$800M Exit: “Shoveling Shit” in Business and Marriage

31:41That's right. And especially with mental health, even more than physical health. I think people are doing better with physical health, but mental health is so scary, so unfamiliar to so many of us. And I know you've mentioned it in your previous interviews that you have each of you dealt separately with mental health diagnosis. And would you mind sharing how you embrace that, how you dealt with it through the whole journey? Absolutely. I'll start with, I've had anxiety and bouts of depression my whole life. It runs in my family of origin. And my symptoms are of, I will start to do more and more and more and more.

32:24That's like a coping mechanism for me. is, like you said, I never wanted to be comfortable with the feelings of being anxious. And so over time, and we're talking like 30 years of working on myself, I've learned to embrace it and then understand what are more positive and more impactful coping mechanisms, right? Because you don't want to be doing more of the stuff that actually increases your anxiety and decreases your mental health. So, um, you know, that, like I said, all the tools that I've mentioned before, but the mental health thing is really scary because it can paralyze you. And the more and more you can get comfortable with, uh, you know, not being shameful about it.

33:11Like I've had, I don't know why, and Mike, maybe you can agree with this or not, but I've never really been ashamed of my anxiety. I've tried to use it as a superpower. And when it's not being used for good, that's when it gets in the way. That's when I know it's taking over, if that makes sense. And I've got to step back and kind of concentrate more on it. So how do you reframe your anxiety as superpower? What do you tell yourself? So the way I've thought about it is, and I think I tell a lot of college kids this, right? I talked to my two sons, you know, friends, is that everybody's got strengths and weaknesses, right?

33:57You're born with whatever it is that you have. And there's a reframing of how you can look at something. My anxiety of trying to make sure that I understand the path and what is the most efficient way to move forward and how do I rally teams to move forward, that is a gift. But my mind could continuously think about the different paths, right? So I chose purposely. And I think mindset is a choice, right? So you have to start to choose how you think and you have to choose what you're going to reframe. So it's not always been like, how do I reframe something? It's the act of reframing that actually has made things better.

34:45Yeah, makes sense. Mike, I heard you mention that you also reframed your ADD as superpower. How did you do that? I knew my brain was different. If I'm very interested in something, I go down a rabbit hole. I can't stop thinking about it. It overtakes my life. If I'm not interested in something, I just don't pay attention. And that was my life experience at school, where if I was interested in a subject, I did great. If I wasn't, I didn't really pay attention. I would forget stuff. And it became even more disastrous in relationships where, you know, it would manifest itself in that I was not always present.

35:27So I was I'd be talking to someone, usually Cass, and what she needed, what she was experiencing wasn't necessarily landing. And so as kind of I was diagnosed shortly after we were married, a lot of things clicked and basically said, oh, yeah, that's how my brain works. And I need to compensate and I need to kind of feed my brain and be proactive and not reactive. And part of the mental health journey for everyone is, I think, understanding how your brain operates and everyone's different. And, you know, some of the smartest people I know have a very busy and noisy and high powered brain that is hard to deal with.

36:15And many of those are entrepreneurs. I also, you know, I spoke about kind of my heart issues earlier, but I also was taught about mental health very early in life. My dad was an entrepreneur and shortly before my 13th birthday, he, you know, had a complete mental breakdown due to a severe cash crunch in his business. And, you know, I was both angry, bitter, and confused as kind of a young kid. But as I kind of have reflected, you know, I learned just this important lesson that, you know, entrepreneurs have mental health challenges that are the combination of a lot of factors that others don't.

37:10So when you think of like what causes people to really worry, it's money issues, it's relationship issues and it's health issues. Yeah. And many entrepreneurs who are facing kind of running out of money, you know, underwater and debt, they start to not only feel the financial pressures, but it seeps into relationships and ultimately their own health, which is what happened to my dad. He bounced back and, you know, was fined and helped others with their mental health struggles. But mental health has been, you know, for at least 30 years of my life, kind of, I've been aware of it in a way that maybe, you know, another generation before me would not have been aware.

37:57Yeah. Yeah, there's obviously really scary statistics about the mental health issues among entrepreneurs. And I've tried to find any statistics specifically about people who had successful exits. I couldn't find any. But my own observation in the last 13 years of, you know, working and meeting lots of post-exit founders is that those rates are even higher. Like if I just look at my podcast guests, like everyone has an issue. There is always something that they have to overcome. So I'm thinking that in overcoming those issues, in understanding ourselves better, we probably actually become better entrepreneurs.

