Never trust a hippy


This is a tricky post to write, because some of my best friends are hippies, I've been accused of being a hippy myself and I live in Boulder, but after reading this article about a first-time entrepreneur's messy breakup with a business partner I couldn't resist.

When it comes to business, pay no attention to what a potential partner says. Judge them on what they do. This is especially important if they're charismatic and overtly spiritual because what they say will be both flattering and very appealing, you'll be tempted to bend over backwards for them. I'm speaking from painful personal experience; my two worst business outcomes were situations where I really liked a partner and stopped thinking critically about what they were offering.

I followed a charismatic hippy manager into his new startup for no equity and worked like a dog for a year. He replaced my friends (he'd needed all our resumes to get the initial contract) with cheap college interns, compressed the schedule and played a lot of other nasty tricks until I finally snapped when a colleague was reprimanded for being late on a Sunday. I'd spent many evenings with the guy and his wife and kids before 'our' startup launched, I really liked him, and he'd painted a beautiful vision of a family-friendly workplace with a great culture. My mistake was that I'd failed to push for any tangible evidence he was serious about his promises. Trust but verify.

The sad thing is, I don't think he was faking the beliefs that he kept talking about, but he was able to use them to convince himself that they justified whatever the most convenient thing for himself was. During the nightmare he often invoked providing for his family as a reason to cut salaries and hoard the benefits of success, which sounds great until you saw it meant a second home for him while employees struggled to afford healthcare for their kids.

Since then I've been much more comfortable with 'coin-operated machines', as a former partner described himself. I find someone who's up-front and honest about their motivations is a lot easier to deal with than anyone who claims they're acting in your best interests.

On Hacker News, a commenter pointed out that Steve Jobs is a hippy, which is true, but I don't think it's possible to find someone who's more blunt and straightforward in his reactions than Steve! All I want is honesty and trust, and I find that's a lot easier to achieve with someone who's unafraid to admit selfish behavior than anyone who's worried about preserving a virtuous self-image.

This is one of the hardest posts I've had to write, I'm admitted a strong prejudice based on a small sample size, and I got a lot of flak when I posted my original comment on HN. In the spirit of openness I'm trying to be honest about what my biases are and how I got to them, even if they aren't particularly flattering. I look forward to the comments!

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