An Update To My Investment Policy

Its the whole serving two masters kind of thing. It rarely works out well. I completely understand Mike's desire to keep on in a role (blogger/pundit) which gives him a lot of satisfaction, and his alternate desire to actually be a mover and shaker rather than a reporter on same, however he should take the clue from some of the small things he's run into (admitting or not admitting he is an investor to a fellow blogger etc) are only going to get worse.

The low point of that road has him losing all credibility as a blogger (since people will accuse him of favoritism based on his investments) and as an investor (as founders discover that his opinions and or presence cause other groups to shun them). $29K here, $100K there, isn't a huge deal but when one of those pops and suddenly the paper value of his holding is $10M and what he says can materially change that, then he has to shut up or defend himself in court.

The subtext of my suggestion was that he may not recognize just how deep the hole goes, nor how easily he can slip into it. Doesn't matter to me of course. I've seen death by conflict of interest and it isn't something I'd wish on anyone. And I recognize it's really really hard sometimes to step away from something you are pretty sure you can pull off. And I'm a huge fan of people who are willing to risk everything for something they truly believe.

But you have to take a cold hard look at the downside and be OK with that outcome. Time will tell.