38:43If it doesn't... If it doesn't kill us. You know, yeah, I mean, you know, as you're talking, I'm thinking about Tony Hsieh, who, you know, Web 1.0, So, you know, I got to know and then, you know, here's a guy who sold Amazon for over a billion dollars. He, you know, revitalized downtown Las Vegas, very wealthy guy. Last time I was with him full of life, you know, was at the Vegas Golden Knights hockey game, which he loved the Golden Knights. little did we know under the surface for this guy whose mission in life was to create happiness exactly he was being eaten inside and i think that i we write about this in the book because there are i don't know the numbers but a hundred percent of entrepreneurs that i speak to the you know you speak to entrepreneurs and it usually goes like this hey how's everything going We're crushing it.

39:45Never been better. I'm like, great. Tell me like, you know, how many employees I, I'm like, are there any issues that I could help out with? Well, I got this, this, this, how are you doing personally? Miserable. My husband hates me. My, you haven't seen my kids. I many days don't want to get out of bed and deal with everything, but I know I have to, And so it's like this, you know, externally crushing it and internally getting crushed, which is typical. And part of writing this book is to tell entrepreneurs that like loving to shovel shit is great and miserable. There's beauty in the suffering and you're not alone in the misery that you're feeling and the weight of your situation, which is oftentimes very weighty.

40:38let's just say. So, you know, you often talk about these sacrifices, right? Like you had to crystallize what made you feel fulfilled. I think one of the other ways that entrepreneurs need to think is, yes, there's a massive discipline in the sacrificing and shoveling. I also think the way Mike goes about things is the way to do it is to, to plan things. You can't do a lot when you're an entrepreneur, but plan things you do look forward to that will allow you to escape the current mindset of an entrepreneur. It's hard to do because, um, I'm very, very disciplined about even kind of rewarding myself.

41:25Again, I think this comes back to being an athlete. Uh, but when I don't have things to look forward to or breaks. And I mean, that has to be breaks away from the kids as well. For me, it's breaks away from people needing me or asking things of me, then it gets really tough. Yeah. Yeah. Cass, I can very much relate to it. And I have to say, to say at this point, I pretty much gave up on being able to have that discipline and I delegated it to my husband. I decided that I'll have this external scaffolding for self-care. So he's responsible for making sure I take care of myself and he gets in trouble if I don't.

42:09You know, another thing which has been kind of amazing that I learned this year was, at least for operators, because you're always looking at like everything that could possibly happen and you're kind of moving different chess pieces up the board, knowing there's going to be sacrifices. Mike and I got into fly fishing, which is kind of micro focusing. And it's allows me like this and, you know, yoga and Pilates, when you have to do something that requires very small movements, and full concentration. It's ironic, but it actually relieves you of thinking about 80 things at once. Yeah. So you know, people talk about meditation, because you're only, you know, doing one thing at a time.

42:55That's hard for someone with a busy mind. But doing these micro focusing things, or trying to get your body in different positions while you're doing yoga or Pilates, that will allow your brain to kind of heal, you know, in those moments. It's interesting that you're a golfer, and lots of golfers say that golf helps, but you're saying for you, fly fishing is better than golf, in this sense? Well, golf, what I do like about golf, There's lots of things I don't like about golf, including how frustrating it is, but you're outside. I think that's what golfers really benefit from. You know, nature is this incredible therapeutic tool, right?

43:38Because when you connect with nature, even if you're just taking a walk, things that you're thinking about kind of fall to the wayside. So golf is definitely one of those things I think people, and definitely Mike, you know, uses as a tool. But for me, it's about only doing one thing at a time, which is not something I do on a daily basis. So how do you structure your days at the moment? Like if you look at your typical day or week, whichever you prefer, how much time you spend on investing entrepreneurship versus family, self-care, fly fishing? Yeah, we work like what we do for living and how we live as we work.

