LMSM 72 | Bad Day


Managers are always on stage. Like it or not, we model behaviors that others emulate. When we are enthusiastic and positive, our teams follow along. And when leaders disengage, it feels like a rainstorm gathering over the office. In this episode, we break down a particularly bad day for Frank and how he snapped himself out of it.

And as a bonus, we dive into a ridiculous example of excess as Frank’s frustration drives him to fly private. How did he book the flight? Where did he fly, and just how much does it cost to book a private jet?

Watch the episode here

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Can Managers Have A Bad Day?

Plus: How To Fly Private If You’re In A Pinch

Frankie, are you okay?

I’m fine, Ian. I had a temporary moment of depression.

I’m worried about you and it sounds like you’re having a tough time over there in that voicemail you left me. Leaving voicemails, especially on personal cell phones is out of style. I almost get no voicemails from anybody. Normally, they’ll call and when they go to voicemail, they’ll text me and say, “Call me.” I get voicemails from Frankie, my parents and Jenny’s dad. That’s about all I get voicemails on my cell phone.

I look forward to Frank’s voicemails because he puts a lot of heart into them. We have this thing. We’ve been doing it for many years. Normally the ones Frank would save were almost always at 3:00 AM and I was hammered and sending him something. Frank’s voicemails are always hilarious. He’s normally telling me about some obnoxious thing that happened in his day.

If you look in my voicemails on my phone, 80% of them are Frank Cava voicemails that I listen to when I need to get a little pump up. I get a voicemail from Frank that is depressing, where he sounds like he’s standing on the edge of a bridge about to jump off. It makes me worried. Frankie, what was going on with you that would get you so down to leave that voicemail?

I’m pretty positive. You caught me at a bad moment. In all seriousness, there was something in there that is worth noting. We were changing around some things that we’re doing in the business. We hired after COVID, a bunch of remote folks who are working for us. We ended up letting a group of people go. Between December 31st, 2021 and the 15th of January 2022, we let 10 people go where 2 people turned over on their own. It’s not an insignificant number. The first time I ever went through reduction force, one of our buddies, Kenny G, said, “If this doesn’t impact you, it’s time to hang it up and do something else.”

Whenever you’re ending someone’s stop in firing them, it sucks. It’s awful. You get excited for the upside of bringing someone onto the team. The other side of that is letting people go, which isn’t fun. I like to build. I don’t like to tear away. That was part of it. I had some executive turnover and then I’ve got six new people reporting to me that weren’t reporting to me before. I had to get back into segments of business that I haven’t touched in a while. These people require guidance so we need to listen to things and go through them. Ultimately, it’s going to end up where it charges me up. You caught me among those moments for I was beaten and exhausted.

You’re hiding behind the veil of running a business. What you’re not telling our loyal readers is that part of your bad day is that you had spent a week eating grandma’s meatballs. You had thrown away two months of hard work with your trainer. You’d gotten off a scale and then called me back. Do you want to be honest with our readers and fess up to what was going on that day?

I love it whenever I hang out with Jenny and she’s like, “Ian was in a bad mood.” I’m like, “Why is that, Jenny?” She’s like, “He had a bad weigh-in.” Keep the scale away from him.

It can throw my whole week off when I have a bad weigh-in.

It’s January of 2022. It’s cold and dark. There’s no sunshine. You did bring up the thing about grandma’s meatballs. Somewhere between the 37th and the 38th meatball, I was like, “This could be a problem. I may come to regret this.”

You’re not going to be better if you’re always thinking you are the worst. Click To Tweet

You were up in the Boston are? How long were you up there with your family?

It was 5 days but plenty of time, just eating 40 meatballs.

It feels like 50 though. You’re up in Springfield. There’s nothing up there. There’s nothing to do other than eat. It’s cold. There are not a lot of places to go see with the kids

The whole story is this. My grandmother’s older and her house will fit a lot of people. We used to pack twenty people in that house. People are sleeping on couches but we’re all married. We all have kids and are older. I don’t want to sleep on a couch. It’s hard to do that with two kids. We had to move somewhere else. We rented this whole Airbnb and got the whole family in it, which was great on the surface.

