Don’t Burn the Boats
Smart Founders Don’t Seek Risk. They Reduce It.
When people think of startup founders, they often picture fearless risk-takers charging into the unknown, ready to burn the boats and never look back. But the best founders I know aren’t drawn to risk—they actively try to reduce it.
“If you want to take the island, burn the boats.” It’s a common entrepreneurial mantra meant to convey total commitment. No retreat. No Plan B. It has to work because there’s no other option.
Some people thrive in that mindset. Matt Higgins, a guest shark on Shark Tank, even wrote a WSJ best-seller about that belief and committing to your Plan A. It works for some people, but most people don’t have the stomach for that, especially at the start.
A better strategy for most aspiring founders is to reduce their downsides. When you do that, starting doesn’t feel like such a leap.
Build Parallel Paths
At The Meet Group, I can’t think of a single actual “burn the boats” moment. We never put all our eggs in one basket. Instead, we built parallel paths.
When we raised our Series A, we also explored other potential deals we could pursue. Could we be acquired? What would we do if we couldn’t raise what we planned?
Similarly, when we acquired Skout and Tagged, we had a thesis: we could layer our live video product on top and grow our Live reach (and revenue). But even if the thesis didn’t work, we priced those acquisitions based on their existing business models. That was all upside. They weren’t burn-the-boats acquisitions. They were thoughtful and calculated, with a low downside and high potential upside.
Even for more day-to-day decisions, we had contingency plans in place. For instance, when pitching a feature to the media, we had a clear plan for who to reach out to next and when, in case the first journalist we pitched to passed or didn’t respond.
I even applied this logic to college. We had already raised venture funding before I arrived at Georgetown. But I still wanted a fallback. Statistically, most startups fail. College gave me another path, in case my startup joined that 75%.
Wade into the Waters
Another way to reduce risk is to take steps in the right direction rather than making a sudden leap.
Mike Schubert, creator of the wildly popular podcasts Potterless, The Newest Olympian, and others, shared how keeping his day job allowed him to build an audience before going full-time on his dream. When he launched Potterless, he was working full-time and used nights and weekends to work on the show. When this became unsustainable, he found a part-time role that allowed him to continue building his business. Only once the podcast had clear traction and was generating enough income for him to be comfortable did he transition to a full-time career as a podcaster. This approach enabled him to maintain financial stability while mitigating the risk associated with the move. He waded into the waters; he didn’t do a cannonball.
Multiple friends have used layoffs as the perfect opportunity to test startup ideas, using severance payments as a runway to experiment and explore new possibilities. Other friends have decreased their hours but stayed employed to carve out time and finance their ideas. Still, others leave their full-time roles but take on consulting opportunities or side gigs as they build their careers.
There is no “right way” to build. Build in a way that works for you.
Reducing risk isn’t just smart—it makes entrepreneurship more accessible. You can hedge. You can test the parachute before you jump.
Don’t burn the boats too soon.
A few things and ways to connect…
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Love this. It's nice to hear this perspective from someone who's done it. When my husband and I watch SharkTank and some of the folks are like "I spent 500k and all of my savings on this!" I have simultaneous admiration and horror (depending on the product). From a product standpoint too, I'm building MapChat for multiple paths to success with this in mind (not going too heavy in on any one)...it meant a lot of thinking at the outset.