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Take Two: Eight Hard-Earned Lessons from Repeat Founders on Starting Over Again
There’s no shortage of advice for first-time founders, but resources for those diving into their second—or third—venture are far scarcer. To help bridge that gap, we spoke with experienced serial founders and distilled eight tactical lessons they applied differently the second time around.
Starting another company is like asking a seasoned marathon runner to lace up, turn around, and tackle another 26.2 miles. Sure, you’ve crossed the finish line before, but that doesn’t make the path ahead any easier. Some early hurdles—like co-founder conflicts or hiring missteps—might be easier to sidestep, but others—like finding product-market fit—can still trip you up. Add to that the risk that your perspective is clouded by old assumptions that no longer serve you. Dennis Pilarinos, two-time founder of Buddybuild and now Unblocked, puts it like this:
“Let’s pretend we’re in an office. If we shut off all the lights and had to walk through, we’d probably bump into desks and chairs, right? Because we don’t know where they are,” Pilarinos says. “But if we’ve been in here before, we have a sense for where things are. The second time, you roughly know where the furniture is—but you’ll still bonk your toe on a few things.”
While there’s a wealth of advice for first-time founders, the road looks different the second time around. That’s why we asked a select group of repeat founders to share their most useful lessons on starting over. Their insights offer a rare window into both the psychological and operational challenges of building a company all over again—and plenty of wisdom first-time founders can apply as well.
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Every repeat founder’s motivation is different. Some are chasing a bigger exit or higher peaks; others simply can’t resist the thrill of building something new. What most founders don’t anticipate is how profoundly doing it again affects your mindset.
Milestones that once felt monumental—closing a seed round, hiring your first engineer, signing your 100th customer—are no longer shiny and new. That can make it harder to tap into the motivation that drove your first venture. Seasoned founders share the baggage they carried into their second ride and the strategies that helped them cope.
Don’t let the past weigh you down. Bob Moore, a rare three-time founder and current CEO of Crossbeam, has scaled and sold companies in 2008, 2016, and now runs his latest venture. One lesson he emphasizes: don’t let the outcome of your previous venture cloud your next one.
“When you get beat, when strategies fail, when you do layoffs, or announce a modest acquisition—it’s easy to hang your head,” Moore says. “After my first startup quietly exited, I questioned if I could ever raise money again. I thought, ‘Have I wasted these years? Is my career as an entrepreneur over?’”
The real takeaway, Moore learned, isn’t the exit—it’s the experience. “It wasn’t until building my second company that I realized the upside of falling on my face so many times the first time.”
Dan Siroker, co-founder and CEO of Limitless, echoes this. Coming off Optimizely, he felt pressure for his second startup to measure up. “I had an irrationally high bar—something a first-time founder doesn’t have. A first-time founder just wants success. The biggest challenge the second time around is psychological: nothing is ever perfect, and you have to embrace that.”
Self-care is crucial. Moore leans on exercise and improv comedy to avoid burnout. “Sometimes operational failures are really outputs of decision fatigue, paranoia, or personal stress. Maintaining your energy is critical to building the support system you need.”
Distance improves decision-making. Dennis Pilarinos recalls his first startup, Buddybuild, where he burned the candle at both ends. “People told me, ‘You’re running a marathon at sprint pace,’ but I was determined. Looking back, that intensity hurt more than it helped.”
Now, Pilarinos is deliberate about time-blocking rest—one full day a week without phone or computer. That buffer gives perspective: “You're never as bad or as good as you think. With Buddybuild, I lived moment to moment. Now, I see that it could be better, it could be worse—and it will be.”
Reshape your quest for fulfillment. Founders invest years of their lives with no guaranteed return, which raises existential questions when starting over. Clay co-founder and CEO Kareem Amin learned this the hard way. His first company, Frame, was acquired in 2014, and when he returned to entrepreneurship, he realized he had to recalibrate:
“A challenge the first time around was treating my company like my art project. It decreased decision-making quality and stressed the team. For the second time, I shifted my mindset: my startup doesn’t need to be the biggest thing. It just needs to be useful to me and others. Approach it with curiosity.”
ON EXPLORING IDEAS AGAIN
Once mentally prepared, the next step is shaping your product. While inspiration may seem random, repeat founders know validation is critical. That means homework, research, and assembling the right team.
A framework for choosing your next idea. After nearly a decade in product-led growth, Neha Narkhede sought a new challenge beyond Confluent, the open-source streaming platform she co-founded and eventually took public. She wanted to build a traditional B2B SaaS company.
“I knew building a closed-source product with early customers would keep me engaged and learning every day,” she says.
Her approach to validating Oscilar, her fraud and risk SaaS startup:
Study the market. “I looked for huge transitions and where we could offer a differentiated product. Fraud and risk were ripe—especially with everything moving online during the pandemic. I also saw pain points firsthand at Confluent and LinkedIn.”
Talk to buyers. “I met with 70–80 heads of risk across industries, showed them a Figma prototype, and validated if they’d pay for a solution. That’s the most critical step in customer research.”
If it ain’t broke, don’t fix your co-founder team. Pilot’s three co-founders—Jessica McKellar, Waseem Daher, and Jeff Arnold—have built three companies together. Their first, KSplice, was acquired by Oracle. The second, Zulip, by Dropbox. Now they run Pilot.
“If your co-founder relationship works, don’t toss it aside,” says Daher. The trio deliberately only pursued ideas all three supported. Their tactical approach:
Constructive tension. Healthy disagreements underpinned by trust.
Shared trust. Each knows what the others will do, reserving discussion for truly important matters.
Energy in the reserves. Less founder drama means more mental energy for building.
Dennis Pilarinos applied a similar philosophy at Unblocked, bringing key Buddybuild team members along. But he emphasizes checking old assumptions: “As we grow, I reassess our predispositions and processes. Make sure you can answer: what makes them special?”
ON STAYING SHARP WHILE BUILDING
Stay in front of customers. Steve Blank recalls a mentor who succeeded with his first startup but ignored customers in the second, focusing on investors instead. The result: a product no one wanted. “Customer insight—not luck or strategy—is the key to success,” Blank says.
Focus, rigorously. Clay’s Amin learned that true focus isn’t just about time management; it’s about mental clarity. “Once we commit to a sprint plan, nothing shifts it. Don’t even imagine other worlds—focus means you don’t think about anything else.”
Play the instrument you’re best at. Lloyd Tabb, Looker co-founder, learned to relinquish the CEO role when it made sense. “Startups are about risks. I could do everything, but Frank was better at enterprise execution. Keep the instrument you’re best at and delegate the rest.”
The journey of a repeat founder is full of nuance: psychological challenges, relational dynamics, and operational lessons that only come from experience. From mindset and idea validation to co-founder chemistry and focus, these eight lessons reveal what it really takes to start over—and thrive—again.
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