The other piece of it that’s interesting, Ian is not being a grandma’s house was depressing. It was nice. It was still Springfield and Christmas but it wasn’t as much fun. There’s that side of it. I ate all the food. I did mention the meatballs. My wife is mostly a vegetarian. Somewhere around her 4th or 5th meatball, she looked at me and goes, “These things are divine.”

I’ve not had grandma’s meatballs. I’ve heard Frank talk about it a lot. When our son was born, IJ, Frank came down with these two platters of her eggplant parmesan. You made grandma’s sauce. This sauce was so freaking incredible. I remember the meatballs and parmesan were great but I remember the sauce more than anything. We made a ton of noodles the next two weeks and put her sauce on it. It’s out of control. If I were there for five days around grandma’s cooking, I could see where I would come home feeling slight bloated.

You feel like you’re leaving money on the table, Ian, if you don’t get every square inch.

You’re not going to get that food for a year so you’re like, “I got to get all this in.”

These moments are dwindling. We’re Italian. We show our love through eating so I ate, Ian. Like Old Tom Joe would eat pork until he won’t pork anymore, Frankie ate meatballs until the meatballs were done.

Frankie, talk about when it was time to go, you couldn’t get out of there fast enough.

Airlines suck. There’s no other way to say but airlines blow. I booked these flights in August of 2021. I booked early. I’ve got two young children. I have a wife who’s militant on a sleep schedule. It took us a week to come up with this strategic plan. We pick the perfect time to fly out of DC, which is a two-hour drive for us. We were going to fly out of DC so it was a direct flight. We were timing naps and threading all these needles. Everything was to a T. The way home was the same.

LMSM 72 | Bad Day

The Snowball: Warren Buffett and the Business of Life

United decides to move the flight from 12:40 to 10:30 AM. If you’re single or you live 30 minutes from the airport, it’s not a big deal. When you’re married with a wife breastfeeding, have a bunch of crap to carry, stuff to lug and kids on schedules, that two hours is a big deal. It went from, “I’m going to get up, have a personal training session and have a cup of coffee to work.” We’re on red alert at 5:30 AM. I get the kids out of bed early. It’s this whole thing. It turned out fine. We got the kids in the car. It was not the end of the world. It worked out great. We pull into the airport. It was a pain in the ass but mostly eventful.

When it’s time to come home and do it, United moves our flight. Our flight was supposed to be at 10:40 AM. They moved to 8:00 AM. We planned around that, “We’ll get the kids up at 5:00 AM. It’s going to be a pain in the ass. We’ll be fine.” They move it to 10:40 AM, the following day. We no longer have a house or anything. It’s all over. We have no place to be at.

I have an assistant. I’m not calling her the day after Christmas and saying, “Will you go deal with United?” I’ll feel like a jerk. I’m second cousins to Satan if I call her up and have her handle that. I’m like, “I’ll do it myself and bite the bullet on this one. I’m sure it’ll be fine.” I’m on hold with United for 1 hour and 45 minutes. I finally get someone to answer who’s clearly from overseas. He asked me two questions and then hung up on me. I go apoplectic and find my wife. I’m like, “That’s it. Fuck it. I’m not doing this.” I went to Google. I googled “private flights.” I was on the phone with someone within a few minutes. Within eleven minutes, I’d booked the plane.

What did you type into Google?

I googled “private flights” and where I wanted to be. I found somebody who was close. What ended up happening was while that was happening, I was like, “This is a process. They got to shop and get back to me.” I texted one of my buddies who live in Pennsylvania, who flies private from time to time. I was like, “Who did you use when you flew to Florida?” He goes, “This guy.” That guy and I were on the phone between fifteen minutes of, “I have this idea,” to texting that guy and getting him on the phone. I was booked in fifteen minutes.

What does it cost to fly private with a family of four?

More than you think and certainly more than he estimates.

Did he estimate? When do you pay?

Here’s a couple of things about private. Number one, it’s great. I’ve never done ecstasy. I’m told it’s amazing. I’m pretty positive flying in either ecstasy or black tar heroin is all as good. The whole reason I never started doing drugs is that if I do drugs, I am never going to stop. It’s the same way I never wanted to get on a private plane. We’re on the plane. My wife looks at me and goes, “You’re never going to want to go back.” I’m like, “Nope.” It’s cost-prohibitive. The point is when you rent the plane, you got to do a few things. You do this all through Venmo. The first thing you do is wire them money for the pilots. I had to wire them $1,200.

