The internet as you know it only exists because someone is paying for your attention. If something is getting propagated, someone is willing to pay their own money to showcase that. Every free product you use, every search you run, every reel you scroll through exists because advertisers subsidize your access with cold hard cash.

Roughly 75% of Google's total revenue comes only from ads. Same story with Meta, X, and most news sites. The free internet is not free. You pay for it with your time and your data. But deep down we know that everything in the world has a cost, sometimes you gotta be happy that it’s just money.

If Google and Meta went subscription-only tomorrow, what would you personally pay monthly? Fifty dollars? A hundred? Most people would not pay a single penny. That gap between perceived value and actual infrastructure cost is the ad subsidy.

It is the greatest value transfer in human history, and nobody acknowledges it.

Now AI is about to break this entire model.

A classic Google search costs roughly $0.0003 to$0.001 per query. A ChatGPT-class AI search costs $0.003 to$0.01 per query. That is a 5 to 15 times multiplier in compute costs. At those economics, ad-supported AI search is mathematically impossible at scale.

AI companies are stuck with limited options. They can eat massive losses like OpenAI. They can charge subscriptions and cut out 95% of users like Anthropic. They can degrade model quality to reduce costs, which every company is quietly doing. Or someone invents a new business model, which is highly unlikely.

There is no scenario where AI remains free and good.

The internet is heading toward one of three futures.

The first is subscription internet. The top 5 to 10% pay for access, everyone else gets locked out. A digital class system, which is worse than discrimination.

The second is degraded AI. Free AI is deliberately crippled to force ad exposure or upsells. Think Spotify ad-tier but worse.

The third is a new extraction model. AI companies find a way to monetize that we have not imagined yet. Behavioral data from AI conversations is potentially 100 times more valuable than search data. They will sell insights, not ads.

But we think the winning model will not be any of these cleanly. It will be a hybrid that nobody has articulated yet because we are still thinking in old paradigms of ads, subscriptions, and data sales.

Meanwhile, browsers are becoming the new walled gardens. Chrome's Privacy Sandbox is not about privacy. It is about Google controlling the ad infrastructure at the protocol level. Dia and Safari are doing the same. The browser wars were never about market share. They were always about vertical integration of the ad stack down to the transport layer.

The actual breakthrough will come when someone realizes that AI does not monetize attention, transactions, or data. AI monetizes decisions.

And that is where all the problems start. Once you start monetizing decisions, AI becomes the closest thing to a propaganda machine that humans have ever built. It can influence choices however it wants and the few people holding the keys will be responsible for how the entire human race behaves.

Most people demanding free AI do not realize they are demanding their own digital alienation. The ad-supported internet was a flawed bargain, but at least the transaction was visible. You saw the ads. You knew the deal. But AI that monetizes decisions operates in the dark. And that is a bargain none of us signed up for.

Free internet sold your attention and now free AI will sell your agency — tell us if we are wrong.

A thought by Shashank & ++Hameed++

"Dude, this feels like a bubble," one of them told me. "You can build fun stuff, but there's nothing meaningful you can build for the long-term."

At first, I thought they were being cynical. Then I noticed a pattern.

They think the hard part is building.

It's not.

Anyone can spin up a testimonial widget. Anyone can code a landing page. Anyone can ship a prototype in a weekend.

Then comes the actual hard part — maintenance.

When volume hits. When edge cases multiply. When the thing that worked at 100 users starts breaking at 10,000.

No engineer wants to sit at 2am debugging a tool they hacked together in Lovable. That's why they pay $10/month for something that actually works.

This is the framework that explains everything:

This creates four quadrants:

1. The Dead Zone (Simple + Low Usage) Where most AI wrapper prototypes live. They don't do much, and nobody uses them. This IS the bubble everyone talks about.

2. At Risk (Complex + Low Usage) You built something heavy and "meaningful," but it's too clunky. Enterprise software graveyard.

3. In Danger (Simple + High Usage) This is where the REAL danger lives. A "simple" tool gets traction, then collapses under its own success. The infrastructure can't handle growth.

4. Safe (Complex + High Usage) The Holy Grail. Handles complex needs at volume. This is why people pay for Zoho instead of building a "simple" version themselves.

Remember when the Y Combinator CEO publicly dismissed Zoho? "Why would a company pay for this?"

Because companies are buying the Safe quadrant. They're paying for someone else to handle maintenance, security, and scale.

The founders I talked to understand this. They don't want to babysit infrastructure. They want to build products.

Don't be the founder who celebrates traction while sitting on a house of cards.

The bubble isn't in the Dead Zone. Everyone already knows those tools are worthless. The bubble is in the "In Danger" quadrant — where success is the thing that kills you.

— Shashank

I usually get stuck in a loop of refining weak ideas instead of exploring new territory. Sound familiar? Then I remembered something important: I was using the wrong thinking mode.

Creativity needs both divergent and convergent thinking — at different times. When I'm divergent, I let my mind run wild.

I ask "what if" and chase unusual connections. My notebook fills with messy sketches and half-formed thoughts. I generate dozens of options without judging them. This is exactly what helps in early branding stages — when you're searching for positioning, voice, or visual identity.

I started doing this with my clients, and suddenly possibilities opened up. But then comes the critical second phase: convergent thinking. This is where you evaluate, filter, and focus.

It's the "what works" phase where you select one direction and refine it relentlessly. For my client, this meant choosing one strategic approach from many options, then aligning all messaging around it. The result?

A whole brand that actually makes sense.

We often use convergent thinking too early. We judge ideas before they've had room to breathe. Or we stay divergent too long and never commit to a direction. Understanding when to use each mode will change your creative process:

Start with divergent thinking when exploring new territory — let quantity beat quality. Switch to convergent thinking when it's time to execute — choose one path and refine it. Return to divergent occasionally when you hit roadblocks. The key is recognizing which mode you need right now.

Are you generating possibilities or making choices? I'd love to hear your experience with these thinking modes. When have you found yourself stuck using the wrong approach? What helps you switch between them? Reply and let me know your perspective. And If you found this helpful, try applying both thinking modes to a current project.

Start with 10 minutes of pure divergent thinking (no judging allowed), then switch to convergent mode.

— Shashank

Francis Zierer is about to ship his 150th issue and hasn't missed a single one."

He runs Creator Spotlight, beehiiv's in-house publication with 400,000+ subscribers. But here's the "positioning" everyone missed. His job isn't to sell beehiiv software. It's to build a brand people actually give a shit about reading.

That distinction --- the gap between "marketing collateral" and "editorial authority", is why beehiiv is winning the category.

I sat down with Francis to deconstruct the "Brick by Brick" manual on how he scaled Creator Spotlight from a side project to a standalone industry power.

Q: How did the internal conversation at beehiiv start regarding the need for a dedicated publication like Creator Spotlight, and what was the "North Star" goal for the brand initially?

The "North Star" was to create a high-quality, well-respected, and widely-read publication covering the creator economy --- entirely owned and operated by beehiiv. Candidly, during the interview process, beehiiv CEO Tyler Denk described it to me like this: "We want to accomplish what HubSpot did in acquiring The Hustle, but in-house from the start."

The first beehiiv creator spotlight was published on March 2, 2022, nearly two years before I joined the company.

Nearly every platform that has creator-users has produced some type of creator spotlight. TikTok has a creator spotlight page, YouTube does. It's a type of case study focused on individual users rather than companies.

That classic creator spotlight format --- and beehiiv's original creator spotlight series --- aims to elevate users, leverage their audiences for distribution, and educate existing and potential users on the accomplishments the platform enables.

Creator Spotlight started in that platform-specific style and grew to around 175k subscribers over the course of 22 months and 71 issues before I took over.

The newsletter had a few different writers during that initial period, and while they produced good work, it was always a side project. Responsibility was shared between a few people based on availability.

Tyler pushed to hire a dedicated editor to own the project. As he first put it to me, with an engaged audience already in place, the project just needed an intrapreneur who could establish and execute against an ambitious vision.

Q: In the "Brick by Brick" spirit, what were the first few foundational elements (the first bricks) you put in place to differentiate Creator Spotlight from other "creator economy" news sources?

The first was to abandon the restriction of only writing about beehiiv users.

This would elevate Creator Spotlight from the platform-specific creator spotlight genre and place us in the broader creator economy resource landscape. More to the point, it would allow us to center creators and their work over beehiiv; to serve creators first and foremost; to expand our total addressable audience.

It would've been redundant and a waste of resources if I only covered beehiiv users; beehiiv already had an exceptional case study program (see this recent example on former "Washington Post TikTok guy" Dave Jorgenson's new company, Local News International).

The second was to focus on a profile format over tactics or news.

There were already high-quality newsletters focused on tactics and news for creators. Most had years of industry specialization and full teams behind them; without those years of industry experience and connections, I knew I wouldn't be able to compete on my own.

There were other products focused on creator profiles, but I know I could compete with them. This was my element, the game I could win. Those were the stories I was driven to tell: how they honed their production, audience development, and business skills; how they identified their place in the broader media landscape; their failures and flaws.

I wanted to produce human-interest journalism, based on the belief I still hold that there is a larger and more sustainable audience for empathetic, anthropological coverage of the people working in the creator economy than for hardcore tactical writeups.

We still interview plenty of beehiiv users and we always aim to provide a tactical education element, but the focus in the profiles specifically is always on the person first, not the platforms they use, not their tactics. Tactical education needs a story to sugar the pill.

Q: Creator Spotlight has a very distinct, polished editorial voice. How did you define this brand persona, and how do you ensure it stays consistent across different writers and interviewers?

At the beginning, for myself and the beehiiv team, I articulated the voice I was after in a couple of documents. After that, as I worked alone, it was all in my head; it was easy to stay consistent when I was the one doing all the work. There was nobody to articulate it to (except our podcast producer and graphic designer, for their parts).

The goal was to produce quality journalism that wouldn't feel out of place in a traditional publication as opposed to commodity lead-gen content that fills the pages of so many corporate blogs.

For interviews, reference points included those published in The Paris Review and The Creative Independent, two outlets I'd loved for years. For profiles, I looked to writers like Jonah Weiner in the Times and many writers producing profiles for The New Yorker . I read a lot of Eli Saslow's work for the Times during my prep.

That's the bar I set. Reaching it every week was impossible, of course.

I always knew I'd be working with a few limitations. When I started, for at least the first year, I would be working alone (save for beehiiv's in-house designer to execute graphics and, eventually, our podcast editor).

With no editor besides myself, I had to publish one interview every week; I'd only be able to put so much time into each edition. I started using Claude as an editor, especially to help me find redundancies in my writing and axe down the word count.

When we brought in another writer full-time last spring, Natalia Pérez-González, I put together a style guide to get her up to speed on the voice and style, but I still edit every edition before we send it out (and she edits my writing). We had around 800 applicants for that Assistant Editor role, and only considered applicants with writing samples; part of why we chose her was because her style was already aligned with the Creator Spotlight style.

For the interviews, though Natalia has joined as co-host a few times, I'm still doing every one (at least, every one we publish on the podcast feed).

Q: Your deep dives often feel more like investigative journalism than standard PR interviews. How do you approach "brand trust" so that high-level creators feel comfortable sharing their specific metrics and tactics?

The audience has to come first --- we aim to deliver entertainment and education in every edition. They wouldn't show up if we just published PR interviews every week. Nor, frankly, would I! If Creator Spotlight is a high-quality product, it's because I'm given creative freedom to make it so. Tyler and team have put that belief in me from the beginning.

I have to be able to ask questions about specific audience or revenue numbers, about flaws and failures. That said, I'm not confrontational with our guests. This is not gotcha journalism; I'm not Isaac Chotiner and this is not The New Yorker .

Anybody we feature should be proud to have participated, to share the interview willingly. That's the catch --- as an interview-based product, we need people to want to sit for an interview.

Guest curation is the most load-bearing part of the job. We are promoting any given interviewee, so I focus, for the most part, on creators with aspirational stories. I spend plenty of time pre-researching potential guests to the point where I can envision the shape and outcome of the interview, to identify people amenable to our desired output.

I have three basic filters for this:

1. The audience demands entertainment and education. Does this person have something unique or otherwise compelling to offer on the topics of media production, audience development, or business development?
2. Every edition includes an audio-video podcast. Can I trust this person to speak articulately about their work, to be generous and transparent with the details, and to be a willing and engaged conversational partner over a 1--2 hour recording?
3. Am I personally compelled by their work and character? Does it feel appropriate to dedicate dozens of hours of my and my team's time to an interview and all related outputs?

There's more to it, plenty of caveats; these are the most basic requirements.

I very rarely book an interview until I've had the chance to meet the person, even just for 15 minutes, to make sure they understand our intentions and our audience. I make it clear that this is not a standard PR interview, that any PR outcome they desire will be increased by the type of questions we ask.

Q: How has the brand identity of Creator Spotlight evolved as the newsletter grew from a "feature" of the platform to a standalone authority in the industry?

Before I took over, the branding was totally aligned with beehiiv's branding. Same purple tones, same fonts. Again, the idea was to cover creators broadly rather than just beehiiv users, so it made no sense to keep that identity.

We completely overhauled the brand on publication of my first issue. Over the month preceding, I worked with beehiiv's in-house designer Laura Calle Puerta, on the details.

Lots of logos in the scrap pile. The one we landed on has a blinking I-beam cursor and a red dot as references to two of the tools creators use most --- word processors and cameras.

The tonal beiges are a nod to publications like the Financial Times and Semafor --- colors we associate with publications serving professional audiences.

The editorial voice, the brand identity --- these decisions were made to elevate what is, for many people, still a frivolous topic. To communicate that we take creators seriously; to communicate creators as a serious topic.

The beehiiv branding is loud and specific, built for a software product people pay to use. We're building a free editorial product. They serve different but overlapping audiences and we did not want Creator Spotlight to be subsumed by the beehiiv brand.

We want our work to be useful to beehiiv users, yes, but equally important is anyone working in or interested in the creator economy.

Q: What is the specific role of visual branding, the layout, typography, and custom imagery in making the Creator Spotlight brand feel premium and "must-read"? Because Creator Spotlight is one of the very few newsletters that quickly pops out when someone takes a look at it, and as a very long-time reader, I feel like it immediately grabs my attention and is very aesthetically pleasing.

The word is texture.

I've already detailed some of the brand decisions in previous answers, but the function of the different sections, the custom-image headers and line breaks --- all of the visual details you listed in the question --- is to create texture.

The newsletter can get quite long --- typically between 1,300 and 2,000 words, including everything from the intro letter to ads the main article. The visual details serve to make the information digestible.

Every issue has to pass the scroll test --- If I open this up and quickly scroll through the whole thing, as plenty readers do (I do this with plenty of newsletters), does anything pop out of the blur and catch my eye, draw me in, get me reading?

A newsletter is a visual product.

My interview with Ernie Smith, creator of the Tedium newsletter, influenced how I think about this. He started his career in newspaper design, and his newsletter is not the most visually complex, but it is visually distinct and deploys relatively straightforward font size, color, and number decisions to elegant effect.

Creator Spotlight has a more involved design than most newsletters --- color-background sections, custom graphic headers. But a well-designed newsletter isn't necessarily about these details, it's about the scroll test , which the detailing serves.

