Just got asked this question on Quora.
If it’s Elon Musk or Jack Dorsey, sure, go ahead and invest in them.
If it’s anyone else, it’s likely not going to work out well as an investment.
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There are some serial founders who specialize in starting and handing off startups to exceptional managers; Sky Dayton (who founded Boingo Wireless, EarthLink and other startups) comes to mind, but these individuals are rare.
You need to ask yourself as an angel investor the following two questions when looking at a founder with “founder ADD”:
- Has this person managed multiple projects before and how did that work out? I’m going to assume they haven’t done this before or you wouldn’t be asking the question.
- Does this person really believe in this startup, product, team and market, and if they do, why are they distracting themselves with other projects?! Perhaps they are hedging their bets.
The second question is the important one here. Perhaps the person started the project, needs to spend time with a sick family member, and they have an exceptional President and management team. In that case, I would evaluate the performance of the team and the likelihood that the President can take over as CEO.
Bottom line: startups are absurdly hard. Running two at the same time is like winning two chess matches at once. Anyone can play two games of chess at the same time, but very few will win both. This is an imperfect analogy, of course, because startups are not “win/lose,” they are more like “win small/win medium/win big/win gigantic/lose.” Even if the person wins both games, perhaps they will just win modestly —- which will suck for you as an angel investor.