This is Probably Your Last Success

"I've got a startup I'm running now that's doing well, but I really want to get out of this and move on to the next one which I think could be a much bigger opportunity. How should I be thinking about a successful startup before I move on to the next one?"

March 8th, 2023   |    By: Wil Schroter    |    Tags: Emotional Support

We need to treat every successful startup like it's our last — because statistically speaking, it probably will be.

In the startup biz, there are tons of second and third acts (I'm on my 9th) but there are very few that are ever equally successful. That's a problem for us as Founders, because we can easily lose sight of how important a single success is, and waste the opportunity thinking there will simply be another.

What if there isn't? What if this startup success, in whatever form it has right now, is the last successful startup we'll ever build? Shouldn't we treat it like gold versus assuming this is "one of many"? What happens if we get this wrong?

The Odds are Stacked Against Us

The first thing we need to understand is that the odds are largely stacked against us. Years ago someone way smarter than me published a Harvard study that did a nice job of summarizing our odds:

"All else equal, a venture-capital-backed entrepreneur who starts a company that goes public has a 30 percent chance of succeeding in his or her next venture. First-time entrepreneurs, on the other hand, have only an 18 percent chance of succeeding, and entrepreneurs who previously failed have a 20 percent chance of succeeding."

Did you catch the part that it's a 30% chance of succeeding if we started a public company on our last go around? Yeah, even if we went IPO we're at a 30% success rate, and I'm guessing most of us reading haven't rung the bell at NASDAQ recently. That's a best-case scenario by far.

Betting Badly on Future Success

The moment we start to risk our current payday for what a future payday might look like, we're putting ourselves in danger. In our minds, we think "Well if this one was successful, then obviously the next one has a higher probability of success because I know so much more than I have before!"

That argument falls apart at so many levels, which is why those second-time success stats are so awful.

Every new startup is a completely new set of conditions, from product/market fit to market timing to team makeup. Getting the right conditions for one startup guarantees absolutely nothing about the next one. When we create this fantasy about future success, we erode the value of our current success and by way of that, often tank the one best shot we had to get paid.

Maximize this Outcome First

We need to treat every success as a single moment in time that may never exist again. As such, we don't have the luxury of betting on the success of the next one — we can only focus on maximizing the value of what we have right in front of us.

Now, this is where it gets tricky. Maybe there doesn't seem like there's a huge upside relative to our expectations. Maybe the amount of time it will take to maximize the outcome feels too long. Or maybe we're just straight-up bored.

It doesn't matter. In this startup life, we typically get one opportunity to make the best of good fortune — one. We can't mess it up for anything. Just because there may be another big idea on the horizon, the one that actually turned into something of value is the only thing that should matter.

Maximize this outcome first — take it as far as it can go — and then, and only then, even consider what comes next.

In Case You Missed It

How to Make Potential Failure Less Scar‪y‬ (podcast) While your mind can make it seem bigger than it is, most people won’t remember when a business shuts down — and processing your emotions includes assessing your failure to get back up!

Optimizing for Productivity. Working through peak productivity is easy. It’s the valleys that we’re concerned about. The key is to plan for and optimize the valleys so we can recharge effectively.

What Will We Regret Risking for Our Startup? Founders are bound to make decisions all the time. These decisions can make or break the Startup, and this is why regret is inevitable.

About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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