Every time we write an issue, we send ourselves a test email and scroll through it, first on our phones and then on our computers. Scroll rapidly. Does anything catch the eye, or does it all blur together?

Most newsletter readers lose loyalty over time (I know my taste for any given newsletter ebbs and flows). Every issue we send, there will be people who open it and barely read, just skimming. The scroll test is about capturing their attention, drawing them in.

Q: How do you balance the Creator Spotlight brand as its own entity versus it being a marketing arm for the beehiiv product?

Simple: my mandate is not to market the beehiiv product, it's to create a high-quality editorial product.

Creator Spotlight is a marketing arm for the beehiiv product in that we use beehiiv to produce a high-quality editorial product; it's a case study itself.

We do keep track of how many beehiiv users enter the ecosystem through Creator Spotlight before eventually becoming paying customers of the product ... but the most important way we market beehiiv through Creator Spotlight is in the type of guest we select and the questions we ask them.

We feature creators who might use competing email service providers or might not have a newsletter at all, maybe their focus is YouTube, but the common thread is that they approach their work seriously as a business .

The most popular creator platforms, the ones that shape the mass definition of "creator," are free to use or take-rate and thus don't require their users to justify an up-front cost. beehiiv has a free offering but is really a pay-to-use tool for customers across the spectrum from prosumer to enterprise.

I seek out people on that spectrum for our interviews. I ask them questions about their business that our audience might learn from; we want our readers to become fluent in the business of being a creator.

In this way, we are propagating a type of "creator" aligned with the beehiiv customer profile; we are encouraging creators to treat their businesses seriously, out of the belief that creators serious about their businesses will benefit from using the beehiiv product over any competing products.

Q: How do you measure "brand equity" for the newsletter? Is it just open rates and subscribers, or are there deeper qualitative signals you look for?

That you reached out to do this interview is one signal!

We have a spreadsheet where I record 42 different metrics 72 hours after we send every edition of the newsletter. But the majority are temperature readings for posterity, to identify patterns over time. I only surface 7 to the broader team each week.

The most important signals we monitor are:

• Monthly active readers (MAR). How many people have opened our emails in the last 31 days? We track 0 unique opens over this period, 1, 2, 4, 7. We send 8 issues in a typical 31-day period, so 4 measures how many people opened half, for example, and 7 means they opened all or close to it.
• Podcast listenership (across both RSS feeds and YouTube). We track listens in the first three days for each episode and across a weekly period for the entire catalog.
• Industry acknowledgement --- requests for interviews like this one, or to speak on panels, aggregation of our writing in other industry newsletters, references to our work on social media, etc.
• Ad revenue. We offer sponsorship packages; our ability to attract the right partners and sell through is a quantifiable measure of brand equity.

Q: What was a significant "pivot" or structural change you made to the brand after seeing how readers responded to early editions?

Brevity.

Some of my earlier issues got up to 3,000 words. This one with Casey Lewis, two months into my tenure, might be the longest. Before the podcast, and into the early days of the podcast, we'd publish excerpts from the interview transcript.

Sections present in that issue that we don't have today include:

• The interview excerpt
• "Zoom out" --- a few distilled takeaways from the interview
• An outro letter with a feedback poll and a preview of the next week's issue
• A what-we're-reading links roundup

Rereading that issue for the first time in at least a year, I love the depth, but most subscribers just aren't going to have time for it. We've sought to streamline the product as much as possible --- brevity is a service we aim to provide our readers. The podcast exists for folks who want more from any given guest.

Q: How does the brand stay relevant in an oversaturated market of "newsletters about newsletters or creators", what is your unique value proposition?

It's a nonstop challenge. Like any newsletter, we lose subscribers with every send.

One of my mottos is: be consistent but not predictable. Consistent in quality, not predictable in the type of guests we curate and the questions we ask them.

We have to take risks with our guest selection. I know not every guest will resonate with every reader, our remit is too wide for that. So we have an appetite for risk there.

We're overdue to shake up the format again. Just like much has changed since that Casey Lewis issue two years ago, if the product doesn't have a few significant differences one year from now compared to today, we've played it too safe.

The unique value proposition, which we do not seek to change, is how we see creators. Creators before platforms, creators as an underserved and overexploited class of worker.Creator Spotlight is an ongoing research project with the goal of making the working creator's job easier.

Q: Can you walk us through the brand's distribution strategy? How do you ensure the Creator Spotlight brand reaches new audiences beyond the existing beehiiv database?

The beehiiv user base remains our important source of growth.

Second is paid growth. We spend thousands of dollars a month on Meta ads.

Third is word-of-mouth. Are we producing work good enough to earn a share? Are we including enough guests with sizable audiences and a willingness to share their interview?

Q: How much of the brand's success is tied to the personal brands of the editors and producers versus the institutional brand of beehiiv?

Our goal is for Creator Spotlight to be the primary brand here. I don't have a major social following --- my biggest is on LinkedIn, where I have 4,600 followers at the time of writing. Nor does Natalia have a major following, nor our podcast editor Tom McCloud, nor our designer Laura Calle Puerta. Tyler Denk, beehiiv's CEO, does have a large personal brand and he lends that weight to us sometimes, but that's separate.

The brand's success is tied entirely to the quality of the product. The guests we curate, the questions I ask them on the podcast, the articles we write. If the quality is there, subscribers stick around, people share our work, advertisers want to spend their budget with us.

The brand's success is certainly connected to my voice as editor, but not irrevocably bound to it.

As my personal brand grows, I'll use it to grow Creator Spotlight and vice versa, but I was not hired for my social following, I was hired for my editorial ability.

Q: What is the most underrated "brick" in building a newsletter brand that most creators ignore or overlook in the beginning?

The most practical thing you can do in building a newsletter brand is to create a simple, outcome-based welcome email. You may eventually need multiple versions as your audience grows, but if you're trying to build an audience in earnest, build a welcome email.

beehiiv has a thorough guide on 11 different types of welcome email.

For Creator Spotlight , we have two variants. One serves subscribers who come to us from beehiiv, the other serves subscribers who come from outside that ecosystem (paid ads, word of mouth).

We introduce the concept, share a few of our most popular pieces to give them an impression, and ask them to reply with a little bit of information about themselves (favorite creators, their own work as a creator). This helps deliverability (signals to Gmail or whichever email client they use that our email should land in the primary inbox) and helps us learn about our subscribers. We've found guests this way!

You might also ask them to fill out a survey in this email, but that can be done separately, as part of a signup flow (here's how to set one up using beehiiv). Set up a survey from the start --- doesn't have to be many questions, but if you plan to work with advertisers, for example, this is where you collect the demographic, income, etc. information that will help you win those deals.

Q: If Francis has to give one piece of advice for people building a brand around newsletters, what would that be?

Newslettering is a long game. I've never missed an issue since I started --- we'll hit 150 in a few weeks, about 25 months after my first one.

Personally, I'm driven by the desire to deliver a quality issue every time. I care about the topic we cover. I love doing these interviews, writing these articles, and editing Natalia's articles. If I didn't --- and if I didn't have license from Tyler and the beehiiv team to execute against my vision --- I wouldn't be here. Probably would've burnt out and left before completing one year.

A newsletter serves at least two parties: the creator and the audience. In the case of Creator Spotlight , there are two more: the publisher (beehiiv) and our advertisers. All parties' incentives have to be aligned long-term for the newsletter to be a success.

Most importantly, the creator has to care deeply about the product to deliver consistent quality, and that product has to fulfill a need for the audience. That's the only way to maintain a great newsletter long-term.

The Brick Worth Stealing

Francis didn't build a 400k-person audience with growth hacks or "one weird trick." He built it through Texture and Tone.

If you're building a brand-led newsletter, stop worrying about being "clever" and start worrying about the Scroll Test. If a reader skims your email and nothing "pops," you haven't built a brand --- you've built a wall of text.

Set up that welcome email, treat your 150th issue with the same respect as your first, and remember that Consistency beats cleverness. Every. Single. Time.

Stay stupid,

Shashank

Your Friendly Neighborhood Brand Architect

P.S. If you're struggling with your own "North Star" positioning, reply to this email. I'm looking to help two more companies fix their revenue-killing brand problems this month.

P.P.S. Seriously, go look at your welcome email right now. Is it a boring receipt, or is it a conversation starter?

Francis is watching.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

But his marketing looked exactly like his competitors'. His positioning was indistinguishable and the pricing followed industry benchmarks.

"So what's the problem?" he asked.

"You have no problem," I said. "You also have no advantage."

Best practices are a trap. They're the default settings of business strategy. And in a world where everyone has access to the same information, following best practices means becoming interchangeable.

The companies that build lasting moats do something different: they treat industry consensus as a signal to investigate, not a playbook to follow.

The best practices paradox

"Best practices" sounds safe. Scientific, even. It's what works. It's been proven.

But a best practice is really just the most common approach among your competitors.

When you adopt a best practice, you're not gaining an advantage. You're eliminating a disadvantage. You're achieving parity. You're running the same operating system as everyone else.

Best practices often become industry standards because they're safe. They spread through mimicry and the original context gets lost.

And then someone comes along who refuses to follow them.

Patagonia: the anti-consumption brand

The marketing best practice is to maximize purchase intent. Never give customers a reason not to buy. Black Friday is for pushing products.

On Black Friday 2011, Patagonia ran a full-page New York Times ad with their best-selling jacket and a simple headline: "Don't Buy This Jacket."

The ad detailed the environmental cost of manufacturing, the waste, and the resources consumed. It explicitly asked customers to think twice before purchasing.

This is marketing malpractice by any traditional standard. You don't suppress demand. You don't highlight negatives. You don't tell people to stop shopping.

Patagonia's revenue increased 30% over the following nine months. A 40% surge over two years.

Trust is scarce. In a world where every brand is screaming for attention, the one that respects your intelligence becomes unforgettable. Patagonia wasn't selling jackets. They were selling a relationship with a company that wouldn't treat you like a mark.

So did Netflix and Costco.

The pattern beneath the stories

These companies aren't randomly rebellious. They share a diagnostic framework.

First, identify the unquestioned assumptions. Every industry has beliefs so deeply embedded they're invisible. "Retail is a margin game." "Tech giants must diversify." "Marketing should drive consumption." These assumptions aren't always wrong. But they're rarely examined.

Second, trace the assumption to its origin. Best practices usually solved real problems in a specific context, at a specific time. Retail margins mattered when differentiation was possible. Diversification made sense when industries were more siloed. But contexts change. The practice often outlives its purpose.

Third, ask the inversion question: what if we did the exact opposite? Most inversions are stupid. Some unlock enormous value.

Fourth, identify the hidden advantage. Anti-default strategies only work when the opposite behavior creates a new source of competitive advantage. Costco's high wages drive retention. Netflix's focus enables mastery. Patagonia's restraint builds trust.

The self-diagnostic

This is where it stops being about other companies.

List five things your company does because "that's how it's done in this industry."

For each, answer: why does this practice exist? What problem was it originally solving? Is that problem still relevant?

For at least one, genuinely explore the inversion. As an actual strategy option. What would have to be true for the opposite approach to work?

Where does the inversion create a hidden advantage?

If you can't answer these questions, you're running on defaults. And somewhere, right now, a competitor is asking them.

The only advantage left

The tools are commoditized. The playbooks are public. The data is available to everyone.

Your competitors can copy your tech stack in a week. They can replicate your marketing tactics in a month. They can match your pricing by tomorrow.

What they can't copy is the courage to reject industry consensus when that consensus has become a trap.

Netflix didn't have better streaming technology than Blockbuster. Costco doesn't have superior warehouses to Sam's Club. Patagonia doesn't have access to manufacturing capabilities that North Face lacks.

They have a different relationship with best practices. They treat "the way things are done" as a hypothesis to test, not a rule to follow.

That's the only sustainable advantage in a world of tool parity. Everyone has access to the same resources. Very few have the nerve to use them differently.

Shashank

P.S.

The safest thing you can do in business is follow best practices. It's also the fastest way to become irrelevant. Safety and differentiation pull in opposite directions. Pick one.

P.P.S.

Worth remembering: when Costco decided to pay workers nearly double the industry average, retail analysts called it "unsustainable." When Netflix bet $100M on original content, entertainment executives called it "reckless." When Patagonia told customers not to buy on Black Friday, marketing experts called it "insane." The people most invested in existing defaults are always the most certain that alternatives won't work.

For decades, brands chased polish. Cleaner logos, smoother transitions, more seamless user experiences. The logic was simple, professionalism signals quality, and quality earns trust.

That logic just broke.

AI flooded the market with perfection. It can generate flawless copy, pixel-perfect designs, and video that looks like it cost a hundred thousand dollars to produce. And in doing so, it devalued the very thing brands spent decades pursuing. When anyone can produce polish in seconds, polish stops meaning anything.

We're watching an economic correction unfold in real time. Attention used to be the scarce resource brands competed for. Now attention is cheap --- algorithms serve endless content to endless eyeballs. What's actually scarce is trust. And trust, it turns out, requires proof of human intent.

This is where imperfection enters as a brand strategy.

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The synthetic fatigue problem

Users are developing what might be called "synthetic fatigue." They've seen enough AI-generated content to recognize the tells --- the slightly-too-clean aesthetic, the generic competence, the feeling that something was assembled rather than created.

This fatigue isn't rational. It's not that AI content is bad. Often it's technically superior. But something about knowing a machine produced it triggers a trust discount. The content might be beautiful, but it doesn't feel meant. There's no one on the other side who cared whether you received it.

Brands are responding by leaving fingerprints. Raw videos where the founder stumbles over words. Behind-the-scenes photos that haven't been color-graded. Employee stories that ramble a bit before landing. Each imperfection says that a human made this, and they chose to show you the seams.

Even Apple, a company that could generate flawless CGI in its sleep made this bet. When they rebranded Apple TV in late 2025, they built a real glass apple sculpture, lit it by hand, and captured every shimmer in-camera. For heavens sake, craftspeople rotating glass under precision lights until they got the shot. As soon as people learned it was done for real, they celebrated. The deliberate rejection of digital perfection became the story.

Why imperfection works

Seamless experiences are forgettable. When everything glides past without resistance, nothing sticks in memory. The brain doesn't flag it as meaningful. But introduce a moment of texture, a pause, an oddity, something that doesn't quite fit the template, attention catches. The user registers that something different is happening.

The path to connection runs through deliberate imperfection. The design world is calling this "post-minimalism." Minimalist structure, but layered with personality that algorithms wouldn't naturally generate. Hand-drawn elements over clean layouts. Bold typography that breaks the grid. Non-linear storytelling that rewards patience rather than optimizing for the scroll.

When a website is too smooth, users glide past without forming memory. When a brand's voice is too polished, it sounds like everyone else's. Imperfection is what makes you pause and that ONE FREAKIN PAUSE is the first step toward trusting.

The human-to-AI ratio

Smart brands are getting explicit about this. They're disclosing their "human-to-AI ratio", which parts of their content were generated, which were human-crafted, which were some blend of both.

This transparency sounds risky, but it's actually a trust accelerant. In a world where users assume everything might be synthetic, declaring your human investment becomes a differentiator. You're not hiding the machine; you're showing where the person is.

The most effective approach treats AI as underpainting. Let the machine handle the mechanical work, resizing, formatting, data analysis, first-draft structure. Free up human time for the parts AI still can't replicate, the joke that lands, the empathy that connects, the cultural reference that signals you're actually paying attention.

