the bossbabe podcast - 466: We Sold a Company for $745M - Here’s the Reality Behind The Scenes: A Raw Conversation with Kass + Mike Lazerow

Episode Date: June 5, 2025

Kass and Mike Lazerow are serial entrepreneurs and investors, best known as the co-founders of Golf.com and Buddy Media, the leading social media marketing platform that sold to Salesforce for $745 million. In this episode, they join Natalie for a raw, unfiltered conversation on the messy reality of building billion-dollar businesses, raising a family, navigating marriage, and staying focused through it all. They don’t hold back. From the tough lessons they’ve learned as partners and parents to the playbook they’ve developed for building a business that lasts, you’ll walk away with the inside scoop on what it really takes to build a wildly successful business… and stay married while doing it. TIMESTAMPS 00:00 - Introduction to Mike and Kass Lazerow 01:22 - Why co-founder partnerships succeed, or fail 02:38 - How to navigate working together as a couple 05:11 - The must-ask questions before choosing a business partner 07:28 - Equity splits, work ethic, and setting expectations 12:03 - The reality of balance for entrepreneurial families 14:27 - Building businesses during early parenting years 21:18 - The V2MOM framework for focus and decision-making 29:17 - Identifying the key levers that drive business growth 32:34 - Common mistakes in hiring and building a team 36:18 - Scripts and frameworks for difficult conversations 40:20 - Legal foundations every founder should know 45:41 - The emotional side of entrepreneurship and building wealth 49:42 - Rethinking money, freedom, and legacy 55:24 - What success really looks like in business and life RESOURCES + LINKS Grab Kass + Mike’s New Book Shoveling Shit Here: kassandmike.com/the-book Get The Small Business Planner Here - The Tool Every Founder Needs To Organize + Run Every Detail Of Their Business, From Legal Documents + Contracts To Systems, SOPs, + Essential Operations. Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).

Welcome back to the Boss Bay podcast. So today's episode, we have Mike and Cass Lazaro who are serial entrepreneurs and investors best known as the co-founders of golf.com and buddy media, which is the leading social media marketing platform that sold to Salesforce for $745 million. This episode was one of my favorites in a really, really long time. And the reason was it was so real and tactical about what it truly takes to build a wildly successful business. And they give so many insights on finding the right partner, on having

hard conversations, on hiring and firing team members, just really diving into the tactical. And they even shared about the book process that they're in and how they're focusing, what they're focusing on, and what their day-to-day looks like. And I think it's quite rare to be able to have these conversations with really successful, really established entrepreneurs

who are so willing to be honest about the realness. They have a brand new book out, Shoveling Shit. So you can kind of guess by the title that they are not sugarcoating any of this. And it really is just such a great conversation. It's one that I'm going to listen to again, because I pulled so much from it. So with that, let's dive into the episode. I know you're really going to love it. Mike and Cass, welcome to the podcast. I'm so excited that you're here. Thanks for having us. Thank you so much.

Big fans and can't wait to get started. So I have to ask, I ask everyone this who comes to the podcast on a book tour, where's the energy at right now? How are you guys feeling? I think we're tired, but we know this grind. We're serial entrepreneurs and this is kind of giving us a different purpose, which is awesome to help as many entrepreneurs as possible. So energy is still there.

I love hearing that. So diving into the serial entrepreneur piece, you don't say that lightly. I mean, when I was prepping for this episode, I was going down so many rabbit holes of the things that you guys do together, which is absolutely phenomenal. And I just have to ask, because I just don't think me and my husband can do it, how do you work together so successfully? Well, I think Mike would say that we don't really work together. The hardest parts for us have been when we parent together and when we wrote the book, because we're very different. He does all the vision, product, fundraising, investor, taking care of the board,

you name it, and I'm more of the operator. So I do everything that's people related, teams, customer success, marketing PR, you name it, HR. I love that and the distinct roles. Whenever I speak to co-founders that are doing it really well, it feels like that's the thing they really echo in on. And I wanted to ask you this because I know I got a copy of your book early, which by the way, I'm obsessed with.

