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The Value of Working with Proven Serial Entrepreneurs

by Brian Flynn

When I graduated in 1995 from Harvard Business School, there was this new thing called the Internet. We all had to figure out how to use it to create new businesses. I watched one classmate build up a company in less than a year that he quickly sold to eBay for quite a nice chunk of change without ever even generating a revenue stream. Another classmate did the same thing with Amazon. Neither of them ever sold another company. I also saw my peers creating products with no markets, answering questions no one was asking, promising to fill needs that didn’t exist. There was suddenly a whole world of information and connectivity at our fingertips, and yet the majority of companies built back then soon faded into oblivion.

Those lessons from the early days really stuck with me, lessons about the difference between generating a quick payday versus building a real business -- one that would yield lasting, sustainable cash flow, which in turn would provide meaningful wealth and security, not to mention professional satisfaction, for everyone involved. Lessons about not only having a good product, but about how to find the right product-market fit, how to strategize going to market. Lessons about bootstrapping vs raising capital, about working lean and being able to pivot, about exiting at the right time.

I learned all those lessons and then I went out and actually started helping founders follow them. First once, and then over and over again.

It’s now 20 years later, but in some respects not much has changed. You still see would-be founders being dazzled by the prospect of a massive VC infusion without understanding the consequences, or being afraid to release their not-yet-perfect product, only to find themselves rendered obsolete by their more nimble, even if inferior, competitors before they ever even got in the game.

Proven serial entrepreneurs understand the journey better than anyone else. Proven serial entrepreneurs are folks that have won the race more than once. They’ve actually built and exited profitably more than one company. It’s about being able to call on real experience to reliably guide founders down the path to success, based on the specific parameters of each particular situation.

For someone to be of real value as an advisor/mentor/guide to your business, that person has to have been successful at least twice. Why is that important?

Well first of all, do you want a one-trick wonder advising you on your business?  That person has only a single data point to rely on. A static, one-size-fits-all approach is not going to help your business, with its unique set of parameters and circumstances, succeed, and isn’t worth the equity it’s going to cost.

Serial entrepreneurs have gone through multiple journeys and therefore have multiple perspectives on pricing strategy, building the right metrics, capital raising, budgeting, recruiting, making quick changes in unexpected market shifts, and a dozen other areas, any of which may be of specific relevance to your business as it grows and changes.

They’re fighters and winners who’ve been in the trenches and know how to solve problems. They can empathize and be a source of understanding and intellectual and emotional support. With their wide prisms of experience, they can help you anticipate and deal with what’s coming in addition to reacting to what’s past.

Many founders seek out former corporate executives or CEOs to advise and guide them, but fail to consider the myopic perspective these individuals typically have. They tend to think within their particular realm of expertise. A CEO from a big company, for example, may be a hired gun whose standard go-to solution for any problem is to throw money and resources at it. That wouldn’t be the right match for a scrappy founder who’s looking to control his own destiny by bootstrapping and working to solve problems on his own. Founders should be especially wary of former executives who think they can advise in areas in which they have no direct expertise, as the ability to pontificate on a topic rarely takes the place of actual know-how borne from experience.

When a serial entrepreneur is faced with a problem, he sees it from all the angles because he’s worked all the angles before. Whether it’s about finance, SLS, products, customers, people, or industry, the serial entrepreneur can see the whole forest, where each tree fits in relation to all the others, and which tree needs pruning so that the whole ecosystem can thrive.

You’re looking for a very specific type of person who has the right expertise and also the right contacts. It’s not always about knowing everything yourself, but knowing who has the right information in any given context.

There are also going to be times in your start-up journey when you hit that brick wall. You may be discouraged, or unsure of the way forward, or even downright depressed. The serial entrepreneur, having seen it all before, can be a real source of inspiration and comfort, the brother/father/coach you never had. Sometimes you need someone to just help you see past a tough part so you can get back on track and keep moving. You want someone who’s going to push you to think differently, and stretch you professionally.

I worked with a pair of co-founders once who had a really brilliant product and a great business plan. Their product was so good, in fact, that one of their former employers tried to intimidate them into selling it by accusing them of having stolen the IP. These guys knew they were innocent, but they were so rattled and stressed by the whole thing that they nearly capitulated to the threat just to get it off their backs.

Luckily, the guys trusted Greg, my partner at FounderPartners, and me to guide them through, and our understanding of the legal landscape and access to the right advisors helped us get rid of the frivolous lawsuit and get back to the real work of growing the company. So instead of being strong-armed out of their creation, these founders ended up reaping the rewards they’d rightfully earned by seeing their company grow and achieve a favorable exit.

Sometimes you can get intellectually stuck into a non-issue (or even a real issue), and you just need someone who can see the big picture to help you through the weeds. It’s important to step back and think about overarching strategic issues and trends, and there’s real value in having a true partner working alongside you who knows how to coach you do just that.

I like to think of serial entrepreneurs like myself and Greg as more than just mentors. For us, working with scrappy, ingenious, motivated technical founders and helping them grow their ideas into viable, sustainable businesses is like raising kids and watching them succeed. It’s an incredibly rewarding and exhilarating thing to do, and I’m grateful I’ve been able to keep doing it.