Think Like a Serial Entrepreneur

[This article was originally published on GeekWire, June 22, 2011. ]

I’m struck by the question of whether, and how, an entrepreneur might act differently if they were mindful that their current startup probably won’t be their last. In other words, chances are you’re likely to continue to be a “serial entrepreneur” whether you like it or not.  This actually might be a good thing to dwell on once in a while. Even if you’re only on your first startup. And even if you’re only just thinking about starting your first one.

So, why not take a moment to consider that you’ll have another startup someday… maybe someday soon?

Whoa, wait a minute, did I just suggest that you may not be working on the next Facebook or Zynga? Is it pessimistic or defeatist to dwell on the thought that your current startup may not be your last? We’re supposed to be eternally optimistic and always be reaching for the brass ring, regardless of what the naysayers tell us, right? I say no.

I’ve long had a penchant for reality-based thinking, influenced by my days as a philosophy grad student where the official department T-shirt slogan was:

“Everything is what it is and not another thing.” — Bishop Joseph Butler, 1692 – 1752

Joseph Butler (Wikipedia image)

How’s that for a hip T-shirt? In any case, you very well may be blessed with the good fortune of Bill Gates, Jeff Bezos, Michael Dell or Mark Zuckerberg. One and done. You might also win the lottery. I sincerely wish you the best of luck with both.

But if you’re like the rest of us poor slobs who didn’t start NextBigThing.com right out of the gate, then you might consider what it means to be signed up as an entrepreneur, i.e., you may be at this for a while and it may take you a few before you land on your crowning achievement.

So what if, upon reflection, it dawns on you that the startup you’re working on right now won’t be your last? Would that recognition cause you to do anything differently? Mind you, I’m not saying that your startup will be a success or a failure (however YOU measure that for yourself).

After all, lots of folks keep going after their next startup even if they do achieve some success. I’m just saying that lots of entrepreneurs end up doing more than one startup and I’m guessing that most (maybe all) of them didn’t really think much about that when they were starting their first one.

It’s a little like asking a 14-year-old holding their first cigarette whether they realize that they are going to be addicted to nicotine for the rest of their lives, that their clothes are going to constantly reek of smoke and that they are likely to eventually develop very serious health problems as a result. It’s just not part of the thought process when you start smoking. And thinking that you’re gonna have another startup after this one is just not part of the thought process for an entrepreneur.

But having a clear understanding that your current startup probably isn’t your last is actually a really positive thing.

For example, I recently met a really smart, aspiring first-time entrepreneur who (in my opinion) was stuck pursuing a problem and a market that would be very hard to create a sustainable business around.

We talked about it at length several times and I really tried to imagine a possible path that would lead to him ending up with what he wanted: Namely a business that could (eventually) make money for him, his team, his family and possibly for investors.

I’m pretty flexible and creative in how I think about problems and markets. But I just couldn’t get this one to fly — even in imaginary flight.

The idea he had was interesting. It was fun. It was even useful. And building the product was well within his team’s reach. But what then?

No matter how we ran the scenarios and crunched the numbers, it was going to require a lot of really hard things to go really, really well and then even if they did (which they just never do) the result at the end of all that just wasn’t likely to get him what he wanted.

As it turns out, I wasn’t the only one who was telling him that. I was, however, the only one suggesting that he consider himself a serial entrepreneur, even though this was his first one. What this did was create the possibility of a conversation about opportunity costs for an entrepreneur who doggedly sticks to an idea that no one is telling him has a decent chance to succeed.

Once he grasped that this was only his first startup and that there would almost certainly be the next one and the next one, then he could begin to take a more objective and critical view of his project.

The realization that his current startup didn’t have to be his last (and probably wouldn’t be anyhow) allowed him to take a more-objective perspective on what he was doing. It also opened him up to considering what might be next. Like lots of entrepreneurs, he had a handful of other ideas that he had been wanting to explore but couldn’t act on them because he was bound up in the current idea.

When we started the conversation, he was struggling figure out how to make his startup work and wasn’t sure himself whether there would ever be a sustainable business even if he did figure it out. But he just wasn’t ready to let it go.

By the end of the conversation, there was a shift of tone to genuine hope and possibility, even excitement.

Am I really saying you should sometimes give up? Admit defeat? Be a quitter? Yeah, I guess I am.

But it’s not a negative thing. Your startup “is what it is and not another thing.”

If you’ve looked out into your future and you cannot see a path that ends up somewhere you think you’d want to be, and if none of the other smart, qualified people you trust can see a path either, then it may just be the case that your working on one of those startups that teaches you some really valuable lessons and adds to your credibility as a “seasoned serial entrepreneur.”

As someone who’s stared that beast in the face a few times, I know it’s not easy. But the alternatives can be worse.

So what do you think?

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About Bob Crimmins

Chronic Technology Entrepreneur, Philosophy Grad, Poker Instigator, Dad View all posts by Bob Crimmins

3 responses to “Think Like a Serial Entrepreneur

  • Startups Play Poker, Big Companies Play Chess « Startup Poker 2.0

    […] you consider that most successful entrepreneurs end up being serial entrepreneurs.  As I wrote for GeekWire last month, I believe it’s useful to think like a serial entrepreneur… even if you aren’t […]

  • J. Shilling

    I wholeheartedly agree with your post. I guess I’ve always been a serial entrepreneur without having defined myself as such. Looking back now I see my first “startup” at age 10 leading up to the 12th startup I’m working on now. The one thing I’d add is “don’t be afraid to fail miserably”. Because as you’ve pointed out, for a serial entrepreneur this won’t be your last go at it ~ and the learning one gets from failing is an excellent teacher on what not to do during the next go round. Cheers!

  • Startup Haven – Startups Play Poker, Big Companies Play Chess

    […] you consider that most successful entrepreneurs end up being serial entrepreneurs.  As I wrote for GeekWire last month, I believe it’s useful to think like a serial entrepreneur… even if you aren’t […]

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