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Our Latest Success May Be Our Last

TL;DR: "I'm getting pretty bored with what my current startup does and I'm thinking about making the leap to get rid of this one and start another. Yeah, it's doing OK, but I bet the next one will be much better. What should I be thinking about before I hit the eject button on my current startup?"

What if our current startup success can't be repeated?

As Founders, we're ridiculous optimists, and for all of our "vision" we're pretty damned short-sighted. In our minds, if things are going this good now, it stands to reason that they will go even better in the future. It has to, right? We'll be better connected, more experienced, and way more prepared than we were for our current startups!

But that's not how startups work. The startup game isn't chess, where the conditions are similar and we're just more experienced. It's more like blackjack, where we know a little bit more, but the variability changes on every hand.


Today’s Advice Sponsored by Aircall

Don't Know What You Got, Til It's Gone

(If you sang this last headline in a Cinderella power-ballad, you are my people).

Early in our career, as Founders or otherwise, one of the big challenges we run into is not realizing how valuable our startup success is, because it may be the only one we've ever had. In our minds, this must just be how startups go, which means if we start another one, we'll just have some version of the same thing — probably bigger.

When I was 26 I lead a $650 million company. I'm 46 and haven't had one since. I had no damn idea what good fortune I had because, at the time, I had nothing to compare it to. Let's just say if hits $650 million in revenue, I'm going to be damn sure to recognize what that really means!

Our challenge in assessing our good fortune is weighted heavily on the fact of understanding how hard it is to replicate. Generally, it's better to bet on the fact that this may be our last winning hand and play it accordingly, then assume we'll just keep coming up aces.

Maximize First, Then Play Again

That's why it's so important to recognize that this may be our last winning hand. Instead of running for the exit on our current gig, we need to take a step back and think about how to milk the current gig for all it's worth! Sometimes that may mean investing some years that suck, just to maximize the ROI, since it may be our last.

Investors have known this strategy for years, but they have the benefit of applying it toward many investments, while we tend to have the purview of only one (ours). From an investor's standpoint, the smartest thing to do, if you have a hit on your hands, is to put all the resources you have toward maximizing the winner since so few startups will ever win.

If investors have 100x the purview that we have (they are actively involved in way more startups) and recognize that nearly all of them take this approach if nothing else we can learn a lesson that they learned long ago — we take our winners for the longest mile.

Our Next Album Guarantees No Hit!

Have you ever noticed how most musicians, after having a single hit album, almost never come back to that former glory? Startups share a similar fate. For every Steve Jobs and Elon Musk there are countless Founders who have had a great hit and never built another. (Although to be fair, any of us would take their failures on our Greatest Hits album any day.)

Startups succeed when a ton of factors all hit at the right time, including product/market fit, funding, team dynamics, and competition. No matter how hard we try, we can't simply replicate them each and every time, and many are out of our hands altogether.

For this reason, we need to recognize that whatever our latest success may be, it may in fact be our last big hit — and that's OK. So long as we intentionally plan on maximizing the value of what we have in hand, we can be sure that when we make our next leap, we're leaving nothing behind.


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In Case You Missed It

Focus On What You Don’t Want To Do. What happens when instead of worrying about the things we want to do, we focus on the things we never, ever want to do again? How can that start to take huge steps in reducing our overall stress?

Build Your Startup Around Your Passion. Not every passion pays well. However, instead of starting with, "what will make the most money?" and hoping we like it, let’s start with what we’re most passionate about and figure out how to do that profitably.

Is Doing Non-Startup Stuff Good For My Startup? (podcast). What if we knew that time away from our startup was the key to actually making it grow faster?
Love this topic? Hate it? Let's chat on social media!

Wil Schroter
Founder & CEO @
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