From a young age, we’re told that quitting is a form of weakness. We learn to equate quitting with losing. When it pertains to school or sports teams, this might be solid advice. But from a professional standpoint, it holds so many people back. Success is all about focusing relentlessly on a few high-ceiling opportunities. And to figure out where to spend your time, you must first try many things (and leave most of them behind).

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The Myth Of “Quitters Never Win”

Why Success People Quit More Than Most


Ian, you son of a bitch.

At least I’m not a quitter.


I have tried to quit a few times. We are getting knee-deep in quitting. It’s fascinating. As we prepared for this episode, we started to put our outline together. We were thinking about this topic, and without even knowing it before we’ve even got into the episode, Frank and I typically spend 30 minutes talking about what’s going on in both of our businesses before we even get into the show. The topic on both of our sides had everything to do with some stuff that we needed to quit doing specifically to business. I’m not talking about Frank eating too many pita chips or something of that nature. We are talking about business.

One of the things Frank was asking me about is would I want to come in and give a keynote at one of his masterminds. I hemmed, hawed, delayed it a little bit and said, “I’m not sure.” The more I’ve got into it, it wasn’t so much that I didn’t want to do it. It was a trade-off of my time of other things that are going on because I know in 2022, I’m going to have far less discretionary time to do things like that. The more we’ve got into it, you started talking about some coaches you are working with. You are going to have to figure out how to change your focus in 2022, which means spending more time in some areas and quitting some other things.

I’m not a gardener. I don’t have a green thumb by any stretch of the imagination. One of the things that happen in a lot of instances like when I bought my newest house, is the landscaper came out and scalped everything to a point where I’m like, “That’s hideous.” I asked him. I was like, “Why?” He’s like, “I’m going to cut back these trees aggressively because they haven’t been properly maintained. If I cut them back aggressively, what you are going to see is they are going to grow and thrive. If I didn’t do anything with them, what they would do is eventually get rotted. Something might fall off, a branch could come out or it could get struck by lightning. There are a bunch of things.”

It’s an analogy that ever since it happened in my backyard, unbeknownst to me with someone else making the decisions, I have used it in business. I always say, “Maybe this is time to either pick the low-hanging fruit or prune the tree.” There are only many hours a day, there’s only so much energy you have, and you can only grow in many ways. Sometimes it makes sense to prune the tree because it’s best for growth.

We are going to talk about quitting because we have both done our share of quitting. The misnomer most of the time is that successful people never quit, and it doesn’t happen. They grind their way to everything. The truth is that everyone successful has quit something to go follow something more important.

It’s a tired trope. Honestly, it’s one of those things that follow you from childhood, “Don’t quit. Quitters never succeed.” The most successful people in the world have quit multiple things. The people who are the most successful, most of them billionaires, have all quit college. That doesn’t work for the lion’s share of us and me but it worked for them because they are much smarter. It wasn’t benefiting them. It’s important to interject that.

Quitters Never Win: The people who are most successful, many of them billionaires, have all quit college.


There are some famous examples that we can start with and talk about. All of them are for a little bit different reasons. Frankie and I were brainstorming on people that we think about when we think of quitting and something where it was shocking that they quit because it seemed like they had everything. They were at the top of the world. Dave Chappelle is one where it was a resounding yes. Chappelle had signed a $50 million deal for his show. It had moved from being a cult classic to the mainstream. Everyone knew Dave Chappelle and his show. When he quit, it was shocking and alarming because people loved the show and looked forward to seeing more.

It wasn’t just alarming. His fans were sad, frustrated, angry, and upset because here’s a guy at his absolute peak. Chappelle’s reasons for quitting, he didn’t come out with them right away. He went away and got quiet. It went dark, he moved back to Ohio, and it took him a while to talk about it. His big thing was he had become bigger than he was comfortable with. He had a show that used satire to explain racial stereotypes. It got to a point where he thought his show was reinforcing racial stereotypes. He talked to Letterman about a moment in the show where they were doing a skit, which had heavy racial undertones in it.

In the skit, folks on the set laughed at a point that he didn’t think was the funny part. It made him feel like he was the clown and the ass of the joke. They weren’t laughing with him. They were laughing at him. He said he felt terrible shame, and it made him think about what has the show become. Very early in a $50 million run, Chappelle left and lost all that money. They took it back. He didn’t fulfill his contractual obligation. A lot of people thought he was crazy. Here we are years later, and he’s bigger than he has ever been because he had the guts to go do something like that. It has made him a legend in the industry that he’s above being owned.

We have talked about this here. I’m sure this is the place where all of you come for news. In his special, he was flying in the face of cancel culture and said that on there, “I don’t give a shit if you cancel me. I have canceled myself. What can you do to me?” It’s like the Eminem moment in 8 Mile, “What can you do to me that I haven’t already done to myself?” It’s one of those things. When you were saying something about Dave Chappelle, I thought of something. When I was growing my business, we were growing pretty quickly. This was years ago. I remember we were bringing somebody on, and I’ve got scared.

I didn’t talk to you about it and certainly didn’t say it to my staff. I remember thinking, “Am I growing too fast?” That person ultimately didn’t start. Something came up. It was a weird thing. Something in my gut was like, “This is wrong.” I remember thinking at that moment of being somewhat scared. It was honest. I had never grown a business like that. Now, I own 300 houses. I’ve got a text message from someone. It happens to Ian and me. It’s like, “You are a beast. I want to work for you. I want to do something with you.”

We are people. We get scared, too. I’ve got freaked out. Some people would go, “They are no Frank Cava.” I don’t think I’m that special. I’m doing something repetitively over and over, and it has had a great result. At the highest level, someone like Dave Chappelle was like, “I’m losing track of my life.” One of the things we are going to talk about in this is it’s the 21st century. We’ve all got cellphones. Technology is different than it has ever been. We are in a place where you get to choose and pick. Life doesn’t have to get dictated to you. You have resources at your fingertips. You could be as famous as Dave Chappelle and say, “This isn’t it for me.”