This is not anti-AI, it's pro-intent. The goal is demonstrating that a human decided this content should exist, shaped it to matter, and released it because they believed it would serve you.

Just like this piece.

The correction continues

We're early in this shift, and the dynamics will keep evolving. As AI-generated content improves, the signals of human creation will need to become more sophisticated. What reads as "authentic" today will calcify into new clichés tomorrow. The grainy founder video, repeated enough times, becomes its own form of polish.

But the underlying economics won't change. Trust remains scarce. Human intent remains valuable. And imperfection remains the proof.

Winners won't be the brands with the best production values. They'll be the ones where you can feel a person behind the pixels --- someone who cared whether you got what you came for.

Perfection used to be the goal, but now it's a liability.

Imperfection is the new brand strategy because they're inherently human. And in an economy where trust is the currency, humanity is what you're actually selling.

--- Shashank

P.S.

If you found this edition valuable, I'd appreciate you forwarding this email to one person who might need this perspective right now.

And if you are the one who received it, you can subscribe here.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

A couple of weeks ago during the year end break, I finished reading Obviously Awesome by April Dunford. Closed the book, stared at the wall and had a deeply unsettling thought:

Did this woman break into my apartment and photocopy my brain?

I'm not saying April Dunford, a positioning consultant with 25 years of experience and 200+ companies under her belt, including Google, IBM, and Epic Games hacked into my Notion workspace. I'm not saying she's been secretly reading every Stupidpreneur newsletter I've published. I'm not making accusations.

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I picked up her book expecting to learn something new about positioning. Instead, I found page after page of ideas I've been preaching for years --- sometimes word-for-word aligned with the Stupidpreneur philosophy.

• The customer-centric approach.

• The death of static positioning.

• The uselessness of fill-in-the-blank positioning statements.

By chapter three, I was highlighting passages and muttering, "I SAID THIS. I LITERALLY SAID THIS." By chapter seven, I'd moved past suspicion into something stranger, validation.

When you spend years sharing ideas that people call "contrarian" or "unconventional" or my personal favorite, "interesting, but that's not how we do things here", you start to wonder. Am I actually onto something? Or am I just a guy yelling into the void?

Then a bestselling author comes along and packages those same ideas into a framework that the business world nods along to. And suddenly your contrarian takes aren't contrarian anymore.

They're best practices.

THE EVIDENCE FILE: EXHIBIT A THROUGH D

Let me walk you through the case file. Four specific overlaps between Stupidpreneur philosophy and Dunford's framework that made me feel like I was reading my own thoughts in someone else's handwriting.

Exhibit A: Customer-Centric Positioning (Not Founder-Ego Positioning)

**Your positioning isn't about what YOU think your product is. It's about what your CUSTOMERS need it to be.**Stop navel-gazing. Stop building positioning around your origin story, your founder journey, your "why I started this company" narrative.

Nobody cares.

Your customers care about their problems. Position yourself as the solution to THEIR context, not as a monument to your vision.

Dunford's take? Almost identical.

She argues that positioning is "context setting", the deliberate act of defining how you're the best at something that a defined market cares a lot about. Not what you care about. What THEY care about.

The reaction I used to get when I said this? "But our story is what makes us unique!" "But investors want to hear your founder's journey!" "But we need to communicate our mission!"

Sure.

And your customers need to understand why they should give you money. Pick one.

Exhibit B: Best-Fit Customers Over "Everyone Is Our Customer"

I've lost count of how many founders I've talked to who say some version of: "Our target market is anyone who needs [extremely broad category]."

My response is always the same, "If everyone is your customer, no one is your customer." You're casting no net. You're standing in the ocean hoping fish jump into your boat.

Dunford calls these "best-fit customers", the specific people who care the most about your unique value. The ones who buy quickly, rarely ask for discounts, and become your biggest advocates. She's ruthless about trying to please everyone.

Find your true believers and position for THEM.

The pushback I've gotten? "But we'll miss out on potential customers!" "But our TAM will look smaller to investors!" "But what if we're wrong about our segment?"

Ahhhhh...

A smaller TAM with 40% conversion beats a massive TAM with 0.4% conversion.

Every.

Single.

Time.

Exhibit C: Competitive Alternatives Aren't Always Competitors

This one made me actually laugh out loud when I read it.

For years, I've told founders: Your competition isn't who you think it is. You're not competing against the other startups in your space.

You're competing against Excel spreadsheets. You're competing against "hire an intern to do it manually." You're competing against "do nothing and hope the problem goes away."

Dunford frames it as "competitive alternatives", whatever your best customers would do if you didn't exist. And she's explicit that often the alternative is a spreadsheet, a manual process, or ignoring the problem entirely.

When I've said this to founders, the response is usually confusion. "But we have direct competitors! We need to differentiate against THEM!"

Do you, though?

If 70% of your lost deals go to "we decided to stick with our current process," your positioning problem isn't differentiation. It's category creation. You're not losing to competitors. You're losing to inertia.

Exhibit D: Positioning Is Not Static

I've been preaching this for years: Your positioning should evolve. Markets shift. Competitors emerge. Customers need change. If your positioning is the same today as it was eighteen months ago, you're probably leaving money on the table or worse, becoming irrelevant.

Dunford agrees. She recommends checking your positioning every six months, or after major market events.

Stupidpreneur has repositioned THREE TIMES in the past year alone. Not because I was wrong before, but the market changed. AI exploded. The creator economy shifted. New opportunities emerged that didn't exist twelve months ago.

Each repositioning was an adaptation and each one drove growth.

The old-school advice? "Find your positioning and stick to it. Consistency builds brand."

The reality? Rigidity kills brands. Responsiveness builds them.

THE EMOTIONAL JOURNEY: FROM HEIST TO VALIDATION

I'll be honest about my emotional arc reading this book.

Stage One: Suspicion. Wait, did someone plagiarize me? These ideas are too similar. This is weird.

Stage Two: Ego Bruise. Okay, no one plagiarized me. These ideas exist independently. Which means... I'm not as original as I thought?

Ouch.

Stage Three: The Reframe. This isn't theft. This is convergent evolution.

When you spend enough time in the trenches, actually working with brands, actually building positioning, actually watching what works and what fails, you arrive at certain truths. Because reality has a way of teaching the same lessons to anyone paying attention.

April Dunford spent 25 years in marketing leadership. I've spent years building and advising brands through Stupidpreneur. We've never met. We've never compared notes. And yet we landed on nearly identical frameworks.

That's a signal.

Stage Four: Bittersweet Acceptance. Look, I'll admit it --- I would have loved to be the one who wrote this book. I would have loved to be the "positioning expert" whose framework gets cited in boardrooms and pitch decks and LinkedIn posts.

But there's something beautiful about seeing your "contradictory takes" validated by someone with 200+ client engagements and two bestselling books. It means the ideas aren't just my opinions. They're patterns. They're truths that emerge from doing the work.

THE POSITIONING STATEMENT IS DEAD (AND WE BOTH KILLED IT)

Let me go deep on one idea that Dunford and I share, because it captures everything wrong with how most people approach positioning.

You've seen the template. Every marketing course, every branding workshop, every "How to Position Your Startup" blog post has some version of it:

"For [target customer] who [statement of need], [product name] is a [market category] that [key benefit]. Unlike [competitors], our product [statement of differentiation]."

Fill in the blanks. Get your positioning. Ship it.

This template is useless.

And it's actively harmful.

Dunford calls it out directly in her book that the traditional positioning statement assumes you already know the answers. It's a formatting exercise disguised as a strategic one. You're just mad-libbing your way to mediocrity.

I've been saying this for years with a different framing: Positioning isn't a SENTENCE. It's a PROCESS.

The fill-in-the-blank approach fails for three reasons:

Reason 1: It skips the hard work. The template assumes you know your target customer, your market category, your key benefit, and your differentiation. But FINDING those answers is the entire challenge. The template is like a recipe that says "Step 1: Obtain a delicious meal. Step 2: Eat a delicious meal." WHERE'S THE COOKING?

Reason 2: It creates Frankenstein language. Have you ever read a positioning statement out loud? "For enterprise HR managers who need streamlined onboarding, TalentFlow is a SaaS platform that reduces time-to-productivity. Unlike legacy HRIS systems, our product leverages AI-powered workflows."

No human talks like this. No customer thinks like this. You've created a sentence that's technically complete and practically useless.

Reason 3: It optimizes for internal alignment, not customer resonance. The positioning statement becomes a thing you put in a slide deck to make executives nod. It doesn't become a thing that actually helps you sell, market, or build. It's a corporate theater.

THE POSITIONING PROCESS FRAMEWORK

So what's the alternative? Both Dunford and I arrive at the same answer: positioning is sequential, not fill-in-the-blank.

Here's how it actually works:

Step 1: Start with your happiest customers. Not your target market. Not your TAM. Your actual, existing, happiest customers. The ones who bought fast, paid full price, and tell their friends about you. They hold the key to your true value.

Step 2: Understand what they would use if you didn't exist. This is your competitive alternative. It might be a competitor. It might be Excel. It might be nothing. But this is your real battleground.

Step 3: Identify what you do that the alternative can't. These are your unique attributes. Factual. Provable. Not "we have better customer service"---that's a claim. "We respond to support tickets in under 4 hours on average"---that's an attribute.

Step 4: Translate attributes into value. For every unique attribute, ask "So what?" until you hit something the customer actually cares about. "We respond in 4 hours" → "So what?" → "You're never blocked waiting for help" → "So what?" → "You ship faster." THAT'S the value.

Step 5: Find the market frame that makes this obvious. Choose a category that makes your value self-evident. Sometimes it's an existing category. Sometimes it's a niche within a category. Sometimes it's a new category entirely.

This is work. This is hard. This is the part that positioning statements skip.

Can you explain your positioning to a stranger in 30 seconds, without using any jargon, in a way that makes them immediately understand why they should care?

If you can't, you don't have positioning. You have a positioning statement.

And this is exactly what I teach in the brand engine as well. I first ask you to research your customers, talk to them and understand them and then come back to the positioning statement and not the other way around.

THE VERDICT: CASE CLOSED

April Dunford didn't steal my ideas. She validated them.

And that validation matters --- not for my ego, but for anyone who's been following Stupidpreneur and wondering if these frameworks actually work.

They do.

They work well enough that someone with 25 years of experience and hundreds of client engagements independently arrived at the same conclusions.

If you've been reading Stupidpreneur, you're already ahead. You've been learning these principles in real-time, applied to real brands, with real results. Keep going.

And if you've been called "contrarian" for believing that positioning should be customer-centric, that it should evolve with the market, and that fill-in-the-blank templates are corporate theater?

Welcome to the club. Turns out we were just early.

But April, if you're reading this, you owe me a coffee. ☕

Your brand philosopher,

Shashank "The Stupidpreneur" SN.

P.S.

Want me to break down YOUR positioning using this framework? Reply to this email with your one-liner and I'll tell you what's working and what's not. First 10 replies get a detailed response.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

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A founder showed me his analytics dashboard last month and it was one of the best ever dashboards that I have ever seen in my life. It had everything:

• Beautiful charts.

• Every metric that a business could possibly track.

• A/B tests running on his headline

• CTA button color

• Email subject lines.

But revenue? Flat for 18 months.

"I don't understand," he said. "I'm doing everything the data tells me."

THE REARVIEW MIRROR PROBLEM

Data only shows you what already happened.

Data is a rearview mirror. It tells you which road you've been on. It cannot tell you which road to take next, especially if that road doesn't exist yet.

When you're "data-driven," you're optimizing for the past. You're making small improvements to a direction that might be fundamentally wrong.

The biggest wins in business don't come from 2% conversion improvements. They come from zigging when everyone else zags.

Data can't tell you when to zag.

THE "FASTER HORSES" PRINCIPLE

Henry Ford allegedly said: "If I had asked people what they wanted, they would have said faster horses."

Whether he actually said it doesn't matter. The insight is real.

Customers can articulate problems. They cannot articulate solutions they've never imagined. Data captures what people do , it cannot capture what people could do if you showed them something new.

The iPhone didn't come from market research. Steve Jobs famously refused to use focus groups. His reasoning? "People don't know what they want until you show it to them."

Jobs killed the stylus when every data point said people wanted one. He removed the keyboard when BlackBerry's data said keyboards were essential.

Steve was right and the data was wrong by trillions of dollars.

WHEN GUT BEATS SPREADSHEET

I'm not saying ignore data. I'm saying know its limits.

Use data for:

• Validating what's already working (double down)

• Identifying what's broken (fix or kill it)

• Measuring progress on a known path

Use gut for:

• Choosing which path to take

• Deciding what to build next

• Making bets the market hasn't validated yet

The founder with the beautiful dashboard? His data was optimizing a product nobody wanted. No amount of A/B testing would fix that. He needed to make a gut decision about a new direction, something no spreadsheet could give him.

THE "INSIGHT VS. INFORMATION" SPLIT

Data gives you information. Gut gives you insight.

Information: "Bounce rate is 67% on mobile." Insight: "Our entire value proposition is wrong for this audience."

Information tells you what . Insight tells you why and what next.

The best founders I've worked with use data to confirm intuition, not replace it. They have a thesis about the market, then look for data to stress-test it. They don't wait for data to hand them a thesis.

THE DIAGNOSTIC

Answer honestly:

When's the last time you made a significant business decision that your data couldn't justify?

If every decision requires a spreadsheet, you're not leading. You're following --- following what already happened, hoping it predicts what's next.

Sometimes it doesn't.

Trust the gut.

Your brand strategist,
Shashank SN

Fractional Chief Brand Officer

P.S.

The most "data-driven" company I ever saw went bankrupt optimizing a product nobody wanted. They had dashboards for everything except the question that mattered: "Should we be doing this at all?"

P.P.S.

If your marketing team says "the data says..." more than "I believe...", you might have a courage problem disguised as a process problem.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

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My friend Sanjeev makes memes about B2B SaaS.

About HRs, sales calls, enterprise software, and the absurdity of corporate life.

People told him it was dumb. "B2B is serious business. No one wants jokes."

Today? Companies put Sanjeev's videos in their pitch decks. His memes get shared in Slack channels at Fortune 500s. He built Supermeme, an AI meme generator, off the back of that audience.

Turns out, B2B buyers are humans. And humans like to laugh.

THE "BORING" LIE

Here's the myth that kills B2B brands: "We sell to businesses, so we need to sound professional."

"Professional" becomes code for:

• Jargon-filled copy nobody reads

• Stock photos of people shaking hands

• A tone so sterile it could pass a hospital inspection

The result? Every B2B company sounds identical. Blue logos. White websites. "Synergy" in the headline.

When everything looks the same, nothing stands out.

THE "MULLET STRATEGY"

The best B2B brands operate on what I call the Mullet Strategy:

Business in the front. Party in the back.

• Front (Product): Your product is serious. It solves real problems. It has enterprise features, SOC 2 compliance, and robust integrations.

• Back (Content): Your content is human. It has personality. It makes people smile, think, or feel something.

The product earns trust. The content earns attention.

Slack does this. Their product is enterprise collaboration software (boring). Their brand voice is playful, witty, and full of personality (not boring).

