Tom Brady left the New England Patriots after 20 years and six championships. He didn’t leave under his terms and tension was bubbling under the surface.

His coach, Bill Belichick: “He looked at his options and he made his decision.”

His owner, Robert Kraft: “If he wanted to be here, we would have put a deal together.”

Tom Brady: “I made a decision to do something different.”

On October 3rd, 2021, Tom Brady faced his former organization with his new team, the Tampa Buccaneers. It was one of the highest viewed NFL games in recent memory because most people can relate to a breakup with a company.

In this episode:

  • Why companies won’t root for you to succeed when you leave them
  • How we are motivated to prove our old company should have done more to keep us
  • Your boss will likely use fear to convince you not to take that competitive offer
  • Yes, the grass CAN be much greener on the other side

Watch the episode here

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Do You Want To Stick It To Your Former Employer?

In this episode, we dive into how your company feels about you when you leave a company. Are they rooting for you? Are they rooting hard against you? Why is it so pleasing and such a motivator for anyone who’s ever left a company to try to stick it to that former company? Whether you’re with a competitor or doing something on your own, why it feels so good to have success after you’ve left? We dive into all of those reasons. We use the example of Tom Brady leaving the New England Patriots in this episode. If you are new, click that subscribe button. If you are one of our loyal readers, go to Apple Podcasts, give us a five-star review and write some nice comments so we know you wrote it.


Ian, you son of a bitch.

How’s it going?

I’ve been catapulted back into the Bronze Age. We’re all locked in the house. There’s nothing better to do with two children under three and a wife walking around with a COVID mask.

For all of our readers, Frank leads a very pampered life. He is in quarantine, which means no help is allowed in his house. You should see his house. It’s literally like Daddy Warbucks. He has staff walking around. There are Punjabs coming around, looking out for you. He got three people in the kitchen cooking. No one’s allowed in Frank’s house. It’s like the end of days. He’s on the last can of beans in a zombie apocalypse right now.

I got my two-year-old running around the house with his iPad, his digital babysitter. It’s great. He’s being raised by YouTube.

We are trying a different format where we’re going to slip in a short show once a week to go along with our long format on Mondays. One of the topics that Frank and I are excited to talk about now is Tom Brady, the key of the seven Super Bowl rings, is returning to New England to face the team that he played for many years before he left for Tampa Bay years ago. The dynamics of this situation are absolutely fascinating with how much seems to be at stake.

When you leave a company, one of the best things you can do is to not trashing anything and just take the high road. It doesn't ever serve you to be bitter grapes and destroy everybody in the company. Click To Tweet

Frank, it’s almost been since his 5th or 6th-year with the Patriots where the dialogue started around who’s the reason the Patriots win. Is it the star quarterback or the brilliant coach? I tend to think it was a little bit of both. Certainly, Brady is winning that argument because he left and proceeded to win a Super Bowl in his first year away from the Patriots. They sucked.

The Patriots were absolutely terrible. Tom Brady has done a lot of things right. He’s old and still a world-class athlete. If you watch us move, we creek and bitch about.

You’re always throwing me in. No, I am athletic. You’re the one creaking.

Ian believes he’s Tom Brady. The point of this is Tom Brady has taken care of himself. He’s done incredible things with his body. He has dedicated himself to his craft. Because he’s done these things, he’s had longevity well past what normal people have longevity. He’s given himself like most quarterbacks, Ben Roethlisberger is seven years younger than Brady, and he is falling apart. He looks like an old man. He’s throwing interceptions at 70-year-olds look like they would throw. He’s younger than Brady because he doesn’t take care of himself. The point is because Brady did all this other stuff and dedicated himself and he is a professional in a different way, he’s had an iteration that most people don’t get. He had a discretionary choice.

I have two young children. People ask me like what I want for my kids. I want them to have a discretionary choice. I want them to struggle and have to work for things. Discretionary choice means you get to pick something that is a good set of choices. He got to a place where he got to leave, be a free agent at 42 and pick the incredible place. He picked a place where retirees go that’s hot, which is better for older people, has no state income tax and is loaded with talent.

They’re aggressive. He went and won a Super Bowl at 43. The fun thing is the NFL is smart. They programmed a game where he gets to go to his old stadium and play in his old stadium against his old team. It’s must-see television. It’s going to be an awesome fucking game. It’s at 8:00 at night. It’s the game of the week. It’s going to be so fun because basically, you got two opposing factions who were very close that are now on opposite sides. What happens when you leave a company is your loyalties go away. People that were huge supporters of you stopping huge supporters of you. They’re now your competitors. They’re doing this and flipping you off. It’s rich with drama.

