Taking the long(er) view

Patience is not my middle name.  As the youngest of three kids I was always in a hurry to grow up so I could do whatever the big kids were doing. And since there’s always someone older, faster, smarter, richer and better-looking than me (especially that last one), there’s never been a natural brake on all my hurrying and striving.

But lately – maybe since I turned forty a few years back – I’ve found myself taking a somewhat longer view. This may come as a surprise to anyone who works closely with me, since it doesn’t translate into taking on any less (more like the opposite, actually). But I now have some goals that are really important to me, and that I know I can’t make happen any faster than they already are. These include:

  1. Helping my kids grow up

    My son just turned six, my daughter is four. They’re completely different from each other, hilarious, fascinating and infuriating all at the same time. Trying to be a good parent – which is a hell of a lot harder than my parents made it look – is the most important thing I’m doing right now.

    Six and four came faster than I expected and I don’t want to hurry through any of my time with them, which means this particular 20-year planning cycle is the through line that the rest of my life has to wrap around for the forseeable future.

  2. Helping our portfolio companies grow up

    I switched from founding + operating to investing in startups about three years ago. In that time I’ve played a role – sometimes very active, sometimes less – in helping more than 30 new startups get off the ground. My longest-running seed investment is over five years old, and my newest hasn’t even shipped yet.

    Once in a rare while the stars will align and a company will get acquired within 6 months (nice work, Dan), but most of the time things take much longer to develop. People quit, strategies change, customers show up slowly, revenues ramp more slowly still. Every time I add a new portfolio company (like I did today), I extend the planning horizon for my life as a professional investor. If I take my job seriously – and if you ask around I hope you’ll hear that I do – I’ll be actively involved in each of these companies, doing whatever I can to help them succeed, until they no longer exist as independent firms. Based on the advice of folks who have done this much longer than I have, I should expect that to be five years on average, seven to ten at the outside.

  3. Building Founders Co-op with my partner Andy

    It’s not quite true that I stopped founding and operating companies when I became an investor. I’m a co-founder (along with Andy Sack) of something called Founders Co-op. Like most of our portfolio companies we’re small (just two people), lean (we don’t take salaries and most of our limited budget goes to lawyers and rent) and hungry (we want to make a big dent in the early-stage investment community in the Pacific Northwest, more on that below).

    Unlike most startups, though, ours has a built-in clock, and it’s a long one. Every fund we raise (we’re on number two) has a 10-year legal life with an optional two-year extension. And the only way we stay in business is to raise a new fund every three or four years. The good news is I’ve never had more fun or felt better-suited to my chosen path. But, unlike most of the startups we work with, ours is a “get rich slow” business at best (and even that is far from guaranteed).

  4. Helping the Pacific Northwest become a kick-ass market for software entrepreneurs

    This isn’t just my project, but it’s one I care passionately about. I grew up in Seattle and – since returning in 2001 – have gone all in on the Pacific Northwest as the place I want to build my life and career. We have great magnet companies, great schools and the kernels of an entrepreneurial ecosystem that can – over time – rival that of any global city. But as I’ve come to appreciate, this is not accomplished overnight.

    The foundation stones for Silicon Valley’s current dominance in software entrepreneurship were laid in the 1940’s and ’50s. Our own roots are not so deep, and it will take sustained effort by many people across the local spectrum to build a similarly rich and diverse ecosystem. As Mark Suster generously pointed out during his recent visit, many of those people are already fully engaged in the project. And by aligning ourselves with similar efforts in other “secondary markets” for entrepreneurship, we can inject greater velocity and excellence into our system than we would have if we tried to do it all ourselves.

If I do them right – and am lucky enough to live a long life – pursuing all of these projects with commitment and purpose could take me into my eighties. A few years back I couldn’t imagine a planning horizon longer than ten years, and now that’s more like a unit of measure. The weirdest thing about it is that it feels pretty good.