44:21So we're friends with people we work with. The inbound is tremendous. So opportunities, people need help. I would say a third of my time is on that, which includes a lot of it, the, the venture business, right? And when I say a third of the time, I'm talking about like 20 hours in a day, you know, we, I get six, seven hours of sleep, but it's not uncommon for us to have dinner and then Cass is back at her desk until nine or 10. If something's going on, we says maybe half the time we then have our proactive stuff. So we're building. So that's the book. We own a healthcare staffing company. We have stuff that we want to build.

45:09So it's not just investments we made, but it's our stuff. And that takes up a portion of time. And any given day, we have close friends, family, kids, and each other that need stuff. We try not to, we try to say no a lot. Okay. We're not, I'm worse at it. Cass is very good at it. And we ask ourselves all the time, if we do this, when we look back on our life, will it be worthwhile? So when we first started thinking about shoveling shit, a love story, is this something that we're going to regret or is this something that's going to be additive that we're going to be like, wow, that was really worthwhile.

45:54And although we're spending a lot of time kind of getting the word out and connecting with people, we love it. And we think that it's going to be an inflection point that opens up tremendous opportunities that we can't even understand or identify today. And so when we commit to do something, we do it. It's our reputation. It's why we get deal flow. if we don't commit we don't do it so if we say no we say no don't you also spend because i i'm actually watching you do this a significant amount of time these days taking care of yourself and you do saunas and cold plunges every day yeah so i you know in my schedule it's a good point Um, like I worked out at 8am with Rico Wesley, my trainer of over 10 years, um, great guy.

46:51Uh, we have a sauna and a cold plunge on our deck here in New York city. Saunas have the data around sauna is I think. Infrared, right? Infrared. Really either one, just heat. It's great for cardiovascular. It's great for mental health. It's great for inflammation. And so I've been trying to do it almost every day. and then I have hobbies. Like I like doing stuff that are creative. I like creating. Mike makes bracelets and, um, you know, to kind of, we have to go into this. I like the bracelets that you make. Here's one of the bracelets. I mean, I like making, like, I like making stuff. It relaxes my brain and drawing you, you often draw.

47:35So yeah, it's about relaxing the brain. Can we talk about that? Let's not kind of share everything. Mike, but I actually do want to talk about your painting career because I know you try to focus on the full time after you exit while you're exploring what else to do in life. So could you share that adventure with us? Yeah. So, you know, after I left Salesforce, you know, I really wanted to get back to creating and I thought that painting was my future. And I really thought that like, maybe I could be a painter. Um, when you love something, but you're not that great at it, it's called a hobby. And so it's something that, you know, helped me realize that what I do for a living is create businesses.

48:27What I do for fun is create art, go and listen to music, fly fish with Cass, play golf, like a few other things. Like entrepreneurs don't have a ton of hobbies. I think I have more than most than I always have. but I think it's important. Like I forget who told us this, but imagine you have a plate and only a certain number of things fit on that plate. Be proactive in putting what you want on your plate and everything that's not on your plate, just don't do it. Yeah. So either do it because it's important to you and it's on your plate or say no to it because it's not important. and be proactive versus reactive.

49:14That's something that comes harder for me, but it's been really important. And so when I say to Cass, listen, you're not going to love this. In January, I'm disappearing for five days to go to Mexico with two of my best friends, one from high school, one from college to see a bunch of 60 year old dudes play music on the beach, Fish, the band that I've had a relationship with before I had a relationship with Cass. So, and we've been married for 25 years. That's on my plate, but I'm very careful not to do that every weekend. Right. Yeah. Mike, how do you figure out what it is you want to do? Because especially for people who go through this transition from, from their business into the rest of their lives, it's often very hard to figure it out.

50:06And I would love Cass to also talk about it. How did you guys figure out what it is you actually wanted? So I'll start, but Cass is really, you know, a better answer. I want to do everything and Cass is my filter. Okay. Literally, we had a meeting yesterday and I'm coming out of it like, let's do it. Like, I'm not going to say what it is, but it's like any other person would be like, this is an incredible opportunity. And Cass is like, you're a fucking idiot. Like, no, like just sit down, shut up. Like, and so I think like, you know, the beauty of my relationship with this incredible woman who will not share an office with me is I got all of the credit for our businesses.