Does that lock in the pilot? They need their cash upfront to say, “We’ll book ourselves. You can book me?”

The first thing you do is lock in the pilot. The second thing is where I’m starting to learn these things but I didn’t know it. They have to fly from Pennsylvania to Hartford where I am to pick me up. It is your responsibility to pay for the gas and also to pay for the docking in Hartford. You know when you get to a crappy terminal and someone’s rude to you with Delta or your airline of choice? In the private world, it’s very different. They’re nice, even in Hartford which is a toilet. The Hartford private airport is incredible. You walk in there and it’s nice. They saw my son and asked him, “Would you some cocoa?” My son’s like, “Yeah.”

If you're the person sitting there worried about losing your job, it's going to happen. Click To Tweet

More important too, with private is you don’t park where everyone else parks. You don’t park in a major parking garage. You have a little lane that pulls off before all the madness you park. You park right next to an office building, you walk in and they’re nice to you. You are on the plane within two minutes of the exit. It’s so fast and outrageous to be on the plane.

I wasn’t sure I was in the right place. It’s the only reason I got out of the car. I brought Max in with me because he was sitting in the car and was irritated. He came in with me and they’re like, “Give him cocoa, get back in the car and drive on to the tarmac.” I drive onto the tarmac. I’m traveling with two kids. They take all of my crap out of the car and put it in the plane. The man said, “Will you hand me your keys?” I said, sure. He goes, “Who did you rent from?” I said, “Hertz.” He goes, “No problem. I’ll return it.” It’s like, “Are you kidding?” He goes, “No.” That all happens and then they’re like, “One last thing, you got to run inside and pay for the gas.” That costs $900.

How many Venmo’s have you sent? You sent $1,200 bucks. They needed money for gas, the docking and all that. Did you have to pay a second time then?

Yes, but I used my credit card for that one so it was $1,200 plus $900. We get onto the tarmac. Everything’s loaded. I pay that entire exchange, including a bathroom visit, which you knew I needed. It took less than six minutes. They’re like, “Buckle in.” Ellie’s like, “Where do we sit?” He goes, “I don’t care. There are eight seats, pick whichever ones you want.” Max sat in front of me with his iPad. Manny was in her lap on a carrier.

Did you mix yourself a bourbon since you paid for it?

I should have but I didn’t. The thing I did do, Ian, I walked on the plane with a bottle of water. Do you know what happened? Nothing. I got to drink it.

When you fly private, there’s no security. You just walk out with your bag. You don’t go through a line. There’s no checking of tickets. They have your name at the desk. You walk in, say your name and walk right back.

My wife and I are both in clear. They’d let anybody on but they check you if you’re on that. We fly through a snowstorm. The pilots are nice as hell. This whole thing is incredible. It’s a small plane. It’s not a jet. It matters because of the amount of time it takes and the winds coming into play. We go up. It’s a normal flight. We land. We’re in this teeny tiny airplane at Washington Dulles Airport, which is one of the busiest and biggest airports in the entire world. We pull off to another private terminal, walk up, people usher us in and they blocked the plane. All of our stuff was taken off of the plane. They help us get off. They put our stuff on a cart and start pushing it. You walk inside. This is Washington DC, which is a major metropolitan. Dignitaries, politicians and big-time deals use this terminal.

This terminal is gorgeous. It’s like walking into a hotel in Vegas. There are fifteen TVs and lounges. The most incredible thing is some people are nice. I’m like, “I don’t know how to handle this but I parked with the commoners because I flew out commercial. I need to get my car. Should I Uber or jog? Can my wife stay here?” They’re like, “The kids and your wife can stay here as long as they want. No rush. We’ll take you.” I’m like, “Pardon me?” You can’t get someone to help you lift a bag. On the other side, they got me in a car, drove me to my car, made sure it started, gave me a thumbs up and then drove me back. When I got back, I had to pay for more gas. Everything I had to pay for was more expensive in DC. It was $1,300.

What was the total all-in?

