Angel investing is a lot like dating. Everyone is different and, in theory, there is someone for everyone. Both romantic and investment relationships are complicated and deeply personal affairs that are dependent on values, personality, and chance.

In dating, there is no one thing that turns everyone on or off. I know a gal who breaks it off with a potential beau if he’s a not a outdoorsy guy and another who is turned off by men who order the domestic beer. Petty details, no? Let’s include in fatal flaws a date who chews loudly, doesn’t tip at restaurants, and who spends all his time talking about the women he has attained.

Oddly enough investor turn-ons look a lot like date-night fails. An attractive founder is unemployed, lives with his mom, and perpetually creates failed inventions. He’s unreasonably optimistic, stubborn, and spends a lot of time with his friends.

How is it that this obvious dating loser looks like a handsome catch to an investor? Let’s dig deeper.

Unemployed – He’s devoting all of his waking hours to the start-up venture. In reality this is very hard to do and I’m certainly not suggesting that founders quit their jobs before talking to an investor. I am suggesting that you make it clear that you are thoroughly devoted to your venture.

Lives with his mom – A founder who has an austere lifestyle with low personal financial needs is way more attractive to an investor than someone who has been living above his means. Start-ups are almost all bootstrapped to some degree and founders don’t get paid for the first year or more. Investors want a founder who will have a long financial burn rate. In other words, investors prefer a cheap date.

Perpetual failed inventions – New ideas and technologies aren’t all winners. A prolific inventor continually bears new ideas, some of which can be commercialized and some of which will go right on the scrap heap. Investors want to avoid the one-hit-wonder who clings to their single so-so idea and go with the inventor who has more in the pipeline.

Unreasonably optimistic – Successful founders are buoyant folks who can take bad news, shift focus, and soldier on in the same day. Bad luck happens.

Stubborn – The business world prefers the term persistent, thank you very much.

Time with friends – It takes a village to raise a start-up company. Founders who have strong social ties with lots of different kinds of people are very attractive to investors. When founders can call in favors, leverage their friends for free labor and services, and surround themselves with smart advisors, they tend to overcome the common struggles easily.

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