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Take Two: Eight Hard-Earned Lessons from Repeat Founders on Starting Over Again
Starting another company is like asking a seasoned marathon runner to lace up their shoes and run another 26.2 miles. You’ve got the muscle memory, sure, but that doesn’t make the next race any easier. Some mistakes from your first go — co-founder drama, rookie hiring missteps — are easier to dodge the second time. Others, like chasing product-market fit, are just as brutal. And then there’s the invisible trap: your brain is full of old assumptions and past priorities that might be useless—or worse, dangerous.
Dennis Pilarinos, two-time founder (Buddybuild, now Unblocked), sums it up:
“Let’s pretend we’re in an office right now. If we shut off all the lights and had to walk through here, we'd probably bump into the desks and chairs, right? Because we don’t know where they are. But if we’ve been in here before, we roughly know where things are… but you’ll still bonk your toe on a few things.”
Translation: experience helps, but it’s not a magic bullet. Here’s what the smartest repeat founders told us about starting over, distilled into eight hard-earned lessons. First-timers, you can crib a lot here too.
1. Don’t Let Past Failures Shadow Your Next Venture
Bob Moore, three-time founder and current Crossbeam CEO, knows this pain intimately. His first startup exited quietly, and it shook his confidence going into number two.
“When you get beat, when your strategies aren’t working, when you have to do layoffs… it’s easy to hang your head. After the modest outcome of my first startup, I was questioning whether I could ever raise money again. What was I going to say? ‘Hey, I’m the guy who pounded his chest before, trust me this time?’”
Moore’s point: the real ROI of your first venture isn’t always the exit—it’s the hard-earned lessons. He only realized this during his second startup.
Dan Siroker, co-founder of Limitless and Optimizely alum, felt a similar weight:
“I had some fear that it wouldn’t live up to my last one. I had an irrationally high bar. A first-time founder just wants success. A repeat founder carries baggage.”
Lesson: don’t let the glow (or trauma) of your first venture distort your second. Embrace imperfection, keep perspective, and protect your mental bandwidth.
2. Distance = Better Decisions
Dennis Pilarinos learned the hard way that burning yourself out doesn’t scale. With Buddybuild, he sprinted like his life depended on it. With Unblocked, he realized stepping back actually helped him move faster.
“Now I take a day away from the things I’m mulling over. I come back, and problems are simpler to resolve. Without that distance, you lose the forest for the trees.”
Practical tip: Pilarinos blocks one day a week for full rest—no phone, no computer. His Saturdays are sacrosanct. Perspective over hustle.
3. Reshape Your Quest for Fulfillment
Founders burn time like it’s money and hope for a return. Kareem Amin, CEO of Clay, says the first startup taught him this the hard way.
“I treated my company like an art project. Too much pressure to make it perfect. It spiraled the team. This time, I focus on curiosity: what does this want to be? Don’t force it to be the biggest thing—just make it useful.”
Lesson: fulfillment isn’t the finish line. It’s the day-to-day grind, done well, without overloading your brain.
4. Do the Homework on Your Next Idea
Neha Narkhede, co-founder of Confluent and now Oscilar, had a clear edge in starting her second venture: experience and rigor.
Her two-pronged framework for choosing a new idea:
- Study the market. Watch transitions, spot gaps, and understand where your differentiated product matters.
- Talk to buyers. She set up 70–80 meetings with prospective customers, even showing prototypes in Figma, to validate willingness to pay.
Lesson: repeat founders don’t guess. They validate.
5. If It Ain’t Broken, Don’t Fix It—Co-Founder Edition
Pilot co-founders Jessica McKellar, Waseem Daher, and Jeff Arnold have been building together since MIT. They’ve started three companies together.
“Far and away, the number one thing I optimized for my next startup was working with smart, talented people who challenged me every day,” says Daher.
Three tactical pillars of co-founder alignment:
- Constructive tension. Healthy conflict keeps you sharp.
- Shared trust. Predictability in each other’s actions prevents founder drama.
- More energy for the business. Less time debugging relationships, more time building.
Pilarinos applied the same principle with Unblocked, bringing former team members along—but cautions to reassess old processes and priors to avoid complacency.
6. Stay in Front of Customers
Steve Blank witnessed a founder succeed once, then watch it crumble the second time because they stopped listening.
“The founder was out in front of customers the first time. The second time? Wining and dining investors. Customers? Not so much. We were building a product no one wanted.”
Lesson: hubris is the silent killer of repeat ventures. Stay obsessed with customers. Teach what you’ve learned; if you can’t explain it, you probably haven’t learned it.
7. Focus Is Your Secret Weapon
Kareem Amin learned the hard way that multitasking kills startups.
“If a customer told us they needed X, we’d switch gears entirely. I had to discipline myself and the team. Once we agreed on a sprint, nothing shifts. No ‘imagine this other world’ thoughts. Focus means zero distractions.”
Lesson: clarity beats ambition. You can dream big, but your day-to-day execution must be ruthlessly aligned.
8. Play the Instrument You’re Best At
Lloyd Tabb, co-founder of Looker, learned that sometimes the best move is giving up control.
“I’m a one-man band. I can do everything, but not well. Frank was better suited as CEO. Startups are about taking risks; this was the right risk for the company.”
Lesson: repeat founders know when to let go and let someone else shine. Focus your energy where it matters most.
TL;DR for Repeat Founders:
- Don’t let past failures haunt your new venture.
- Step back to gain perspective.
- Redefine what fulfillment means.
- Validate your idea rigorously.
- Keep the co-founder magic if it exists.
- Stay customer-obsessed.
- Focus like your company depends on it (because it does).
- Play your strengths, delegate the rest.
Starting over is hard. Starting smarter is possible. These eight lessons are your cheat sheet.