The reason why we’re talking about it on this show, we talk about careers, management, leadership, startups, all that stuff on this show, but the parallels to anybody leaving any company they’ve been with for a significant period of time are so incredible. You don’t have to make $30 million a year and be Tom Brady and famous for recognizing the dynamics between ownership, management, your coach, yourself and who gets the credit. Frank, who’s the last Super Bowl-winning quarterback for the Miami Dolphins, your favorite team?

It was Bob Griese and Earl Morrall, but it was Earl Morrall was Griese got hurt.

What year was that?

It’s ‘72.

LMSM 52 | Former Employer

Former Employer: Most times when you leave a company, people are going to create their own narrative, no matter what you say. You just have to get over that.


It would be Bobby Layne for the Detroit Lions in 1957. If a quarterback came along and won six Super Bowl championships for Miami after that drought, could you see any way that Miami would let him retire with any other company?

It’s hard to believe. They’re so incompetent in everything else, why would they have gotten that right?

Detroit hasn’t had a quarterback win in a playoff game since 1991. If you want a few playoff games, I can’t see you leaving our franchise, but the Patriots let him go. They didn’t make a big effort to keep them. At the time when Brady left, this was his quote. This is 2018. He was talking to Sports Illustrated. “I made a decision to do something different. It was a very thoughtful decision. It wasn’t spur of the moment. Since this moment I’ve got here, they’ve embraced me with the opportunity.” He’s talking about Tampa. “I spent twenty years in one place. I left on great terms and I have a lot of respect for everybody in that organization.”

He took the high road, which it’s worth stopping right there. As an employee, when you have been with a company a long time, you’ve built a certain cachet, a personal brand within the organization with hundreds of people within that company. I think one of the best things you can do is leave the way Brady did by not trashing anything.

Take the high road and say, “It was my time. I wanted to do something different.” It doesn’t ever serve you to destroy everybody in the company or to be bitter grapes. I’ve seen a lot of people leave with scorched earth. I rarely see the employee coming out looking positive when they do something like that. In my perspective here, Brady did it very well. He took the high road. What do you think?

He took the high road. It’s the smart move for him. I think that’s not how he feels. No fucking chance on Earth that’s how he feels. For Ian’s 40th birthday, we went up and saw Hamilton and we got good and smashed. We acted like bros that are in a frat. We would scream at the top of our lungs as much as humanly possible, but there’s a scene in Hamilton. It’s one of the songs. It’s called The Room Where It Happens.

The entire song talks about these outsiders who are not in the room where it happens. What Ian and I try and talk about in this show is management and conversation happen. People are thinking, talking and gossiping behind your back. If you don’t think it, leave the room. It happens to all of us, but what The Room Where It Happens is it shows that there’s the perception where things get done.

Brady went the high road here. He’s like, “It’s great. It’s all this thing.” He didn’t want to give the Patriots any bulletin board material, but there is absolutely no freaking doubt in my mind that Brady was pissed at the Patriots for letting him go, not surrounding him with talent. He wanted to do one of these to them and he did it. He could say what he wants publicly, but there’s no way that’s how he feels or what’s happening behind the scenes.

All of this started when they drafted Garoppolo, who is a young guy. They drafted him in the draft and started giving him a lot of reps in training camp and practice. It sent a message to Brady that Belichick thought that the success of the company was his and the organizational strength and not the quarterback. Belichick went as far as pushing Kraft to trade Brady at the time. This was a few years ago. That all came out in the wash and Kraft wouldn’t do it. Kraft went to Brady and worked a deal out for two years. I think it pissed Belichick off, who is the head coach. He is a very good coach in his way.

Everybody thinks they have great perspective, but most people don't. It's very hard to see anything past the end of your own posts, because you're the most important person in your story. Click To Tweet

Belichick’s quote, “He looked at his options and he made his decision. We weren’t as good an option as Tampa, so you’d have to ask Tom about that, but it wasn’t a question about not wanting him. That’s for sure.” Kraft, the owner said, “If he wanted to be here, we would have put a deal together.” The truth is somewhere in between, when you’ve been somewhere that long and you’ve had so much success, there’s a lot more there.

When Frank says, “It all comes out in the wash,” what tends to happen with these kinds of things as you take the high road, but the truth comes out through people around you. People that are your close confidence. You’ve shared things with me. It’s very funny, Frank, and I’m sure you’ve had the same thing happen. I heard ten reasons why I left GE. Some of them were months later where people go in and be like, “I heard you got into a fight.” I was like, “I swear to God, I never got in a fight.” You’d hear these stories that people try to fill in.