Chappelle left because he felt like he was selling out and his purpose was wrong, and he had steered off track. You take someone like Garth Brooks, who at his peak was the biggest star in music, not just country music. He walked off the face of the map.

Before you get into reasons why he walked off, I want to put this in perspective. He was such a big star. He hadn’t played baseball since middle school. He was 50 pounds overweight. For five years in a row, baseball teams let him come to spring training. I don’t know if you remember that. He got to go to spring training. He has no earthly right in the world to be taking batting practice. Your son is a better hitter but Garth Brooks can sing better, so he got to go to spring training.

Garth was the man. We are going to get into the whys of quitting. Garth Brooks had all the money, the fame, and everything in the world. It was just more. A little bit for him was, he had kids. He wasn’t spending enough time with them. The trade-off for him to continue down that life and what he was missing wasn’t worth it for him. He chose to go spend more time with his family and spend his time differently. When you have all the money in the world, the only thing you can’t buy more of is time. He had all the money in the world, and yet his time was being used by other people. That’s why he chose to do something different. Do you want to talk about the R.E.M. drummer?

Garth Brooks came back. He won the Entertainer of the Year two times in a row. He immediately was back where he was and did it on his terms. It was pretty incredible but it was courageous to walk away. Most of you know who R.E.M. is. That’s number one. Number two, who the drummer is completely inconsequential. His name is Bill Berry. One of my favorite bands growing up was R.E.M. Somewhere in the mid to late ’90s, he had an aneurysm and fell over on stage. They postponed the tour, got him vertical and back into a place where he could play the drums, and finished the tour.

He then stepped away from the band and ultimately retired. Years later, he came back and played a handful of gigs but he was no longer their drummer until they discontinued as a band. What he decided was, “I’m happiest when I’m in Georgia and on my tractor. I have been behind this drum set for 20 to 30 years. It’s enough.” R.E.M. was the band. They were one of the absolute hottest bands at the end of the ’90s. He did not partake and walked away because he had a scare. That scare woke him up. With that scare, he decided to refocus his life.

When you have all the money in the world, the only thing you can't buy more of is time. Click To Tweet

In the news was Simone Biles, an Olympic gold medalist. Her reason is multifaceted but a lot of it was mental health. There’s so much pressure on that young lady. She was a superstar in the previous Olympics. She won everything and was being hyped as the greatest gymnast of all time. I have thought about her a lot. Michael Phelps had the same issue. That was a no-win situation.

You are expected to go in and win 4 or 5 gold medals, and anything less, you failed. If you are up against the greatest in the world at what you do, even if you are that good, that’s pretty tough to go through some of that. Her even bigger issue is she got what’s called, in gymnastics, the twisties, where in mid-air you lose track of where you are at.

It’s incredibly dangerous to not know where you are at when you are spinning eighteen times in mid-air the way that girl can fly. She stepped away, and a lot of people were pissed off. This theme is going to go through this whole episode. It’s all these pissed-off and outraged people of, “You are a quitter. You turned your back on your country.” Who gives a shit what any of them say? We all live our own lives.

If you live it based on what other people may or may not say about you, you are not going to end up being happy. To me, I was not outraged and on the camp of, “I can’t believe it.” It’s the frigging Olympics. Give me a break. It’s a big corporate bamboozle for people to make money in advertising. If she didn’t feel like taking part, then who gives a damn?

I thought of it while you were talking about her. There was a meme I saw. It was something to the effect of, “All of you on social media saying Simone Biles is a quitter but you can’t even wear a damn mask when you go to the grocery store.”

God bless her. She made a decision for her. We want to talk a lot about these things. I’m a Detroit Lions fan. I talk about it a lot. Barry Sanders broke my heart when he retired because it felt like he was still at his prime and peak. He had rushed for 1,700 yards, was an MVP candidate, and walked away. His quote has always resonated with me. Barry didn’t talk much either and was a little bit like Chappelle. He went quiet. He released it at an Oklahoma newspaper.

He didn’t even announce it at ESPN or something big. He said, “My desire to quit is now greater than my desire to play.” That line is so beautiful and simple, yet it cuts through all the clutter of why people get themselves caught up with sunk costs and all these things. Barry’s answer is honest, “You don’t have to like that. You don’t have to love my decision but it’s my decision and I’m going to live with it for the rest of my life. I’m good with it.”

Ian was tasking me with coming up with some names on this. We were trying to think of people who weren’t just in sports. Chappelle popped up there, which we thought was a good one, and the R.E.M. drummer. I remember reading that being young and like, “It doesn’t make sense to me.” I was in my twenties, and I had my health. I never had anything like that. As I’m in my late 40s, I get it. Things hurt more. The best example I could think about of someone who was quitting was George Washington.

Hopefully, they are still teaching that in school. He was the first President of the United States. I don’t know if that has been replaced by the Underground Railroad. The point is George Washington was in charge of this incredible Republic. We had term limits of four years but we didn’t have a maximum amount of terms. He had a four-year term but it didn’t say he had to end after four years. He goes, “Two is enough.” The King of England, who we had defeated years earlier, was like, “That is a man who would walk away from all of that power.”

What George Washington was saying is, “This place is bigger than me.” The person who left and fought to leave in England is saying, “How could someone do that? What a man.” You think about what that has done. It’s loosely defined. If you can serve a third term, some people tried to push it. They have made amendments after the fact but the point is he didn’t have an amendment in place at that time. He thought, “This is it. This has been a good run. This is a good time to walk away.”