50:57I was named Ernst & Runck Young Entrepreneur of the Year. I was named Fortune Magazine's 40 Under 40. Well, Cass is older, so maybe she didn't qualify. You know, I got all of the credit, but we were equal partners. Neither of us would have been able to build any of the businesses alone. And so part of writing the book was exposing Cass' behind-the-scenes work that has created the life we have today. And I think any entrepreneur who's thinking about a co-founder needs to really dial into how do you choose someone who complements your weaknesses and your strengths negate their weaknesses? So together, you're stronger and you can build a foundation of trust, empathy, compassion, respect, which only happens over time.

51:57Yeah. Like you may be friends with someone, but until you start a company with them and literally get work married to them, you really don't build an enduring relationship. And, you know, some relationships are built on interests, hobbies, religions, way of lives. Our 30-year love affair is based on just the hard work of building companies and families and, you know, homes and memories and, you know, and a life. You did mention that after the sale of golf.com, you went through a rough patch together. What helped you get out of that? Because again, this is very common after exits, right? There are so many divorces or difficult years for couples.

52:47How did you guys handle it? And are there lessons you could share with others who are going through this? I think it's cliche, but it really is communication. Mike and I have always talked about like the kitchen table. That's where we bring everything and just sit down and dump and, you know, dump it all, And it wasn't easy, right? So there's a lot of miscommunication when you get to that point. But it is about unpacking everything, listening, and then rebuilding. And I think often, you know, you forget the simple part of what makes relationships grow, and that's communication, right? And we're so good at knowing each other's lanes that when we're disconnected, it's because we haven't communicated and we haven't shared on a deeper or more meaningful level.

53:48We've checked boxes. We've told each other the things we've done. We've shared to-do lists. I'm very good at giving Mike to-do lists and priorities. But we haven't really talked about the feelings underneath it. And I think that's really how you start to rebuild. And you have to do that because, you know, I remember both times after selling the company, Mike being really grumpy, right? And it wasn't because he had to go work at Time Inc. or go work at Salesforce. You actually, I think, enjoyed your time at Salesforce and learning there because it was a different, there were different things you were learning.

54:25but he was, I think, you know, going through an identity shift and instead of, you know, I think we could have gotten stuck not talking about his feelings of grumpiness and what was causing it. And, and, you know, those start to pile up and then you think those feelings are going to last forever. Right. And both sides say, oh my God, he's going to be grumpy forever. Or Mike's thinking, I'm going to feel like crap forever. You've got to acknowledge the little feelings along the way, the mishaps along the way, so that the intention is there and then you can move forward. And then the healing, you want to heal the little cracks, right?

55:05If you think about a foundation, if you have little cracks, you want to put, you know, the glue back in because otherwise they become big cracks. Yeah. So yesterday I interviewed another amazing entrepreneur who created his business with his wife, Adam Rossi. And he said that the venture community really dislikes businesses run by couples. And I'd love to share that experience and how you handled that. Mike, why don't you tell the story about us trying to raise money for golf.com. Yeah. So yeah, we've seen everything we've, we've had investors who absolutely embraced us from day one. And we've had investors who we've made trips to Silicon Valley to pitch them.

56:01And literally we walk in and they hadn't paid attention. One in particular, a very like well-known firm and the head person, the person whose name is on the firm basically says after the first slide, wait, you're married. Like, yes. Like that's the same last name. Like we've set up this meeting. Um, we don't invest in married founders. Now, mind you, we'd flown from Chicago to Silicon Valley to meet with them. Wow. And so what I did is I didn't even respond. I closed up the computer. I said, Cass, let's go. We didn't say goodbye. We just got up and walked out. I'm sure they'd regret it. I think I said, well, I think I said to him, well, we're not changing our status.

56:58So thank you. That's definitely what you said. You know, So I have talked to a lot of up and coming entrepreneurs who are couples and doing this together. And I've always told them that, especially the ones that are in different lanes, right? I think that's how it has to be for success. You don't want like two product people, because I think micromanaging starts to happen. But it is a superpower when you meet a couple who compliments each other's strengths. And it becomes a real superpower for investors. And I think all investors should look at it that way. Because you know that this couple is pot committed, right?

57:43100 % in. And you never have to worry about work ethic, right? With a couple that complements each other's strengths and weaknesses and are running a company together. So I, again, I look at it as a superpower. So talking about superpowers, how do you think about your parental strategy in this sense? Are you, would you prefer your kids to be entrepreneurs as well? Do you want them to do whatever they want? I, what I always tell them, I mean, they've had these discussions all the time of like, how did you know you were going to do this? Like, how did you know? For Mike, I think it's a little different.