Mailchimp did this for years. Email marketing (boring). A cartoon chimp and weird animations (memorable).

Clay, the CRM platform, does this right now. The product is sales intelligence (boring). Their content is memes, chaos, and internet culture (magnetic).

WHY HUMOR WORKS IN B2B

Three reasons:

• Pattern interrupt. When everyone zigs (corporate), you zag (human). Humor makes you the one people remember.

• Shareability. Nobody forwards a whitepaper to their colleague with "lol you have to see this." They do forward memes.

• Trust signal. If you're confident enough to have fun, you must be good at what you do. Insecure brands hide behind jargon.

Sanjeev understood this instinctively. By making B2B people laugh at themselves, he became the insider, not the outsider trying to sell them something.

HOW TO ADD PERSONALITY (WITHOUT BEING CRINGE)

The fear is: "If we joke around, people won't take us seriously."

Here's the trick: Be serious about your product. Be human everywhere else.

• Keep product pages clear and direct. Features, benefits, pricing. No jokes needed.

• Let content breathe. Blog posts, social media, newsletters---this is where personality lives.

• Find your "inside joke." Every industry has absurdities everyone knows but nobody says. Say them.

• Hire for voice. Your content person should actually be funny. You can't fake this.

THE DIAGNOSTIC

Answer honestly:

If you removed your logo from your website, could anyone tell it was you?

If your copy, tone, and visuals could belong to any competitor --- you don't have a brand, you have a template.

B2B doesn't mean boring. It means your buyers sign contracts instead of clicking checkout.

They're still humans. Talk to them like it.

Your brand strategist,
Shashank SN

Fractional Chief Brand Officer

P.S.

Sanjeev's "dumb" meme account became the foundation for a real SaaS company. The people who told him B2B is serious? They're still writing whitepapers nobody reads.

P.P.S.

If your marketing team is scared to post anything "too fun," that fear is the problem. The safest path in B2B is now the riskiest, because everyone's on it.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

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El Mejor Coffee: Spanish for "The Best." People read it as "El Major." They called it El Major. I didn't correct them. We still sold coffee.

Happy Beginnings: I got the name from "Happy Endings" --- which sounds wildly inappropriate for a wedding invitations company. Didn't matter. Still India's first wedding invites e-commerce.

Stupidpreneur: The word has "stupid" right in it. People ask, "Who's the stupid one?" I tell them: everyone building something worth building.

Tbh, your company name matters about 0.01% as much as you think it does.

THE NAME OBSESSION TRAP

I've watched founders spend 6 months choosing a name. Domain hunting. Trademark searches. Focus groups with friends. Endless debates about "vibes."

Meanwhile, their competitor shipped a product, got customers, and owns the market.

The delay just killed them.

THE "RADIO TEST" (AND WHY IT'S OVERRATED)

You've probably heard this advice: "If you say your name on a podcast, can people spell it?"

It's decent advice. But most successful companies fail this test.

• Airbnb (AirBNB? Air B and B? AirBed?)

• Lyft (Lift? Lifft?)

• Flickr (Flicker? Flickr? Where's the E?)

They figured it out. So will you.

If your name is somewhat pronounceable and not actively offensive, you're fine. Move on.

WHY YOU SHOULDN'T BUY THE .COM (YET)

Founders blow 1000$+ on premium domains before they have a single customer.

Here's what I recommend instead:

• Start with a workaround. Use .co, .io, or add "get" or "try" to the front.

• Prove the business first. Get to 50k+ revenue.

• Then acquire the .com. You'll have leverage (and cash) to negotiate.

Nobody ever said, "I love this product but I won't buy because the domain has 'get' in front of it."

THE "REBRAND LATER" SAFETY NET

You can always change your name later.

And when you do? It's a PR opportunity.

"We started as Old Name. As we grew, we evolved. Today, we're proud to announce New Name --- a reflection of our journey, our values, and our commitment to whatever sounds good."

Companies do this constantly. It's free press. It signals growth and maturity.

So stop treating your first name like a permanent tattoo. It's a sticky note. You can peel it off when you're ready.

THE "STUPID" NAMING PROCESS

Here's my actual process:

• Spend one day brainstorming.

• Check if the name is taken. Basic trademark search, domain availability.

• Say it out loud 10 times. Does it feel weird? Can you introduce your company without cringing?

• Ship. Fix it later if needed.

The bar is low.

Go build something.

THE DIAGNOSTIC

Answer honestly:

Have you spent more time on your company name than talking to potential customers?

If yes, you're hiding from the hard work. Naming feels productive.

It isn't.

The name doesn't make the company, the company makes the name.

Your brand strategist,
Shashank SN

Fractional Chief Brand Officer

P.S.

"Stupidpreneur" breaks every naming rule. Has a negative word. Hard to take seriously. Sounds unprofessional. It's also the name behind a 20,000+ subscriber newsletter read by people at Coca-Cola, LinkedIn, and Amazon.

I let you be the judge of whether this name is good or not.

There's a man who built a billion-dollar company, created a platform that changed how startups get funded, and somehow became more famous for his tweets than his exits.

Naval Ravikant doesn't fit into a box. He's a tech investor who reads philosophy for breakfast. A startup founder who quotes Buddha in board meetings. A capitalist who talks about happiness like a monk.

And that's exactly why you can't look away.

His approach to brand-building isn't in any marketing textbook. It doesn't involve personas or positioning statements or carefully crafted brand guidelines. What he's built and what he teaches is something far more radical:

The most powerful brand you can build is one that cannot be replicated. Because it is you.

Here are ten principles from Naval's philosophy that will change how you think about building a brand.

PRINCIPLE 1: THE BEAR ON A UNICYCLE

"If you go to a circus and you see a bear, that's kind of interesting but not that much. If you see a unicycle, that's interesting. But you see a bear on a unicycle, that's really interesting."

Naval uses this metaphor to explain his own unlikely appeal. He combines things you're not supposed to combine: hard-nosed investing with Eastern philosophy. Startup hustle with inner peace. Wealth creation with wisdom literature.

The most memorable brands aren't the ones that fit neatly into a category. They're the ones that create a new category by combining things nobody thought to combine.

Think about it: What two worlds do you live in that most people keep separate?

Maybe you're an accountant who also does improv comedy. A software engineer who's obsessed with Renaissance art. A corporate lawyer who grows mushrooms on the weekend.

The combination is the brand. The weirder the intersection, the more interesting you become.

Diagnostic question: What are two things you're genuinely obsessed with that seem like they don't belong together? That's your bear on a unicycle.

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PRINCIPLE 2: SPECIFIC KNOWLEDGE CANNOT BE TRAINED

Naval makes a crucial distinction: there's generic knowledge (anyone can learn it) and there's specific knowledge (it can only be developed through lived experience).

Generic knowledge creates competition. Specific knowledge creates monopoly.

"If society can train you, it can train someone else and replace you."

But specific knowledge? It's the stuff you picked up because you couldn't help yourself. The rabbit holes you went down when nobody was watching. The skills you developed because you were obsessed, not because it was on a syllabus.

Here's the framework:

THE SPECIFIC KNOWLEDGE HIERARCHY:

• Level 1: Trained skills (replaceable, low value)

• Level 2: Experience-based skills (harder to copy, medium value)

• Level 3: Obsession-based knowledge (nearly impossible to copy, high value)

• Level 4: Identity-fused knowledge (truly irreplaceable, maximum value)

Level 4 is where the magic happens. It's when your knowledge becomes so fused with who you are that separating the two is impossible.

Naval's specific knowledge isn't "investing." It's the specific intersection of tech evaluation, philosophical frameworks, and first-principles thinking that he's been building since he was 13 years old.

Diagnostic question: What do you know that you've never been formally trained in, but you've been learning your entire life?

PRINCIPLE 3: ACCOUNTABILITY IS THE UNLOCK

The people who build the biggest brands are the ones willing to put their name on the line.

"The most powerful money makers are actually individual brands, people like Elon or Kanye or Oprah or Trump. These are individual brands, eponymous name brands who themselves are leveraged."

Naval isn't hiding behind a corporate veneer. He's not "the founder of AngelList." He's Naval. The brand and the person are one.

This is terrifying for most people. If you fail publicly, it's your failure. If you say something wrong, your name is attached to it. If things go sideways, you can't disappear into the corporate machine.

But here's what accountability unlocks: trust at scale.

When you put your name on something, people know you have skin in the game. They know you're not going to disappear. They know that your reputation is tied to delivery.

The formula: Accountability + Skin in Game + Public Name = Trust Multiplier

Anonymous operators don't build brands. People who hide behind corporate masks don't build followings. The willingness to be personally accountable is the price of admission.

PRINCIPLE 4: AUTHENTICITY IS YOUR MOAT

Naval says something that sounds almost too simple to be true: "No one can compete with you if you love to do it."

Read that again.

If you're doing something because you think you should, you're vulnerable. Someone who actually loves it will outwork you every time.

"If they want to compete with me and they're going to work, they're going to lose. Because they're not going to do it 16 hours a day, 7 days a week."

This flips the entire competitive landscape.

Most people ask: "What should I do to get ahead?"

Naval asks: "What would I do for 16 hours a day without getting tired?"

Because that thing --- the thing you'd do even if nobody paid you, is your unfair advantage. It's where authenticity becomes a moat.

The imitators will burn out. The grinders will fade. But you'll still be here, doing what you love, getting better every day.

Diagnostic question: What could you do for 16 hours a day, 7 days a week, and still call it play?

PRINCIPLE 5: LEVERAGE CREATES REACH

Here's where Naval gets practical. Having a unique voice means nothing if nobody can hear it.

"We live in an age of infinite leverage. Your actions can be multiplied a thousand fold, either by broadcasting on a podcast, or by investing capital, or by having people work for you, or by writing code."

THE LEVERAGE HIERARCHY:

• Labor (people working for you) --- Limited, requires management

• Capital (money working for you) --- Requires money to start

• Code (software working for you) --- Scalable, requires technical skill

• Media (content working for you) --- Most accessible, scales infinitely

Naval built his personal brand primarily through Level 4: Media.

His tweets, his podcast, his appearances on other shows, all of it is content that works while he sleeps.

The magic of media leverage: every tweet is a seed. Every podcast episode is an asset. Every piece of content is working for your brand 24/7, multiplying your reach without multiplying your effort.

The modern brand equation: Specific Knowledge + Accountability + Media Leverage = Exponential Reach

You don't need a massive team. You don't need venture capital. You need a microphone, a keyboard, and ideas worth sharing.

PRINCIPLE 6: THE LONG GAME IS THE ONLY GAME

Naval explicitly rejects short-term thinking:

"Build wealth in a very long-term kind of way. Not the banker crash-the-economy, bail-out kind of way. But build businesses and help people and provide value kind of way."

Most people are playing checkers. Naval is playing a multi-decade game of chess.

He doesn't optimize for this quarter's numbers. He builds relationships that compound over years. He creates content that becomes more valuable over time, not less. He invests in his reputation the way others invest in stocks, patiently, consistently, with an eye toward decades, not quarters.

The Long Game Framework:

• Short-term players optimize for attention → Their brand is noise

• Medium-term players optimize for transactions → Their brand is transactional

• Long-term players optimize for trust → Their brand is durable

The compounding effect is real. Every truthful thing Naval has said adds to his credibility. Every accurate prediction builds his track record. Every valuable insight compounds his reputation.

Short-term games attract short-term people. Long-term games attract the people you actually want.

PRINCIPLE 7: SPECIALIZATION IS FOR INSECTS

Naval quotes Robert Heinlein: "Specialization is for insects."

And he means it. His interests span tech investing, philosophy, happiness research, fitness, meditation, wealth creation, and a dozen other domains.

This is a direct challenge to the "niche down" advice you've heard a thousand times.

"Every human basically is capable of every experience and every thought. I like the model of life that the Ancients had, the Greeks, the Romans, where you would start out young, then you're going to war, then you're running a business, then you're supposed to serve in the senate, then you become a philosopher."

The brand you're building isn't a narrow slice. It's a whole person with multiple dimensions.

The Polymath Brand Advantage:

• Unique combinations (bear on unicycle)

• Cross-domain insights (pattern recognition)

• Resistance to obsolescence (multiple skills)

• Human relatability (people are multidimensional too)

The specialist is replaceable. The polymath who can synthesize across domains? That's rare. That's valuable. That's a brand.

PRINCIPLE 8: POSITIVE-SUM GAMES ONLY

Naval draws a hard line between two types of games:

Zero-sum games: Your gain is my loss. Status games. Political games. Win-lose dynamics.

Positive-sum games: Your gain is also my gain. Wealth creation. Value building. Win-win dynamics.

"You should all be for playing positive-sum ethical games."

Zero-sum players eventually run out of people to extract from. Their reputation becomes toxic. Their network atrophies. They win battles but lose the war.

Positive-sum players attract other positive-sum players. Their network grows. Their reputation compounds. They become known as people who create value rather than capture it.

The Brand Litmus Test:

• When you win, do others also win?

• Are you creating value or just redistributing it?

• Would the people you work with recommend you?

Naval's brand isn't built on defeating competitors. It's built on helping founders succeed. That generosity of spirit is felt by everyone who encounters him.

PRINCIPLE 9: THE BEGINNER'S MIND

Naval admires Elon Musk for something most people overlook: his willingness to look stupid.

"The greatest artists and creators have this ability to start over that nobody else does. Elon will be called an idiot and start over with something brand-new that he's supposedly not qualified for."

Most people who build an initial success get trapped by it. They're afraid to start over because starting over means being a beginner again.

But beginners are free. Beginners ask the questions experts have forgotten. Beginners see solutions that experience has blinded others to.

The Beginner's Mind Paradox: The more you're willing to look foolish, the faster you can learn. The faster you learn, the more formidable you become.

Madonna. Paul Simon. Elon Musk. These aren't people who peaked and plateaued. They're people who abandoned the peak to find another mountain.

Diagnostic question: What are you avoiding learning because you're afraid to be a beginner again?

PRINCIPLE 10: PEACE IS THE ULTIMATE LEVERAGE

This might be Naval's most counterintuitive insight.

"A happy, calm, peaceful person will make better decisions and have better outcomes. So if you want to operate at peak performance, you have to learn how to tame your mind just like you have to learn how to tame your body."

Most entrepreneurs think stress is the price of success. Naval disagrees. He thinks stress is a tax on success.

"Warren Buffett plays bridge all day long and goes for walks outside. He doesn't sit around constantly loading his brain with non-stop information and getting worked up about every little thing."

The Peace-Performance Framework:

• Cluttered mind → Poor judgment → Worse outcomes

• Clear mind → Better judgment → Better outcomes

• Better outcomes → More success → More resources

The stressed-out founder making reactive decisions is losing to the calm founder making deliberate ones.

This is Naval's ultimate brand insight: the internal state creates the external result.

Your brand isn't just what you say. It's the energy you bring. It's whether people feel calm or chaotic around you. It's whether your presence creates clarity or confusion.

Naval's calm confidence is part of his brand. It's not separate from his investing success, it's a precondition of it.

THE META-PRINCIPLE: YOUR BRAND IS YOUR LIFE'S WORK

When you step back from these ten principles, a larger pattern emerges.

Naval isn't building a brand. He's becoming someone. He's doing the internal work. He's developing unique knowledge. He's playing the long game. He's staying peaceful while others burn out.

