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Boardroom Q&A With Mike Tannenbaum, NFL Front Office Insider

“Be the first one in and the last to leave,” the former Jets GM tells Boardroom. “Meet and exceed your boss’s expectations and create value. You’ll be indispensable.”

Few could match Mike Tannenbaum’s wealth of expertise on the business of the NFL for one big reason: It comes from all angles.

The man who would become New York Jets general manager and Miami Dolphins vice president knew he wanted a career in sports, so he worked day and night to make it happen. Eventually, his sweat equity earned him personnel positions with the Saints and Browns before leading front offices with Gang Green and the Fins.

Today, Tannenbaum’s been outside the NFL for almost four years, but he’s perhaps got more on his plate than ever before. He’s become an ESPN front office insider, a professor at Columbia University, an advisor at Bruin Sports Capital and Patricof Co, and founder of a new media venture, The 33rd Team.

He found time to discuss it all with Boardroom — including his Super Bowl LVI prediction. The following is our Zoom conversation with Mike Tannenbaum lightly edited for length and clarity.

RANDALL WILLIAMS: You started your sports career at the Pittsfield Mets, who are now called Tri-City Valley Cats. Talk to me about your first experience with a professional sports team.

MIKE TANNENBAUM: I graduated from UMass in 1991 with a degree in accounting and I absolutely hated it. So one of the very few connections I had in life was a fraternity brother of mine whose father worked at the Pittsfield, Massachusetts post office. I was able to convince the Pittsfield Mets to let me work for free and I worked there during the day.

My parents paid for college and they said, ‘hey, look, we’re going to pay for college but… if you want to pursue this crazy dream of working in sports, you’re on your own.’ So I’m stubborn and I told my parents, ‘no problem.” And I worked for the Mets during the day, and from 11:00 at night until 7:00 in the morning, I sorted mail.

RW: So then you eventually jumped to working for the Browns and the Saints. Talk to me about those experiences that really got you into football?

MT: When I graduated from law school, I sent out 60 binders to every team in the league about how I would build the team under the salary cap, which had just started. I got 59 rejection letters and Coach [Bill] Belichick hired me in Cleveland, and it was incredible. My job was to basically drive people to the airport and research contracts.

RW: The NFL’s brand is bigger than it’s ever been — the league just signed a $110 billion media deal. For newcomers who want to work for a team or the league, what advice do you have for them?

MT: A couple fundamental things: Be the first one in and the last to leave. Meet and exceed your boss’s expectations and create value. You’ll be indispensable.

For example, understand what’s the pain point of your boss. What’s something that keeps them up at night? What’s one thing that they’d like to read, or maybe two podcasts that they’d like to hear? Make sure that you’re creating value, so when they’re looking at things and saying, “hey, we can only keep one intern,” you’re the man or woman that they absolutely have to keep.

When people walk into a room they either add or create energy — or they are what we call “energy vampires.” Make sure you’re adding energy.

RW: You spent a pretty long time in the NFL. How would you describe your experience?

MT: Winning is really like the relief of agony. One of the things that was really hard in my career was that the expectations were so high. For a lot of points in my career, we had so much success that if we had a good year but didn’t get to the Super Bowl, it was considered a disappointment.

I think for me what’s been the most fulfilling thing is the relationships. Just being inspired by so many people like Curtis Martin, Laveranues Coles, Laremy Tunsil, guys that came from challenging backgrounds and had any excuse to fail, but exceeded expectations and created generational wealth. It just brought out the best in me. 

RW: What do you miss about being involved in football every day?

MT: I’d still say the relationships. Coming back after a loss on a  Sunday night at 3:00 in the morning, falling asleep on the plane, and then getting into your car. Just looking at all the people who got off the plane that have the same jersey you do and knowing that we just have to be a little bit better or smarter this week. It’s us against the world and nobody else believes in us.

It’s just like those moments of camaraderie that’s really hard to replicate, and I’ve had a lot of fulfilling experiences and I get to do a lot of different things that are engaging and very rewarding, but those moments of camaraderie are the ones I miss. 

RW: Let’s talk ESPN — what were your motivations for joining ‘the Worldwide Leader?

MT: Bill Polian, a Hall of Fame general manager, retired. The timing worked out perfectly. And with anything I get in life, I feel like I want to meet or exceed expectations.

Bill set an incredibly high bar and he’s been a guy that’s been a mentor to me and someone I greatly admire, and when they gave me the opportunity to replace him, it was an unbelievable opportunity. If my wife [were] on this Zoom, she would say the only thing I’m capable of is asking others to get work done (which unfortunately is probably true at this point in my career).

I was able to get two incredible interns from UMass that helped me become a better broadcaster, and I hired a broadcast coach. I wanted to be the best broadcaster I could possibly be and take what Bill Polian did, crush it, add to it, and drive that bar even higher to make sure that ESPN knew they made a great decision when they hired me. 

RW: It’s always interesting to watch former players and front office execs discuss the NFL as media members, because at one point, you were the ones being covered. How does your experience dealing with the New York media spotlight affect the way you speak about the league now?

MT: I always feel like I need to have justification for my view. Right now, I’m not very popular in Pittsburgh — I think they are going to have a losing season. I think Mike Tomlin is a great coach, and even though he’s never had a losing season, I think they are going to be bad this year and worse next year. But I can talk about how they lost three offensive linemen and I know how hard it is to replace offensive linemen. I can talk about how they have a 39-year-old quarterback who is speed deficient.