58:27For me, you know, I had to try a lot of things and cross things off and figure out what I'm really good at. So I would prefer that our three kids spend their 20s really honing what they're good at and identifying their weaknesses and then figuring out how to surround themselves with people who fill in their gaps, right? And especially with their careers, because I think they have to understand what that's like. And this generation of kids, our kids are in their 20s and our daughter is almost 18. They've lost that sense of community because of COVID and technology. So in terms of what I want them to be or not be, I think I want them to know who they are based on what their strengths are.

59:22I think that's my answer. Mike, what would be your answer? I mean, it's really the same. We've lived our life, and it's been a great life. I think we've modeled hard work and ethics that we want them to carry forward. At the end of the day, it's their life and we want them to be productive and to have purpose and to have impact however they choose to define that.

59:53And there's no pressure. Find your path and attack it. And I tell them all the time, part of, you know, college and being an early professional is learning what your superpowers are and then exploit those superpowers to the benefit of others. And you will receive whatever your goals are. It could be money, could be, you know, doing good, could be recognition, could be balanced, could be just a comfortable, just a happy life. And so it's kind of the key is like understanding yourself, what makes you tick, what you're good at. And then from there, you can figure out how you can be service in service to others, which is really what a company is.

1:00:49You know, you are providing a service or a product that will benefit others. And if you don't, it's probably not going to be a great company. And if you want to be a change maker, if you want to be a therapist, if you want to be an accountant, if you want to cut hair, all of that is identifying stuff you're good at and literally exploiting it to help others. And I often, I would add to that, I often tell our kids as well as all their friends, you don't have to know what you want to be now. Mike and I are still reinventing ourselves, right? And we plan to continue to do so. And while that may seem scary, you know, again, if you focus back and you go in as opposed to worrying about going outward and you understand who you are and you know your strengths, it's fine to not know what you want to be when you grow up.

1:01:50It's fine to try on 10 different kind of experiences in a career until you settle on what that is. And do I want them to be entrepreneurs? I only want them to be entrepreneurs if they want to love to shovel, right? If that's what gives them purpose. So how do you approach the whole crazy challenge of raising kids with wealth? It's definitely not easy and it's amplified in New York City. I can tell you that. I think we've done as best as we can do and we could have done, but it's about, you know, unlike most of, I think, our kids' friends who have often, you know, they tell us that they have unlimited budgets and credit cards and things like that.

1:02:47Our kids don't. So they, you know, have to live within their means. Obviously, when they're with us, they have, you know, nicer experiences, nicer hotel rooms. But we've always tried to tell them that this is, you know, life is much better when you learn how to earn the things that you have. Are you open with them about what the family has financially? For the most part, I think, you know, they've read enough, they're old enough to know. Uh, but they also, I think are, you know, have a front row seat to how we decide to spend that money. Right. We're not, we're, we're, you know, I, I'm a hermit.

1:03:28Like I, I'm a homebody, right? Like I, I enjoy being home and creating spaces that are cozy and warm and traditions and things like that. So they see how we spend our money on experiences and family, right? Um, we're not extravagant people? So I found that there are two schools of thought on this. Some people are saying, including lots of professionals in the space, are saying it's extremely important to start training children on how to manage wealth and prepare them psychologically to having to deal with wealth in the future. While there is another school of thought where many entrepreneurs belong to, which is absolutely not.

1:04:14Kids need to be hungry. They need to experience this hunger and they need to go and earn their own money, even if we know that we are leaving enough for them. So which school you feel you would, you belong to if, if either. The latter. We want our kids to earn it themselves, even if there's a small parachute at the end that, that we will help them with. I think that people in general who earn their keep and understand, again, it's about the struggles, right? And the failures, living with uncertainty, learning kind of financial literacy, right? I think those are really important skill sets that provide a lot of confidence as you grow and go through changes, especially in life with careers.

