Flip or Last? VC or Bootstrap?

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Was chatting with a friend about the dynamics of those questions, and wrote it out for myself, so figured I’d share those thoughts here.

1. There is nothing wrong with building a company to flip, per se. A $50 million dollar acquisition is life-changing for an entrepreneur – its often an incredible marginal return on the amount of work you put in, and part of the promise of a start-up dream is, to many, making a lot of money quickly, so that’s a fine way of doing it. (see 4 and 5)
2. Some companies just aren’t built to become ultra massive – either based on how they’re capitalized, management style, or the size of the market. So for these, a flip is the only real option for liquidation event save “dividends” or “revenue share” which takes years of profits to be viable. Smart VCs filter those companies out of their dealflow, see 3 and 6.
3. Institutional venture capital simply can’t return their funds if they don’t get a couple >$100M hits. So for them, “last” HAS to be the bet (they raise $500M to return 2x over 4 years, that means you need a $1B in exits…) Seed and angel investors have different math – that is, a combination of luck, network effect (so, getting good deal flow and that bringing more deal flow) and for some just simply realizing they’re losing money, but it being worth it for vanity’s sake. And honestly in institutional VC, only the top 10-15 firms do well, anyway. (Nut they do well enough to make the entire 400 VC industry look like a profitable asset class. thank you Facebook, etc.) Dave McClure at 500 startups has a different philosophy on all this – on his view, take a TON of really small bets and see what happens. YC is a version of this, though not as many bets, and not quite as small. VC’s respond to that with “YC is just doing what we’re doing – Airbnb and Dropbox are carrying the whole portfolio”. I’m not sure where i stand on all of this. I guess we’ll have to see how this incubator wave matures in the coming years.
4. The mindset of building to last often (though not always – see #2) makes a business better to flip than the mindset of building to flip does. If you build valuable pieces, companies that last want them anyway…
5. I feel more strongly that entrepreneurs should be more ambitious than money, and this is sort of a riff on 4. Money is a byproduct, not a goal. Even if its an essential byproduct, its still just that.
6. So where does someone who isn’t aiming all that high go for capital? The answers are angel, seed, incubators (sometimes), heck – go to the bank and get a loan. Mostly – dream big. It’s the effin interent! You can get to a billion people if you build something cool enough. and a billion people using something is important!

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