Profitably financing war stories, and investor advice

From the Department of Oversharing: Since we love being candid about ourselves at Profitably, Adam decided to write up a warts-and-all account of the things we’ve learned from the time spent fundraising over the past year. Well, mostly what he’s learned, because during most of this he’s worked hard to bear the brunt of the stress and the time-sink while leaving the rest of the team relatively insulated so we can trucking on the product. It’s long and detailed and worth a read if you think you’ll ever have to raise an investment round, especially if you’ll have to do it in NYC:

A Tale of Two Financings

One smallish side point that re-occurred to me as I was reviewing this is on the value of advice from investors. The best investors are the ones who figure out how to be open about their doubts, even if they can’t be bothered to be diplomatic about it. And I know, speaking for myself, it was very difficult to not get defensive about any advice that would result from those doubts. It’s easy to think “screw you, you’ve thought about my company for all of ten minutes, I quit my last gig and I’ve been doing this full-time for months now”, and use that position to dismiss the difficult advice you may have received.

But in the past year, there have been multiple times when we started to hear the same advice from multiple investors or advisors—whether on product or market or people—and we resisted, and then after a little while we realized, “Damn it, those guys are right.” This is just my banal point about the whole smart money vs. dumb money thing: The best investors don’t just have cash, they have experience and perspective that can be helpful in more profound ways than just paying for your salary. Unfortunately, some investors are actually just jackasses. But the good advice is out there, and it’s far more plentiful than investment cash—and if you can figure out how to get good advice, that’s just as valuable to your company as anything else.

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