Give Me 30 Minutes, and I Will Kill Your Entrepreneurial Dream
The Hard Truth About Hustle Culture
Tech entrepreneurship is the modern American fairy tale, a shimmering promise that you, yes you, can defy the odds, rewrite the rules and become the next Jeff, Steve, or Mark. It’s the intellectual equivalent of buying scratch-offs at a gas station and calling it investment strategy. Only here, the stakes aren’t a $20 loss and some sticker residue. The stakes are your life, your sanity, and your life savings—if you have those, which you may not, if you’re already Googling how to quiet quit your job as a CPA and get VC funding.
In America, land of freedom fries and dystopian optimism, the entrepreneur is our ultimate folk hero. The rugged individualist who “grinds” until their knuckles bleed and their marriage collapses. We don’t idolize teamwork or sustainability here; we idolize the loner in a hoodie, scribbling on a whiteboard in a garage they likely don’t own.
It’s all absurd, of course. But absurdity is our national pastime.
The Cult of the American Founder: Or, Why We Worship People Who Don’t Sleep
Americans love a narrative. We’re a country built on storytelling—Horatio Alger, rags to riches, manifest destiny, all that jazz. But we’ve taken it to pathological extremes. We’ve replaced our old heroes—explorers, pioneers, generals—with founders and business leaders. And not just any of the above, but the rare, mythic few who we elevate to demigod status.
We frame these people as prophets, geniuses who emerged fully formed from the primordial ooze with nothing but their vision and winning spirit. Never mind that Steve Jobs was ousted from his own company, Jack Ma failed his college entrance exams, Elizabeth Holmes is in jail, Henry Ford tried to build an utopia in the Amazon called Fordlandia. Blockbuster’s John Antioco passed on buying Netflix for $50M. Sam Bankman-Fried is in jail. Bill Gates didn’t believe mobile was going to take off. Henry Ford bankrupted two auto companies early on, Oprah was fired from her first TV anchor job, and Elon Musk’s kids hate him. We gloss over the inconvenient truths because they make terrible LinkedIn posts.
The “leader as savior” narrative is so deeply embedded in our culture that we’ve started to mistake wealth for wisdom. Want proof? WeWork’s Adam Neumann once tried to trademark the word “We” and Gwyneth Paltrow’s company sold a $75 candle called “This Smells Like My Vagina”.
Entrepreneurship Is Just the Lottery, but with More Meetings
Here’s the fact: almost every startup fails. Starting a business in America is like attempting to climb Everest in flip-flops with Aaron Rodgers as your Sherpa. The odds are comically bad. Roughly 90% of startups end up going belly-up.
Failure isn’t just likely—it’s the default. But we don’t talk about that because the American dream isn’t built on math; it’s built on hope. We are a country of delusional optimists, cheerfully ignoring facts while shouting things like, “What if we’re the exception?”
Spoiler: you’re probably not.
Failure isn’t a quirky learning experience; it’s a slow, suffocating ordeal. Most entrepreneurs don’t go out in a blaze of glory. They go out with a whisper, one rejected pitch at a time. You keep telling yourself the next pivot, the next round of funding, the next Instagram ad will save you. It doesn’t. Meanwhile, your friends stop inviting you out because they’re tired of hearing about your “runway”, your debt balloons, and you start to wonder if it’s too late to move back in with your parents.
Here’s a particularly bleak statistic: a 2021 report showed that almost half of all entrepreneurs earn less than $30,000 a year. That’s less than the average kindergarten teacher—except kindergarten teachers don’t have to explain to their spouses why they spent $10,000 on a logo redesign.
The Cult of Hustle: How to Burn Out in Style
Hustle culture is America’s unofficial religion. “Rise and grind,” we say, as if grinding is somehow inherently virtuous. Forget sleep, forget joy, forget human connection—sacrifice them all on the altar of the grind. If you’re not answering emails at 3 a.m. or eating ramen out of a mug, are you even trying?
It’s nonsense, of course. But we’ve glorified burnout as the price of admission. People wear their exhaustion like a badge of honor, bragging about how they haven’t taken a day off in five years, as if that’s admirable, and not just deeply sad.
And here’s the kicker: this obsession with hustle doesn’t lead to better outcomes. Studies show that overwork leads to diminished productivity, impaired decision-making, and increased rates of depression. But hey, at least you’ve got your motivational Post-it notes.
Why I Love Destroying Dreams
This is why, when people come to me with their big ideas, I do what any responsible human would do: I try to kill them.
I’ll try to tear it apart piece by piece, pointing out the risks, the flaws, and the staggering unlikelihood of success. I’ll tell them why the world probably doesn’t need another app for artisanal dog treats or an Uber for high-fives.
I’ve killed the “dreams” of many entrepreneurs in such sessions.
Why? Because it’s the most useful thing I can do. Either I succeed in talking them out of it—saving them years of pain, financial ruin, and late-night cries into their steering wheel—or I fail, and they tell me to f*** off. And when that happens, I’ve probably found a real entrepreneur, and I may even cut a check.
Here’s the punchline: if a stranger can kill someone’s dream in 30 minutes, it’s not a real dream. I probably just saved them an incredible amount of heartache.
Real entrepreneurs can’t be swayed, especially by a stranger over a coffee or a post on Substack. My words of warning will be adrenaline to their heart. My facts about failure will be a dare for them to prove me wrong. My dosage of truth about their idea probably not being as good as they think will be motivation to improve it.
Real entrepreneurs (in the same way I used to react to all of the people telling me I can’t do it) want to prove the world wrong. All I am doing is validating that urge, and giving them some helpful insight that I wish someone had told me at that age.
A real entrepreneur doesn’t need my approval, even though I may have earned the right. I’ve defied the advice and odds of this article my whole life. I grew up with nothing and made enough wealth to retire at 30. I started and exited a company to Salesforce. I told those very same people to f*** off who told me I couldn’t do it.
Entrepreneurship isn’t about ideas, funding, or the perfect pitch. It’s about stubbornness. It’s about having the sheer, unrelenting audacity to keep going even when the world—and people like me—tell you to stop.
To those individuals — who are fired up by this post and currently writing a rage comment telling me how wrong and dumb I am — you go girl. Hell yeah. We are lucky to have you. We need you. Keep going. Godspeed.
John Roa is the CEO of AnthologyAI, a NYC-based consumer intelligence company.
Have thoughts? Hate my take? Love the tough love? Let me know! Leave a comment below, share this post with your fellow dreamers, or send me a message explaining why your app for organizing kitchen spices isn’t destined for failure. I’m always up for a good debate.
This post is an adapation of my original Medium post.
Sources
No thank you sir. I did that this morning reading my latest post.
You really had me in the first half there... But then you had to go an perpetuate this concept of a "real entrepreneur". I agree there are people that are more suited to the life but even still I can't understand how people can't see the facts:
90% of people that are successful come from money and the other 10% are 100% the lucky few that have won the proverbial lottery. The are no real and fake entrepreneurs. Just people with money and resources and the rest of us.