I’ve had older quarterbacks on my teams like Jay Cutler, Vinny Testeverde, and Brett Favre. I know what they were like at the end of their career. I feel like if I’m going to criticize a person, a player, a transaction, or whatever it may be, it better be well thought out and have foundation.

RW: Are you more sensitive to what you say and how you say it because you’ve seen how it can affect players, teams, and organizations?

MT: Absolutely. I have a level of professionalism up there. There’s a standard; I just can’t be like, “Pittsburgh sucks!”

I try to put a lot of time into explaining why I think the things that I do. It’s a little bit about having the privilege of running a team and negotiating on behalf of the team, which is I can make you an offer, you can disagree, and that’s fine. It’s a part of the process of a negotiation. But I have to be able to look you in the eye and say, ‘hey, we think this compensation is appropriate for these three reasons.’ Now you can disagree, but there’s a reason we are offering you this. 

RW: On HBO and Uninterrupted’s The Shop, Tom Brady said 90% of what he says is not what he’s actually thinking. What percentage is it for you?

MT: It started at 50-50, but it’s probably 70-30 or 80-20.

I think there are some things that aren’t constructive to the conversation. My role in the play is when the former players are like, “oh, just give him the money,” I’m like, “hey guys, there’s a salary cap. If we pay this player, here’s what we can’t do.’

I try not to get bogged down in the details because I don’t think that’s really constructive, but I try to give a little bit of a different point of view. ‘Look he may be a really good player, but the team’s resources are limited and we just can’t pay them all.’ We usually have a lot of fun talking about the contracts. 

RW: You joined Bruin Sports Capital earlier this year. How did that come about?

MT: I got to know [founder and CEO] George Pyne through a gentleman named Stan Kasten, who is president of the Dodgers. I admired George from afar for a number of years. If there was a hall of fame in sports business and sports marketing, he is an inaugural member.

I think the part that has been so special is I get to contribute ideas and some leads on deals. But just to be around George and to be able to sit in on some meetings — he is more kind than he is smart, and he’s really smart. It’s inspiring to see someone who’s so successful and such a thought leader that is unbelievably kind and committed to his family. I have to tell you that 100% of our conversations, not 99%, he’s giving me a recap on what his children are doing. He won’t let me talk about business until I give him a detailed update on what’s going on with my kids. 

RW: Your official role is senior advisor. What are you most hoping to help Bruin accomplish?

MT: I want to exceed expectations. We’ve just talked about what a meaningful advisory role is; I sit at the cross-section of some interesting deal flow and having a really good understanding of technology and how it can enhance performance. And with everything going on in the world with gambling, fantasy, and the NFL, it kind of ties everything together.

RW: You also started a website geared toward front office/insider content called The 33rd Team. What’s the story there?

MT: When I was fortunate enough to become the GM of the Jets, my family and I started a foundation at the University of Massachusetts where we provided scholarships for people that wanted to work in sports but couldn’t afford to. Instead of them taking a job as a waiter or waitress or bartender, we gave them living wages so they could go work for free.

But we’re building the plane after we have taken off; there’s this massive void in the marketplace of really good coaches who are in between opportunities. A great example of that is Dan Quinn — he gets let go in Atlanta, he wants to stay current and research new ideas, so he comes to us for six months, we pair him with world class graduate students such as math majors, physics majors, and people that love football. And they do meaningful research for him and we put it all out for free.

Our website is free. We have over 50,000 people subscribed to our newsletter, and through that process, we’ve put eight students in the NFL. That is unbelievable validation for what we’re doing. For the coaches, they’re getting this sort of research department where we can talk about things like clock management, roster management, contracts, injuries, health, and safety, officiating, and more.

We have a weekly call every Wednesday from 5:00 to 6:00 that’s totally open to people. Our standard is when we are done in that hour, we have to get a little bit smarter from when we started.

RW: And you’re now a professor at Columbia as well.

MT: I am. I’ll be going into my sophomore year this year. I was a rookie last year, but Columbia has a masters in sports management program and they asked me to start teaching a course on the business of the NFL a year ago. We have a great curriculum. We go a mile wide and an inch deep.

RW: “The business of the NFL” sounds vast. What types of assignments are you giving out? What do you do if someone wants to give a sixth-round receiver $90 million?

MT: Last year with everything going on with all the social injustice causes, the pandemic, gambling, we packed it all into the curriculum. But $90 million to a sixth-round receiver is unacceptable!

RW: Would you like to see more courses like this? Countless young people want to work in football, but most don’t know how to get a foot in the door.

MT: You have to make sure you have a really good path. Maybe it’s a masters in sports business. Maybe it’s a masters in business administration or a simple MBA. I think these programs sort of help students clarify what they want to do, and I always say go in with a plan because grad school takes a lot of resources with time and money.

RW: Now that the NFL is back, I gotta have your Super Bowl prediction.

MT: It’s going to be unbelievably plain and vanilla, but I have Tom Brady and the Buccaneers.

I’ll give you one sleeper team: I think the Chargers are going to make a lot of noise this year. I don’t know if they’re going to win the Super Bowl, but we’re going to be talking about a great young coach in Brandon Staley and a great young quarterback in Justin Herbert for years to come.

RW: Who will “Tompa Bay” match up against?

MT: The Chiefs are going to beat the Chargers in the AFC championship game and the Buccaneers will beat the Chiefs once again.