Entrepreneurship is often glamorized, but the truth is far grittier. Throughout my career, I’ve launched 30 businesses. Twenty of them failed. Ten found success. In baseball, a .333 batting average earns you a spot in the Hall of Fame. In business, it means you’ve failed two-thirds of the time—and yet, you’re still standing.
Later this year, I’m publishing my next book: FAIL HARD. WIN BIG. REPEAT. It’s built around one central belief: Failure is not the end. It’s the fuel. These are some of the key lessons I unpack in the book—hard-earned truths from the entrepreneurial frontlines that I wish someone had told me before I took my first swing.
This isn’t about statistics. It’s about survival, resilience and learning the hard way. Every strikeout sharpened my instincts. Every win proved that the pain was worth it. Entrepreneurship is a relentless game—no timeouts, no shortcuts and no sympathy. The mental load is real. My brain never stops. Sleep is a luxury, and switching off is next to impossible.
But if there’s one truth I’ve earned through the fire, it’s this: You only lose if you quit.
Here are 10 brutal truths I wish someone had told me before I took my first swing.
1. Custom software is the cheat code most founders aren’t using.
Passion is the spark, but process is the engine—and custom software is the system that keeps it running. Early in my career, I ran on energy and instinct. It led to chaos: missed deadlines, burnout and “almost” businesses that never scaled.
The shift came when I started using custom software to build repeatable systems—tracking KPIs, automating workflows and creating operational clarity. Off-the-shelf tools can help you start. Custom software helps you scale. It streamlines execution, improves customer experience and attracts both clients and investors. If you’re trying to grow without it, you’re playing the game on hard mode.
2. No one cares about your business.
Not until it solves a painful, urgent problem. I launched companies I loved—ideas that my team and friends swore would be hits. They weren’t. Why? Because nobody needed them badly enough.
The market doesn’t care about your pitch deck or passion. It cares about what you can fix. Until your product saves time, makes money or removes pain, you’re invisible. Launch early. Iterate fast. Validate demand. Because without traction, your business is just noise.
3. Failure doesn’t teach you anything—until you own it.
For years, I blamed external factors: the economy, the team, the timing. It wasn’t until I looked in the mirror that I grew.
Failure isn’t a teacher until you’re willing to be the student. Own your missteps. Rewrite the story with yourself as both the problem and the solution. Growth starts the moment you stop outsourcing responsibility.
4. Equal partnerships rarely work.
50/50 sounds fair. But when no one has the final say, everything slows down. I’ve seen great partnerships crumble when the pressure hit—and no one could make a call.
If you’re starting a company with a partner, define roles, equity and decision rights early. Think of it like a business prenup. Because if you don’t, a judge might write one for you later.
5. ‘Build it, and they will come’ is a fantasy.
A product without a go-to-market plan is just overhead. I’ve seen brilliant tech gather dust because the founders had no clue how to reach customers.
It’s not enough to build. You have to drag people to the door and show them why it matters. Know your customer, where they are and how you’ll get in front of them. Marketing isn’t optional. It’s the game.
6. Investors aren’t partners—they’re position holders.
When things are going well, investors feel like partners. When the numbers dip, you’ll remember they’re not. They’re managing portfolios. You’re managing survival.
The best investors offer more than money. But even then, don’t confuse support with safety. You carry the weight. Own your decisions.
7. ‘I’ll just do it myself’ is a dead-end strategy.
Early on, I wore every hat. It felt scrappy. It felt noble. But it was fear in disguise—fear of losing control.
If your company collapses when you step away, you haven’t built a business; you’ve built a job. Delegation isn’t a luxury—it’s a necessity. Build teams. Empower them. Your job is to lead, not to do it all.
8. Revenue solves a lot—but not everything.
Revenue feels like validation, but it can hide a broken model. I’ve chased top-line growth only to realize I was losing money on every deal.
Margins matter. CAC matters. Churn matters. Revenue buys you time, leverage and options—but only if it’s healthy and scalable. Know your numbers. Celebrate wins—but inspect the foundation.
9. Everyone’s metrics are inflated.
I’ve seen pitch decks that looked like they were built by NASA. Most of them? Theater. Reality always catches up.
Focus on the boring numbers: retention, time-to-value, customer satisfaction. You won’t find them on TechCrunch, but they’re the numbers that build companies.
10. If you can’t sell, your business is already dead—you just don’t know it yet.
I’ve met brilliant founders who went broke because they couldn’t close a deal. I used to think products sold themselves. They don’t.
Sales isn’t optional. It’s the lifeline. Learn to pitch. Learn to handle rejection. Learn to follow up. If you can’t sell, find someone who can—because nothing moves until someone says yes.
The journey of launching 30 companies (missing on 20, landing on 10) taught me that success in business isn’t about being flawless—it’s about being relentless. It’s about showing up after every miss, learning the lesson and taking another swing.
Because in this game, the only way to lose is to quit.