Advisors are as valuable as you make them out to be. The answer to whether you should remain CEO as a young entrepreneur is part psychology, part experience.
We had a good 2020. I emailed my list of formal and informal advisors to relay the high level results. One of them replied with a nice note, which let me down memory lane:
Great news on [the results]: a lot of hard work and smart decisions to get to this point and to let WatchMojo grow into its next phase. On a personal note, you have been great to work with, an inspirational leader, true to your word every step of the way and built an impressive business and culture. Not many people can check all those boxes. For me it has been a great privilege to get to know and work with you! Thank you for the opportunity.
That’s Ted Prince, former AOL exec and president of NatGeo from 2006-12. He’s now president at Neustar. How I got to know Ted in 2011 isn’t dissimilar to how many young entrepreneurs meet more seasoned veterans: an investor was looking to invest and have him take my job (in essence).
From the 10-Year Overnight Success:
"I was reading Business Insider when I came across an article by Bo Peabody in which he examined why VCs tended to shy away from backing content companies. Peabody was the founder of the dot-com era’s Tripod and had made a ton of money before going off the grid to party. He was now back as a VC at New York-based Village Ventures.
Peabody was trying to recruit National Geographic's former CEO Ted Prince. A Yale graduate, Prince had worked at Aol. before National Geographic. To his credit, Peabody asked me openly how I felt about bringing on Prince as a possible CEO if he were to invest.
When a VC asks a founder about the CEO role, it’s more psychology than actual negotiation. I think that if a founder insists on retaining the CEO role, the VC may view it as a turn off. Alternatively, if a founder is too eager to relinquish the role, then the VC may insist that without the founder in the CEO role, they’d balk. So I was open to any scenario, stressing my desire to run WatchMojo for the foreseeable future, but willing to do anything reasonable that would benefit the company and its stakeholders.
I’d explained that I was open to it for the right candidate, but for Prince to come in and run WatchMojo, it would be like taking the pilot of a Boeing 767 and suddenly asking them to operate a Cessna. I was being modest and even gracious to some extent, since at the time WatchMojo had more operational heft (in terms of production and distribution) than most of our peers, but financially it was a bit light.
I sincerely felt that if we were to do something like that, we’d ought to set up Prince (or anyone else) to succeed, meaning they should come on in one role for three, six, or even twelve months, after which point I’d hand off the baton, moving to some kind of (strategy or business development) role. I really didn’t have any objections because I’d run WatchMojo for over five years and felt that if someone was willing to invest and another person was willing to come in and run it, everyone should do what was best for the company, starting with me. But we never struck a deal.
Prince and I developed a great rapport over the years, and I even retained him as an advisor in 2011."
In 2011 we’d just completed our sixth year of operations in the red, with aggregate losses reaching $900,000. Between that reality and my Nature and Nurture, Bo could’ve asked me if I’d be open to Bozo the clown running day-today affairs, and I may have said “sure, I hear he’s amazing at Powerpoint.”
Like most advisors, Prince wasn’t necessarily super hands-on and involved at all times. We spent a good amount of time early on thinking of where to take the business, and he was very helpful introducing me to the Washington DC media world. By 2013, when WatchMojo embraced YouTube took off like a rocketship, I was admittedly focused more on internal operations and navigating day-to-day on a platform that was figuring out the balance with regards to the DMCA and Fair Use. But, when I needed advice he was there.
Most importantly, back in 2012, he helped me conclude that my understanding and interpretation of Fair Use wasn’t off. It wasn’t so much that Prince was a fair use guru (I had others to turn to for that), I thought he had a unique background and perch to “stress test” my thesis. A Yale law grad, I first asked his thoughts on how I was interpreting and defending the relationship and dynamics between Fair Use’s four tests:
Then, given his tenure at Aol (an ad-supported publisher) I asked about the risk appetite big platforms and publishers had with any risk, let alone copyright, and the indemnifications required to build a business around said risk. Finally, and critically, wearing the president of NatGeo hat, how would he feel, for example, if he saw one of our fair use clips excerpting NatGeo intellectual property without a license. Would he be upset? Angry? Would he sue? Would his counsel want to use? Would he hold back counsel or vice-versa? That was the arithmetic that would dictate the viability of the business plan I’d envisioned. Trivial as it seems today, at the time, I knew the law was on our side, I needed to “stress-test” my hypothesis and hunch.
After all, when we launched in 2006, we covered a wide array of verticals before making our four big bets, one of which was Fair Use. In 2012, Prince wanted to lean on his past experiences at NatGeo and push WatchMojo down towards such factual editorial; which were two of many categories we covered. Of course, I’d spotted another macro-trend: that geek culture would overtake pop culture, so instead of history and science, we pushed towards entertainment. I’m not sure if WatchMojo would be as big as it is today had we not. It’s worth noting that the investor Peabody hated YouTube as a platform, whereas I was adamant it was going to take over the whole world. Peabody did fine with his thesis, mine with mine.
The lesson: people will walk into your life for a myriad of reasons. I would have had every right to be turned off when an investor suggested Prince be CEO. But I had an open mind, and in the end, it all worked out.