It's so good. It's so real. And I wish I had it a decade ago because it would have saved me many headaches. But in one chapter, you talk specifically about business partners and choosing the right partner. And I have had business partners, I have a business partner, it's been part of my journey,

some successful, some not. And I would have loved to have these conversations before I even knew what I was getting into with business partnerships. So can we start there and kind of talk about what you guys feel like are the golden rules for building a really good partnership? Sure, I'll take that. I got very lucky. I met Cass when I was very young and not only did I

think she was beautiful and smart, but she's the best operator I know. And I'm the worst operator, you know, and I'm a visionary. I can sell. I wasn't self-aware for many years. After 30 years with CAS, I've become much more self-aware in all the best ways. And that difference between us is really what we love about co-founder relationships. You need a partner who you have the same foundation of values, trust, how hard you're gonna work, vision for the company, but your actual skillsets have to be very different.

So if you're both programmers, it's gonna be very hard to get on the same page about what tech to use, how to build it, just because you'll have so many ideas. Cass and I stay in our lanes, and we think all co-founders should. So typically you have someone who's more technical or operational,

and then someone who's more of the visionary and more external, and that's what I've always been. I also have gotten this wrong. I've started one business with a friend and I lost a friendship over it. And it was a painful experience and it was an experience that, you know, shouldn't have reminded me of how special

the co-founder relationship is with Cass, but what I have with Cass just wasn't there. And that was, you know, mutual respect, the idea that if I say I'm gonna to do something, I'd do it. That wasn't happening. And we just had a different vision for the business. So the business is still around, but I had to step back. And it was a really painful experience because it's very easy to pivot a company. So business models, it's very hard to pivot a co-founder. It's very hard to change a co-founder. And so we think it's worth having the hard conversations before you start.

Otherwise you land in a pool of mud like I did. Well, here's why I've messed up the avoidance of hard conversations, especially in the early days when you don't really know what a hard conversation should look like. You know, I started one of my first companies early twenties and I co-founded with a friend and we didn't really know what questions we should be asking or what the conversation looked like. So what do you think some of those initial questions should be when you're

getting into business with someone? I think the first question should be obviously after you figured out your strengths, right? Each of your strengths and the lanes. The first question should be about how hard do you want to work? Because you both should be making sure that you guys are going to put everything you have into this. We see a lot of founders or a lot of companies and most, you know, I would say most 99% of the time we're not investing in them because there's a difference, right? There's this huge difference and gap

between how excited, passionate, and you can tell this person's always on with the company and the other one's kind of sitting back. So that's the first thing. And that kind of goes to work ethic, right? And then why are you doing this? So what if someone really wants to make an impact and solve a problem and the other one really is in it for, you know, making the most money they can. It doesn't mean that that's bad, but you need to know that about each other because it also

teaches you data points about what motivates the person. And sometimes you'll hear things that you didn't know, and that's a good reason to just say, no, this is not a good partnership. But those are the two big ones that we do. Mike, do you have another one? Yeah, one of the biggest ones that I, it hit me the other day and we write about it in the book, working with two co-founders and I met with them separately, just to understand what was going on. And their vision for the business was completely and we write about it in the book, working with two co-founders, and I met with them separately just to understand what was going on, and their vision for the business was completely different.

