The easiest thing to do is check out my LinkedIn profile, but it doesn’t tell the whole story.

I dropped out of college in 1995 and moved across the county to put some gaming magazines online. This was when there were only five videogame sites on the entire World Wide Web. In the following 25 years, I started numerous companies that you may have heard of, including IGN, MyBlogLog and Gnip.

More importantly, I started a bunch of companies you never heard of, because they were stupid and I should never have launched them. That is where I learned the most about startups, in the “oh god, oh god, please don’t do that because I’ve tried it four times and it never works.”

EXPERIENCE

Companies I’ve started have exited for nearly a billion dollars of value (one IPO, two meaningful exits, one turnaround). That said, most of my value comes from my many failed projects. I can’t tell you why my successes happened (so much of that is built on other people’s efforts and straight-up luck), but I can tell you what killed all of my failures.

I am not smarter than you, I just have more battle scars and more experiences to pattern match against. Basically, I’m you from the future.

SUCCESSES

IGN

I dropped out of college in 1995 to come up with a web strategy for publisher Imagine Media. Launched IGN, the web’s first videogame news network, a year later. IGN grew to a Top 50 web site, went public in 2000 and eventually sold to News Corp for $650M.

Gnip

Founding CEO of big data provider Gnip. Initially founded on the belief that social APIs were going to take over the web. Raised capital with a 12-page Powerpoint deck and a dream. Sold to Twitter for $150M. Straight up, smarter people than I made that acquisition happen.

MyBlogLog

Co-founding product guy. We started out as a blog stats company and pivoted into a distributed social media company at the suggestion of a random dude who cold-emailed us (we hired him as our CEO). Sold to Yahoo for $12M without ever taking funding.

Beatport

Provided strategic consulting on an e-commerce turnaround. Simply asked “hey, what are you doing with these 40 million fans who visit every year? Let’s tell a story about them.” Went from an $8M acquisition offer to $52M acquisition in 14 months.

FAILURES (abbreviated)

OneTrueFan

Co-founding Co-CEO. Tried to recapture the zeitgeist of MyBlogLog while failing to recognize that blogging had ceded the market to microblogging platforms. Also spent way too much time on a strategic partnership that failed to materialize. Lost $1.2M of investor money.

Zentact

My white whale. I still think this thing should exist, a software consiglieri that reads the news and helps you strengthen your network by suggesting opportunities to reach out to people you haven’t connected with in a while. As co-founder, I assembled the team and raised capital and lost $250k of investor money.

Minerva Software

Founding CEO of a videogame-based training platform back when “Serious Games” were a thing. Landed a multi-million dollar contract with Best Buy and was unable to raise capital because I could never land a second customer. Beware outliers. Put a second mortgage on my house to finance the company.

BuzzSite

Launched an entertainment aggregator in 2000 because 1) IGN had moved away from the network play and 2) I was pissed that I wasn’t given an executive role in IGN’s spin-out. Effectively my rebound/revenge girlfriend. You know how well those work out.

Atlas Consulting

Tried to launch a digital media agency back in 1994, selling to radio stations and publishing companies. We could have been Razorfish or Agency.com. Crowning moment was when I landed my first meeting and brought my desktop PC to their office to run a demo.

Additional Experience & Projects

Startup Coach

Yeah, what I’m doing now. I’ve worked with more than a hundred startup CEOs, learning from their experiences and helping them create world-changing businesses. This has given me X-ray vision :)

Thunderview CEO Dinners

I throw a monthly dinner specifically for Colorado-based startups CEOs who are looking for a community of other folk going through the same crazy journey. Check it out here.

Techstars Mentor

I was a mentor with the Techstars accelerator starting with their very first cohort in Boulder in 2007. Over the years I’ve work with many, many Techstars companies in Boulder, Denver, New York, Philadelphia and Seattle.

Cloudspace

I co-owned a software development shop for four years and worked with dozens of companies, from startups to tech darlings like SoundCloud to Fortune 50 companies like AIG. It doesn’t matter what size the company, people make the same mistakes.

Investment and Advising

Very occasionally I invest in a company. Slightly less occasionally I accept stock options for advising. I was the first advisor to Zynga. That was neat.