LMSM 72 | Bad Day

Bad Day: When you invite someone to work for you, you are also making a commitment to their spouse and children. It’s your job to keep those checks keep coming.


The adventure is not over. The plane has to fly back from Pennsylvania.

You’re paying for that flight, the gas and everything going back? Could they go right back to the airport they started at?

He flew back and told me it was $1,500 bucks a flight hour. He’s like, “It’ll probably be 2 hours, maybe 2.5 hours.” It turned out it was almost four because of the winds. He’s like, “The pilots said you and your family were very nice. I’m going to take $100 an hour off.” I’m like, “Awesome.” Ian, it’s probably $9,000. Here’s the best part. My wife’s like, “Frank, hurry up.”

We had this incredible experience but my youngest son needed to nap. I knew that portion of my day was over and I had to hurry up and get gas in the car because I had two hours to drive home. I needed to get a sandwich from Wawa because I was starving. The only thing was she’s like, “You got to get in the car by this time because we got to make sure he falls asleep.” We go through this incredible thing. I have a sandwich from Wawa which fires me up. I spend four hours driving home.

I live close to the Dulles Airport. It normally takes me about an hour and a half to get to Frank’s house down to Richmond when I leave at a normal time. You can get some shitty traffic before. You pay all that money to fly private but then you get stuck in a car with kids for four hours.

By the time we get home, everybody wants to kill themselves anyway.

It’s almost better you weren’t boozing up on the scotch with a four-hour drive ahead of you.

That was the main reason.

I flew private with NVR a couple of times to small airports where I would go with one of the executives. It was never terribly exciting. My favorite private experience was a good friend of mine who also invest with Frank and me, Tim McHenry, who started a restaurant chain. It’s quite large to the point where he has his nice jet. He calls me one night and had a few glasses of wine. He’s all fired up and he’s like, “I miss you. I’m going to fly out there and we’re going to go somewhere.” I didn’t even call him. The next day, he calls me back. He’s like, “Did you get my message?” I’m like, “I didn’t think you were serious. I thought you had a load out and having a good time.” He’s like, “No. We’re doing this.”

He flies from Chicago in his jet to Dulles. He has a driver waiting. He gets in the car because he’s never seen my house. He wants to see my house. He drives 30 minutes to my house in Vienna. He sees Jenny, the kids and my house. He hangs out. We have a glass of wine. His driver is waiting. We get back in. My friend is very rich. There are levels of rich where I’m like, “I feel poor.”

We get to Dulles. It’s the same. We zoom right through and get right on the plane. I didn’t even pack anything. I’m in a shirt and jeans. He’s like, “We’re going to Philly.” I’m like, “Why Philly? What are we going to do there?” He’s like, “I’ve never been to Philly and I want to see the Rocky Statue.” I’m like, “That’s why we’re going to Philly?” He’s like, “Yeah. There are some good restaurants.” We fly, drank a bunch on the way there and land. He’s got two pilots. He knows these guys and he’s like, “Go get me my buddy some Philly steaks.” They’re like, “What kind? Pat’s is popular and so is Gino’s.” He’s like, “You go to Pat’s and Gino’s. Get us a bunch of them.”

The only thing you can do during challenging business situations is to be real. Try not to put up a shield and be corporate. Click To Tweet

We take a car, have dinner, see the Rocky Statue, take pictures, come back and two dozen Philly steaks are waiting for us. These guys have gone and got our Philly steaks. We flew back. I left my house, Frankie, at 5:30 PM to go to the airport. I was in bed at 12:00 AM. We had an incredible dinner. I’d come home with all these cheesesteaks to give my kids. I was up at 7:00 AM like it was nothing. That side of the world that flies private, it’s amazing what is available to that elite group of people that can do it. I would travel a lot more if I didn’t have to deal with airports and the way they treat you in airports. Compared to that experience, I’d be on a plane all the freaking time.

It’s a completely different experience. The best thing I can summarize it with is what they said in The Snowball, the Warren Buffett book. Warren Buffett asks somebody, “How do you justify having an airplane?” He goes, “Warren, you don’t justify it. You rationalize it.”