The brand is a side effect.

You can't shortcut authenticity. You can't fake specific knowledge. You can't pretend to be playing the long game while secretly optimizing for this quarter.

The best brands are built by people who would be interesting even if nobody was watching. People who are doing the work because the work matters to them.

Naval's brand works because Naval is genuinely trying to figure things out about wealth, about happiness, about life. The brand is just the broadcast of that genuine quest.

Your final diagnostic question.

If you knew nobody would ever see your work, would you still do it?

Because that stuff you'd do anyway is where your brand begins.

Everything else is just marketing.

And marketing fades. Authenticity compounds.

That's the Naval doctrine.

Now go find your bear. Find your unicycle. And get to work combining them.

--- Shashank

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

"Seven things that make Apple's branding GENIUS, and number four will blow your mind."

You've seen this thumbnail. You've clicked it. You felt cheated twelve minutes later when "number four" turned out to be "they focus on simplicity."

This is what passes for storytelling now.

Companies are hiring "storytellers" at $274,000 a year. LinkedIn job postings with the word "storyteller" doubled in the past year. Executives said "storytelling" on earnings calls 469 times this year, up from 147 times in 2015.

Everyone wants storytellers. Nobody knows what storytelling means.

We've confused hooks with stories. We've mistaken tension-bait for tension. We've turned narrative, the oldest human technology for transferring emotion into a cheap trick for harvesting clicks.

The YouTube formula is seductive. Open with a promise so outrageous the viewer can't scroll past. Tease a revelation that never comes. Pad the middle with filler. End with a subscribe button.

If you roll back this all started with the clickbaity lifestyle blogs that were just making money on ads.

I'm not against one platform. But this is a slot machine dressed in a narrative costume.

Real storytelling looks nothing like this.

Consider the moment Darth Vader first confronts Obi-Wan Kenobi after becoming more machine than man. The anger. The vulnerability. The desperate need to prove he made the right choice by destroying everything he loved.

You feel all of it.

And here's the thing, you can't see the actor's face. Vader wears a helmet. No eyebrows to furrow. No tears to well up. No micro-expressions to read.

The emotion comes from somewhere else entirely.

It comes from the cadence of his breathing. The controlled menace in his voice. The way his body moves, mechanical yet somehow betraying the broken human underneath. And underneath it all, John Williams' score tells you exactly what Vader cannot say.

That's craft.

That's decades of filmmakers understanding how humans process emotion and engineering every frame to trigger it.

No "wait for it." No "you won't believe what happens next."

The modern internet has strip-mined storytelling for parts. Content creators discovered that certain narrative structures trigger dopamine responses. The open loop. The curiosity gap. The promise of transformation. These are legitimate storytelling tools and screenwriters have used them for a century.

But there's a difference between using tension to serve a story and using the appearance of story to manufacture engagement.

The first approach respects the audience. It says that I have something meaningful to share, and I'll use craft to help you receive it.

The second approach exploits the audience. It says that I know which buttons to push in your brain, and I'll push them to extract your attention.

One builds trust.

The other burns it.

You can feel the difference, even if you can't articulate it.

When someone opens with "I was $50,000 in debt, sleeping in my car, about to give up forever, then I discovered this ONE trick" your brain lights up.

Three minutes later, you realize the "trick" is posting consistently on LinkedIn. The debt was student loans. The car was where they napped between meetings.

You've been had.

The storyteller used narrative scaffolding without narrative substance. They built a beautiful frame around an empty room.

Companies are now building entire teams around "storytelling." USAA has four staff storytellers. Google has a "Cloud storytelling team." Microsoft is hiring a "senior director overseeing narrative and storytelling."

The word appears in 50,000 marketing job listings and 20,000 communications roles.

When everyone claims to be a storyteller, the word means nothing. And when companies hire "storytellers" who learned the craft from YouTube thumbnails instead of actual narratives, they get content that feels like content.

The irony is brutal, in an age where AI can generate infinite content slop, authentic storytelling --- the kind that makes you feel something real is the only competitive advantage left.

And we're teaching an entire generation that storytelling means "hook harder."

Real storytellers understand something the content mills don't.

A story isn't a trick to capture attention. It's a vehicle for transferring emotional truth from one human to another.

Darth Vader's confrontation with Obi-Wan works because George Lucas spent three films building the relationship. Because the audience knows what Anakin sacrificed to become Vader. Because every element, the dialogue, the pacing, the music, the silence serves the emotional truth of that moment.

You can't replicate that with a clickbait template.

Let the hook emerge from the story, not the other way around.

The filmmakers who made you cry during a Pixar movie didn't start with "what thumbnail will get clicks?" They started with "what human experience are we illuminating?"

That's the difference between storytelling and story-shaped content.

One changes how people see the world. The other changes your impression count for the next 48 hours.

Companies hiring "storytellers" at six figures should ask one question in every interview: "Tell me about a time you made someone feel something they weren't expecting to feel."

If the candidate talks about open loops and curiosity gaps and optimized hooks, they're a content technician.

If they talk about a moment when craft and truth combined to create something that stayed with the audience long after they stopped watching, that's a storyteller.

The internet has enough technicians.

It's desperate for people who understand that storytelling is the oldest human technology for transferring what it feels like to be alive and that no amount of hook optimization can replicate what happens when that technology is used with skill and intention.

The seven-point listicle won't save your brand.

But one true story might.

Based on: https://www.wsj.com/articles/companies-are-desperately-seeking-storytellers-7b79f54e

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

Every business thinks they're selling a product.

They're wrong.

They're selling a future. A transformed state. A possibility that didn't exist before.

The product is just the artifact. The receipt. The thing that sits in a folder somewhere, unopened, while the real value compounds in ways no deliverable can capture.

This is the hidden logic behind the most valuable companies on the planet. And it's the insight that changed how I run my own business.

Let me show you what I mean.

THE MOMENT I REALIZED I WAS IN THE WRONG BUSINESS

A few years ago, an edtech company hired me for brand strategy.

They were about to take some massive risks. The kind of bold moves that either define a category or become cautionary tales. They wanted someone to build the foundation.

So I did what strategists do. Built the framework. Developed the positioning. Created the campaign roadmap.

Three months in, we were reviewing progress. I asked about the strategy document.

"Oh," the founder said.

"I'm not sure where that is. Maybe Google Drive?"

The engagement was a success. The risks worked. The brand broke through.

But no one had opened the strategy document since month two.

I could have been offended. Instead, I got curious. If they weren't using the document, what were they using?

The answer changed everything.

They were using me.

Not my deliverable. Me.

The strategy document was the excuse. The real product was having one sane person in the room while they took crazy risks. Someone who could look at their wildest ideas and say, "Here's how we make this work."

I wasn't selling strategy. I was selling the possibility of confident risk-taking.

The document was the artifact. The possibility was the product.

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THE COMPANIES THAT UNDERSTAND THIS

Once you see this pattern, you can't unsee it.

Amazon Web Services (AWS) gives away nearly $1 billion in credits every year, which is free infrastructure for startups.

Why?

Because 80% of the world's unicorns run on AWS. Every startup that got free credits and became a billion-dollar company now pays millions annually for the infrastructure they built on.

The credits aren't the product. The credits are the wedge. What the credits make possible, entire companies that couldn't exist without scalable infrastructure --- that's the product.

Canva has 260 million monthly users. $3.5 billion in annual revenue.

Canva has never designed anything.

Every design on Canva was made by someone else. Canva just made it possible. They turned "I'm not a designer" into "I just designed this."

The tool isn't the product. The capability isn't even the product. The identity shift, from non-designer to designer --- that's the product.

Stripe and Twilio are billion-dollar companies built on APIs. Lines of code that do one thing: make other things possible.

Stripe makes it possible to accept money with a few lines of code. Twilio makes it possible to build communication into anything.

They don't sell features. They sell removal of friction. The distance between "I have an idea" and "I'm getting paid for it" just collapsed. The distance between "I need to call my customers" and "I'm calling my customers from my app" just collapsed.

That collapse --- that's the product.

THE POSSIBILITY HIERARCHY

Here's the framework. I call it The Possibility Hierarchy.

Most businesses operate at Level 1. The most valuable operate at Level 5.

Level 1: The Artifact

The tangible deliverable. The thing with a name and edges.

→ A strategy document. A SaaS subscription. A line of code. A designed logo.

Level 2: The Capability

What the artifact enables someone to DO.

→ Make informed decisions. Accept payments. Design graphics. Send messages at scale.

Level 3: The Confidence

What the capability makes them FEEL.

→ Safe to act. Competent to compete. Ready to scale. Willing to risk.

Level 4: The Behavior Change

What the confidence makes them DO differently.

→ Take bigger bets. Move faster. Invest more. Attempt things they wouldn't have before.

Level 5: The Transformed Future

What their changed behavior makes POSSIBLE.

→ Category leadership. Exponential growth. Market dominance. Legacy.

The gap between Level 1 and Level 5 is where all the real value lives.

AWS sells at Level 5. Server credits (Level 1) → Build without infrastructure limits (Level 2) → Confidence to scale (Level 3) → Attempt rapid growth (Level 4) → Build billion-dollar companies (Level 5).

Canva sells at Level 5. Design software (Level 1) → Create professional visuals (Level 2) → Feel like a designer (Level 3) → Create your own marketing (Level 4) → Professional brand presence without hiring designers (Level 5).

That edtech company paid me at Level 5. Strategy document (Level 1) → Strategic framework (Level 2) → Confidence in the plan (Level 3) → Take bold market risks (Level 4) → Category breakthrough (Level 5).

THE DIAGNOSTIC: WHAT LEVEL ARE YOU SELLING?

Let me ask you some uncomfortable questions.

Question 1: How do you describe your work?

• If you describe deliverables, you're selling at Level 1.

• If you describe capabilities, you're selling at Level 2.

• If you describe confidence, you're selling at Level 3.

• If you describe behavior change, you're selling at Level 4.

• If you describe transformed futures, you're selling at Level 5.

Most professionals sell at Level 1. "I deliver strategy." "I build websites." "I write code."

That's fine.

But you'll always be competing with everyone else who delivers strategy, builds websites, and writes code.

Question 2: What's your 100x gap?

What do you charge for your work?

Now: What's the value of what your work makes possible?

If you charge $10,000 for work that makes a $1,000,000 outcome possible, you have a 100x gap.

That gap is either:

• An opportunity (you could capture more value)

• A strategy (you're using it as a wedge to bigger things)

• A problem (you don't understand your own value)

Question 3: What would your clients never attempt without you?

This is the real question.

What do they ATTEMPT because of what you represent?

For me, the answer became clear, my clients attempt things they'd otherwise consider too risky. They made market moves that make competitors nervous.

The document is the artifact. The risk tolerance is the product.

WHY MOST PEOPLE GET THIS WRONG

There's a reason most businesses, consultants, and creators sell at Level 1.

It's safer.

Products are tangible. You can point at them. You can compare them. You can put them in a contract and say, "Hey, this is what you get."

Possibilities are scary. They're intangible. They require trust. They force you to make promises about outcomes you can't fully control.

But the best companies figured out that the more intangible your value, the more defensible your position.

Anyone can copy a product. No one can copy the possibility you represent.

Stripe's code could theoretically be replicated. The possibility of effortless payments and the trust that Stripe represents cannot be.

Canva's features could be duplicated. The possibility of creative confidence for non-designers, the identity shift Canva enables, cannot be.

My strategy frameworks could be stolen. The possibility of having one sane person in your corner while you take risks --- that's irreplaceable.

The thing that feels hardest to sell is actually the thing that's hardest to compete with.

When you sell at Level 1, you're in a race to the bottom. Better features.

When you sell at Level 5, you're in a category of one. No one else can offer the exact future you make possible.

THE POSITIONING

This insight is why I call myself the stupidpreneur.

I work with businesses that want to stand out instead of fit in. Companies that have wild ideas but need someone slightly sane to make them work in the market. Not to make them safe, but to make them survive contact with reality.

This positioning does something important; it describes Level 5 value, not Level 1 deliverables.

"Brand strategist" describes deliverables. "Stupidpreneur" describes what becomes possible.

THE CAREER APPLICATION

This isn't just for businesses. It's also for careers.

What do you make possible?

A manager doesn't deliver task assignments. They make initiative safe, growth possible, and autonomy rewarded.

A teacher doesn't deliver information. They make curiosity rewarding, mistakes productive, and learning sustainable.

A consultant doesn't deliver recommendations. They make bold decisions defensible, strategic risks intelligent, and ambitious visions achievable.

A developer doesn't sell code. They sell the possibility of ideas becoming real.

A designer doesn't sell visuals. They sell the possibility of being understood at first glance.

If I were you, here is how I'd reframe things:

Old question: What do I do?

New question: What becomes possible because I exist?

Old question: What are my deliverables?

New question: What futures do my clients build that they couldn't build without me?

Old question: What should I charge?

New question: What's the value of what I make possible?

That edtech company didn't hire me for a strategy document. They hired me for permission. For validation. For the confidence that comes from having someone in your corner who gets what you're trying to do.

WHY THE BEST COMPANIES GIVE THINGS AWAY

The companies that understand the Possibility Hierarchy often give away the lower levels for free.

AWS gives away credits (Level 1). Captures value at Level 5 (billion-dollar company infrastructure).

Canva gives away the basic tool (Level 1). Captures value at Level 5 (professional brand presence for teams).

Stripe charges almost nothing on transactions (Level 1). Captures value at Level 5 (owning the commerce layer of the internet).

They understand that the artifact is the wedge, and the possibility is the product.

This is why "freemium" works. This is why content marketing works. This is why giving away knowledge builds consulting businesses.

You're not giving away the value. You're giving away the artifact to capture the possibility.

SIGNS YOU'RE SELLING AT THE WRONG LEVEL

How do you know if you're stuck at Level 1 when you should be selling at Level 5?

Here are the warning signs:

You compete on price.

When clients compare you to competitors based on cost, you're selling at the artifact level. At Level 5, price comparisons don't make sense, you're not selling the same thing as anyone else.

You get asked for revisions, not results.

When clients focus on the deliverable itself ("Can you change this section?") rather than the outcome ("Will this help us achieve X?"), you've positioned yourself as an artifact producer, not a possibility enabler.

Your proposals describe activities.

"We will conduct research, develop a framework, and deliver a report." That's Level 1. Level 5 sounds like, "You'll be able to make $10M decisions with confidence."

Clients don't refer you.

When you sell artifacts, clients say, "They delivered a good strategy." When you sell possibilities, clients say, "They changed how we think about risk." One of those generates referrals. The other doesn't.

You feel replaceable.

If you worry that a cheaper freelancer or an AI tool could do what you do, you're selling at the wrong level. No one can replace the specific possibility you represent.

The fix isn't to work harder on your deliverables. It's to climb the hierarchy, to understand and communicate the transformation your work enables.

THE PRICING IMPLICATION

This changes how you think about money.

Level 1 pricing is cost-plus. What does it take to produce this deliverable? Add a margin. That's your price.

Level 5 pricing is value-based. What does the transformed future look like for your client? What's that worth to them? Price as a fraction of that value.

Here's a concrete example:

A brand strategy document takes me about 40 hours to produce. At Level 1 pricing, let's say $200/hour --- that's $8,000.

