What I Learned Each Time My Startups Failed

In a 20-year career as an entrepreneur, I’ve been lucky enough to have a few wins, including two big exits within 12 months. But I’ve also had my share of startup failures, and I learned more with those than I did with the successes.

This isn’t going to be a bleed-all-over-the-page confessional. I’ve read those, and they’re great, if you’re into that sort of thing. Instead, I’d like to get pragmatic and tell you exactly why I think each startup failed and what I should have done differently.

Intrepid Media Grows and Grows and Then Doesn’t

When I talk about Intrepid Media, I don’t call it a failure. I call it a stagnation or even a success, but it wasn’t a success in the traditional sense. Looking back, now about 15 years removed from its peak, it was great experience, but I could have done it differently.

Intrepid started in 1999 as a website that hosted repurposed content back when traditional media companies saw the web as a home for alternative content. When these alt.stories ran their course, they’d be removed from the website. So I built a site to host my own orphaned stories and then started hosting for my friends as well.

Soon, a bunch of us stopped writing for traditional media companies and we started writing just for Intrepid Media. Then, I started letting anyone write for Intrepid, and I wrote a bunch of algorithms that bubbled up the best content — meaning the most well-written and highly-rated — to the top of the site.

Look, I was a coder, and I had never even worked for a media company, so a lot of what I was doing was counter to the strategy of most media companies. They were doing eyeballs and ads, I was doing quality and optional paid membership — a lot like Medium, but with a really clunky CMS.

Within four years, Intrepid Media would explode. We had tens of thousands of members, and they stuck. We had annual conventions in places like New York, DC, and Las Vegas. And a crucial component of that success was the Intrepid Boards, a sort of cross between what Reddit and Facebook are today, and they had millions of threads and posts.

Mistake: Lack of faith

Simply put, Intrepid Media failed because I adopted the Facebook model over the Medium model. I went for the lower-hanging fruit because I stopped believing my instincts were right, even though they had gotten me where I was.

As Intrepid grew, I could see an end to the growth, or at least to the ridiculous intensity of the growth. Blogs were appearing, Facebook was coming, Twitter was a thing. Quality content had become an afterthought.

So I made the decision that Facebook was going to be the new medium for content. Pun intended. I focused more on the Intrepid Boards and the networking aspects of the site, less on the quality measures around the content. I got more eyeballs. I threw ads everywhere. The money spiked, then cratered.

You can’t really blame me, can you? Medium wasn’t even an idea yet, let alone viable. But that’s what my model was and where it should have remained. I was about five years ahead of the curve, exactly where an entrepreneur wants to be. Had I remained faithful to the original mission of Intrepid Media, it’d be a Medium competitor today. Maybe.

Zoom Culture Takes On Traditional TV

In 2000, Zoom Culture was an independent video production company that had some crazy ideas about the Internet. I was brought on to build out those crazy ideas into ZC.TV, a website where anyone with a digital video camera could upload their work and we’d stream it.

Does that sound like YouTube? Because it freakin’ was.

The company ended up raising around $15 million on the promise of disrupting television, and the investors brought in former television executives to fill the C-Suite. The goal was to dig through the tons of video content on ZC.TV and stitch together enough of it to sell to the networks.

In 2002, this wasn’t just a risky idea, it was a crazy idea. Television networks wanted nothing to do with content that got its first run on the Internet.

In 2018, I give you the Emmy nominations.

Mistake: Lack of confidence

At the time, I was leading a faction of the company who was arguing that we didn’t need television networks. Mainstream access to proper digital video equipment was imminent, and in the meantime, we knew anecdotally that people were sinking thousands of dollars into top-of-the-line digital cameras just to be on our platform. Viewership was off the charts.

But our faction was young, we weren’t very convincing, and we were kind of punks about it. We lost the argument.

When the company ran out of money, I had already moved on, but I was asked to come back to make one last pitch to the investors to build a new company around the platform I had built. I said I would, but as young as I was, I didn’t want to lead it. An older employee stepped in to give the pitch. It failed. Months later, one of the investors told me we would have gotten the green light if I had agreed to run the show.

Two years later, almost to the day, YouTube was founded in San Mateo.

Teaching Startup Wants to Be Everything Startup

I founded Teaching Startup in 2015 as a research project. Having recently sold both Automated Insights and ExitEvent and realizing I was a terrible investor, I decided that I would try to give back by educating potential entrepreneurs in a way that wasn’t about TAMs and P&L.

Teaching Startup was a little like what I’m doing here on Medium, but the crown jewel, so to speak, was a weekly video show (I don’t want to use the term “vlog” because I’ll vomit) where I round-tabled a group of slightly off-kilter but definitely hands-on entrepreneurs to discuss everything from getting your first sale to the plague of sexual harassment.

Basically, we wanted to talk startup without talking startup, and bring startup to a more mainstream audience.

Then, taking a page from ExitEvent, I’d build a funnel of entrepreneurs, stocking it with a huge base of potential founders all the way down to serial exiters. I’d code in tools for them to communicate without it being overwhelming, and it’d be a University of Life approach to making more and better entrepreneurs.

Mistake: Lack of market

I did all the right things before I launched Teaching Startup. I talked to everyone from fellow entrepreneurs to YouTube stars and podcasters to educators.

I launched everything at once, and it did nothing. Well, not totally nothing, but not much more than nothing.

What happened here was that for as much as I tried to set Teaching Startup apart from everything else out there that was startup-related or startup-labeled, the market, the ecosystem, was so small and disjointed and localized that trying to stitch it together was going to take more money than it would make. Forever.

People who saw it loved it. It would have been a cult classic. But that’s not a startup. I knew that going in, but I was so in love with the mission that I ignored it until it slapped me in the face.

The thing about these failures is they ultimately brought about successes over time. The tech I built for Intrepid Media was the foundation for ExitEvent, which I sold a year after shuttering Intrepid. Zoom Culture taught me that if you’re going to disrupt an industry, you don’t need to do it from within the industry. And Teaching Startup taught me that if you’re going to run a passion project, you run it way differently than a startup.

These failures are all still painful when I look back, nostalgia does not heal all wounds. But if these are going to be my misses, I’m proud of them, and that’s something you should take out of every failure.