Tools #Opinion
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25 February 2020

When to believe in an entrepreneur and when to run away

Last week, one of the founders I’m advising landed a lucrative and potentially game-changing customer. This was a moment of truth in more ways than one. First of all, it staved off what had been a downward spiral of unfortunate events in the life of her company. But more importantly, it reestablished her faith in herself — faith that, by that point, seemingly no one else had. Joe Procopio tells us more about what makes an entrepreneur stand out.

She may not ultimately succeed, but at least now she has a fighting chance. For entrepreneurs, that fighting chance is usually all we need. Oh, and as an advisor, witnessing that kind of redemptive win — when nobody else believed in her — is one of the best experiences in the world.

Why did I believe in this particular entrepreneur?

One of the primary reasons I’ve been successful is an ability to spot faith-worthy entrepreneurial talent quickly — in terms of picking people to work with, work for, invest in, or just stake a vouch on.

I’ll admit that there isn’t a template or checklist that I go through to decide if I’m going to believe in someone’s entrepreneurial talent. Hell, if I had that, I’d just sell the template. I’ve been wrong with initial calls on people. I’ve even reversed positive calls into negative calls when I started seeing things I didn’t like.

For the record, I’ve never reversed a negative call into a positive call — which just shows it’s much easier to go bad than turn good.

I’m also not talking about picking obvious winners and losers. Anyone can do that math. I’m talking about finding maximum value early because that’s essentially the game we’re all playing. If I see value where no one else does or before anyone else can, that’s worth so much more than making a bet that Mark Zuckerberg might just do okay the next time he starts a company.

Entrepreneurial talent means someone who can solve problems and get results on their own.

If I had to break down how I spot entrepreneurial talent, I’d start by describing the person in hindsight: Entrepreneurial talent means someone who can solve problems and get results on their own; someone who I don’t feel like I have to pick them up and place them back down every step of the journey.

It’s someone who is creative in finding solutions and is not afraid to admit and fix their own mistakes. It’s someone who can explain complicated concepts simply, and not make you feel stupid while they do it. It’s confidence without arrogance, street smarts balanced with book smarts, scientific acumen paired with the passion of an artist.

So… when you find that person, let me know.

Yeah, all of what I just described sounds great and is certainly 100% true, but it takes a long time and a sixth sense to truly make a call on whether or not a person fits any of that description, let alone all of it.

You have to take a leap of faith every time you stick your neck out for someone, whether that’s with your time, your money, your actions, or your words. Sometimes you get lucky, but most of the time you rely on your gut, that background processing your brain does that you can’t quite put into words.

But I’ll try to put it into words anyway.

It’s not necessarily the serial entrepreneurs

I’m going to use conventional wisdom to fight conventional wisdom here, and I’ll get detractors on both sides.

Just because you’ve been a successful entrepreneur doesn’t mean you’ll ever be a successful entrepreneur ever again.

First, let me say that I totally understand why repeat entrepreneurs are sought after. I’ve done 11 startups from start to finish as an employee or a founder, and each time it’s gotten much easier.

Don’t put your faith in a serial entrepreneur unless they can talk about their current startup with as much knowledge as they can talk about their past successes.

If you’re going to perform surgery, fly on a plane, or argue before a jury, you want as much experience as possible beforehand. But imagine if every time a pilot flew a plane, every system on that plane would be markedly different than the last flight. The physics would still work the same, but the controls, the electrical, the instruments were all brand new.

That’s a freaking startup.

Don’t put your faith in a serial entrepreneur unless they can talk about their current startup with as much knowledge as they can talk about their past successes.

It’s not necessarily the rock stars

After I got a couple successes under my belt, I learned really quickly that people would want to throw money at me. In fact, right after my last startup got acquired, I jumped into a new idea I had been working on, and the investment offers came in before I even had any code written. But the idea was so half-baked that I couldn’t take the money. And I’m glad I didn’t. It was bad money.

Before I got into startup, I had a career in music. There, I learned that your name fades really quickly. It took me a lot longer to understand that the same is true in startup, or in business, or for that matter in any vocation.

Developers, marketers, salespeople, local big shots, chief executives, tech evangelists, big name press, market makers, investors — name recognition has a sneaky half-life that starts with someone’s last success and bleeds out until their next success.

If they ever get there.

Fame is fleeting. What people do remember is your impact on them the first time they meet you. If a startup rock star can’t hold that mantle up, if all you hear is eyes-glazed-over buzzspeak when they’re talking about their company, don’t put your faith in them.

The entrepreneur doing entrepreneurship to be an entrepreneur

It’s never the ones who have memorized the startup playbook and are running it step by step. These are the folks who have a passion for the process, the ones who can name every lauded founder from Jobs on, the ones who follow in those footsteps because they believe that if they can emulate the person, they can replicate the results.

Nope. This is how you end up with Theranos and WeWork and the cult of entrepreneurship. They can fool a lot of people, because they exude confidence and competence, and they surround themselves with smart people who talk about them as visionaries. They spend a ton of time talking about the company, the mission, the story — not so much about the product.

Some of this is healthy, of course, but I’m always skeptical of entrepreneurship for entrepreneurship’s sake. It takes a while to figure these folks out, because they spend so much time and energy looking the part that they mask whether or not they can actually play the part.

But usually, you can see it in their mannerisms, what they care about, and often how they treat other people when they think no one is watching. Don’t put your faith in fakery.

I believe in the crafters

A friend of mine who happens to be a successful entrepreneur once told me that startup makes the most sense to him when he looks at it as a craft.

That’s such a great way to put it.

Going back to music, the reason I wanted a career was because I wanted to be a musician. But musicians don’t have careers — well, some of them do, but those careers suck. Rock stars have careers, as long as they hop from success to success. This is why the dustbin of music history is filled with one-hit wonders.

Most other vocations outside of entertainment aren’t like that, but every single vocation, whether it’s in startups or medicine or plumbing, has its experience factor, its rock star factor, and its passion-for-the-process factor. Some more than others, startups more than most.

So when you’re deciding who to trust, start by making sure that you — whether you’re an entrepreneur or not — are into what you do for the love of the craft. Because just like a liar believes everyone is lying to them, someone worthy of your trust is much easier to spot when you’re trustworthy yourself.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is currently the Chief Product Officer at Spiffy, a startup focusing on on-demand vehicle care and maintenance. In 2015, he sold Automated Insights to Vista Equity Partners. In 2013, he sold ExitEvent to Capitol Broadcasting. Before that, he built Intrepid Media, the first social network for writers. You can read more and sign up for his newsletter at