If you have ever read about him or seen that incredible series called John Adams. John Adams gets up in this incredible order. George Washington was a huge man but he was not as loud of a speaker. It’s incredible what he did by making that decision to step away. He set a tone for a place where it made a lot of sense. Until FDR in World War II, nobody had ever challenged it.

Quitters Never Win: You need to look at things and say, “Does this serve me anymore?”


Washington is a good example, too, because George is a pretty simple dude. He wasn’t a real politician. He was voted in because he was a great general, warrior, and leader. He didn’t necessarily like the politics, the office, and the decisions he had to make on a regular basis. He was uncomfortable in that job from day one and thought there would be better people to do the next step. There are so many reasons it’s cool that he stepped away but it comes back to he didn’t think that position was serving him anymore either. He wasn’t having the best time. He did it out of duty for his country and mission. He didn’t think it served him.

Frank, you talked a little bit about how you grew up with, “Quitters never win. Quitting equates to failure, weakness, and dropping your dream.” Both of our parents were pretty similar, and they were similar to all American parents, which is, “If you start something, finish it.” I feel like that still makes sense for me as a parent. I’m that way on team sports because if you quit a team sport in the season, that leaves your teammates, coach, and other people in bad positions. It’s completely silly when it comes to individual activities or something where you don’t impact anyone else if you quit. Most things in life are usually along the line of, “It doesn’t impact other people much if you quit,” but if you do have some team things, that’s not the right thing.

My son played tackle football for the first time. August tackle football is the worst. It’s two-hour practices in 100 degrees, and you are hitting for the first time. If I had have given him a chance anytime in those first three weeks of practice to quit, he would have taken it in a second. This was not a discussion, “You started this, you signed up, and you are going to finish the season.” It’s a great life lesson for him. His team came together and won a little county championship. If I would have let him, he would have quit. I still feel strongly on some of that stuff with teams where if you are letting someone down, you should stick it out as long as you can, at least until they are in a good place to move.

It’s a parenting trope, “You don’t want to quit. I’m not going to raise a quitter.” It’s these things. At its core, I haven’t gotten to this place yet where my kids have discretionary decision-making. They do what they are told. It’s like, “You are going to do what we tell you.” That’s what it goes down to. The reason that this, “Quitters never win,” is still in our parlance and used regularly has a lot to do with the fact that parents don’t want their kids to have momentum or inertia going in the wrong direction. What you hear is, “You should never quit. I’m not a quitter.”

It makes sense because when you were a young kid, you didn’t want momentum in the direction of, “I’m quitting. This is a quitter. I can start but I cannot finish.” There’s a good lesson for a time. There comes a time when you need to look at things and say, “Does this serve me anymore?” I will give you the best example for me. I dated a woman starting when I was 27 and broke up with her when I was 35. I knew it was the wrong relationship ten months in, and I was in that relationship for years. I was doing it because I thought I could make it better, it was okay, and I didn’t want to quit it.

The longer it went, the more sunk cost you added to it.

In the end, I remember we broke up, and there were a lot of nasty words and feelings. It didn’t work. It was nothing catastrophic. It was a wrong relationship for both of us. I remember telling a friend of mine, “I wasted eight years of her life.” He looked at me and goes, “You wasted eight years of yours, too.” I had never thought about that and allowed that to get into my head that I also had sunk cost and lost time. I was 27 when it started and 35 when it ended. That’s real.

One of the things that have changed me is realizing I didn’t get that time back. Ian and I look at successful businesses. I’m not going to quit the business but there are parts of the business that I may or may not keep. I ask myself, as a business owner all the time, “Does this serve us? Is this sensible? Is this where we should be spending our energy, money and capital? Would we be better-suited repositioning?” Those are good questions to ask. That isn’t quitting. That’s evolving. That is a different thing.

You said something about how pretty much forward momentum is a big reason why we did that. We have enough data to say that your odds of succeeding in life are better if you finish the fifth grade than if you get tired of your teacher and quit halfway through. That’s an obvious one but we know the material they are teaching in fifth grade is stuff you are going to need. It’s good for you to stick this thing out one more year. We know better than you as a parent. We know that if you make it through a baseball season, you didn’t like your coach and finish it, you are going to be proud of yourself for finishing it.

There’s a lot of data that goes around there. I would say the same thing about high school. Your chances in life are dramatically higher if you finish high school than if you drop out early. After high school, it starts to get a lot more blurry. Does making your kid finish college mean they are going to be more successful than if they were to quit their sophomore year and start a business? Times have changed so much since the ’50s, ’60s and ’70s. There was a time where getting a college degree gave you a huge advantage over someone else but now, it comes with a lot of debt. It doesn’t come with a lot of promises of more income.

I don’t know that it translates to the same level as it used to. With some of those things that you learn as a youngster of quitting or sticking through things, in the business world, nothing is guaranteed. Everything you do in business has an uncertain conclusion that you are hoping for, especially if you start something, but even which company or job you choose, “Should I stay in this job long enough? I’m in sales. If I take this marketing approach, will it work?” Everything is uncertain. To have this mindset of, “If I started it, I have to finish it,” when does that end? Who gains?

Anything worth having takes time, effort, and a bunch of embarrassing setbacks, mistakes, and miscues. Click To Tweet

There’s a book called Tightrope. It’s in the same spirit of Hillbilly Elegy or Dopesick. It talks about how much on the razor’s edge people live with their finances. It talks about three things. I can only recall two of them. The three things were finishing high school and not getting pregnant before you finish high school. God forbid you don’t finish high school and either get someone pregnant or you are pregnant before that, those are two things that put you behind the eight ball. From a financial standpoint, it’s hard to recover from. Once you get to a certain age, and especially if you have a certain amount of gumption, there is a world out there where it doesn’t necessarily make sense to keep pushing through college.