But what does that strategy make possible? For the edtech company, it enabled a market move that captured significant share in a competitive category.

The possibility? Worth millions.

I'm not saying I charge millions. I'm saying the conversation changes entirely when you understand the gap between the artifact's cost and the possibility's value.

Clients who understand they're buying a $10M possibility don't haggle over $50K. Clients who think they're buying a strategy document absolutely will.

THE PLATFORM LESSON FOR NON-PLATFORMS

You might be thinking, "Great, but I'm not AWS. I'm not building a billion-dollar platform."

Fair.

But the thinking still applies.

Even if you're a solo consultant, a freelancer, or a small agency, you can think in possibilities instead of deliverables.

Positioning: Describe the future you make possible, not the work you deliver.

Pricing: Price based on the value of the possibility, not the cost of the artifact.

Marketing: Share the transformation, not the process.

Sales: Sell the destination, not the vehicle.

It changes who you're competing against.

AWS isn't competing with other cloud providers. They're competing with the question "Should I build this myself?" And they win by making the alternative feel impossible.

Canva isn't competing with Adobe. They're competing with "I can't design." And they win by making that statement feel outdated.

When you sell at Level 5, you're not competing with others who do what you do. You're competing with the version of your client's life where you don't exist. And you win by making that version feel unacceptable.

THE COMPOUNDING NATURE OF POSSIBILITY

One more thing.

Possibilities compound in ways deliverables don't.

That edtech company took one big risk with me as a safety net. It worked. Now they take big risks as standard operating procedure. They don't need me for every decision, but that first possibility unlocked a permanent expansion of what they believe they can do.

AWS enabled Netflix to stream at scale. That possibility, once proven, changed what every media company believed was achievable. Streaming became the default. AWS made an entire industry possible.

Canva enabled millions of non-designers to create professional visuals. That possibility, once proven, changed what every small business believed about in-house capability. The marketing team stopped waiting for designers.

When you sell possibilities, you don't just change what someone does. You change what they believe they can do.

That belief outlasts any deliverable.

YOUR POSSIBILITY AUDIT

I'll leave you with a practical exercise.

• Step 1: List your deliverables. What do you actually hand over?

• Step 2: Map each deliverable to a capability. What can they do because of it?

• Step 3: Map each capability to a confidence. What do they feel safe attempting?

• Step 4: Map each confidence to a behavior change. What do they actually do differently?

• Step 5: Map each behavior change to a transformed future. What becomes possible in their life or business?

• Step 6: Look at the gap. Where are you positioning? Where are you pricing? Where should you be?

THE BOTTOM LINE

The product was never the product.

The deliverable was never the value.

What you make possible --- that's where the real leverage lives.

AWS figured this out. Canva figured this out. Stripe figured this out.

Every time you think about your business, your career, or your offering, ask:

"What becomes possible because of me?"

Answer that question honestly, and you'll understand your real value.

Answer it compellingly, and you'll never compete on price again.

Answer it consistently, and you'll build something no one can copy.

The product was never the product.

The possibility was the product all along.

Stay a little stupid,
Shashank

Your Stupidpreneur

P.S.

What's the biggest decision a client made AFTER working with you that they wouldn't have made before? That's your Level 5 value.

P.P.S.

When prospects default to price, it's not because you're expensive. It's because your positioning is unclear.

Click here and get your free 5-day brand diagnosis.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

Seven years ago, an accident ended my cricket career.

I didn't have a backup plan. I had a laptop and a lot of free time. So I started making posters on Instagram. The first $15 that hit my PayPal felt like winning the World Cup.

Since then, I've built El Mejor Coffee and sold it. Started Happy Beginnings with my dad's printing press, still running at $30k a month. Grew Two Paise Club to 10K subscribers in six months, then let it go when HCL GUVI hired me.

Now I run The Stupidpreneur with 20k subscribers and work as a fractional chief brand officer.

Some of it worked. A lot of it didn't. All of it taught me something.

But before I get into the lessons ---

Happy New Year. 🎉

(Yes, I know you've already heard this 47 times from brands trying to sell you something. This isn't that. These are just 25 things that slapped some sense into me this year.)

Shoppers are adding to cart for the holidays

Over the next year, Roku predicts that 100% of the streaming audience will see ads. For growth marketers in 2026, CTV will remain an important "safe space" as AI creates widespread disruption in the search and social channels. Plus, easier access to self-serve CTV ad buying tools and targeting options will lead to a surge in locally-targeted streaming campaigns.

Read our guide to find out why growth marketers should make sure CTV is part of their 2026 media mix.

Learn more.

Here we go:

• Scalability beats perfection. I spent months building a service that required me on every call. Revenue maxed out at my hourly capacity. I was the bottleneck. The business couldn't grow without me drowning.

• Your first dollar proves nothing except someone paid you once. Your tenth customer coming back proves you might have something. Your hundredth referral proves you built a brand.

• Distribution beats quality. I've seen mediocre products with great distribution destroy superior products with no distribution. The storyteller without a megaphone is just talking to themselves.

• Boring consistency quietly beats genius. The newsletter that goes out every week will outperform the one that's "perfect" but irregular.

• Cash flow is more honest than brand love. If people clap but don't pay, you built content, not a business.

• Most positioning fails because founders describe what they do, not who changes. "We're innovative" could be anyone. "We cut churn by 70% in 90 days" is a position.

• Brand isn't your logo. It's what customers say at dinner tables when you're not there. If they can't explain why you're different in one sentence, you don't have a brand.

• Pricing is positioning. Charge 5k, and you're another freelancer. Charge 50k, and suddenly people think you know something. The price communicates value before they read a word.

• Product-market fit comes before brand work. Fix your product first. Brand strategy on a broken product is cologne on a corpse.

• I wasted 6 months debating two approaches when I could've tested both in week one for 2k. The cost of choosing slowly killed more businesses than choosing wrong.

• Trust isn't built by claiming you're trustworthy. It's built when customers tell other people you delivered what you promised.

• Most founders don't have a marketing problem. They have a differentiation problem. You can't advertise your way out of confusion.

• Frameworks don't sell. Results sell. Frameworks just help you deliver those results repeatedly. I stopped selling "the method" and started selling "cut your sales cycle by 40%."

• Communities die when you optimize for size over engagement. 10 people who actually implement beat 1,000 lurkers who "love the content."

• First-principles thinking beats best practices. Best practices are what worked for someone else's business in different conditions. First principles let you build what works for yours.

• The hardest person to position is yourself. Because you're too close to your own BS.

• Big leaps came from conversations, not courses. Every meaningful insight this year came from a human, not a module.

• Creativity is seasonal. Systems aren't. Rely on systems. Let creativity be the bonus, not the backbone.

• People don't buy expertise. They buy certainty. Branding exists to make people feel the decision is safe.

• Work-life balance is a myth that makes you feel guilty. Work-life harmony means some weeks are work-heavy, some are life-heavy, and that's okay. Learned this in February. Changed everything.

• The creator economy rewards the prolific, not the perfect. Volume beats polishing. Every time.

• Failure hurts less when you fail in public. When you share the lessons, the loss at least compounds into audience trust.

• AI is a thought partner, not a replacement. I use it to structure my ideas, not generate them. My work comes from experience. The tools help me organize it clearly.

• Nobody is coming to save you. The day you stop expecting a "lucky break" and start treating your career like a product you're building, everything gets easier.

• Nobody remembers your mistakes except you. Your customers care about whether you solve their problem today. Not what you messed up last year.

That's it.

25 lessons from building, failing, selling, and doing it again.

The only thing that matters: keep building.

Happy 2026. Make it satisfying.

Yours,

Shashank "Santa Clause" SN

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

Ayush Agarwal had a million users on his gaming platform, Tournafest.

40% of them were outside India.

And he couldn't make a single penny from them. 😤😤😤

Bangladesh. Europe. The Middle East. Users everywhere, wanting to pay, credit cards in hand and he had to tell them no.

Why?

Because gaming was a "restricted category" in half these countries. Compliance nightmares. Tax labyrinths. Payment gateways that looked at his use case and said, "lol nope."

His small team didn't have the bandwidth to become regulatory experts in 47 different jurisdictions.

So they did what most founders do in that situation:

They gave up on 40% of their market.

AND THAT'S WHERE THIS STORY REALLY BEGINS.

In 2023, Ayush teamed up with Rishabh Goel, a guy who'd spent years in the payments trenches at Wise and Prodigy Finance.

Rishabh had seen the problem from the infrastructure side.

Ayush had lived it as a founder.

Together, they decided to build the solution they both wished existed.

Fast forward to early 2025: Dodo Payments raised $1.1M in pre-seed funding from Antler, 9Unicorns, and Venture Catalysts. Angel investors included folks from PayU, Oyo, Flipkart, and a16z. 💰💰💰

But here's what's interesting about that fundraise:

It wasn't about the money. It was about the signal.

When people who've built PayU and worked at a16z write you angel checks, they're not just betting on your product. They're betting on YOU understanding the problem better than anyone else.

And Ayush understood it because he'd FELT it.

That authenticity, that founder-problem fit --- it's something you can't fake.

Brands built on real pain solve real problems

Because that pain, that specific, visceral frustration of watching revenue slip through your fingers because of backend complexity, became the foundation of Dodo Payments.

Now, before we dive deep into how they built this brand...

Let me be crystal clear about something:

This isn't another breakdown cobbled together from random blog posts and LinkedIn stalking.

This is the latest edition of Brick by Brick , where I sat down with the people who actually built Dodo Payments from scratch. Asked them the uncomfortable questions and got the real answers.

This is a breakdown BY the company and me, not a secondhand interpretation of their marketing copy.

That distinction matters.

Because when you're learning how to build a brand, you don't want the polished PR version.

You want the architecture. The decisions. The philosophy.

Let's get into it.

Part 1: The Name Nobody Forgets

Here's a question nobody asks enough when starting a company:

"Will people feel intimidated just LOOKING at our brand?"

Fintech companies love sounding serious.

"Apex Financial Solutions."

"GlobalTrust Payments."

"SecureCore Technologies."

You know the vibe. 🙄

It's just forgettable.

The Dodo Payments team went a different direction entirely:

THEY NAMED THEMSELVES AFTER AN EXTINCT BIRD.

I asked them about this.

Here's what they told me:

Read that again.

In an industry where everyone's trying to sound like a Goldman Sachs subsidiary, these guys chose a name that makes you smile.

And that's not an accident; it's the whole strategy. Because their target customer isn't a Fortune 500 CFO with a legal team on speed dial. Their target customer is a solo developer who built an AI tool in their bedroom and needs to start charging for it by Tuesday.

Different customers = Different brand energy.

The Dodo Payments brand says, "We're not going to make this complicated. We're not going to talk down to you. We're going to help you get paid."

THAT'S THE FOUNDATION EVERYTHING ELSE IS BUILT ON.​

Part 2: The Mission

Most company mission statements read like they were written by a committee of lawyers having a stroke.

"We leverage synergistic solutions to optimize stakeholder value across vertical integrations..."

🤮🤮🤮

Dodo Payments's mission?

That's it.

And this mission --- it's SPECIFIC.

They're not trying to be everything to everyone. They're not chasing offline retailers or restaurant POS systems or enterprise ERP integrations. They picked a lane: Digital and AI-native products.

And they're going ALL IN on that lane. This specificity shows up everywhere in their brand:

• The messaging

• The product design

• The partnerships they pursue

• The content they create

When you know exactly who you serve, every decision becomes easier.

When you try to serve everyone?

You end up serving no one well.​

LESSON: SPECIFICITY ISN'T LIMITING. IT'S LIBERATING.

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Part 3: How They Talk (Without Sounding Like Robots)

Fintech has a jargon problem.

Payment rails. Merchant acquiring. PCI-DSS compliance. Settlement windows. Interchange fees.

Uhhhh....

The average founder hears this stuff and their eyes glaze over faster than a Krispy Kreme donut. 🍩

They made a conscious decision to speak differently.

Here's how they described it to me:

Did you catch that?

Outcomes, not features.

They don't say, "We provide multi-currency payment processing with automatic FX conversion and real-time settlement across 80+ currencies."

They say, "Sell to customers in 150+ countries without worrying about currency or compliance."

And they adapt this messaging for different markets:

One truth. Many expressions.

That's the formula.

Part 4: The Consistency Principle

Here's where most startups completely fall apart with branding:

They nail the website copy.

Then someone writes support docs that sound like a different company.

Then the sales deck uses different language entirely.

Then social media goes rogue with its own vibe.

Result? 🤦🤦🤦

A brand that feels schizophrenic.

They built systems to prevent this:

They maintain:

• A central messaging guide

• A visual library

• UX patterns that carry across every touchpoint

So whether you're on their website, inside their dashboard, reading their docs, talking to support, or seeing their content on social, it all feels unmistakably like Dodo Payments.

THIS DOESN'T HAPPEN BY ACCIDENT.

It happens because someone sat down and created the infrastructure for consistency, and yet most founders think branding is a logo and a color palette. Real branding is a SYSTEM that ensures every customer interaction reinforces the same story.

Part 5: UX as Brand Proof

Here's something most founders miss:

Your product experience IS your brand.

You can claim "simplicity" in your marketing all day long.

But if your dashboard looks like it was designed by a committee of confused engineers...

If your onboarding takes 47 steps and three blood samples...

If your documentation reads like stereo instructions from 1987...

Then your REAL brand is "complicated." No matter what your tagline says.

Dodo Payments gets this:

And then they dropped this gem:

UX IS NOT DECORATION.

IT'S PROOF.

That's such a powerful reframe.

Quick personal aside:

I'm not easily impressed by companies. Most fintech brands feel interchangeable to me.

But Dodo? They made me feel seen as a customer.

Like I actually matter. Like someone's listening.

I don't get paid to say this. I just genuinely tell people, "Use Dodo Payments."

When a brand makes you want to spread the word for free, that's the ultimate proof their product matches their promise.

Every design decision is a chance to either prove or disprove what your brand claims to be.

If you say you're simple, every interaction better FEEL simple.

If you say you're transparent, every screen better SHOW transparency.

The product IS the brand. 🎯🎯🎯

Part 6: Dancing With Giants

Now let's address the elephant in the room.

Or rather, the GIANTS in the room.

Stripe. Razorpay. PayPal. Adyen.

These are companies with billions in funding, thousands of employees, and decade-long head starts.

So how does a startup founded in 2023 with $1.1M in pre-seed funding even begin to compete? 😅

Here's how Dodo Payments thinks about differentiation:

See what they did there?

They didn't try to be a "better Stripe."

They redefined the category entirely.

Stripe = Payment processor.

Dodo Payments = Monetisation engine.

Different positioning.

And they got even more specific:

This is the classic "niche to win" strategy.

Don't try to serve everyone.

Serve a specific customer SO WELL that the giants can't match you, because they're too busy serving everyone else.

The USP?

FOCUS.

Here's how they put it, and this is where being small actually becomes an advantage:

When you're Stripe, you have to build features that work for millions of merchants across every industry imaginable. When you're Dodo Payments, you can build features specifically for the solo AI developer who needs to go live in 48 hours.

That's the superpower. 💪💪💪

Part 7: Storytelling as Strategy

Fintech is confusing.

