late bloomer, not a loser. (I hope)
most of the time I think of myself as a failure.
when I'm optimistic, I think maybe I'm just a late bloomer.
I know a lot of folks won't understand this perspective, but when I was growing up I was always the smartest kid around. it was expected that I would do great things, by my mom, by my teachers, and most importantly, by me. I don't know whether that's a good thing or bad thing, but high expectations were always around me, and for the first 10-15 years, the results would seem to indicate that was a likely thing.
but after lots of good grades and academic achievement (I skipped 8th grade and another in high school), that kind of stopped happening. I went to college early, and found out that performing well wasn't always based on being smart. hard work and regular, consistent effort was also required… and I wasn't really very good at those things. I also had a lot of trouble in college with too many fun things to do… many of which didn't involve school. I got really good at playing foosball, pool, frisbee, and going to lots of parties and making friends, but I kind of barely made it to graduation. altho I did make dean's list later in college, I was also on probation a few times, and I spent a lot of time doing “recreational activities” (ahem) which caused a lot of pain and hassle for me, and probably even more for my family. I got through those times, but I started to think about all the things I was supposed to be, and the reality was that I wasn't quite getting to the goals that had been expected. I didn't become an astronaut, or an astrophysicist, or a great singer or dancer or pianist, I didn't end up in politics, I didn't join the peace corps, I didnt get a Phd or even a masters degree. by my mid-twenties, I headed west to California in search of myself, barely managed to become a decent programmer who bounced around a few jobs, and wasn't really sure where I was going next.
by my late twenties, I stumbled into running my own consulting firm, which sort of became my first startup. we had a lot of ups and downs, and altho we won a few awards and did some interesting and innovative work, after 5-6 years of trials & tribulations and serious questioning of my own ability as an entrepreneur and leader, I barely escaped bankruptcy multiple times and ended up with only a very small and desperate acquisition that was hardly anything to brag about. I didn't take the job with Microsoft or Intel in the early 90's, and I didn't join Yahoo or Netscape in the late 90's. i had applied to business school at Stanford, but didn't get in. I was fortunate to get a job at PayPal in 2001 after the first dot-com blowup, but it wasn't with any fanfare, and I was struggling to adjust to a new career in marketing, working with people ten years younger than me from Stanford and MIT who seemed to have their shit together a lot more than I did. after 3 years hard work at PayPal, I made some progress, but didn't get any promotions and mostly got shuffled around working with 3 different bosses who really didn't know what to do with me. in fact, I felt lucky I didn't get fired during my time there, and as I walked out the door I was relieved no one had figured out I was a lame duck who didn't know where the hell I was going.
don't get me wrong: PayPal was a great place and I made some wonderful friendships and learned a hell of a lot. my own startup had been a comedy of errs, but i did learn a lot about running a business (mostly what not to do) and learned a lot about myself in the process. I also ran a lot of user groups and events, and realized I was pretty good at marketing, and I really loved technology and the silicon valley culture. but I still felt like an unfocused underachiever, and at 40 hadn't accomplished much other than finding a good woman foolish enough to marry me, and somehow managed to father two wonderful children I was vastly unqualified to raise. I joined Simply Hired for a few years and did some work I was proud of there, but then continued bouncing around at consulting gigs with oDesk, Mint.com, O'Reilly Media and others where I still felt like I didn't quite fit in, and wasn't making the impact I had hoped. at Mint, I was again fortunate to work with some amazing people, but Aaron correctly assessed I wasn't really the right guy for the job, and I felt lucky to just play a small part in a decent success story (Aaron did let me invest some money in the company, which worked out pretty well for me; thanks Aaron :)
so after twenty years in the valley, I had made only a little bit of money, had some modest accomplishments as a programmer, an entrepreneur, and a marketer. meanwhile my peers at PayPal had gone on to create incredible businesses like LinkedIn, YouTube, Yelp, and Yammer, and other kids half my age were seemingly even more ambitious. most folks thought I was a decent fellow, but over the hill with my best days behind me… and I guess I thought so too. I watched as other friends helped make companies like Google and Facebook and Twitter into juggernauts, but mostly I was on the sidelines, only peripherally involved in their big ideas. but I had started doing some angel investing when I left PayPal in 2004, and after finding Mint.com, SlideShare, & Mashery, I figured maybe I had some talent as an investor… since it seemed like I was only a half-assed entrepreneur.
so after some small notoriety in 2007 teaching a class on Facebook at Stanford (strangely, a school where I wasn't good enough to get accepted as a student, somehow let me become a visiting lecturer), I decided I'd try to become a venture capitalist. my timing was of course impeccable, and as i was attempting to raise a small fund in summer 2008 the next huge financial crisis hit, and the bottom fell out of the market. again I was fortunate, and my plan B was to humbly say yes to a job offer by Sean Parker to help do some marketing and investing at Founders Fund. I was likely the only person hired in the entire venture industry in Q4 of 2008 (thanks Sean, I owe you one). I threw myself into the job, and after a year and a half had made some decent picks investing in Twilio, SendGrid, Wildfire, and TaskRabbit among others. along the way, I also got the opportunity to run the Facebook fbFund for a short time, and made some friends at Accel and Redpoint and BlueRun. these folks, along with Founders Fund, Mitch Kapor, Michael Birch, Fred Wilson, Brad Feld, Marc Andreessen, and several other generous souls helped me to finally and barely raise a small fund in 2010 that I brazenly named 500 Startups.
it would have been easy at any point in this journey to rationalize my limited success, and accept being a small cog in a bigger wheel, at likely much better pay and much less stress. but I was still hoping I had a little fire in the belly, and maybe some gas left in the tank to make something more of myself, before I ended up with just a broken spirit and a comfortable life.
and so here I am: still standing in the arena, in hand-to-hand combat with demons mostly of my own making, aiming to make a small dent in the universe. nowhere near a great success story, yet fighting the good fight and perhaps helping others to achieve greatness as I attempt a bit of my own. I'll be 46 in a month, well past the age when most folks have already shown what they're made of. but I'm still grasping for that brass ring.
I don't mean to whine or bemoan my lot in life – I've been far more than lucky, and I've had a great time on this planet. I have nothing to complain about, nor will it be the end of the world if all I get to do in the next 30-40 years is to breathe in the air. all things said, it's been a wonderful life.
but I'm not giving up yet.
I'm still betting my epitaph will read “late bloomer”, and not “failure”.
wish me luck :)