When you take the high road and say, “It was my time,” what people try to do is create a narrative. They guess, especially in sports because of Talk Radio. Here we are talking about it, so we can only assume but when you get to it, some of the close confidence come out. Joe Montana, Hall of Famer, a champion quarterback in the ‘80s, came out on someone’s radio show and said, “I spoke to Tom while we were back at a Super Bowl. I don’t think he was happy with the way things were progressing. He wasn’t having the input that he wanted. I think that was a big decision for him.”

He told me, “They’d ask my advice,” they being the Patriots. “I would tell them my advice and then they wouldn’t take it. I think he would have liked to have had more input. That’s probably why he went to Tampa.” Another person who came out and made news is Brady’s personal trainer, Alex Guerrero. He came out and said, “The interesting thing I think as an outsider was Bill’s emotions or feelings never evolved with age.” I think in time with Tom, as Tom got into his late 30s or early 40s, Bill was still trying to treat him like a twenty-year-old that he drafted. All the other players realized Tom was different.

You have Tom taking the high road. “It was time for me to go,” ownership, coach, taking the high road, “We wanted him to stay if he wanted to stay,” but then you have all these little side factions coming out about Belichick wanted Garoppolo. Tom wasn’t happy with the way he was treated. The truth came out in the middle somewhere. If you try to read between the lines, but most times when you leave a company, people are going to read between the lines and they’re going to create their own narrative, no matter what you say.

You have to get over that. There are going to be your haters. There are going to be people that hate management for letting you leave that are going to create narratives that are some true and some are not true. For me personally, I try to ignore all of them and not give a damn what the narrative is and let people do whatever they want.

Perspective is incredibly hard. Most people don’t have a very good perspective. Everybody thinks they have a great perspective, but most people don’t. It’s very hard to see anything past the end because you’re the most important person in your story. I can remember with lower stakes than what anybody in the NFL deals with. I would go back to events and interact with people from NVR when I was there.

They would all look down their nose at me and think as life ended. Life is over. I am significantly happier that I don’t work there. They’re fucking miserable in most instances and I still feel all the things that caused me any of both to quit and they’re living through it. They’re telling themselves this story of, “It can’t be better over there because if it was, I would leave and they haven’t left.” That’s their reality.

It isn’t true. Some people are destined to work at companies. That’s how they’re wired and how you’re built. That’s okay. Embrace it. Be cool with that. Take the ups and downs. You get a lot of things I don’t get by being an employee because you don’t have to deal with certain stresses, but no one’s going to understand what it feels like for you. What they’re going to do is if they feel self-conscious or they feel like, “Maybe he’s making a better decision than me,” that’s where this stuff comes from. They then get defensive like, “How could he live without me?”

LMSM 52 | Former Employer

Former Employer: Today, there’s just such a world of abundance to care so much about someone losing after they go. It’s very short-sighted.


You broke their narrative, Frank. They had told themselves a narrative about, “Grin and bear it, drive with it and make good money. This is what a career looks like.” You broke the narrative and it scared them. They wanted you to lose. This is worth asking this question. Do companies root for people who leave? When I say companies, I mean managers and employees. When they see someone break off into what looks like a better opportunity, do you think all of those folks are rooting for that person to have incredible success?

I’m going to answer that question with a quote from you from years ago. You and I were having a conversation. I’ve been gone for several years. We were talking about somebody and you’re like, “That person would love it if you turn up as a division manager for Beazer Homes.” To them, that would be a failure, like, “Frank couldn’t make it.” They’re secretly rooting for it. I was an outsider. I was doing something different.

People who we’ve referenced in that instance are like, “They’re rooting for you to fail,” some of them have quit and it’s hysterical. Twenty-four months after they quit, they call me or text me. They want me to help them with something. They want to ask me a question and all the bullshit is gone. There’s this inertia of crap that follows you. Everybody who’s on the Patriots, but the people who are out of the fray, the Guerreros and the Montanas, are not in the same mindset, so they don’t ever have the brainwashing. They’re already able to get through a different truth.

Our ancestors were in tribes if you go back thousands and thousands of years ago. If you left the tribe to join someone else’s tribe, you’re for us or against us. The world is so different from what it was then. The truth is back then, it could be life or death. Losing a strong member of your tribe, who was a good hunter, could be life or death for the weaker people and them going to another tribe. You would root against them because there was a scarcity of resources. Now, there is such a world of abundance to have that mindset of caring so much about someone losing after they go. It’s very short-sighted but I see how it happens because it breaks the narrative.

Another thing, Frank, and I think I’ve been guilty of this. If someone leaves and goes, let’s say a competitor. You want it not to work well because if it works great, 4 or 5 other people are going to follow along. I ended up at NVR because McCauley came to NVR. Everyone was rooting for him when he left GE to fail and come back to GE, but he made a ton of money. The stock went up and went crazy. Guess where I followed? As soon as the CEO called me, I was enamored by it because I had social proof. That was bad for GE that it worked out for McCauley because that meant I came along to now. Now, they didn’t lose one talented executive, they lost two.

