The Exit Nobody Tweets About

There's a moment in my conversation with Caique Carvalho, founder and ex-CPO of a brazilian super app for drivers Gringo, that gets to the heart of why startups fail. He's describing his journey through two ventures that went under—one in South African auto sales, another in Brazilian tattoo marketplaces—and instead of the usual founder narrative of perseverance, he says this:

"You cannot fake product-market fit."

Not shouldn't. Not it's hard to. Cannot.

In an ecosystem drowning in growth hacks and blitzscaling mantras, here's a founder who spent a year in Cape Town learning that all the operational excellence in the world means nothing if you're solving the wrong problem. Who came back to Brazil to start a tattoo marketplace on WhatsApp—manually matching artists to clients—only to discover that even perfect execution can't save a flawed thesis.

Most founders would have taken the hint. Caique started company number three.

Five years later, Sem Parar (Corpay's Brazilian arm) would acquire that third company for $200 million.

THE EXIT NOBODY TWEETS ABOUT

We obsess over unicorns in Latin America. We celebrate funding announcements like they're cash exits. But here's what we don't talk about enough: most unicorns never actually leave the stable.

The real backbone of our ecosystem are strategic M&As—the deals that return capital, recycle talent, and prove you can build, scale, and exit here. Gringo's $200 million acquisition by Sem Parar won't spawn Twitter threads about generational wealth. But the value of mid-market exits in Brazil and emerging markets goes beyond cash-on-cash multiples.

These exits create something more valuable than paper unicorns: founders who've completed the full cycle of build, scale, exit, repeat. And the repeat part is what matters. When you've put real money in the bank—money that compounds at Brazil's double-digit interest rates—you gain the financial cushion to take bigger risks, solve harder problems, think globally instead of locally.

The founders who exit at $200 million don't retire. They start their second companies with their own capital, longer time horizons, and the earned confidence that comes from having done it before. They become the angel investors who write first checks. They mentor without needing immediate wins to justify their time.

This is how ecosystems actually mature: not through mythical valuations that never materialize, but through completed cycles that create financially secure founders ready to bet bigger.

THE BORING WEDGE THEORY

When startups look at automotive, they see buy-and-sell. That's where the money is—the transaction, the financing, the cross-sell. Carvana, Kavak, Auto1 all went there first.

Buy-and-sell has downsides though. Huge CAC, low recurrence. You acquire a customer for thousands, sell them one car, wait five years to see them again. You stop being a software company and become a car dealer with better UI.

Gringo wanted to build something different: a consumer company with software DNA. High engagement. Recurring touchpoints. Compounding network effects. The question was where to start.

So they wandered—deliberately. Gas station price comparisons. Parking solutions. DMV documentation. Three different wedges into a $300 billion market, each tested with the sophistication of a WhatsApp group chat and zero infrastructure.

This is where most founders get it wrong. They fall in love with their first idea. They confuse persistence with stubbornness. To avoid this trap, the Gringo team defined three success criteria before picking a solution - scale, recurrency (frequency) and strategic value. They weren't looking for a business model. They were looking for a user behavior that mattered enough to build a business model around.

Gas stations had frequency but no differentiation—pure commodity play. Parking was a real pain point but only in São Paulo and Rio, not nationwide. Then they hit DMV documentation and discovered something beautiful: universal need (every driver has it), natural frequency (pain points every 60 days), and hidden strategic value (all the data for insurance, credit, and transactions lives in these documents).

"When we fell in love with documentation," Caique recalls, they weren't falling for the problem—they were falling for the characteristics. The boring surface hid perfect unit economics underneath.

The lesson isn't "pick boring problems." It's test until you find problems with software physics: frequency that creates habits, habits that create retention, retention that creates runway to expand.

THE INDEPENDENCE THESIS

"You need to be independent as a company," Caique tells me.

Not profitable. Not sustainable. Independent.

Caique articulates something I've observed but couldn't name: the most successful companies in emerging markets aren't just building products—they're building sovereignty. The ability to survive when venture capital dries up. The capacity to grow when international funds flee to safer shores. The power to say no to a term sheet because you don't need the money.

Gringo charged users early—not because they needed the revenue (they had raised angel money), but because they needed validation. Would people pay? How much? For what?

This is the inverse of the Silicon Valley playbook: growth first, monetization later, figure it out at scale. That model assumes infinite capital patience. It assumes markets that won't turn. It assumes you'll always have access to the next round.

In São Paulo, you assume nothing.

THE DISCIPLINE OF SEQUENTIAL MASTERY

"Normally when you talk to people about growth, they do everything," Caique observes. "SEO, paid, branding, influencers, podcast, newsletter—everything. But 80% of your acquisition comes from one channel."

The insight isn't that you should focus—everyone says focus. The insight is that you should focus sequentially. Master one channel completely before adding the next. Excellence in one channel teaches you principles that transfer. The discipline, the data analysis, the optimization mindset—these become organizational capabilities. Your second channel benefits from everything you learned perfecting the first.

But there's another principle to GTM mastery: mental plasticity. Channels aren't permanent infrastructure—they're temporary opportunities. PIX transformed Brazil's payment landscape overnight, making some business models obsolete while creating entirely new categories. WhatsApp became Brazil's OS, enabling Gringo to test MVPs with nothing but a phone number and message threads. Tomorrow, it could be something else entirely.