Especially a guy like that who’s got businesses all over the world. The amount of time that would save someone like him getting around is incredible. You go through this miserable travel experience that you’re dealing with. You come back and got a key executive who’s out. I’m still trying to unpack your voicemail. You are the owner of a company. Let’s talk about laying off ten people. What’s going on in your business that precipitated making that move in the first place?

I was asleep by 9:15 PM on New Year’s Eve. Ellie was like, “Can you stay up until 10:00 PM?” I’m like, “Yes.” Out cold. The next day, I wake up and good friends of ours come over. I make a cioppino and it was delicious. It didn’t help me with the weight. We had eight bottles of wine. I’m pushing the weight limit even further but the holidays are a lot of fun.

Reality sets in. Private plane and New Year are over. It’s ice-cold in January of 2022. I’m fat again. I got to lose the same 15 pounds that I’ve been losing for the last decades. The reality of it is I kick the can down the road on some people because I want to get through the holidays. It’s come up and it’s time to get serious about what we’re doing. The plan with the staffing changes was something that I knew about. I’ve been thinking about it for a significant time.

It’s a nonsense move to lay off a bunch of people before Thanksgiving or Christmas unless you’re a big heartless company but that’s not something a small company is typically going to do.

We waited until the New Year. In the New Year, I no longer had this executive whose last day was December 31st. I’ve got new people reporting to me. I’m looking at a whole bunch of new things I’ve got to deal with that I haven’t touched in some time. The harsh reality of it is I’ve got to let a bunch of people go and it doesn’t fit well with my grain. It works against me. I was in a shitty space. People talk about how incredible it is in a business. The Warren Buffetts of the world that fly private all the time, not once in a while, comes with the cost that strains the ever-living shit out of you. That was one of those moments where I was tapped out.

I’m pretty sure I called you on a Friday driving home. I don’t think I made it to 9:00 PM. I was asleep on a Friday at 8:45 PM. I have beaten the hell. I was super tired, emotional and drained. At the end of it, the thing that’s important to note is I’m the one who still had a job. I needed to go through this and do this to other people. Ian can tell you this. We did an episode about raising money. I didn’t go out and raise money until I knew I could pay people back. I didn’t go out and start hiring people until I knew I couldn’t pay and employ them.

For the first four years of Cava Companies or Cava Capital back then, it was me and a bunch of VA’s or temps and 1099s because it’s a big responsibility. When you look someone in the eye and say, “I want you to come work here,” you’re not only making a commitment to them but you’re making a commitment to their spouse and children. You’re entering a contract. It’s your job to make sure those checks keep coming. That’s not something I take lightly. When it flips and I need to let people go, I understand the gravity with which the decision is. It’s not something to be taken lightly. It has a drain because that’s not my comfort zone. My comfort zone is the growth side, not this side. It’s very hard.

When you’re the decision-maker or the boss, the higher up you go in a company whether it’s a big company or you own your own company, it’s a lonely place to be when you got a lot on your shoulders. There are not a lot of people in your company that you can talk to. When you’re worried about your business and you’re down, the last thing you want to do is go vent to people who work for you. They’re thinking, “Why do I want to be here if the boss is feeling that way?”

LMSM 72 | Bad Day

Bad Day: It’s a lonely place to be at the higher up of a company when you got a lot on your shoulders.


I always felt this way as a Senior Executive. You were having a day and left me that voicemail. I couldn’t have many days like that. If I was feeling that way, I had to find a way to quit dragging my ass around no matter what. If my boss was on the rampage, I felt like shit, I had things going on at home or I hadn’t slept in two weeks because I got two little kids at home, I couldn’t go down to Richmond in the office or to Orlando, sulk around and feel bad for myself.

When they saw me, they had to see energy, excitement and enthusiasm. They had to see a guy that loved his company, loved his job and believed in the mission. Even if I woke up not feeling any three of those things, they had to see it. I always had to find outside of my organization because I couldn’t vent out to people. A lot of times, if your boss is the reason you’re feeling that way, you can’t vent to him about it. I would have to surround myself with positive people outside of the company or positive messages. What were the books I was reading? What were the podcasts I was listening to? I always leaned on you for perspective when I was feeling crappy.