My dad went to a high school that was called Tech. It was Technical Institution. He never went to college but what they did at Tech is they taught him about the Electrical Trade. He was already doing it with my granddad, and now they are going to teach him about the Technical Trade. When he was a junior, he was able to leave midday and go to work. He worked on his trade, and it served him very well. He has had a great career in life. One of the things we get away from is we want to push everybody into this four-year college experience where sometimes that isn’t the sensible move. It’s not the right thing for people. As a society, we have gotten away from that. It makes sense. Colleges are big businesses.

I think about things that I have quit and when I have wanted to quit and haven’t. There are some times where quitting is not okay. We have touched on a couple of the obvious ones. A lot of people quit too early, and their issue is more of impatience. They try something, and it doesn’t work, “I’m not good at this. I’m going to try something else.” The truth is anything worth having is going to take time, effort, and a bunch of embarrassing setbacks, mistakes, and miscues. That’s normal.

If you want to learn how to golf, you are going to hit a bunch of balls in the woods before you get good at dropping it on the green. The part that everyone and I struggle with is, “How much time do I give this before I realize I’m not good at it? I’m never going to like it.” You can’t start everything, put 10,000 hours in, and Malcolm Gladwell everything. You have to choose which things you dive deep in to become an expert in or, “Is it something I’m going to delegate for life and something I’m never going to want to do a lot of?”

You’ve got to gut certain things out. That comes down to parenting. You have to be confident. When you or your child has the ability to make decisions, you have to be comfortable there to allow them to make them. What I want to pivot into quickly is when it is okay to quit. It pivots with this even when it’s not. I had a mentor early in my career. He was someone that I met when I was still in college. I flew up to NVR. He figured out before me and showed me the roadmap of, “Come and work here. You build yourself a house. You can trade the house into another house. Do it 2 or 3 times. You make $1 million.”

It was not an original idea that I had. I copied somebody else who did it. This person meant a lot to me. I was unhappy at NVR in 2004. One of the things that he told me in 2004 was, “If you quit now, you will be fine. If you quit in five years, you are going to be great.” I was like, “Why?” He was like, “It’s because, in five years, you are going to go from being where you are as Production Manager to most likely running a division.” If you are a vice president with a publicly-traded company, it’s a lot different spot than if you are simply a middle manager. The world is going to open up to you in different ways because you are going to see things in different ways than you do now.

There is a statistic out there of people who start their businesses in their 50s, 40s, 30s and 20s. I did it in that order on purpose. The older you are when you start a business, at about 60, it inverts. In your 50s, 40s or 30s, you are way more likely to succeed as a business owner than you are if you start something in your 20s and 30s. The reason for it is you have more experience and money. If you wait, grind and do these things, it gives you a much better chance of being successful long-term because you waited. It wasn’t because it was hard or you disliked it. You set yourself up. It becomes positioning. You are not quitting. You are positioning.

When you say quitting is not okay, the lesson learned there is leaving NVR too early wouldn’t have served you because you wouldn’t have got as much out of NVR as NVR got out of you. When you are young in a company, and especially if you are with a good company, the company is going to take everything it can from you. It’s going to let you work 80-hour weeks, let you grind, and do twice the work of a normal person because you are ambitious. It takes a while to get the full value of a great company. That comes with learning, experience, the responsibility they give you, and the decisions you make.

It’s getting to be there long enough to see, “My decisions, were they fruitful? Did I make mistakes?” If you are there for a short period, how do you know if any of your decisions were worth a damn? You weren’t there long enough to see them out? You were getting moved all over the place. That’s pretty insightful to think about. If you work for a great company and you are thinking about, “Should I quit, go work for another company or start my own thing?” Ask yourself, “Does the company still have more to give me? Can I still grow here and learn?”

When Frank says leaving as a project manager versus leaving as a division manager, the value of those two things is not 20%. It’s 3, 4 or 5X what he was making years before. You have to ask yourself, “With another 3 or 5 years, what could I attain at this company? What kind of multiples of income could I make if I stuck it out and got that extra experience and not just with someone hiring me?” That’s important. Your resume will look better if you have different positions, “If I were to go work for that company, how much more valuable would I be because of the experience and stuff I have learned and the skills I have gained by sticking out?”

In those five years, I went from a Production Manager to a Sales Manager, General Manager, and Division Manager. I was Division Manager for two and a half years before I ultimately quit. Had I stayed another five, I would not have gotten promoted again. You don’t get promoted out of a division manager role in less than somewhere between 7 and 12 years on the norm. If I had stayed there for another five years, I would have been doing the same stuff. Would I have been better? Perhaps. Would I have more money? Yes. Would I have any new skills? The answer to that for me was no.

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I could have gotten better with some of the skills that I have. I had all the exposures already. I had developed land, built things, hired and recruited. When it came down to it, I was like, “This does make me happy. I can continue to be on the gravy train but I have the skillset.” I remember years later when Ian called me up and he’s like, “I’m thinking of quitting.” We had a similar conversation of, “You have been in that role for so much time. What’s next?” He goes, “It’s more people, responsibility and travel. It’s not exciting. There’s nothing new. I’m not growing. It’s just more money.”

It’s more of the same. It’s like Garth Brooks. It’s more concerts and tours. It’s international. I’m flying more. It’s more money and bigger record albums. That’s all it is. If you are excited about those things, that’s awesome. I’m sure there was a point in time where Garth was like, “I’m going to Japan. This is amazing.” The fifth time going to Japan, he was like, “I can’t believe I’m going to Japan again. What a pain in the ass for me.” It gets to that place where you are not excited and enthused.