Tax codes. Compliance frameworks. Currency regulations. MoR structures.

The average founder would rather get a root canal than read a white paper about cross-border VAT compliance.

So how do you communicate complex stuff without losing people?

Dodo Payments' answer: Story.

And they have a simple framework for every piece of content:

Three questions.

Problem. Stakes. Speed.

THAT'S THE FORMULA FOR CUTTING THROUGH COMPLEXITY.​

Whether it's a new feature announcement, a compliance update, or a launch post, the story always ties back to the founder's journey.

Because founders don't care about payment rails. They care about getting their product into customers' hands and getting paid for it.

Lead with their story, not your technology.

Think about that for a second.

Most companies lead with "Here's our cool new feature!" and expect customers to figure out why they should care.

Dodo Payments flips the script: Start with the founder's struggle. Connect to their pain. THEN reveal how you solve it.

That's empathy operationalized. ❤️

Part 8: What Actually Works (Marketing Edition)

I asked them about marketing campaigns and initiatives that moved the needle.

Here's what they said:

Notice what's NOT on that list?

Paid ads.

Cold outreach.

Influencer partnerships.

Instead:

• Founder-led content. The actual founders sharing insights from their journey.

• Product-led launches. Let the product speak for itself.

• Educational content. Teach people what you know.

REAL VALUE > AD SPEND.

Every. Single. Time.

This isn't revolutionary advice.

But it IS advice that most companies ignore because creating real value is HARD. It's easier to throw money at Facebook ads than to sit down and create genuinely useful content.

But the companies that invest in value creation build something that paid acquisition can never buy:

Trust. Authority. Community.

Part 9: Community as Moat

Speaking of community...

Here's maybe the most important thing they told me:

Any competitor with enough engineering talent can build payment infrastructure.

But community? Relationships? Trust?

Those take YEARS to build.

And they can't be copied.

Read that again and let it sink in. 🧠

Two different functions:

Partnerships = Reach

Community = Relevance

You need both.

Partnerships get you in front of new audiences.

Community keeps you deeply connected to what those audiences actually need.

Most startups focus exclusively on reach.​

Here's what most founders get wrong:

They treat community as a marketing channel. Something to "do" after the product is built.

But Dodo Payments treats community as a product development input. They're not just broadcasting TO developers, they're learning FROM developers.

That's a fundamentally different orientation.

And it shows in how closely their product matches their users' actual needs.

The smart ones invest equally in relevance.

Part 10: The Trust Playbook

We're talking about money here.

People's revenue. Their livelihoods. Their businesses.

Trust isn't a nice-to-have in fintech.

It's EVERYTHING.

So how does a young startup build trust against established players?

They has three pillars:

Let's break these down:

• Predictability: No surprises. What you see is what you get. Pricing is clear. Processes are consistent.

• Transparency: Nothing hidden. Everything is auditable. Clear contracts. Explicit tax handling.

• Compliance: They're not cutting corners on regulations. They're not in a gray zone. They're doing things properly.

TRUST COMPOUNDS.​

Because trust isn't built through one big gesture, it's built through hundreds of small moments where you do what you said you'd do.

Most payment companies try to win with speed or price. Those are table stakes.

Dodo Payments wins with trust. And trust can't be bought with money or engineering hours. It can only be earned through consistency.

Over time, those moments stack up.

And eventually, you have something competitors can't touch.

Part 11: The Vision (And Where They're Headed)

Every brand needs a north star.

Something bigger than quarterly metrics.

Dodo Payments' Vision:

"To create a world where any builder can open their laptop, create value, and instantly monetize across borders without understanding tax codes, currency rules, or compliance frameworks."

That's a beautiful vision.

Because it's not about Dodo Payments.

It's about what Dodo Payments ENABLES.

The solo developer in Nigeria who builds an AI tool.

The indie hacker in Vietnam with a SaaS product.

The creator in Brazil with digital courses.

All of them are able to sell globally, instantly, without becoming regulatory experts.

THAT'S THE WORLD DODO IS BUILDING TOWARD.

And they're making progress.

Part 12: The Customer Story That Says It All

I always ask for customer stories.

Because they reveal what the brand actually delivers versus what it claims to deliver.

Here's the one they shared:

A solo AI developer who built a niche product but couldn't sell globally because of compliance and tax obstacles. With Dodo Payments, he went live in less than a week and scaled to customers in more than 20 countries without touching a single payment, tax, or currency workflow.

It is a simple story, but it captures our purpose perfectly.

THAT'S THE BRAND PROMISE IN ACTION.

🤪 The Stupid Take

Alright, you've made it this far.

You've seen the origin story.

The naming philosophy.

The messaging strategy.

The differentiation playbook.

The trust framework.

Now here's my take on what this all actually MEANS for founders and marketers. 👇👇👇​

THE BIG LESSON ISN'T ABOUT PAYMENTS.

It's about this:

Dodo Payments succeeded by refusing to play someone else's game.

When you're entering a market with giants, the temptation is to compete on THEIR terms.

• Better features than Stripe!

• Lower fees than Razorpay!

• Faster than PayPal!

That's a losing game.

Because giants have more resources.

So Dodo Payments did something smarter:

They defined a NEW game.

• Not "payment processor" → "Monetisation engine."

• Not "everyone" → "AI-native products."

• Not "scale" → "Agility."

And here's the thing, this applies to ANY industry.

If you're a freelance designer competing with Fiverr on price, you'll lose.

If you're a SaaS startup competing with Salesforce on features, you'll lose.

If you're a content creator competing with MrBeast on production value, you'll lose.

BUT...

If you define a different game --- a game where YOUR strengths matter, you can win.

Maybe you're the designer who only works with Web3 startups.

Maybe you're the SaaS that only serves solo consultants.

Maybe you're the creator who goes deep on one weird niche.

SPECIFICITY ISN'T LIMITATION.

IT'S LIBERATION.

The brand works because every decision flows from a clear understanding of:

• WHO they serve (AI-native, digital-first products)

• WHAT they believe (monetisation shouldn't be the hardest part)

• HOW they're different (end-to-end engine, not just transactions)

That's it.

That's the whole framework.

Who. What. How.

Get those three right, and every other branding decision becomes obvious.

The name? Should reflect what you believe.

The messaging? Should speak to who you serve.

The product? Should prove how you're different.

Dodo Payments got all three.

And that's why they're building something real in a market where most startups get crushed by the giants.

DON'T PLAY THEIR GAME.

DEFINE YOUR OWN.

Your Brand-Building Checklist (Steal This)

Before I wrap up, let me give you something practical.

Based on everything Dodo Payments taught me, here's a checklist you can use for YOUR brand: 📋📋📋

• The Founder-Problem Fit Test: Did you personally experience the problem you're solving? Not "I noticed a market gap" but "I felt this pain so deeply I had to fix it." Ayush couldn't monetize 40% of his users. That's not market research, that's a scar, and scars make better brands than spreadsheets.

• The Name Energy Test: Does your brand name match your customer's emotional state? Dodo Payments' target customer is overwhelmed by complexity. The name promises approachability. Match made in heaven. If you're selling to stressed-out founders, maybe don't call yourself "Apex Ultimate Solutions Pro." 😅

• The Mission Specificity Test: Can you state your mission in under 15 words without using any jargon? If your mission statement needs a glossary, rewrite it.

• The Outcomes vs. Features Test: Take your website copy. Count how many times you talk about features vs. outcomes. "Multi-currency processing" = feature. "Sell globally without thinking about currency" = outcome. Outcomes win every time.

• The Product-Brand Alignment Test: If you claim simplicity but your onboarding takes 30 minutes, you're lying to your customers. Your product experience IS your brand. No exceptions.

• The Category Reframe Test: What category do giants own? Now, can you create a NEW category where you're the obvious winner? Payment processor → Monetization engine. CRM → Revenue intelligence platform. Whatever your space, find your reframe.

• The Trust Audit: Are your fees obvious? Is everything auditable? Do you communicate changes before they happen? Trust compounds. Every hidden fee or surprise policy erodes it.

• The Community Investment Test: Are you building a community or just a customer list? Customer lists can be bought. Communities can't. Which one are you investing in?

THAT'S THE PLAYBOOK.

Use it. Adapt it. Build something worth talking about.

The world doesn't need more companies. The world needs more companies that give a damn.

Dodo Payments gives a damn.

Does your brand?

🔥🔥🔥​

Until next time --- your brand-obsessed friend,

Shashank "Brick by Brick" SN

P.S.

If you know a founder building something cool who needs to hear this breakdown, forward it to them. Good ideas deserve to spread. 🔥

P.P.S.

TheDodo Payments team was incredibly generous with their time and insights. If you're building digital or AI products and struggling with global payments, give them a look. Sometimes the small players really ARE better for your specific situation.

P.P.P.S.

If you've got a brand you want me to break down in a future edition, hit reply. I'm always hunting for companies doing branding differently.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

Quick test.

Think of a business you'd recommend to a friend without hesitation. One where you'd say, "You HAVE to work with them," and stake your credibility on it.

Got one?

Now count how many you can think of.

Total.

Most people land somewhere between three and five.

Out of every business you've ever bought from, every purchase, every subscription, and every service, fewer than five earned the right to borrow your reputation.

That ratio tells you everything about why customer retention is broken.

Because most businesses are building for a transaction, not a relationship. They're stuck on the first rung of a ladder they've never even seen.

Let me show you the whole structure.

Before we move on, wishing you a Merry Christmas✨

The Three Rungs of Trust

Every customer relationship sits on a ladder.

Three rungs.

Each one harder to reach. Each one is worth exponentially more.

Most businesses only see the first rung. They optimize for it, celebrate it, and build their entire operation around it.

Then wonder why everyone keeps disappearing.

Rung One: The Purchase

Someone exchanges money for a solution.

They saw your marketing. They believed the claim. They thought, "Maybe this works," and tested that theory with their credit card.

That's it.

That's the whole rung.

A transaction that proved one thing: you weren't lying.

The bar for Rung One is "not a scam." You delivered what you advertised.

The thing worked.

Congratulations. You've proven you're not a fraud.

But Rung One customer is a renter. They're not committed. One bad experience, one slightly better offer, one moment of indifference, and they're gone.

80% of first-time customers never come back.

Never.

They bought once, got what they paid for, and moved on.

Most businesses lose 80% of everyone they acquire.

That's the ladder problem.

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Rung Two: The Return

A customer comes back because you proved something competence can never prove.

Motive.

Rung Two is when a customer believes you'll act in their interest, even when it costs you something.

That distinction changes everything.

Competence says, "They can do the job."

Motive says, "They actually want what's best for me."

You prove competence by delivering results. You prove motive by sacrificing for someone else's outcome.

The sacrifice is the signal. Without it, you're just competent. And competent businesses are replaceable.

I watched a software founder leave $50K on the table last year.

"You don't need our premium plan," he said. "Start with the basic tier. You'll know in three months if you need more."

His sales team thought he was insane.

That company stayed for two years. Upgraded twice. Referred four other customers.

Because that one conversation proved motive. It showed he cared more about their outcome than his revenue.

Rung Three: The Referral

Now we reach rare air.

Rung Three customers don't just trust you. They stake their own reputation on you.

Think about that.

When someone says "you HAVE to work with them," they're putting their credibility on the line. If you screw up, they look bad. They've attached their name to yours.

That's BRAND.

Because a brand is when someone borrows their own reputation to recommend you.

It can't be bought.

Referral programs don't create Rung Three customers, they create mercenaries who'll switch the moment someone offers better incentives.

Rung Three is earned.

By proving motive so many times, so consistently, that a customer stops questioning whether you're on their side.

They just know.

The Numbers That Matter

This isn't philosophy. It's economics.

Rung One business:

• 20% of customers return

• Customer acquisition cost: recovered after 3-4 purchases

• Problem: most customers never make 3-4 purchases

• Reality: constant bleeding, constant replacing

Rung Two business:

• 40-60% of customers return

• Customer acquisition cost: recovered after 1-2 purchases

• Lifetime value: 3-5x higher than Rung One

• Reality: sustainable, profitable growth

Rung Three business:

• 30-50% of customers actively refer

• Cost per referred customer: near zero

• Referred customer retention: 37% higher than paid acquisition

• Lifetime value: 6-10x higher than Rung One

• Reality: compounding, self-sustaining growth

The gap isn't marginal.

A Rung Three customer is worth ten Rung One customers, and they arrive without acquisition cost.

This is why some businesses scale effortlessly while others grind forever on the acquisition treadmill.

They're not better at marketing. They're better at the ladder.

The Rung One Trap

Most businesses are architecturally designed to stay stuck.

Look at your incentives.

Sales gets paid on new deals. Marketing reports on acquisition metrics. Your board deck shows new customer growth, not trust depth.

The whole machine optimizes for getting people ON the ladder. Nobody's measured on moving them UP.

And the standard "retention tactics"? They're usually Rung One tactics in disguise.

Loyalty programs: Bribery. You're paying them to transact again. The moment someone offers better points, they vanish.

Satisfaction surveys: Competence checks. "Did we meet your expectations?" is a Rung One question. It measures whether you delivered the basics, not whether you've proven motive.

Personalization: Expected. "You bought X, you might like Y" is baseline competence now. It proves you have software, not that you care.

None of these build trust. They just make Rung One slightly stickier.

To actually move up?

You need sacrifice.

The Sacrifice Test

When was the last time you cost yourself something for a customer's benefit?

Actually sacrificed.

• Told them NOT to buy something

• Refunded them before they asked

• Fixed a problem they didn't know about

• Sent something valuable with no pitch attached

• Turned down money that wasn't right

If you can't remember the last time, you're stuck on Rung One.

Because motive is only proven through sacrifice. Words mean nothing. Policies mean nothing. The sacrifice is the signal.

The Motive Audit

Three questions. Answer honestly.

Question 1: What's your "wrong customer" rate?

How often does your team turn away money that isn't the right fit?

If the answer is "rarely" or "never," you're not proving motive. You're just taking whatever comes through the door.

Track this.

If your sales team isn't turning away at least 10% of leads, you're optimizing for Rung One.

Question 2: What's your value-to-ask ratio?

Look at your last 20 customer touchpoints. How many were "asks" (buy this, review us, refer someone) vs. "gives" (pure value, no strings)?

If more than half are asks, you're extracting value from the relationship faster than you're depositing it.

Fix the ratio.

Aim for 50/50 at minimum.

Question 3: Would your top 10 customers stake their reputation on you?

Would they look someone they respect in the eye and say, "You HAVE to work with them" knowing their credibility depends on you not screwing up?

List your top 10.

Count the definite yeses.

If fewer than 3, you haven't reached Rung Three with anyone.

The Plays: Moving Up

Enough diagnosis. Here's the playbook.

Rung One Foundation (do these first):

• Map "time to first win." How long until a customer gets actual value? Measure it. Then cut it in half.

• Build proactive rescue. Track signals that predict churn, low usage, support tickets, and silence. Reach out before they decide to leave.

• Deliver slightly early. Every timeline beat, even small ones, builds evidence of competence.

Rung Two Ascent (the unlock):

• Institute the "not for you" script. Train everyone to recognize mismatches and turn them away. Track it weekly. If nobody's doing it, incentivize it.

