Doing a startup – Should you bootstrap it or VC it?

1377964_tightened_100_dollar_roll_So, you want to “do a startup”?

First big, huge, life-changing question: Should you bootstrap it, or VC it?

And I’m about to say something entirely heretical.

In a world where that question typically gets what I call a “religious” response – on par with the Mac versus PC question – I’m going to give you the craziest answer you’re going to get…

You need to try it both ways.

Not on the same startup. Two different startups, probably two different time periods in your life.

I’ve done both, and I wouldn’t trade it for anything.

There’s a ton of stuff – and I mean a TON – that you can’t learn from doing it just one way.

I know lots of people who’ve bootstrapped themselves into very successful multi-million-dollar businesses that they’ve built for decades or sold for millions.

And I know lots of people who spend their time building VC-backed startups, that they run for several years, grow, make millions, and then leave for the next thing.

Here’s why you need to do it both ways:

There’s just no good way to learn the independence, the confidence, the no-time-to-hesitate decision-making, dollar-stretching, seat-of-your-pants entrepreneurship that bootstrapping teaches, other than doing it.  Not knowing where your next payroll is going to come from, and then making it happen, month after month, for several years, teaches you lessons that are priceless. There’s just nothing like it in the world.

At the same time, there’s absolutely no way to learn about the high-hurdle, high-octane, high-demand, high-performance, 24/7 roller-coaster thrill ride that a VC-backed startup provides. You learn a lot about business – and about yourself – when you’ve got to be in three different cities in a day, convincing “Masters of the Universe” that you and your crappy little startup are the hottest thing on the planet, and then hosting a cocktail party in the evening, while trying to manage your startup and your team on your cell phone, from the taxi and the airport lounge. There’s nothing like it in the world.

And the only way to see both sides of the fence is to do both – at some point.

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This blog is dedicated to providing advice, tools and encouragement from one entrepreneur to another. I want to keep this practical and accessible for the new entrepreneur while also providing enough sophistication and depth to prove useful to the successful serial entrepreneur. My target rests somewhere between the garage and the board room, where the work gets done and the hockey stick emerges.