One of them wanted to create a business that was very profitable, didn't raise any money, and just grew slowly. The other was interested in raising $30 million to surge the business, and had come to me to talk about that fundraise, because we know a lot of investors and one of the things we do when we invest in any company

is we take responsibility for making intros to the next investor, right, the next round. And I said, I'm not making another intro or having another conversation until you're on the same page with the co-founder. And that opened up a whole host of discussions that the truth came out. They hadn't talked in a week,

they weren't on the same page. One was working much harder than the other. And most importantly, where they wanted to take the business wasn't on the same page. And so it's just gonna be a very painful relationship if you're not over-communicating and getting on the same page and having that dance of those conversations. On that lens of communication, what do you think about equity

splits and valuing the work that each person is bringing to the table? You know, for me, when I first got into business, I just assumed, well, everything's 50-50. I didn't really think to dig into all those different things and ask those hard questions and have those conversations, which it sounds like you're saying there was probably resentments building up. I know I've seen that a lot with co-founders I've talked to. How do you think about that kind of thing? I have a very specific way I'd answer this. Mike, you probably will have a different lens

on this, but I think if you've had the right conversation. So like for me, I'm always looking at like, if we're going to invest in a team, I'm looking at do they have separate skill sets, right? So that they're never going to be paralyzed with decision making or micromanagement and do they know what they don't know? So I think, you know, that's, that's really a big thing for me to see that they know what they don't know, and they're willing to go outside of that. So then when it comes to having the difficult conversations of like, okay, how hard are you working? Why are you doing this? What's our vision? And you're kind of working that all out. Then I think it is going to be 50-50. You know, if you have two founders, I think you got to split it down, but you've got to have those conversations

first and not everyone is going to be working at the same intensity level, the entire journey of a company, but you have to have the intensity level be the same about what you want to happen in the company. And oh, sorry, Mike, were you going to say something? No, it's really well said. And we used to show up to investors and we'd sit down to pitch, they'd be like, wait, are you brother, sister, are you married? And we'd say we're married.

And a lot of them would say, we don't invest in kind of couples. And we would turn around and walk out, oftentimes not even saying goodbye because we're not going to change or if we said anything, it'd be like, you know, unless you change your policies, like we're not planning to get divorced. And we've come to realize that people who start businesses with people they love, so spouses, brothers, sisters, parents, it's actually a superpower. And it hit me today, we spoke at an event and met the founder of Van Lewin, the ice cream company who we love. It was in our neighborhood on the Upper West Side. We saw them build their business.

I remember when they bought a truck off of eBay for $2,500 and it was two brothers who started it and another founder. When you have history of being able to fight and then go to sleep without being resentful and having love that will never be broken no matter how hard the conversation, I find that much better than what I had in the business that didn't work out, Shape Matrix, where I was walking on eggshells.

And so having someone like Cass who is aggressive, meaning she's not passive aggressive, I know where I stand and I've gotten better at communicating my feelings and what I need and that takes time. It takes a lot of shoveling shit together. I could not agree more with that. And I mean, for me, it's even extended to working with family. I work with family.

In fact, my longest employee is my cousin. We've worked together in every business and so many people have said, isn't that a mistake hiring family? And for us, we're just very honest with each other. We know exactly where we stand and we can be really, really honest with each other. And there's a lot of family that I would never dream of working with, but I think you, you can make that decision and have that discernment. And I actually think it can be amazing.

And do you think part of that is, you know, how you were brought up and where you came from and kind of like family, you had to have been a big part, you know, coming from a smaller town and kind of go setting out on your own? Probably. Yeah. I mean, she was my older cousin, someone that I just always looked up to. We just had a really close relationship. And I think we also fought a lot. We were cousins. We were both to. We just had a really close relationship. And I think we also

fought a lot. We were cousins. We were both girls. We fought a lot. And by the time we decided to work together, it was like, like you said, we kind of learned how to fight. We learned what was important to each other. We learned, we learned a lot about each other. And what's also really interesting is we can trust each other. I was going to say there's implicit trust. I mean, we met identical twin, like one of the identical twin brothers who's running a company and his twin actually was in India. And he just said, but there's nothing better than knowing someone so well and trusting them when you work with them. I really, really agree with that.

