The Greatest Adventure Ever

I had coffee with a 22-year-old founder last week who reminded me of myself 15 years ago. Full of fire, convinced his technical innovation would change the world, and completely blind to the landmines I could see scattered in his path.

I wanted to warn him, but realized he wouldn't hear me. Some lessons you can only learn by experiencing them.

At 20, you're dangerous because you don't know what's impossible.

Every founder around you is building "AI for X" - meanwhile, you're asking why Visa still holds your money for 3 days, or why Instagram doesn't feel like a social app for friends anymore.

Your naivety is your secret weapon. You question industry norms that veterans have long accepted as immutable laws. The establishment looks at you with amusement, but you don't notice because you're too busy building. Plus, you're probably pretty broke, which gives you a hunger that well-funded founders can't manufacture. When ramen is your only food group, your ambition tends to run hot.

Then reality teaches you expensive lessons.

You launch a technically "worse" product but get distribution right, and it works. Your "MVP" gets surprising traction but can't scale when real users show up. Users love the product but absolutely refuse to pay what it costs to deliver it. The feature everyone said they needed in customer interviews? No one uses it once you ship.

Your "dumb" buddy from high school sold his company for $15M because he knew the director of product at Google. Meanwhile, your technically superior product struggles to get a meeting.

You discover your biggest competitor isn't other startups - it's inertia. Users hate their current solution but hate changing more. Customers enthusiastically saying "yes" in meetings never write checks. Your perfectly scalable tech stack doesn't matter when you can't find users. Your product never really answered the "why now" question, and the market refuses to forgive you for it.

By age 30, the game reveals itself. You start seeing patterns others miss: Paper valuation of your startup is kind of BS, and optimizing for it is a trap. The best companies start by solving a small, boring problem perfectly. Consumer social is the hardest game in town (but endlessly alluring). "X" is a bubble (fill in with: crypto, AI, no-code, etc.). Failing marketplaces become SaaS companies. Growing SaaS companies build marketplaces. Every big company is a distribution company wearing product company clothes. Your "clean" architecture matters less than your first 100 customers. Most startup ideas are timing mistakes, not product mistakes.

But you do start getting more jaded. The unicorn dreams start fading, replaced by more practical ambitions. You can't help noticing that many "overnight successes" have powerful networks, family money, or industry connections. The playing field isn't level, and pretending it is becomes exhausting.

At thirty-five, you can't unsee these lessons: Profitability gives you ultimate leverage to do what you want in life. Bad UI with distribution beats great UI without it every single time. Consumer indifference kills more startups than competition. The best products look like toys to incumbents. If you plan on selling your company one day, it's probably good to know the people in charge of making those decisions. What you can't measure is usually what matters most. Market timing beats execution every time. Edge cases reveal your true moat. The best products solve problems so fundamental, they look obvious in retrospect.

The words "cash-flow positive" start sounding better than "Series A." You find yourself drawn to boring industries with real problems rather than crowded spaces with manufactured ones. You understand that fundraising isn't validation - paying customers are.

If you're lucky, you learn the 35-year-old lessons at 21. Not by reading posts like this one - these words will sound hollow until you've felt the sting of reality yourself. But maybe by finding the right mentors. By studying failures more than successes. By questioning the startup gospel that everyone around you recites without thinking.

The irony is that the 20-year-old's naivety combined with the 35-year-old's wisdom creates the most dangerous founder of all - someone who questions everything but knows where the landmines are buried. Someone who brings fresh eyes to old problems but understands that distribution trumps innovation, that timing beats brilliance, and that the most elegant solution is worthless if users don't care enough to change. Someone who knows that the game is unfair but plays anyway, because building something from nothing remains the greatest adventure available.

I ended up sharing some of this with that 22-year-old founder. He nodded politely, clearly thinking "that won't happen to me." And maybe it won't. Maybe he'll be one of the rare ones who gets to skip some of these lessons.

But as I watched him walk away, I couldn't help but think: we all have to earn our scars. The question isn't whether you'll learn these lessons , it's how expensive they'll be when you do.

The good news is: he's on the greatest adventure ever.

Note: I write posts like this every week, packed with free startup ideas, insights on business building, and strategies for succeeding in the online world. It’s called Greg’s letter.

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