A lot of people think quitting is not okay because you are going to let the team down. I have already talked about how as kids, we don’t want to let a team down. You don’t want to quit the soccer team in the middle of the year because that leaves them in a bad place. That’s true but there’s also not another soccer team you can join. You are not getting paid. You did that and made that commitment. It’s a little bit different when you work because you are a free agent. Every day that you work, you get paid for. The company pays you for your services. There are no long-term contracts.

To an extent, no matter when you leave a company, quit a job or stop doing something, there are going to be people inconvenienced. There was no time for me in leaving GE or NVR where it was not going to be a pain in the ass for a while. I was doing a lot of work. That meant a lot of that now fell on my boss’ shoulders and the managers underneath me who were already overwhelmed. They had to do a lot of things that I used to do. The company had to find my replacement. Some people left because they didn’t like the new leadership.

It inconvenienced the company for a while but after a few months, everyone got used to it. There’s almost no position anywhere where if you leave, the company has been in dire straits for years and all of the people left in the team. Usually, the group figures out how to handle what you were doing and move on. A big reason why most people don’t quit companies is they give too much of a weighting of how bad they are leaving their company and how inconvenienced everyone is going to be. A lot of that is ego. You think you are more important than you are.

I remember quitting my job in January of 2009. It’s going to be hard for me to articulate this in a way but it’s this. I remember I didn’t sleep. I quit. I went and got a Starbucks. It was 5:00 or 6:00 in the morning. Nobody was on job sites yet. I remember driving through job sites and seeing a heater. It’s January. It’s cold in Virginia. I remember seeing a heater in a house. The heater in the house means the heater is on, so all the mud and ice is on the drywall. I quit, and the drywall heater was still going.

At some point in the not too distant future, the drywallers were going to show up, move the heater, sand that house, and paint it. That house was going to get finished. It didn’t matter if I sat in that chair anymore or not. The world moves on without you. We tell ourselves these bullshit stories, and sometimes you tell yourself these bullshit stories when you were a little kid because you need to get through football practice. At some point, it’s like, “Everyone else is going to be fine. Let’s focus on me a little bit.” There’s a fine line with that.

Let’s talk about when it is okay to quit. First is when it’s clear you are no longer wanted. That should be pretty obvious but a lot of people do stick around much longer than that. One of the most miserable times you should stay at a place is when it’s clear that you are not wanted.

I will tell a story about this. I have a friend who worked for a company, and they were pretty high up within that company. They did so at a young age and did it very well. They are well thought of. They were small equity owners in a small company but it was a big deal. They were kind of an owner and were treated as such. The management team that owned the company or the majority stakeholders sold to somebody else. This person decided to hang around for a long time. There were a bunch of employees who were there but this person was the last. All of a sudden, the job was gone. They were told they no longer had a job. It came as a surprise.

As an outsider looking in, my opinion was, “They have been telling you for years they want you to go do something else. You came from the old regime. There were signs.” What ended up happening was the person walked in, got fired, and had to pick up the pieces. What could have happened is you could have looked and said, “I’m going to look at this objectively.” I realize what happened.

I have seen this in books, stories and movies. When something gets purchased, the only thing that’s usually left is the basket of money the owners got, and everybody else has got to fend for themselves. In some instances, you’ve got to look at that and be honest, “I need to be selfish, prioritize me and figure out where the right spot is for me.”

Sometimes you need to prioritize yourself and figure out where the right spot is for you. Click To Tweet

The nature of business is you can be the most important person in a company now and next week not be wanted. That’s hard for people to grapple with. Your story resonates with me. I saw it happen. I was only at GE for six years but I went through three reorganizations, which are largely like acquisitions. When a big company reorganizes, all that means is a bigger part of the company takes over a smaller part of the company. Those managers have all the power. The whole point of reorganizing is to wipe out layers of management and redundant accountants and analysts. Every time it happened, managers who were like gods in my little business all of a sudden were clearly not wanted.

Some of them didn’t know how to handle it and what to do. They couldn’t see it. I was a kid, and I could see it like, “You have no power anymore. The new managers talk over you in meetings. You are not invited to some meetings that I’m going to. It’s pretty clear.” Some of them would, like your friend, hang around and hope that the power dynamic would change but it’s not going to change. That sucks that happened. It’s not the same company you thought it was. Some people that I knew were talented and more talented than the group that came in and took over. They laughed and were like, “Screw it. If I’m not wanted, I will go somewhere else.”

There were no hard feelings, and our business kept rolling right along without these talented people. It wasn’t as fun for me when that happened but they saw it. They could read it right out of the gate, “We have reorganized. You can call it whatever you want. I’m not wanted the way I was a week ago. I’m going to take steps to protect myself and my family. There’s a new regime. I’m going to go find somewhere else to work rather than waiting and having this contentious relationship for 1, 2,or 3 years.” One day, you finally have the guts to say, “I want you out or I can see I’m not as wanted as I was before. I’m not going anywhere and start looking for what’s next for me while you are paying me. That’s what I’m going to do.”

The thing that I would challenge anybody who finds himself in this situation is most likely, you are not passionate about it either. You are staying there because of fear, “How do I pay the bills? How do I put my kids through college? How do I do this or that?” You are thinking of it from the capitalistic aspect of it. It most likely no longer serves you either. You are bored. You are not into it as much. You are doing it on a routine. I wasn’t at GE with Ian but I was at NVR. I watched the same thing happen with a couple of different mergers. You saw the most important people.

Some fought it and some were like, “I’m going to immersively sit on the sword. This has been a good run.” In some instances, I have done this before where I have someone who’s not the right fit. Instead of bringing them in and being like, “I’m going to lock your head off,” I will ask, “I feel like this isn’t working. Doesn’t it make sense to be proactive? How do I as an employer help you get to a place where it could make sense for you?” That’s a good spot to be and a good dialogue to have with somebody. It sucks but it’s one of those things where you get to refocus and reevaluate.

