For the fourth time in an hour, my car was stuck in the snow on a February morning in 2006. My usual 11-minute door-to-door commute from Lexington to Waltham, Mass., was going on an hour-plus. One of the people pushing my car into a spot was a product manager from a big media company whom I had met all of six minutes before. He had leapt from his car, which he had just parked, when he saw me spinning my tires helplessly. Even though he had driven from somewhere in Connecticut that morning in a blinding snowstorm, he was on time for our 9:30 a.m. meeting, while I, despite my short commute, was late.
“So how did you manage to get here?” I inquired.
“I saw the forecast and left at 5 a.m. I knew it would be a slow go, and it was. Took me just over four hours to drive what usually takes two, but I made it.”
“Great,” I said, taking the measure of him. “Why didn’t you postpone?” I asked
“I couldn’t, and I was awake anyway.”
“Oh,” I replied. “Great, let’s talk about your idea.”
John had been recommended to me a week earlier by Sam, a mutual friend. I had recently helped Sam exit his sports tech company at a great return, and John had called him to hear the story of the deal. Now John had a big idea and wanted help in bringing his idea to fruition. A recommendation from Sam was meaningful to me, so I was happy to meet.
“I want to build sports talk radio for the Internet,” John started. “I want a place that can find the most relevant sports information instantly and provide a forum for people to interact with that info and each other.”
“And how is it different from Google or an online chat room?” I inquired.
“Well, it combines everything in one place, and it limits the information scrape to high-quality, trusted sites,” John explained. “Today, if you want to know if Tom Brady’s ankle is healed enough to start him in your fantasy lineup, you Google his name and up pop 10 pages on Gisele’s latest fashions, game tickets, Tom Brady t-shirts and bobbleheads—useless stuff. I just want to know if he is healthy enough to play, and I need to know now, because we are late for church and my wife is yelling at me to help the kids get ready to get out the door. I need the latest info from the best sources that cover football up to the minute.”
I was intrigued by the idea—and by the fact that this guy fought through a blinding snowstorm for four hours to come see me.
We talked for another hour, and I could sense his smarts about the space and his vision about the consumer experience. I also got a growing sense that this guy was determined. I asked him why he wanted to leave his very prestigious, comfortable job for this risky endeavor when there was a 90 percent chance of failure, and I asked him how much he was currently making.
Answering that he makes just under $250k, he said, “I like my job, but I feel constrained, and I feel that this idea has huge potential.”
I looked at his projections and noted that he was going to pay himself $100k. Before I could ask him about this, his phone rang. It was his wife. He told her that he would be home to shovel the driveway and get his daughter to dress rehearsal that evening.
“How old is your daughter?” I asked.
He laughed. “Which one?”
“How many do you have?”
“Four, and a boy, with one more on the way.”
My jaw dropped.
“Wait, wait. You have five kids and another one on the way, and you’re leaving a $250k job to reduce your salary to $100k to build a startup?”
“Yes, if you help me find the money,” he responded.
I paused for 10 seconds, dumbfounded, and replied: “I’m in.”
I usually mull pitches over for days and weeks, but the four-hour storm drive and the fact that he had enough kids to field an entire hockey line with a goalie on the way and was still up for the huge salary reduction led me to one conclusion: John was a “boat burner.”
We have a saying in our office: “Burn the boats.” It’s shorthand for a mentality. When building a startup or completing any task, it is critical to “go to the island and burn the boats.” You and your team are staying until the job is done. No hedging, no contingency plan. No one is leaving the island. This guy was a bona fide boat burner.
I have worked with numerous boat burners and consider them my most trusted friends. Boat burners win. Gandhi was a boat burner. Muhammad Ali was a boat burner. Steve Jobs was a boat burner. No matter what challenges they faced, they stuck it out on the island and found a way. I have also worked with pretenders, those who spoke of boat burning but only did so when it was easy for them. They ensured that their interests were always placed above the team’s sworn pact. I no longer work with them.
John went on to build his 10-person startup in a true boat-burning manner until he sold it just over a year later for $25 million after an initial post-money funding valuation $4.5 million—a 5.5-time return for investors in 12 months. That $150k reduction in salary was a bet on himself that turned out to be a good one—he made $10 million in 12 months.
He was awake that snowy morning because he was up feeding his 1-year-old at 4:30 a.m. He could not postpone because his calendar was filled up with his children’s commitments and work for the next 45 days. He put himself in a spot where he had no choice but to succeed, and he was smart enough, skilled enough and determined enough to do it.
He was 100 percent sure that he would find a team of fellow boat burners. He was 100 percent sure that he would be fulfilled by his work. He was 100 percent sure that he had to feed his family. He was 100 percent sure that he was burning the boats.
Looking back years later, I am 100 percent sure of one thing—I will do everything in my power to continue to fill my teams with boat burners.