You’ve always been great at helping me see like, “You come to do what I’m doing. You know what I’m doing now?” You’d tell some joke about what it’s like to start a company and get your ass kicked around. It would give me perspective and make me feel better. For me, I have a great wife who’s good at this. She could tell when I was leaving the house looking like that. She’d be like, “You all right? You sure you’re going to go to that meeting in that mood?” She’d be good at calling me out on it or I’d be like, “I got to get my shit together. I’m going in front of 30 people. They need to see someone different.”

It’s like a football game or in sports. You might not be the most confident now because you’re in a slump but you’re not going to be better if you go into that game thinking you’re the worst. You need to look in a mirror and convince yourself, “I’m going to have a different game.” When I heard that voicemail, it was funny because when I called you back, I was like, “You all right?” I wasn’t overreacting to you being miserable. What’s funny is before that, Frank was like, “This is great. We’re going to do more of these deals. Let’s get down and do dinner at Naples.”

I get this voicemail and it’s like, “You can send an email to the investors or not. Send some checks.” I’m like, “What is going on with Frankie?” I had done that to you right before we did the investment. I was like, “Frank, I might be out on everything. Maybe we’ll stop this.” You call me and you’re like, “What is wrong with you?” I was like, “I don’t know. I’m having a bad day.” It’s good to have positive influences around you that can call out that behavior and remind you of it like, “Things aren’t so bad. You flew private. You know how many people would love to do that?” Have a laugh when you go through it.

The thing that was causing the stress is I turned over a high-powered executive for this company. That’s hard to do but people leave. People have other visions, goals and desires. It’s the right thing for them but a pain in the ass for me. What happened is a retrench. I’m digging in and seeing things. I’m getting excited about things. I wasn’t excited then. At that moment when I left you that voicemail, I wasn’t anything. At the same time, that’s where I’m getting to. I’m seeing things, feeling them, touching them and getting new people involved. That’s all growth. That’s exciting and positive stuff that comes from it.

The day that we let a bunch of people go was awful. It was a terrible day. There was someone in there stealing. That was easy but everybody else was harder. Carla knew this. I’m like, “My schedule is free starting at 1:00 PM.” She’s like, “What are you going to do?” I’m like, “I’m free at 1:00 PM. Don’t schedule it. I’m leaving at 1:00 PM.” Will come back here and goes, “It’s almost like a mantra. You keep telling us you’re going to leave at 1:00 PM.” I say it all the time. I don’t do it. I walked down to Eddie’s office and said, “I’m going to see a movie at 1:20 PM. Do you want to come with me?” He goes, “Yeah.” We got two big buckets of popcorn and sat there. I don’t know about him but I cried like a little girl. I saw American Underdog: The Kurt Warner Story. I felt better and I left. Whatever was bullshit was gone.

I was home by 5:00 PM. My son said, “Daddy, will you get on your hands and knees and play with me?” I did. The next morning I delivered a message to my team. I told my team, “This is important. I want to deal with this head-on. We went through something somewhat traumatic. We needed to do it.” I explained the reasons why and I told the story. I’ll tell you the story now. In 2006, home billing sectors are getting decimated. I drive an hour from work. Nobody showed up at my office. It was in the middle of nowhere. It’s in cold weather Virginia. I get to my desk at whatever time I was supposed to be there.

I walk in and my boss is at my desk. My heart is in my throat. I take one more step and I realize his boss is at the table next to me. I look at them and freeze. He goes, “You’re fine. Close the door.” I closed the door and I looked at them like I just pooped. He giggled and it was Kenny. He goes, “Take a seat.” He explained to me what was happening. He told me, “We’re closing this division. Your job is fine. We’re letting a bunch of people go.” What I told my staff is, “This is the moment. You’re fine. Take a seat. The people we need to get rid of are gone. This is the direction. We got thirteen people we’re hiring in the next months. We’re growing and in a great cash position.”

I went through all these things. I said this, “This is not the moment to be freshening up your resume. You’re here because you’re doing a great job and I see a huge future for you. What I think at the moment is you to do an incredible job at your job. What we’re going to notice is your performance and this is what spurs other opportunities.” That’s how I handled it. I told that story and got a bunch of texts and feedback about it. Those are things that you must do. It’s a hard conversation. You got to get through that moment.