The companies that survive aren't the ones who master a channel forever. They're the ones who master the meta-skill of mastering channels. "You're gonna have to find new acquisition levers," Caique notes.

This is harder than it sounds. When you have 20 million users, the temptation to monetize everything immediately must be overwhelming. When you've proven product-market fit, every growth channel looks attractive. The discipline to say "not yet" might be Gringo's most underappreciated asset.

THE INTELLECTUAL HONESTY PREMIUM

Midway through our conversation, I ask about co-founder dynamics. Caique's answer surprised me: "Best idea wins. Everyone says that, but when you go deeper, it's not how it works."

The gap between what we say and what we do—that's where companies die.

Here's why "best idea wins" usually fails: it requires intellectual honesty, and intellectual honesty requires people to lose gracefully. Most cultures can't handle that. They have the posters, the values deck, the open-door policies. But watch a real decision get made: the idea that wins is usually whoever's loudest, most senior, or best at politics.

Building actual meritocracy is brutally hard because when the best idea truly wins, most ideas lose. Your ideas. The CEO's ideas. The investor's ideas. Can you handle being wrong five times a day? Can your co-founder? Can your board?

This only works with radical transparency—and transparency requires trust. You can't have real debates if people fear the consequences of winning. You can't find truth if ego fills the room. The best idea can only win when losing an argument doesn't mean losing face.

Caique's chargeback story illustrates the point. In the early days, they're processing payments through WhatsApp with Mercado Pago links. No fraud protection. They celebrate hitting 100,000 reais in GMV—then get slammed with 50,000 in chargebacks. Half their revenue, gone. Ten percent of their cash reserves, evaporated. Most founders would bury this story. Caique tells it laughing.

That laugh is worth more than any mission statement. It says: we can admit we were stupid because we know we're smart enough to fix it. Most founder stories are sanitized victories. This one includes the word "chargeback" as a punchline.

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THE QUESTION BEHIND THE QUESTION

There's a moment near the end when I ask what question Caique wishes people would ask more often. His response: "What is the question that we're trying to answer?"

Not the solution. Not the strategy. The question itself.

Gringo's question was: "How do we make drivers' lives easier?" not "How do we disrupt transportation?"

That word—easier—did all the work. It pointed them to documentation, not to building the next Uber. To removing friction, not adding features. To boring problems with beautiful unit economics. Every decision filtered through that lens: does this make driving easier or just different?

Here's the thing about simple questions: they're hard to hide behind. Complex questions create wiggle room. "How do we revolutionize transportation through AI-enabled blockchain solutions?" can mean anything, so it means nothing. "How do we make drivers' lives easier?" demands specificity. You either do or you don't.

Most founders think they need better answers. When in fact what they need are better questions.

HAVE FUN DOING IT

I keep thinking about Caique's answer to my "What would you ask your future self?" question.

His actual answer was: "Did you have fun doing it?"

Not "did you succeed?" Not "was it worth it?" But "did you have fun?"

It's a curious question because it cuts through all the performance metrics we wrap around entrepreneurship. The valuations, the press releases, the LinkedIn humble-brags. It asks whether the journey itself—the actual daily experience of building—brought joy.

Most founders can't answer this honestly. They're so focused on the destination that they forget to design a journey they'd want to repeat. They optimize for outcomes instead of experiences. They build companies they'd want to exit rather than companies they'd want to run.

This matters more in Latin America, where the journey is objectively harder. The capital is scarcer. The infrastructure is weaker. The bureaucracy is byzantine. You're not just building a company—you're building the ecosystem around it. When tourist VCs flee at the first rate hike, when the currency swings 30% in a quarter, when you have to explain to Silicon Valley why Brazil isn't Argentina isn't Mexico—the external validation disappears.

What's left is the work itself. The daily grind of solving problems that matter to people who need them solved. Either that brings you energy, or it doesn't. Either you find joy in making DMV paperwork slightly less painful for 20 million people, or you're in the wrong game.

The paradox of entrepreneurship is that the people who succeed aren't necessarily the ones who want it most. They're the ones who can sustain themselves on the process when the outcomes are uncertain. Who find meaning in the attempt, not just the achievement.

Fun is a radical metric. It doesn't scale. It doesn't compound. VCs can't model it. But it might be the only metric that matters when you're five years into building something and wondering why you started.

Because here's the sobering thought for you: the destination might never arrive. The exit might not happen. The unicorn might remain mythical. But the days—all those accumulated days of building, testing, failing, adjusting—those are guaranteed. Those are what your life actually consists of.

Caique built something worth $200 million. But I suspect that's not why he's smiling when he tells the chargeback story. He's smiling because he got to play a game he designed, with people he chose, solving problems he cared about.

The rest is just scorecard.

THE J CURVE HALL OF FAME

Last week we celebrated a new (and very ambitious) milestone — 100K views on YouTube for a single episode. Pure wow. Pure joy.

The story of Piero Contezini and Asaas is so unique, different, and inspiring that I’m not entirely surprised it resonated this deeply. If you haven’t seen it yet, watch the full interview here:

Or if you’d rather read it, The Insider edition has you covered

Thanks for reading,

Olga 

 P.S. If this issue was valuable to you please share it with a founder who needs to hear it. Let’s build LATAM’s next tech leaders—together

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