If your gut tells you something changed dramatically, maybe someone got promoted into a position of power that’s over your boss or your boss’s boss, and it feels immediately like things have changed, “I don’t think this individual wants me anymore,” you should listen to your gut. For years, I was fortunate. I was promoted a lot of times over businesses. If I made you feel that way, it’s because I did feel that way. It wasn’t by accident if I made you feel like you were no longer wanted.

There were times where I was promoted into positions to make big changes in a company. When I was promoted into positions, almost every time, it was because something was failing. The boss that put me in charge of it said, “Go make changes and fix it.” I had already been watching that business. I knew how it operated. I was in a sister business or I was a peer to the person that was running it before. I knew who was doing the job there and who wasn’t. I had a strong opinion for every job I came into. If I didn’t have an opinion of you right away, I usually made one within 30 minutes.

I needed about 30 minutes to 1 hour with you, looking at some of your numbers and then talking to you directly to form an opinion. If you ever felt like you weren’t wanted, it was intentional. You should trust your gut because if a new manager comes in, they can’t wipe out the whole staff. They are going to do a piecemeal over time and go after the most obvious actors. Over time, they are going to get the people they want in place. If you feel like you are not going to be one of those people, you should act on it to protect your self-interest.

There are two sides to this. There are people who were the sacred cows before and were loved and adored by the previous regime. There are two camps. I always assumed when there was somebody new coming in that they were trying to push me out but they didn’t usually push me out. What they did instead is they embraced me and let me know like, “I had that conversation with the new manager and impressed them. We want to keep this guy.”

I felt it quickly because a new manager needs someone good under them who supports the mission who’s onboard and producing. You need that. The other side is, “I was one of the sacred cows, and now I no longer am.” There’s a third group that is often overlooked. It’s the person who was talented but for some reason, the previous regime missed. That happens. There’s a fresh look at things. They are like, “This person has been pushed aside but I see a reason to not push this person aside and empower them.”

You can think of it all the time in sports. It usually happens through an injury, and they promote somebody. Tom Brady got promoted when someone else above him was the highest-paid player. They never gave the job back. It happens in business, too. The new manager looks at you and says, “I could work with this guy or girl. I can help them. They can help me.” Those things happen, too. It’s not like the new management ran out. Think about where you are. If you are not being embraced in those first 30 days, this is coming.

An obvious time when it’s okay to quit is when you are doing something that no longer serves you. Using the word quit, in general, is a mistake. That’s the name of this episode. Our and responsibilities change. My life in 2012 was different than it was in ’17. It’s going to be different in 2022. There are lots of things that I have done in the past that I enjoy doing and don’t consider them to be mistakes. I don’t look at quitting as a negative thing. I no longer have time to do certain things that I used to do and now I have other things that are filling my time up.

Quitters Never Win: If what you’re doing doesn’t make you happy Quitters Never Win: If what you’re doing doesn’t make you happy.


If it doesn’t serve you or make you happy and you are not excited about it, find something else to do. That’s not just in career. That’s everything. Don’t keep doing something. If running is making your hips and knee hurt, you’ve got to get surgery because you were running in your 20s and now in your 40s the same distance, and you keep doing it because you are not a quitter, in my opinion, that’s ignorant. Go swim, get into Pilates, and do something different. Your life is different. Don’t keep doing something just because you are not a quitter.

It’s part of that. It’s not quittable. I want to say something else about what you are talking about how it’s no longer serving you. We had a person who worked here. He no longer works here. He was mid-twenties when he started. He was going to school to get a degree in Accounting. He was doing entry-level data entry for us. I knew he had an expiration date on it. When he graduated from college, six weeks later, he came back and goes, “This has been a great run. I loved the company. I’ve got to try something else. That’s why I’ve got the degree.” I get it. That made sense. He was making moves. He worked and deserved what we paid him.

It was one of those things where he’s not a lifer in that role. We have done a good enough job as a business where he has told me point blank, “Maybe there will be a chance in the future. I like it here. Maybe I will come back.” I can live with that. That’s also part of it. As the person who’s in the role, you need to realize it may be best for you to leave. As the owner, you are not signing people up for life sentences. I live and work in Virginia. It’s a right-to-work state. People can come, people can go. That’s part of life. Your team is going through change over time. Sometimes you want to see people go. Sometimes you don’t. It’s part of life.

I also think there are times where you are doing something fine, working well for you, and paying you well that you are good at and you think is okay but you have an opportunity to do something that gets you much more excited. This gets into regrets a little bit of, “I’m doing something safe and working but in ten years, am I going to look back and say that I wish I would have taken that swing?”

If that’s the case and you feel like, “I’m going to regret not trying this one day,” that’s a beautiful time to quit, especially if you ask yourself, “If quitting and trying this new thing doesn’t work, could I find something comparable to what I’m doing a few years from now?” If the answer is yes to that, all day long, quitting is a good idea. It makes sense. At least changing switching your time to something different makes sense all day.

Let’s flip to the opposite side of this and talk about building a culture where people don’t want to quit. We have a pretty great culture and retention in our company. There were three years where nobody quit. It’s a good culture, company, and a place to be. What we try and focus on is you, your career and goals, what you are interested in, and are you bought in? As we get bigger as a company, we do other stuff. We have community service events. We do community outreach and attract a lot of younger people to work here. Giving back is big for them. Being a part of something bigger than themselves is part of the problem.