There's just something about that trust that is like, I've got you, you've got me, we can make it through whatever. There's going to be lots of shit that comes you, you've got me, we can make it through whatever. There's going to be lots of shit that comes your way. You're like, we can make it through. So speaking of working hard and those things, another thing that you guys talk about, which Cass we kind of talked about in our last conversation, you guys named it in the chapter as the imbalanced life and I know you built your businesses while also raising a family. How did that look and how has that looked for you?

I'm in the thick of that right now and it is not for the faint of heart. I think you're totally right. So let's see. We started all of our companies right around the births of our three children, which is kind of crazy when you think about it, but I don't think I'd change anything if we had a chance to go back because I really, I said this to another entrepreneur today that, and she was like struggling with whether she should have kids now or wait like five or six years to see how the company does. And I said to her, if you don't want to miss out on kids, have them as early as you can

because you don't know how long it's going to take to get pregnant and there will never be a great time. The truth from our side is when they're younger, there are, and I'm talking like, you know, five, six years and under, there's a lot of people who can be in your community, in your village that can love them and do what you would do at their age. When they get older, I really think that's when you need to think about how many hours away you are from them because it's your values that you need to lead by example with. We kind of made that bet when they were little that if we could afford a babysitter, get

some family in every now and then that we would work really hard and prioritize the work so that we could get back to them when they were older. But there is no balance. And I don't care if you're an entrepreneur or if you're working a nine to five job, there is no balance. Right. You only can do one thing well at a time. I really like that perspective.

And it's so helpful for me to hearing, cause I have a toddler baby on the way. And I've heard people say that a lot of it is very different when they start getting a little bit older and their needs towards you actually do shift. And so for you guys, I love the word harmony because I really do think like every season is so different and it just requires such different things from you. Like I don't know what it is, but every time I'm pregnant, I'm like, I have so much energy. I'm like running full force. Then I'm going to slow down a little bit and then I'm going to go back at it. Like I kind of run with the season and the energy. I'm like running full force. Then I'm going to slow down a little bit and then I'm going to go back at it. Like I kind of run with the season and the energy that I'm given. Is that

the way that you guys have thought about it? Have you really built with that in mind? Yeah. I mean, what's interesting is that entrepreneurs, when they're at their best, feel like they found their purpose. And from there becomes you get your passion, you get your energy, and it's from everything starts there. And there are other people who get it from their kids or get it from giving away or church or temple or whatever it is. But the entrepreneurs that we speak to and definitely for us, it was all about kind of the reason we got up in the morning was because of work. It was our love language. We love entrepreneurs, we love growth, they're growing the businesses.

And then we have these kids who come along and you just have to be very honest in their trade-offs. And Cass talks about this a lot, it's much harder on moms. It's harder for Cass to turn off her brain, it's harder for Cass to not get through her to-do list at the end of the day. It's relatively easy for me, and I think a lot of guys, to just compartmentalize. And what we realize is that that passion that we bring to work, we just

have to make sure that we schedule the time and we set structure for everything else. Otherwise we get lost. And so it's not on the calendar. It doesn't exist. We, and I speak to my friend Gary Vaynerchuk about this all the time, who has now two kids who are older and we saw those kids born and you know, we've seen him grow his empire as he's grown And I speak to my friend Gary Vaynerchuk about this all the time, who has now two kids who are older. And we saw those kids born and we've seen him grow his empire as he's grown his life. And the book is, they're all the cheat codes that we use to grow the business, but also to grow a life. And it's not only about kids, it's also about your spouse.

It's about relationships that matter. So I had Saturday mornings, Cass would sleep, I would take the kids, we'd go get pancakes, we'd go somewhere in the city, we live in New York City, we'd have fun, I loved it. And Wednesday and so that was like how I filled my cup with kids. When they were young, that's what I could give them. I couldn't give them every day, right? I was lucky I got half an hour before they went to bed at 8 p.m. Cass and I had a date night every Wednesday and Sunday night, Saturday night, which we recommend to all entrepreneurs.