1:05:07If you lose jobs, have to find new jobs, you know, when big stressors happen, it's important to know that you can count on yourself and you have those skills. So we, we strongly believe in that. So a common argument against this school, which by the way, I also belong to, the common argument is that we we may be kind of setting up our kids for failure because if they at some point suddenly have to manage money and they don't know how to do it and we supported their entrepreneurial mind mindset they may have the problem which as I'm sure you know is very common for post exit founders when it's so hard to switch from entrepreneurial thinking into investors thinking and so many people lose money because entrepreneurial mindset is so different from investors mindset what would you say about that because you did go through this transition yourself successfully I like a lot of stuff Cass asked the important questions And part of being a good investor is trusting your gut both ways.

1:06:27You know, so I can look at any deal and give 100 reasons why it won't work. The question to ask isn't why will it not work? What happens if it does work? so okay uber it's not going to work because they don't have licenses they're not gonna be able to hire drivers they're going to be category categorized as employees there's no way that you can employ thousands and thousands of people as drivers and manage them well if they pull it off they can be one of the largest transportation companies the world has ever seen right but i I think she was asking more about the kids, right? When I look at the kids.

1:07:11Basically, yeah, the kids. And I wanted to transition into talking about entrepreneurial versus investors mindset, because I think this argument that people who belong to the other school of thought about kids often make is, it's very hard for kids to then suddenly be in a position to have to manage their own personal wealth if we don't prepare and train them to do that as opposed to being entrepreneurs. So everything Cass said about how we approach money and kids, we're on the same page, right? I mean, how could we not be? It's one of the most important things. And we have prepared them and And we've prepared them because we have the head of our state, who's my brother, who's a money manager, who set up the trust, who knows everything about it, who, if God forbid anything happens, will be there to steward them and teach them.

1:08:14And we have backup plans for that, right? At the end of the day, it's very hard to teach people concepts, especially your kids. who naturally tune you out, right? At least our kids do. So you can talk, but the only way they're going to learn is through modeling of behavior. How can you model behavior? Absolutely. And I think we've modeled ethics, we've modeled hard work, and we've modeled practicality in a way that we hope they have a foundation that they'll take forward regardless of our involvement with their life. I do agree. And I think they're well prepared, while also knowing that their life is going to be about earning it.

1:09:04I really want to quickly talk about your book again. And what it is like, why are you reading it? What is it? What is it given to you personally? At this point in our career, and because we often, on a weekly basis, talk to entrepreneurs who have questions, need our support, were often asked like, oh, can you talk to this person? Or, you know, I'd really love if you could help out this person. This next 50 years of our life, we really wanted to give back to the entrepreneurial community. And so for us, this book is a chance to provide the 50 plus cheat codes that we've learned over the last 30 years together in hopes that we can be supportive as well as so that entrepreneurs don't feel alone in these struggles.

1:09:55So that was the purpose of this book. And to share like the real gritty part of being an entrepreneur, the shoveling part, and why those who actually learn to love to shovel are the unstoppable ones out there. So that's why we wrote this book. I love that. Those who love, who, who, uh, learn to love to shovel shit on Sopperbill. Yeah. I'm, I'm so using the quote, you know, and as entrepreneurs have to hustle. And so my sales pitch is go to shoveling shit.com, buy a copy of the book, pre-order it. there's$350 worth of benefits and our benefits are real. So when you start a company, you got to have budgets, you got to have planning documents.

1:10:47Like we've included everything we use to start our companies. We, you have access to the founder's farm. We're doing an event with the community where we get together on zoom and we shoot the shit entrepreneurs, helping entrepreneurs and interview with Seth Meyers, where he really goes deep with us about the book, the concepts, among other things. So if you want to join the community, pre-order the book, benefits start right away. And we look forward to meeting all of you virtually or in person at some point, we hope. Brilliant. I'll definitely add a link to the interview. I'm so grateful for you.

1:11:26So much wisdom, so much authenticity. Can I ask you just one last question? Because it's the question I ask everyone on this show. How do you want to be remembered? I would like to be remembered as someone who gave back more than they received. Beautiful. And I think I haven't really thought that much about it. But I think at the end of the day, I just want to be remembered as a good guy. Someone who did the right thing. And that's enough. Like we don't put our names on buildings. We don't like when we donate, you know, we fund scholarships now at Northwestern in the name of my advisor from college.

1:12:11Like we don't want to be named. We don't want to be remembered for the stuff and the things. It's just how do we make people feel when they interact with us, which is really important to us. This is so wonderful. Thank you to so very much. Thank you for having us. Thank you. Bye.