The other thing is I had to reset my head. I’m not taking it not seriously because I went to a movie but I’m a mess. I needed to go somewhere and check out for a few minutes because I’m a dad and an employer. I needed to be right. I went home. I was in the right mindset. The next day, I delivered the right message, “We’re building from here.” Those are the things you must do. People don’t tell you to reset. The last message I left for Ian was way more upbeat than that one because I got my head right.

If you want to lead people, find a way to get your mind right. Click To Tweet

The downturn of the financial crisis started for people in the real estate industry peaked in 2006 staffing-wise and sales-wise. A lot of people when they think of the financial crisis, they think of 2009. We started going through it three years before it. My region, in particular, the Virginia-Maryland region at the peak, had 8 offices and 260 people. I came into 2009 with 60. When I manage people, I know their names and their wives’ names. I know that they have kids and what their kids like to do. These are all people that I had hired and I had gotten to know well.

I didn’t lay all of them off. I didn’t have a conversation with all of them because there were so many going on. You couldn’t go around to every office. The suspense and stress would build. You had to coordinate it so that chunks would go at a time. It was a stressful time. The number one question everyone would have after a layoff especially during that time was, “Is this the last of it?” I don’t know if you remember that but I remember that question every single time. When I would pull everyone together, they would say, “Is this the end of it?”

The worst thing you could say there is, “We got it.” That’s a lie. Our sales are plummeting. You have to say, “I have no idea. I don’t know if my job is safe. No one knows anything. What I do know is us sitting around worrying about it is going to make us all perform worse. If you’re the person sitting there worried about losing your job, it’s going to happen. The only thing you can control is kicking ass. If this thing goes down another, here are the criteria we made.”

“Production, positive attitude, good teammate and leadership. Do you do more than the other people? Do you make your teammates better? If you control those things, you’ll be one of the last ten standing out of this whole region. If you can’t do those things and all you can think about is, ‘Am I going to lose my job in the next round,’ it’s going to happen. We have to make decisions.” I always looked at it like, “I have 260 people. If I’m going to have 60 and I’m going into a dark alley with only 60 people, lean and mean fighting machine, who can I take?”

It’s going to be my absolute best. The people that can do lots of different things. The people never say, “That’s not my job.” The people that are willing to jump in and do someone else’s job when we’re running lean and someone doesn’t come into the office. Those are the people that stay. All you can communicate to people when you do lay off is, “Here’s why we decided to keep the group we have. The people in this room that demonstrated these behaviors, that’s who we’re going to continue to keep. It’s people that produce and then have these behaviors. I can’t tell you if the market’s going to go up, down or stay flat but I do know that when I have employees, here’s who I have. These are the people that I value the most.”

That sucked. I had to go to Gaithersburg, Maryland and shut an office of 30 people. I kept 3 and had to tell 27 people in 1 day that they were gone. It was awful. It was just me. I didn’t have any help. I went up and told the three that were staying, “You can stay or leave. You can keep working or get out but this could be a bloody day. There’s going to be a lot of tears.” I called people in one by one. By the third person that I laid off, they were all crying when they came in.

You could say, “Why didn’t you pull all 27 together?” I was young. If I had to do that again, I might do that. I felt like they should all hear it directly from me. I look them in the eyes and tell them why they’re not staying. It was a shitty day. It took 3 hours to get 27 people through my office. Some people were like, “Screw you. Give me my papers,” the second they walked in. Other people were crying, “Why me? I’ve been doing a good job.” It was an awful day.

That does sound selfish because for them it was a lot worse day but Christ, it was not a fun day for me because I liked those people. More than half of them, I would give a glowing reference letter to. I didn’t have any work for them. We weren’t selling any houses. You don’t pay $100,000 for a loan officer when you don’t have any houses to do a mortgage on. “Sorry, but we don’t have work for you.”

We started this as a joke but you need to realize a couple of things. No matter what you’re going through, someone else is going through something else. I was having those rough days when I left you that message. My son doesn’t know that and neither of my kids realized dad’s having a tough day at work. There’s no time for it at home. You must have friends that you can talk to about it. That’s part of it. You’re going through a shit economy and we’re going to go through one again soon. It’s pretty strong.