You're gonna be married to your work, but if you don't wanna be single, if you don't wanna be divorced, like schedule time, it doesn't sound sexy, but it's required because you'll just sit at your desk, you'll just make another call. And so it's this idea that you're never gonna be more passionate about much other than the company,

and I see what you've done, and the reason why you have so much energy is you've found your purpose. Like you are living your life. If you weren't, you wouldn't feel that. You'd feel tired. You wouldn't be able to get out of bed and schedule the stuff's important so you don't lose it. I love that. Do you know something me and my husband have started doing, which has been a game changer? We have our date night and we've started doing a weekly family meeting on a Friday so that date nights don't become about the family meeting.

Yeah, 100%. Right. Right. It's been a game changer because both entrepreneurs, both incredibly busy, we can turn date nights very much into like calendar checking and scheduling and like, tell me what's going on for you. So we started doing the Friday morning family meeting. And so date nights actually like real connection.

And it's been a game changer. Like, why didn't I start doing this five years ago? And trips, right? So, you know, when we could actually afford it, we would get away for a night or two nights. I think that was really important. But the other part is as a mom, there's gonna be no like bigger guilt

than you're not doing everything you write or as you're not enough as a mom, there's going to be no bigger guilt than you're not doing everything you write or you're not enough as a mom to the kids or whatever. And you have to realize that they will be okay. I am a mom, an example of looking at three kids that we have raised and they're great human beings. And we did the best we could and we didn't have a hundred percent focus on them, you know, for many differently, you called it seasons, for many different seasons. So good hearing that too. I always love talking to entrepreneurs who are also parents of kids

that are a little bit older to be able to have that perspective because sometimes when you're in the thick of it, you're like, am I doing a good job at anything? You just don't know. So I really, really love that. Are there other things that the two of you have done to be able to really prioritize the strength of your marriage alongside working together and raising kids and all the other demands of being together? Well, I think one of the things is we are very into health and I think having some shared interests outside of work has really been helpful. Now, I also think, and Mike will probably agree with this, to strengthen your marriage, you have to have your own interests. It can't be against each other. It's got to be like,

okay, Mike has his stuff, I have my stuff, and then we have our stuff. And for us, when you work with your spouse, you can't always have the together stuff be about work. We have, you know, we have pickleball, we have golf, when I'm playing it, because it sometimes takes too long. Yes, Mike, that's the truth. And we, you know, we work out together. And so I think we have a lot that we share, obviously, outside of kids, family, homes, and work. And that's important. I think I could definitely do a better job of the hobbies part. So I'm going to put that on there.

It's hard. It's hard when you're, uh, let me, let me make sure I, I don't, I don't have hobbies. Like Mike has hobbies and passions. I want to make sure everybody hears me that I am a mom and I have an operator's mind and people who are like me that are all about to do's and, and they kind of execute ideas. They're not going to have a lot of hobbies. They're going to have things they like to do such as me sitting in silence with my dogs. I love sitting in silence. You know, like silence is my favorite music. Whereas Mike, if you said like, what's a hobby, it would be like playing the drums and what's your passion, going to fish shows. Like I don't have

those things. That's a really good distinction actually, because I do think men and women are really different in that way. So I think that's a really, really good distinction. And also my husband just finds it a lot easier to leave the house when he's not working to do things. And I'm like, but the kids and da-da-da. Oh yeah. Yeah.

You always hear the story of the husband leaves the house for a trip and just walks out the door. We are getting ready for three weeks before we would ever leave on a trip and just walks out the door, we are getting ready for three weeks before we would ever leave on a trip. I know. And you'll leave the door and you're still texting. What about thinking about this? Have I done this?

There's all the things. There's so many things. There's something else that I want to talk to you about too, which was in your book that, again, I feel like I learned a little bit too late, but I'm really glad that I've learned this lesson. And it's something that I feel like every three months I have to keep reminding myself this, but you talk about hyper focus and I feel like it's still something every three months I'm like, Natalie focus, bring it in.

