Seeing Vice Media need to scale back their expansion by reducing headcount by 15% and Defy Media shut down serve as cautionary tales. I will leave the lessons for another day, but here are two excerpts from my third book The 10-Year Overnight Success that cover my dalliances with both, when WatchMojo was essentially a money-losing, insolvent “going concern.”

re: Vice Media, which touch on some of the issues that now haunt them today:

“For such an anti-establishment venture, Vice has more than its share of corporate investors. Today those investors include Disney, A&E, and News Corp. to name a few. But at the time, in 2011, the main corporate backer was WPP. I’d met a gentleman named Bill Lederer years before at some New York shindig, he worked for WPP’s Kantar Media and sat on WPP Digital’s board. The following is only a guess, but I presume that WPP was nervous about its investment in Vice (which had had a reputation for being the bad boy of the media world) and he’d encouraged Smith to invest or acquire WatchMojo, so that we might help their online video efforts.”

re: Defy Media, then known as Alloy Media:

“By spring of 2011, Alloy’s Christian Busch boomeranged back and inquired about a possible deal. If you recall back in 2009, I’d reduced my asking price of $10 million to $6 million, but that went nowhere. This time, we’d reached a tentative deal that called for $2 million in Alloy stock and $1 million in cash. At the last second, Busch advised me that Alloy’s CEO Matt Diamond was taking the cash component off the table. I was disappointed, because I’d owned Alloy shares and really admired Diamond as an executive; he reminded me of a young Kirk Kerkorian, the legendary investor who bought and sold MGM three times, because it seemed like Diamond had launched, sold, and taken private Alloy repeatedly over the course of a decade.

Their explanation was that since a chunk of the debt on the books was owed to me personally, he didn’t feel compelled to include any cash in the deal. Since I’d taken out credit lines and mortgages in my name, I would want those paid off in any change of control deal. The $1 million in cash would net me about $500,000 pre-tax, which was the least I’d accept in a deal. The $2 million in Alloy stock would be too speculative to rely on and with no cash, I’d have to use my salary to pay off the interest and principal on the personal debts that had been used to finance the company. It made no sense to me. When Diamond wouldn’t budge, I balked. It’s a shame, as I really liked Busch and respected Diamond quite a bit. Had that deal been consummated, we’d likely be one of (if not the) biggest asset they’d own, with Smosh having set their sights on Hollywood and sparingly publishing on YouTube.

Sometimes the best deals are the ones you don’t make.”