Ian and I were talking during the pandemic about how many jobs were getting cut. It’s usually measured in numbers around 100,000. Fifteen million people were fired in one day. Those are astronomically big numbers. It’s those moments like that where your company is going through a restructure or something happens. I have a friend who’s an alcoholic. What he says is that all you can do is control the controllable.

To that point, if you’re going through something that’s seismic and your industry is being affected, you’re probably going to get affected. There are always the last people off the boat. The people who were the ones off the boat are the ones who control the controllable. The one who does the best job, performs and give the best metrics are people you want to have on the team. Our office manager and my chief of staff said on the call the day after we did this, “It comes down to how you’re doing. Are you doing a good job? This is a sad day but it’s one of those things where we know those people should go and we have the right people.” That’s coming from someone, not me, who gave a voice.

The other thing I’ll tell you is a fun story. It sucks but it’s got a funny twist. We were on our fourth round of layoffs. My division went from 75 to 23. Every time there was this kid, everybody loved. He was right on the line, every time. Somehow or another, we always kept him above the line. Finally, his number got called. There was nobody else left. He walked into my office. He had his hat pulled all the way down to his eyebrows. You couldn’t see a thing. I looked at him and said, “Buddy.” He goes, “Frank, you kept me into the end.” He gave me a huge hug and he goes, “I know it was you.” For a second, there was a little bit of levity. I still text and call that guy. I haven’t worked with him in many years at this point.

LMSM 72 | Bad Day

Bad Day: There are people who are willing to jump in and do someone else’s job when the team’s running lean. Those are the people that stay.


The same guy that I’m talking about that we went to Philadelphia with, when COVID hit, the state shut his restaurants down. The choice was bankruptcy or getting lean and cutting a lot of people. He had to have a call with over 1,000 people to tell them that they no longer had jobs. “We have to change things. We got to figure out how to deliver food.” He called me the day before and was like, “Ian, what do I say?” I was like, “I’m not going to tell you words to say but all I can tell you is the more genuine and authentic you are about how you feel about this, the better they’ll accept it. You have to tell them how you feel and why you had to make this decision. The only thing you can do in a situation like that is to be real, not try to put up a shield and be corporate.”

That’s where people get into a lot of trouble. Be real. Be yourself. You were yourself when you hired them so be yourself when you have to make decisions that are this tough. He went through a real funk there for a while where he was struggling to keep himself positive. I was talking to him a lot more than I normally do. Not just me, there were a few of our other friends that were calling me, “Have you talked to Tim? He’s pretty bummed.” I’d be like, “I talked to him a few times.”

He was reaching out to people outside of his company because there was no one for him to talk to within his company. He was trying to get perspectives to pump himself up to get energy. That’s what leadership is. If you want to lead people, you have to find a way to get your mind right. I worked for someone who would go through months-long sulk. It would cast this pale over the whole organization where a dark cloud would go over the organization because he was in one of his moods. He would go 4 or 5 months where he was the happiest. It was this bipolar, crazy situation.

It would wreck the organization when he was in a bad mood. It would rumble all the way through. What you have is you lose a lot of people on the front line because they’re the ones that have the least to lose. They’re like, “Screw it. I’m not putting up with it.” Executives like me, I got stock options and handcuffs to the company. I have to deal with it. As you get down the line and there’s less and less staff to deal with, “Peace. I’m out.”

He couldn’t control it, put on a face and get his energy right. It would then go through the whole company, which is the opposite of Billy, the Founder. When he was in a bad mood, you caught it like crazy. You woke up in the morning and it was like it never happened. He was like that old Adam Sandler movie with Drew Barrymore where every day she wakes up and doesn’t remember the last day. That’s how he was and I loved him for it.

He never took a bad day or a bad conversation with me into the next day. It was always starting over. He had a goldfish mindset ready and the five-second memory. He made his point and moved on. He wouldn’t let it cast over his organization for a long time. Kudos to you, my brother, for not letting a couple of bad weigh-ins, bad flight and some issues in your business linger on for months because that’s only going to make it worse. It’s pretty cool that you’re back smiling and having a good time.

I’ll leave you with another quote from a movie. Ferris Bueller once said, “It is so choice. If you have the means, I highly recommended it.”

It’s great talking to you.

It’s always a pleasure, Ian.

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