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, turn around and tackle another 26.2 miles — it takes an extraordinary level of determination and perseverance. While there is clarity and wisdom that comes from the experience of crossing the finish line before, that doesn't mean the path ahead will be easy.
While some of the challenges that plague the first-time founder — like co-founder conflicts and hiring missteps — might be easier to sidestep, others — like the struggle to find product-market fit — are likely to still rear their ugly heads. Then there’s the added difficulty that the repeat founder’s perspective may be clouded by past priorities and assumptions that no longer serve them. Here’s how Dennis Pilarinos, two-time founder of Buddybuild and now Unblocked, likes to analogize it:
“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,” Pilarnos says. “But if we’ve been in here before and we shut off the lights, we probably have some sense for where things are. So the second time, you roughly know where the furniture is, but you’ll still bonk your toe on a few things.”