A lot of the people who we are recruiting are into it. Nicely, it lines with my core values. Those are things that we try and build. This is a culture where you don’t want to quit, where you want to grow, and where you are challenged. People quit for a bunch of reasons. Money is usually fifth. It’s usually not feeling challenged, not being wanted, not feeling enriched, and not feeling like you are growing. Those are the types of things that, as an employer, you want to make sure you have, so your employee base is continuing to strive.

We are talking about it all the time. It’s okay to quit when you are not happy, motivated, stretched and growing. If you are a manager in your company and want to keep employees, don’t let that happen to people and show them a career path. One thing you do better than anything, forget planting trees, is you have a clear success path. You have entry-level, second-level, and third-level jobs. If I start for Frank and I’m good at what I do, I can see the next 2 or 3 jobs ahead of me if I want to earn them.

That is more important than anything else you do. You give people a chance to grow, not stagnate and be bored. If I start at Cava Companies five years later, I’m worth dramatically more than when I started as an entry-level person. We can say that unequivocally. If you started at an entry-level lower-paid position in your job, made it through five years, and took some multiple promotions, you are way more valuable to the next company that hires you or you are closer to starting your own thing and being more responsible than beforehand. That’s why you retain people.

You are migrating into a role that retains you here because you are continuing to be challenged, grow, and get better. I will ask this several times a year, “By a show of hands, who wants to be doing the same thing in two years?” Nobody raises their hand. That’s like, “I don’t want to be doing the same thing in two years. I want to be evolving.”

Even people that do will raise their hand and even people that are like, “I’m pretty cool where I’m at.” I find people raise their hand from the social pressure of, “I should be growing,” because we were taught that as kids by our parents always moving forward. You go to promote someone, and they were like, “I raised my hand because everyone else was.” There’s this social pressure of, “I should always be advancing.” Your family, friends, and everyone is pushing you for it.

Evolve to get better and become more efficient. Click To Tweet

There is a way to not change jobs or positions within the same company and evolve to do things, get better and become more efficient. Those things are rewarded and become fun. You know this. I have a three-year-old. He has fun doing everything, getting in the shower and pooping. He has fun doing everything.

I have fun pooping, too. That’s not a three-year-old thing.

He’s like, “Dada, that would hurt.” “Drink more water, buddy.” The point is he’s always doing stuff that is mundane. Getting dressed, he laughs. Getting into the showers, he giggles. He runs around and makes it fun. Going to bed, he runs laps up and down the hallway. What we can learn from three-year-olds is they figure out how to make shit entertaining. If you are in this rut and thinking about it, maybe it’s you. Maybe there’s a way to make things entertaining so you don’t have to quit. It goes through this list of things we have talked about. Maybe it is the right time.

You see people that are jumping around, looking at things, throwing money at people, signing bonuses, and all these things. If you are in a place where you feel like you are growing every day, getting better, and there are opportunities to take bigger jobs, and you leave for an incremental pay raise, you are a moron unless that company can also offer the same skill growth and opportunity growth.

Especially if you are younger, you should be thinking hard about, “How am I making myself more marketable?” It’s not 5%, 10% or 15% more marketable, “How am I making myself 3, 4 or 5 times more valuable to someone who would hire me?” If your company can give you those things, quitting is silly. Suck it up and eat ramen noodles. If that company is making you more valuable, you have to understand what the long game is.

You and I have talked early in the history of this show about something similar. Sometimes you’ve got to embrace the suck. If you are in your twenties, it’s going to suck. You are not doing great jobs because you are learning the skillset that gives you the ability to do the more fun stuff. That’s true unless you are Zuckerberg or somebody like that, and you can build something. For most of us, there’s a process. I was at a family wedding and shipped them a bunch of wine in June 2021. I was there with my family.

I was like, “This is going to last my uncle months.” We had enough people there where we drank it in minutes. I called my uncle and said, “We are having this wedding. I’m going to send you up some more wine.” He’s like, “That’s cool.” I was like, “Drink it.” He’s like, “I’m going to wait for you. We are going to do a wine tasting.” What was funny about it is my cousin that got married was 27. She’s a woman. There are a bunch of her friends, girls, and women. When you have wine, people immediately assume you are rich. It’s hysterical.

You understand why I’m like, “You are rich. You are doing better than me.” Several of them asked me, “How did you get to a point where you had money?” That’s what they are getting at. I’m like, “Your twenties sucks. You are not supposed to have this in your twenties.” It doesn’t happen that way. It happens if you do all the right stuff in your 20s and 30s that gives you an opportunity in your 40s, 50s, and 60s to ring the bell.

I remember where I was sitting in the conversation you had with me about when you turned 40, how life was changing, and how you wanted to look at your career differently. You had that conversation with your boss about, “This is the time for me to ring the bell.” What I want to say going into this regression is there are times to quit but there are also times to roll up your sleeves, keep going forward and make sure that you are doing so in a way that is prudent, smart, and will serve you long-term.

If you do have the skillset, you are at the right place, and you can cultivate your skills, stay. If you are at a bad company that’s poorly run, get the hell out. If you can have continuity at a certain place and you are being enriched and growing, that’s a time to slow down, look at it, and say, “Does it make sense for me to go?” If you are talented or being an entrepreneur is something you ultimately strive to, you are going to have to make that decision at some point but you don’t necessarily need to make it every 12 to 24 months.

We have talked about this. Both of us knew we wanted to leave our last company 4 or 5 years before we did it. Yours was smart because you took multiple promotions. I was in the same position those last 3 or 4 years. I wasn’t growing. I was stagnating. If I left even two years before, the amount of money I would have left on the table is insane. For me, there are also times where quitting would be ignorant. It would be not even ignorant. It would have been irresponsible for me to leave a few years before when I did because I owed it to my family to stick around and get the equity payment. A time not to quit is if you have equity or some type of large bonus that could change your life in a meaningful way. It will either let you start a business or invest differently.

