LUCKY OR SMART? Ordinary People Would Be Nuts To Work At Startups

Bo Peabody

Below is the 5th chapter of entrepreneur and VC Bo Peabody’s book, LUCKY OR SMART: Secrets For An Entrepreneurial Life.

Before you read this chapter, you might want to read a quick overview of Bo’s experience of founding his first company, Tripod: How To Start A Company In Your Dorm Room And Make $580 Million.

You might also want to read the Introduction, Chapter 1, Chapter 2, Chapter 3 and Chapter 4.

Chapter 5

so-cio-path (noun): a person who is unwilling to behave in a way that is acceptable to society.

The first person I hired at Tripod was a complete sociopath. He avoided all social gatherings. He claimed to have played a key role in the actual creation of the Internet. He stole a framed picture from the desk of a colleague because he did not like the way he looked in it. He ultimately snookered me out of $60,000 of Tripod’s capital we only had $87,000 at the  time), declared personal bankruptcy, and has managed since then, until this very day 10 years later, to avoid even bumping into me in a town of six thousand people.

And I really like this guy.

Ordinary people don’t agree to work for start-ups. They go get ordinary jobs. So, as an entrepreneur, you’d better like odd people, because that’s who is going to agree to work with you. This is particularly true  in  the  restaurant  business. If  you  think computer  programmers  are lawless, long-haired, multi-pierced, tattooed  hooligans, try hanging out with a crew of cooks for a night. At restaurants and technology companies, the drug-testing policy is: Bring your drugs in on Friday and we’ll test them over the weekend.

In order to like odd people, you need not be odd yourself. I’m not. In fact, assuming you genuinely like odd people, the more ordinary you are, the more odd people will like you. It is an absolute sociological truth that odd people and ordinary people get a co-dependent kick out of being needed and liked by each other. But you can’t fake it. If you’re faking it, the odd people will know. They are smarter than you. Ordinary people get B’s. Odd people get A’s.

My all-time favourite odd person is Ethan Zuckerman, the leader of the first team of crazy programmers I hired and the individual most responsible for Tripod’s success. When I first met Ethan, he was a radical leftist graduate student living in an upstate New York town of conservative farmers. Ethan was trying to complete what would have been the first master’s in multimedia art ever awarded. I convinced him to come work at Tripod instead. Ethan is a six-foot-three, 275-pound black belt who always wears karate pants, hardly ever wears shoes, drinks two litres of Diet Pepsi a day, and is the drum master of a small tribe in central Ghana. A veritable God of Odd. Ethan was my utility player, my most trusted executive, and to this day is a very good friend.

After many long discussions, Ethan, Dick Sabot, and I decided that if Tripod was going to be a high-powered media company, it needed a high-powered editor. Enter Brian Hecht, one more in my great soaring circus of sociopaths.

Pat Sajak buys A’s from Brian. He is a fascinating character: frighteningly smart, neurotic, mercurial, and sidesplittingly funny. Brian and I drank together all the time, went to parties together in New york City’s Silicon Alley, and shared coaching duties for an elementary school soccer team in Williamstown. Brian was a trusted colleague, and we became good friends. Ethan, however, was sceptical, his finely tuned “oddar” having picked up trouble in the ranks.

Brian had been the editor of The Harvard Crimson and was, until he came to Tripod, working at ABC News in New york. Brian is a high-strung city kid. He talks a mile a minute, copyedits birthday cards he receives from friends, and has several life-threatening allergies. In the big city, he fit right in. But when someone with this particular cocktail of neuroses works fifteen-hour days in a small, traditional, isolated town in the mountains of northwestern Massachusetts, chaos is bound to ensue.

My most gruelling test as an ordinary, odd-people-loving entrepreneur arrived with the clash of Brian and Ethan. It was a Tuesday at four in the morning, and I was asleep in my rarely visited bed. Nate Kurz was, on the other hand, wide-awake, programming at the office. While he worked at Tripod, Nate—number three on my all-time “Odd Guys I Love” list—lived out of a 1983 Aries K car, kept a “vacation” home in a depressed, old South Dakota farming town of two hundred people, and did not cash paychecks for years at a time. While making some routine updates, Nate tried to visit a story that he had posted a few months earlier on the main portion of the Tripod site, which was reserved for edited content rather  than  our  members’ unedited personal homepages. The story was an intimate account of how World War II had affected Nate’s family. Brian, being the A-student editor that I was paying him to be, had removed Nate’s story from the site.

I walked six miles with Nate that morning, from four until sunrise,  talking him off the “Brian goes or I go” ledge. Nate and I ultimately agreed that everyone was wrong. He shouldn’t have put the story on the site without Brian’s approval, and Brian shouldn’t have removed it without speaking to Nate — or at least to me—especially given the nature of the piece. Whatever. I could finally go to bed.

By the time I arrived at the office, at eleven, I could already sense I was about to enter a shit storm. Ethan, having enjoyed the luxury of a full five hours of sleep, had arrived at 10, just before Nate’s bedtime. Ethan heard only Nate’s side of the story, peppered, I’m sure, with a few unrelated “Brian is evil” rants. Ethan and I discussed the situation. Three hours later, we came to the same conclusion that Nate and I had come to seven hours before.

Now it was two o’clock in the afternoon, my workday had not yet begun, and I knew that the Brian vs. Ethan clash was about to come to its inevitable head.

Sure enough, it did. For the next two months, Brian and Ethan were at each other’s throats. They argued about every conceivable issue (and many inconceivable ones), and their arguments slowly halted all of Tripod’s progress.

When the A-student odd people start to quarrel—I mean really fight—us ordinary B-student folk are in trouble. I needed both of these A-student sociopaths to make Tripod succeed; living without one of them was not an option. I had no choice but to pull out my most trusted odd-people-tricking trick. I was desperate. And I had built up enough trust with these guys that a little disingenuous  dramatics  wasn’t  going  to  discredit  me.  I  called  them  both into my office, and after a good fifteen-minute soliloquy about how their infighting was crushing Tripod’s unlimited potential to positively impact the lives of millions of people, I cried.

They never fought again.Ordinary people are repressed, and therefore cry less than odd people. So when ordinary people do in fact cry, odd people get  really  worried.  And  watching  a  six-foot-two,  two-hundred-pound, blond-haired, blue-eyed, khaki-shorts-and-J.Crew-golf-shirt-wearing entrepreneur cry brought these guys to their knees.

If you’re going to be an entrepreneur, be prepared to work with people who not only don’t follow the rutted path of the masses but openly shun it. After all, that’s why these people are willing to listen to you and your fundamentally innovative ideas in the first place. In working with odd people, you are in for some serious challenges. But you’re also in for some serious treats. These are the smartest, most interesting people on the planet, and the fact that they are willing to give your ordinary B-getting arse the time of day should flatter you. And, occasionally, bring you to tears.

Reprinted from Lucky or Smart? Secrets to an Entrepreneurial Life by Bo Peabody.