Yes. Ideas are great, but really bring it in. How are you hyper focusing on what is really, really working? And I'm just curious for you guys, how you think about focus and how you think about as visionaries and entrepreneurs, we have a lot of ideas and that can be really fun and it can be really energizing. But we also know that the best results are gonna come from when you double down and you're really optimizing.

And so how have you thought about that in all of the companies that you've been building? So I'll take that because I struggle with it the most. I mean, Cass is hyper-focused and as kind of the companies that you've been building? So I'll take that because I struggle with it the most. I mean, Cass is hyper-focused and as kind of the visionary and salesperson and person who makes things happen just from a business like revenue perspective, I'm constantly talking to people, bouncing off people. And it took me a good 10 years to figure out how to focus. And what I realized is that we together can do anything we want. We can't do everything.

And we learned from Mark Benioff after we sold Buddy Media to Salesforce, a system called the V2 Mom, which he has started. He started when he launched the company, which is vision, values, methods, obstacles, metrics. And it doesn't matter what you use, but it forces you to write down what kind of company do you want to be? What's your vision? What are some of the things that are important to you, those values? And then most importantly, like what are the five things you have to do to achieve the vision?

So if your vision is to be a top 10 podcast or launch a number one Netflix show or launch a number one carbon capture company, you then have to figure out, okay, for me to do that, what do I need to hyper focus on? As a software company at Buddy Media, we have to build the software right, for me to do that, what do I need to hyper focus on? As a software company at Buddy Media, we had to build the software right before we could sell it. So that was number one until we got customers, then selling was number one, and then our customers started leaving. So we had to kind of figure out this customer success and support function. And so it's a constantly changing, but at any given time, everyone in your organization needs to know where you're going and what you have to do to get

there. If you don't, you're all paddling in different directions and you don't get anywhere. And I spent a lot of days in my career, not focused and just wasting time. And I regret those days. Some of it hopefully ended up with kind of some business models or something that benefited us. But when we go all in, we write a V2 mom and we're going. This book, we basically are not doing a lot, but what we're doing is a lot of speaking. We're doing podcasts. We're asking friends for bulk orders. And those three things, we think, will propel the book to a success because we wanted it to be a best seller. Why write a book if no one reads it, right? And so everything we do, we sit down and we're

like, hey, what do we need to do to win? And every time we don't do that, we end up in this murky middle and we're confused. And how are you balancing that, let's say with the book, alongside all the other things that I'm sure you do have going on, other responsibilities or things coming at you, how are you thinking about, okay, my time needs to go here, so that's how I'm going you do have going on other responsibilities or things coming at you. How are you thinking about, okay, my time needs to go here. So that's how I'm going to do it. It's hard. I mean, Cass has a lot of stuff on her plate for our companies.

You know, we have a hundred investments and if anyone needs help with reorgs or layoffs or anything that's HR and ops related, if anyone needs help with fundraising or, you know, I comes to me, you know, last week we had tons of stuff for the book, but we also had four board meetings I had to do Thursday and Friday, right? So that's our day job. We're fiduciaries of other people's capital. We also bought businesses, we own businesses, and the CEOs and COOs who are running those businesses are our customers, not the other way around. Like when they ask me for something, yes, sir, yes, ma'am, whatever you need. Like we're here to work for you. And so we only have 24 hours in the day.

We haven't been sleeping a lot. You know, it was a very big decision to decide to greenlight a project. Like a book, it takes so much time to write it, but most importantly, it takes time to like promote it and get it out there. And it's so personal that it's a really exciting project for us, but we didn't exactly, we weren't sitting around with a lot of time. And so I think some things have struggled. We haven't seen a lot of our friends as much as we have wanted.

We were just with some friends Memorial Day weekend. They're like, where have you been? We're like, well, you'll see, we're about to launch the book. And we've just been working hard. And so any entrepreneur out there, it doesn't matter what you use, but get hyper, hyper focused and really focusing on the two or three things. Because saying I'm focused on these 10 things as an entrepreneur means you're focused on none of them.