Quitters Never Win: If you have the skillset and you can cultivate your skills, stay.


It’s worth it to suck it up sometimes for a few years if you are in a profitable situation and if it will help you live the next few years a lot easier. For me, I’m glad that I didn’t quit. There were many days where I came home, and I was at my wit’s end. I didn’t want to be there but I sucked it up. I had a glass of wine and a whiskey. I went to bed.

I’ve got up in the morning and went and grinded more because I knew if I keep doing this for a few more years, the next two decades were going to be amazing. I will do whatever I want to do and all that flexibility. You don’t want to be obstinate either if financially, it makes sense. There are times where it does make sense to work for money. Forget your passion. If the money is that big, you should stick around for it because it does make your life a lot better.

As we are getting close to wrapping this, there are two things I want to go over. It’s putting things on the ice and knowing where you are in the generational cycle. What I want to say about putting it on ice is this. There’s an article that I read. It was Kenny Chesney, a country singer. He’s one of my favorites. He covered a Bruce Springsteen song years ago. He and Bruce Springsteen became friends. Bruce Springsteen is married and has grown children. One of his children was in the past Olympics with Simone Biles. She’s talented on the horse and does equestrian.

The point of the matter is Bruce Springsteen had a family. Kenny Chesney is a lifelong bachelor. What Bruce Springsteen said to Kenny Chesney is this, “You can write part of a song and stick it in a drawer in your bedside table. It will still be there for you in ten years when you come back to it because your family won’t be.” I thought that was incredible advice because there are certain parts of our lives that we could stop, mothball or put on ice, and there are certain parts of our lives that we can’t.

People take for granted. I did when I was younger age. As I get into my 40s and I don’t have to have kids, I’m a lot more sensitive to the fact of how old I will be when my kids are certain ages, very much so like, “I will be 60, and my kid will only be X. I hope I’m still fit so I can do fun things.” You start thinking about it differently. What we trade in a lot of instances are money, job, and things. We do the anti-Garth Brooks or the anti-Dave Chappelle. Instead, what we do is keep grinding where we said, “Maybe I should pause.”

I love that advice because you have given that to me a few times. Over the years, I have figured out ways to make money in a lot of different ways. There are times where I’m doing well with one avenue of revenue and another one, I’m frustrated with. I will grumble to you, and you always have a great perspective when you talk to me. It’s like, “You don’t need to be great at all of them all the time. You don’t have time to be great at all of them all the time. You can always put it on ice.”

I always remember you saying that to me, “If that business isn’t working well, it will be there for you in 1 or 2 years if you want to go back to it. You can always go back to doing something else. If you have a better opportunity right in front of you, you should take advantage of it. You can always come back to that if you are passionate enough about it. If you are not passionate, don’t ruin the better opportunity to try to do everything.”

That advice serves me well all the time because I feel like I’m always playing a game of arbitrage with my time, “Where is my time best served both personally and from a profitability standpoint? Where can I spend my time best?” That normally means stopping doing something else with my time that is keeping me from doing the most profitable things.

I remember people would talk to me about how important time was. I didn’t have money. I would hear that about time and be like, “I have to grind for money.” You do. That’s part of it. You don’t get to have the discussion about time until you get to a certain spot. If you are in the spot where money is more important to you than time, you should be critical of where you are spending your time. If you are not critical of it, you might be doing things that you shouldn’t be doing and aren’t going to ultimately get you where you want to go.

That’s part of the program. You need to fully understand that. There’s a great movie with Jim Carrey called Yes Man. He goes to this seminar, and all he can say is yes. He was a no-man before. He wouldn’t do anything and get off the couch. He says yes to all this stuff and ends up with all these incredibly ridiculous situations. The guy who talked in the event was like, “You idiot. You don’t say yes to everything. You say yes to more because it opens doors.”

Every time you say yes to something, you close doors to something else. Every time you say no to something, you can open doors to other things that you might be able to say yes to but you can’t now. There’s no perfect solution, remedy or scoring sheet. You have to make these decisions as you go. Steve Jobs had a great quote. He goes, “If I looked in the mirror more days in a row than I like and I don’t like what I’m doing, I change it.” That is what we are trying to drive at.

Take us home, Frankie.

If you have a better opportunity right in front of you, take advantage of it. Click To Tweet

Ian and I talked about this, and I’m passionate about this. Ian and I are both third-generation kids in this country. His parents came from Slovakia. My grandparents came from Italy. Knowing where you are in the birth order makes a lot of sense, and you need to be mindful of it. What we are talking about with discretionary choice with time is something we get to do because of where we are. We did not come here from Haiti on a boat. We are not someone whose parents or grandparents speak with an incredibly thick accent because they immigrated here. We get to have a choice.

Most likely, if you are reading this, you get to have a choice. Our grandparents didn’t. Our parents, to most degrees, didn’t. Two things have changed. It’s their birth order and the times. The times with the internet and what you are able to do are certainly different. This dawned on me. I buy a lot of houses in all kinds of neighborhoods but I usually don’t buy in the rich ones. I buy more in the poor ones. What I noticed was this. I would see all these yard signs, urns, and figurines of Jesus.

I was at my grandmother’s house and she had the same stuff in her yard. It made me realize where I was in the birth cycle. It made me humble and realize maybe there’s some luck that plays into this where I was born because I get to make these choices. My landscaper speaks with an incredibly thick accent. He comes from a shitty part of the world. He’s an incredible guy. He doesn’t get to make these choices because he survived. He doesn’t read this either. If you are reading this or if you are in this spot and thinking about this, you have great fortune, and you get to make decisions. You don’t have to.

On that note, it would be a good time to quit this episode.

It’s a good thing we didn’t quit.

I’m glad we did this episode.

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