Four takeaways from an honest and open startup community gathering

I had the opportunity to join an intimate conversation last night with a variety of folks from the startup community, both Portland and otherwise. It was very much a “Chatham House Rule” sort of vibe to the event, so in keeping with that, I’ll reveal neither who was there nor who said what. But suffice it to say that it was a well rounded group of founders, investors, and support organizations.

I didn’t really talk much. I may have made a few comments. So I did what I do best: listen. (Because talking and writing are very much not what I do best.) And in so doing, I continued to hear four very specific themes that I thought would be important for you to hear.

1. There is a fundamental and pervasive misunderstanding ignorance of how the business of Venture Capital works. Part of this is due to the prevailing mythology around how businesses are built. Part of this is due to the obfuscation by VCs about how they do what they do and why they do what they do. And part of it — are you sitting down? — are those two elements further exacerbated by “Portland nice.”
2. Founders aren’t ready to hear what they need to hear until they’re ready to hear it. (But they’re often more ready to hear it from other founders.) I’ve struggled with this for years at PIE. It’s not a criticism. It’s just a fundamental human dynamic that comes into sharp relief with startups. I always use the analogy of the way we learned as children. Where a parent or guardian cautioned “Don’t do that. You’re going to get hurt.” And yet we kept doing it until — in fact — we got hurt. But the memory of that scrape or bruise or scar made us pay slightly more attention the next time. Same with founders. Until they’ve been through it and scraped a knee or two — or worse — it’s difficult for them to believe that the horror stories are actually horror facts.
3. Great founders are magnets for great founders. Or, curate the company you keep to enhance your chances of success — as well as the success of your immediate peers — and vice versa. It’s the hokey old “birds of a feather flock together.” But it’s a platitude because it’s so true so often. Find your people. Keep them safe. Trust them. And protect the trust they have in you.
4. Research, research, research. This is really the key to everything. Do your research. Follow it up with deeper research. Develop a strategy. Continue to inform that strategy with research. Try a tactic or two. Research. Iterate. Research. Lose. Research. Win. Research. No one “takes a swing at it” and actually succeeds. Do your research. Whether you’re trying to build a product, trying to secure customers, or trying to raise money.

As anyone who’s spent more than a few seconds with me realizes, my head is a bag full of cats. So sometimes, it takes me a while to process and come up with deeper insights. If that actually happens, I’ll share more. But even if it doesn’t, I hope you find these off the cuff observations helpful.

Oh. And one more thing… do your research.

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