• Create zero-ask touchpoints. Helpful emails, resources, and check-ins where you want nothing in return. These prove you're thinking about their outcome when they're not even thinking about you.

• Make sacrifice visible. When you absorb a cost or fix something proactively, say so. "We're crediting your account because our onboarding took longer than it should have." Visible sacrifice is what proves motive.

Rung Three Endgame (the compound):

• Replace referral bonuses with access. "Your friend skips the waitlist." Status is more valuable than cash. It also proves you're not trying to buy advocacy, you're rewarding it.

• Give advocates a flag. People who stake their reputation want to feel part of something. A point of view. A movement. Give them language for what they believe, and they'll carry that flag.

• Protect their credibility. If an advocate sends someone who isn't a fit, handle it gracefully. Don't let their reputation suffer for your benefit.

The Different Game

It's not about your product being better or your price being lower

It's about which rung you're building for.

Rung One business grinds forever. They acquire, lose, replace, and repeat. They're on a treadmill they can never escape because their customers have no reason to stay.

Rung Two businesses grow sustainably. They retain. They profit. They stop bleeding.

Rung Three businesses compound. They grow themselves. Customers arrive for free, stay longer, and spend more.

The only difference is the ladder.

The Choice In Front of You

You're building for one of three rungs right now. Whether you've thought about it or not.

If you're optimizing for acquisition and ignoring retention, you're building for Rung One.

If you're willing to sacrifice short-term revenue to prove you're on the customer's side, you're building for Rung Two.

If everything you do is designed to be worth staking a reputation on, you're building for Rung Three.

The ladder exists in every business. Most founders only see the first rung because that's all their metrics show them.

But now you see all three.

What are you going to build?

--- Shashank

P.S.

Here's the exercise: Pick one current customer this week. Do one thing that costs you something and benefits them. A sacrifice. An admission, a fix, a proactive upgrade, a piece of help with no pitch attached.

Don't tell anyone you're doing it. Just watch what happens.

P.P.S.

The next time someone on your team says, "We need more leads," you'll hear it differently. You'll ask, "Or do we need more movement up the ladder?"

That's when you know.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

"The most powerful person in the world is the storyteller."

Steve Jobs said this.

LinkedIn regurgitates it daily.

And it's actively ruining your brand strategy.

I've spent seven years watching founders pour months into crafting the "perfect" brand story, hiring agencies, workshopping narratives, and perfecting their "why."

Then they launch into the VOID.

Because Jobs was only half-right.

The most powerful person isn't the storyteller; it's whoever controls what story gets told.

And that distinction is worth millions.

I'm a die-hard Jobs fan myself. If I get stuck on any business decision, I've always asked, "What would Steve do?"

But I wholeheartedly cannot agree on this one.

THE LIE BENEATH

Jobs didn't just tell Apple's story. He controlled every single touchpoint where it could be told.

• Product launches

• Retail environments

• Packaging

• Advertising channels

• The keynote stage itself

He wasn't the storyteller.

He was the studio executive.

Think about Hollywood for a second. The screenwriter writes the story. But the studio executive decides if that story ever sees the light of day. The algorithm engineer at YouTube has more power over which creators succeed than the creators themselves. The media mogul who owns the platform controls the journalist's reach.

A storyteller without distribution is just someone talking to themselves.

Jobs understood this. He built distribution infrastructure disguised as product launches. He created events that became their own distribution channels. He made the announcement of the announcement newsworthy.

Most founders?

They perfect their story, then pray the algorithm gods smile upon them.

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THE BRAND POWER HIERARCHY

After working with brands across revenue stages, from pre-launch to eight figures, I've noticed a pattern. There's a hierarchy of power in brand distribution. And most founders are stuck at the bottom without realizing it.

Level 1: Distribution Owners

These are the platforms. Meta. Google. LinkedIn. YouTube. Amazon's algorithm. They decide what millions of people see every single day. They write the rules. They change the rules. And they don't ask permission.

When Facebook's algorithm shifted in 2018, media companies lost 50%+ of their traffic overnight. That's Level 1 power.

Level 2: Gatekeepers

Editors who decide what gets published. Executives who greenlight projects. Curators who decide what gets featured. Podcast hosts who choose their guests.

They control access to Level 1's distribution. They're the bouncers at the club. And if you want in, you need their approval.

Level 3: Storytellers with Audience

Creators with earned distribution through trust. Brands with owned communities. Influencers with loyal followings.

They have power.

Real power.

But it's fragile.

One algorithm change can cut their reach in half. One platform shift can make their audience disappear.

They're one step above powerless, but they're still dependent on Levels 1 and 2.

Level 4: Storytellers without Audience

Everyone starting out. Brands with great stories and zero reach. The "undiscovered genius" waiting to be found.

Powerless until they climb to Level 3 or buy access to Levels 1-2.

But most founders think they're building Level 3 (audience). But they're actually stuck at Level 4 (obscurity) while renting access to Level 1 (paying Meta and Google for ads, this includes me as well).

They're not building anything. They're paying rent.

And rent goes up.

Look at the brands you admire.

Nike sits at Level 3 with massive Level 2 influence, they ARE the gatekeeper in athletic culture.

Your favorite DTC brand? Level 4, spending 40% of revenue renting Level 1 through Meta ads.

Tesla? Musk was at Level 3, then bought Level 1 when he acquired Twitter.

He stopped renting. He bought the DAMN building.

THE THREE PATHS OUT OF DISTRIBUTION HELL

So you understand the hierarchy.

You're probably at Level 4, renting access to Level 1, hoping to build Level 3.

What do you actually do?

There are three paths. Two of them are traps.

Path 1: Build Your Own Distribution

This means assets you control. Email list. Community you own. Platform you build. Media property with your name on it.

Morning Brew built email distribution, then sold for $75 million. Glossier built community before products. Stratechery built a subscription audience of enterprise buyers willing to pay $120/year for analysis.

They can't be taken away.

YOU OWN IT.

A little reality check is that it takes 2-5 years and requires consistent output. But most founders quit before reaching escape velocity.

The trap: Thinking "building an audience" equals posting on social media.

It doesn't.

Posting on LinkedIn is renting. Your followers are LinkedIn's users. The algorithm decides if they see you.

You own nothing.

Building an email list of 10,000 people who actually open your emails? That's ownership. That's Path 1. (I'm lucky I have over 19k)

Path 2: Rent Distribution Strategically

This means

• Paid ads

• Influencer partnerships

• Platform algorithms

• PR & media placement.

Every DTC brand you know uses this. SaaS companies with venture funding use this. Anyone running Facebook ads uses this.

It's fast, predictable (until it isn't) and scalable if the economics work.

The downside: Costs rise over time. Platform changes kill businesses overnight. Stop paying and you disappear immediately.

I've watched brands with $2M/month in Meta ad spend panic when CPMs jumped 40% in Q4.

THis is exactly what happens when you confuse "growth" with "building a brand."

When you're running ads, you're not building anything. You're renting shelf space. The moment you stop paying, you don't exist.

Path 3: Become the Story Others Can't Ignore

This is the highest leverage path and the hardest to execute.

It means creating something so compelling that distribution comes to YOU.

They are

• Movements, not messages.

• Controversy that forces conversation.

• Novelty that demands attention.

• Utility so high it creates organic sharing.

Liquid Death made water controversial. Duolingo became a meme. Oatly created a culture war over oat milk. Teslamade electric cars aspirational instead of environmental.

When this happens, distribution becomes free. Platforms feature you, and media covers you. Customers evangelize without being asked.

But their behavior can't be templated. It requires genuine insight into culture with a high risk of failure.

The trap: Thinking "going viral" is a strategy.

It's not.

It's an outcome of strategic positioning.

You can't plan virality. You can only create conditions where it becomes possible.

THE REALITY MOST FOUNDERS IGNORE

Most successful brands use all three paths simultaneously.

Path 1 for stability (owned audience). Path 2 for scale (paid acquisition). Path 3 for efficiency (earned distribution).

Which one are you building FIRST?

Because starting with Path 2 (renting distribution) without Path 1 (owned distribution) is building a house on rented land.

The landlord can raise rent. The landlord can evict you. The landlord can change the rules.

And you'll have nothing to show for it except a really good brand story that nobody hears anymore.

THREE QUESTIONS THAT MATTER MORE THAN YOUR STORY

Your brand story is probably fine.

Maybe even great.

But it doesn't matter until you can answer these three questions.

Question 1: Who controls whether anyone hears it?

Bad answers: "We'll post on social media." "We'll do content marketing." "We'll build a community." "Our story is so good it'll spread organically."

Good answers: "We're spending $50K/month on Meta ads with a 3x ROAS." "We have 10,000 email subscribers who open at 40%." "We have partnerships with five influencers who reach 2M combined." "Our product has a viral coefficient of 1.4."

See the difference?

Good answers have numbers, systems, and control.

If you stopped creating content today, would anyone still hear your brand story in six months?

If yes, you have distribution.

If no, you have a content treadmill.

Question 2: What makes someone share this?

Your brand story needs to do work beyond "communicating who you are." It needs to make people want to spread it.

What doesn't make people share: "We're authentic." "We care about quality." "We're customer-focused." "We're different." (While looking identical to everyone else.)

What makes people share:

• Identity signaling - "This says something about who I am." (Patagonia, Tesla)

• Social currency - "This makes me look smart or informed." (Liquid Death, Oatly)

• Utility - "This solves a problem my friend has."

• Emotion - "I need others to feel what I felt."

• Novelty - "No one has seen this before."

When someone encounters your brand, what do they GET from telling someone else about it?

If the answer is "nothing," your story won't spread no matter how good it is.

Question 3: What position are you actually fighting for?

Most founders confuse "brand story" with "brand strategy."

Your story is WHAT you say. Your strategy is WHICH position you're claiming in the market.

Telling a beautiful story while fighting for a position you can't win.

Unwinnable positions:

• "High quality, affordable, sustainable fashion." (You're describing 10,000 brands.)

• "We help businesses grow." (Consultant-speak for "we're undifferentiated.")

• "The Airbnb of X." (You're literally saying you're not original.)

Winnable positions:

• Starling Bank owned "the boring bank."

• Ugly Drinks owned "no added nonsense."

• Liquid Death owned "water for people who hate wellness culture."

Complete this sentence: "We're the only _____ that _____." If you can't fill that in with something defensible and ownable, your brand story is noise in a crowded market.

THE GATEKEEPER MOVE

Even at Level 3, as a storyteller with an audience, you're vulnerable. Algorithms change, and your reach dies. Platforms shift, and your distribution evaporates. You stop creating, and you stop existing. Competitors copy, and you lose differentiation.

You're on a content treadmill. The moment you stop running, you disappear.

Gatekeepers don't have this problem.

Gatekeepers don't create dependency on their content. They create dependency on their INFRASTRUCTURE.

Level 2 power means other people need to go THROUGH you to reach their goals. You control access to something valuable. Your position exists independent of your daily output.

There are four gatekeeper positions you can build:

Credentialing: Create certification that the market recognizes. StoryBrand certification for agencies. HubSpot certification for marketers. Employers filter for your credentials. Practitioners must go through you to get validated. You control the standard.

Marketplace: Build a platform that connects buyers and sellers. Upwork for freelancers. Behance for designers. Clients come to your platform first. You control deal flow.

Methodology Licensing: Make your framework the industry standard. EOS for business management. Jobs-to-be-Done for product strategy. Agencies license your methodology. Consultants get trained in your framework. Can't operate at scale without your system.

Editorial Platform: Turn your brand into a multi-contributor media property. First Round Review. Stratechery. HBR. Best thinkers pitch YOU to get featured. Your platform becomes THE place to get discovered. You control whose ideas get amplified.

THE ASYMMETRY THAT CHANGES EVERYTHING

Storyteller math: Stop creating = stop earning.

Linear relationship between effort and outcome and can be easily replaced by the next storyteller.

But infrastructure earns independently of daily output. Network effects compound over time, which makes it nearly impossible to replace once established.

That's why an AI coding tool can build the next LinkedIn or Gumroad in seconds but can never replicate the network effect these platforms have.

So sre you building a storytelling business that depends on your continued output? Or are you building infrastructure that controls which stories get told in your market?

Because a mediocre story with great distribution beats a great story with no distribution.

Every.

Single.

Time.

Pick one gatekeeper position. Build it quietly while you storytell publicly.

In three years, you'll own a position no one can take from you.

That's when you stop being a storyteller.

And become the person who decides which stories get told.

Your fractional CBO,

Shashank

P.S.

If you're still explaining what you do to prospects, you've already lost.

Clear brands don't explain. They own a category in the customer's mind.

Unclear brands spend every sales call trying to differentiate themselves. Then they lose to competitors who charge 2.5x more with worse products.

I built a free 5-day email course called The Brand Diagnosis that shows you what's actually broken. Takes 10 minutes per day. By Day 5, you'll know whether it's positioning, messaging, or differentiation and how to fix it.

▶▶ Sign up and get Day 1 tomorrow.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

I'm ending the daily emails.

It's because I care about building something that lasts longer than an inbox habit.

Here's what's changing:

My primary content moves to X/Twitter. If you want to see how I think through positioning problems as they happen, that's where it lives now.

Tuesday deep dives start next week. No more bite-sized daily hits. One strategic breakdown every Tuesday, either a brick-by-brick brand teardown or a concept breakdown that takes 10 minutes to read but changes how you think.

And there are two secret projects I'm not announcing yet. You'll know when it's ready.

If you want the unfiltered version of how I think, follow me on X.

If you want the weekly strategic depth bomb, you're already on the list. The first one drops next week.

Your brand strategist,

Shashank

P.S.

Gimme one last chance.

11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

I'm ending the daily emails.

It's because I care about building something that lasts longer than an inbox habit.

Here's what's changing:

My primary content moves to X/Twitter. If you want to see how I think through positioning problems as they happen, that's where it lives now.

Tuesday deep dives start next week. No more bite-sized daily hits. One strategic breakdown every Tuesday, either a brick-by-brick brand teardown or a concept breakdown that takes 10 minutes to read but changes how you think.

And there are two secret projects I'm not announcing yet. You'll know when it's ready.

This isn't me ghosting you.

This is me building for the long game instead of the engagement game.

If you want the unfiltered version of how I think, follow me on X.

If you want the weekly strategic depth bomb, you're already on the list. The first one drops next week.

Your brand strategist,

Shashank

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11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service

That tells me something, and I love you for it.

Next Tuesday, the first deep dive lands: Why did Steve Jobs lie to you?

Here's what it covers:

Why most brands fuck up distribution by treating it as a tactic instead of a strategic positioning decision. I'll walk through three companies, one that nailed it and two that died because they got it backwards.

This isn't a 2-minute skim piece. It's 2000+ words. It'll take you 15 minutes to read. And if you actually apply the framework, it'll change how you make channel decisions for the next decade.

The quick observations **move to X**. Follow there if you want that feed.

The strategic depth stays on Tuesdays. That doesn't change. These are the deep breakdowns that show you HOW to think, not just WHAT to think.

But really, it's about how to make strategic bets when conventional wisdom tells you to follow "best practices."

(Spoiler: Best practices are where differentiation goes to die.)

If you're still here, you're the right audience for what's next.

Your brand strategist,

Shashank

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11, PNR Nagar

Dindigul, Tamil Nadu 624001, India

Terms of Service