Optimize Relationships, Not Transactions

What I learned from Robert Kraft.

Published in
5 min readOct 12, 2016

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Robert Kraft is one of my personal heroes. For a Rhode Island kid growing up in the shadow of the perennially pathetic New England Patriots, he’s the savior that showed up, cleaned house, built a world-class organization, and delivered the greatest franchise the sport has ever known. With character and faith, he and his family persevered in the face of withering townie cynicism, achieving on- and off-field triumphs no self-respecting Masshole could have dreamt of back in 1988. And he did it all with style and grace, a firm hand and a human touch; a husband, father, and citizen that set an example for us all.

In 2007 I had the opportunity to work closely with Robert and Jonathan Kraft on a startup called Matchmine. The project was ill-fated for reasons worthy of another blog post, but it gave me a chance to get to know these men on a personal basis. It was something I couldn’t pass up.

Good business is personal.

Early in our relationship, at Robert’s tidy and tasteful home in Chestnut Hill, we hunkered down in his study one night to get to know each other. We moved quickly past the pleasantries, talking about business and life, just a couple of football fans who played some Ivy League ball back in the day, wiser and wider after some mellowing in the real world. We talked about family and faith — the only things more important to him than football — about the common threads of Italian and Jewish culture (“Mediterraneans,” he called us…), and the demands and joys of fatherhood. It was wonderful, and after a while I began to relax and he began to accept me into the tribe.

“There’s something I’d like to ask you,” I said, after working up the courage.

“Shoot,” he said.

“I’ve had some success, Robert, and known many people who were successful. But I’ve only known a few folks as successful as you. Now we’re sitting here, just a couple old lineman, shooting the shit about Gino Cappelletti. It’s great, but I guess I just expected you to be… different. As a kid from the burbs, there’s something I always wondered about people who were able to succeed at your level.”

“OK. What?”

“Well… we both come from families and traditions that value relationships, and it’s obvious we both look at business through that lens. I guess what I’m wondering as we sit here is whether that philosophy holds up at your level? I mean… if you want to be a Billionaire, if you really want to reach the top… do you have to come to terms with the need to be — well — a dick sometimes?”

He looked away for just a moment, reflecting on the question. “I hope not,” he said, turning back to me.

“People are people,” he continued, “and the same dynamics are at play at any level of business. It’s hard sometimes, you have to make hard choices to win. But I don’t think you need to be a dick. Doing right by people is a good strategy because, in the long run, good business is personal.”

“But you have to play hardball sometimes,” I pressed, “Right? I know you’ve found yourselves in situations where your personal loyalties were in conflict with what the team needed to do. Look at the situation with Drew (Bledsoe.) Cutting him must have been hard, even though going with Tom (Brady) set up all the success that followed.”

Relationships last, among people who value them.

“That’s true,” he said, “but I don’t think I was a dick about it. I felt a personal debt to Drew, who was a great guy and had been the face of our organization for many years. When it was time for him to move on, we worked to do the right thing for him. In the end we traded him to a big AFC rival, which was clearly not in the interests of our team. But we knew it was the right thing for Drew, and that’s why we made that deal happen.”

“I guess there are relationship people, and there are transaction people,” he said, digging deeper into his own thoughts. “In business you need to deal with both, but I’ve always tried to be a relationship person. I don’t know if that’s always the better way. You leave something on the table sometimes. But things are going pretty good so far, so I’m sticking with it.”

Not a family. But a team.

A year or so later, as the credit crunch took hold of the economy in 2008, we shut that business down. We did it despite having achieved all the milestones we set for ourselves at the beginning, and I’d be lying if I said it didn’t upset me at the time. It was one of the hardest things I’ve ever had to do, but it helped to have Robert and Jonathan’s personal support throughout.

We did what we could to take care of people, to help get them into jobs elsewhere and move on. I’m proud of the way that team came together, actually, networking and supporting each other in the search for new opportunities. We met socially, created a group thread to share who was hiring, and kept in touch as each person, inevitably, landed successfully someplace new. Many went on to great success at other companies, and remain friends to this day.

As Netflix put it so beautifully a while back, a business is not a family, in the end, but a team. A pro team, in fact, but a team that can look out for each other even when the game is over.

Take care of your teammates.

Companies come and go in our business, and to lead one you need to come to terms with hard choices that will effect the lives of people you care about. The solution isn’t not to care, though, it’s to reconcile what is necessary for the business with what is right for the people, and to apply yourself equally in service to both.

That’s how it works in the pros. According to one of the best ever, that’s what it takes to get to the top.

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Mike Troiano
The Startup

Storyteller. Consiglieri. Lyrical gangsta. Partner, G20 Ventures, thoughts here are my own. https://nf.td/miketrap