In the startup world, we have people we like to call “serial entrepreneurs.”
A serial entrepreneur is basically a startup founder who has ridden the entrepreneurial merry-go-round more than once.
That’s because founding a startup that makes it to a big exit is an extremely profitable (though grueling) endeavor. A really skilled founder can make hundreds of millions of dollars or more, doing just that.
That’s why, when I see a truly talented entrepreneur, I’ll often jump on the deal – even if I don’t quite “get” their business plan.
Take serial entrepreneur Jack Dorsey, for example. When he first started his business – a mobile credit card processing platform called Square – some investors weren’t so sure about the idea.
But they backed him anyway. Why? Because Dorsey is the man behind Twitter, one of the most successful tech companies of all time.
Trusting in the founder’s expertise turned out to be the right move. Today, Square is worth more than $30 billion.
Of course, even the greats come up with bad ideas sometimes. That’s why I run every single pitch through my 7-question gauntlet, which you can find here.
But a skilled founder knows the intricacies of steering a startup towards success, and that counts for a lot.
In addition to “street cred,” serial entrepreneurs have a Rolodex full of past investors, advisors, venture capitalists and board members.
And, since they all made money the last time they backed this founding team, they’re more likely than not to sign on again.
That’s because, in startup-land, it’s just part of the unspoken law: if an entrepreneur you backed rewards you with a big return, it’s good form to support them in their future endeavors.
On the other hand, if you’ve never invested in a startup before…
Backing an entrepreneur with a history of big exits is a pretty reliable way to succeed.
Until next time,
34 responses to “Your Angel Investing Philosophy: Back the Jockey, Not the Horse”
April 23 2019