I think this is worth talking about. This shit happens. It’s a tide. It can pull you in or out. If you get caught up in the tide, you lose control of yourself. What’s important here is to realize this stuff is going to happen and none of it matters. Tom Brady’s Wikipedia page will forever note that he’s a seven-time Super Bowl winner unless he wins more. That’s the narrative for him. It doesn’t affect my life. It doesn’t affect Ian’s life. It’s Tom Brady’s life.

If you get caught up in this crap and you get caught up in the water cooler talk from your employers, the company that you work at, you’re not being truthful to you. You’re not serving yourself and getting yourself to that point where you are going to get what you ultimately want because you’re getting caught up in this crap tide. I think what Brady was able to do has he deserved it because he kept himself in the game. He made a discretionary choice to move. He is now above the fray. He doesn’t need to get in and throw elbows. He already won. He moved to a better place, climate and temperature. He has another Super Bowl and won. If he does nothing else and his career ends, he already won because he was able to rise above it.

I think it’s worth noting that when you leave a company, the way most companies are going to try to convince you to stay is through fear. They’re going to say, “You’ve done so much here. You’re giving up so much. What if it doesn’t work?” Everyone always says, “The grass isn’t always greener.” They’ll say that to you every single time. They will try to prey on your fears, which is what kept you in that company so long and kept you from looking somewhere else.

When it doesn’t work for you, they can then go spread that narrative across the rest of their team and say, “See what happens when you leave a good-paying job with benefits and you go out there to the scary world? Look what happened to him. Let this be a lesson to you.” Managers don’t like turnover. They liked the status quo. They don’t want people hopping in and out. They will use fear when you leave for something else.

Former Employer: When you leave a company, the way most companies are going to try to convince you to stay is through fear.


One of the things that happened in my life is I started to become more successful, make more money and started the floor when I stopped worrying about what other people said. This is an example, but it’s worth noting. This doesn’t happen to me as much anymore, but maybe a few years ago, this always happened. People would try and control my schedule. You’re trying to control my time. When I got honest, I looked at it, and I said, “This person isn’t as successful. They haven’t accomplished as much. They don’t make nearly as much money.” They’re trying to dictate their schedule to me. “No way. I’m not letting that happen. I’m going to dictate my schedule to you puff shit.”

When Ian quit, when I quit, almost everybody told us it was a mistake because all of those people had jobs. They couldn’t see what we could see. The 3 or 4 pieces of input that we used were from people who quit or people who retired and who built something else. They said, “There is another world out there.” A lot of the other stuff, we either didn’t seek it or we didn’t listen to it and retain it because it didn’t serve us.

That’s the thing here. There’s bitterness because you’re scorned. “How can this person do this without us?” The Patriot way worked. Their best pupil took it to Tampa and won. That doesn’t feel great for the people that imparted it. Because of the acrimony that’s happening, Brady isn’t celebrating these guys and saying, “I became Tom Brady by being there. There’s bitterness.” All truth be told, he probably did learn a ton of this stuff from Belichick and Kraft, but he’s smart enough to take it somewhere else and implement it. That gets lost and there’s a lot of hard feelings.

There’s a lot of narratives that will be created, but the truth is, Bob Kraft has an incredible NFL owner. Bill Belichick is an incredible coach. Tom Brady is an incredible quarterback. When you leave a company, there’s going to be a strong feeling. A lot of people leave for the same reason as Brady is you want to be able to show that it wasn’t the company that gave me success. I’m a successful person. I could have done this anywhere I went. I need to prove it to myself.

Whether you go work for yourself or you go to another company, that’s important. It’s important to Brady to come back and show, “I learned some things from you guys, but I’m good with or without you.” It was important for him to win a championship like it’s important for Kraft and Belichick. They feel like they would love to stick it to Brady and say, “This is what you had. You’re not the same without us.” That’s going to be natural on both sides but I think through all three of these, it’s a fascinating dynamic. To me, it doesn’t matter who wins or loses. All of the parallels in a career are about the same.

I’m going to finish Frankie, with an Eric Church lyric. The song lyric for Eric Church is, “I bet you thought before you left, I’d sit in silence by myself. Turn this house into a jail, dying slow in a living hell. But love’s got a funny way of keeping score, and your leaving’ lit up my scoreboard. One bourbon, one scotch, one beer, I’m having a record year.” It’s an awesome lyric. I think it sums up the situation pretty well. It’s great talking to you.

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