I really appreciate that honesty too. Cause I feel like a lot of people aren't fully honest about what it really takes. But when you're saying we're not sleeping a lot, we are doing a lot. We are giving it everything we've got. I think people need to be honest about, cause this is essentially like a launch. And it's the same whether you're launching a business, whatever you are all in. In our community, we talk a lot about freedom based businesses. So a lot of women in our community, they're not raising money.

They're building businesses around their lives. But I always say, don't get that confused with lack of hustle or lack of hard work or the need to put hours in because that's going to be something that happens in every single business if you want it to be a success. There's really, I don't think any way around that. And there's ways in which you can build it so it can support your life if that's a goal, but there's no way around the time it takes.

We had an event last night and we got back around 10 and I quickly changed and then sat down at the computer and went to bed at two just to make sure I got everything I needed to get done. And you're right. It's all about hard work and reps, right? There's no shortcuts when you are an entrepreneur. I think our cheat codes in our book will help you not step in it and not make the same mistakes we did, but at the end of the day, it is the work that you're putting in. That's what equates to any success that you will have.

I could not agree more. Another thing that I wanted to talk to you guys about, because you obviously, you've said you're an investor in a hundred companies, you've seen a lot. From growing your own companies to being part of many, many companies, you've seen a lot. And I'm curious, the companies that are in, like they've made, they're probably averaging a few million a year, and they really want to take it

to the next level. Have you seen that there's a pretty standard playbook? Like you come into that company, there's ways in which you coach those CEOs to start really growing. So we do. And we basically, we believe that every company has levers and your job, your job when you start a startup is to not be a startup, right?

Your job is to go from like, oh, I don't know what I'm doing, I don't product market fit to like, oh, I know what I'm doing. Now, if you're a pizzeria, if you're cutting hair, it's a little easier, but you can understand what drives the business. We own a healthcare staffing business

and our recruiters are really our clients, meaning like we need to onboard more recruiters and the more recruiters we have, the bigger the company grows. And it's been around for 25 years, very profitable. And we're really making that concerted effort effort and we just know that the lever for that business is recruiters, others it may be customers, others it may be partners or channels if you're selling through like the supplement business you that you've

experienced and like you know that's a totally different series of levers and once you understand them I think it's important to realize that there's only so much you can do today. So think about doing what you need to do to kind of push those buttons and kind of pull those levers to grow, but do it over years, decades even. Like that's how big businesses are built. It's not about kind of being patient and not working.

It's about doing the right things every day. So when you look back in the year, you're like, wow, I got a lot done. Any given week, you're not gonna be able to look back and say that you did that much, right? Any quarter, you're not gonna do a lot. But if you do the right things every year for several years, like do that for five years,

you're gonna wake up with an audience of 100 million people if you're in the podcast business. You're gonna wake up with 100 customers of 100 million people if you're in the podcast business. You're going to wake up with 100 customers from zero if you're an accountant. So just continue doing the right things every day and letting the value of time compound to create returns for you. What I don't like when I see on resumes entrepreneurs who launch something and then ditch it and launch something and ditch it, it may not go your way, but figure out what is going to drive the business and just stay at it.

Winners never quit, quitters never win. Like you've got to keep going every time you restart, you're starting at zero, basically. And how can someone be thinking about identifying those levers and making sure that they're really knowing what moves the needle and what things they can do now that five years from now will be making a difference. They're not hitting stagnation. Cass, do you want to take that or should I continue? I mean, you can continue and I'll add, I have a thought, but it's not quite on that, but keep going. Yes. So we are fundamentalists. We believe that businesses are systems. We believe that the inputs drive the outcomes.

What you focus on, your priorities determine what happens in the business. And a lot of companies end up focused on the wrong things. For instance, the biggest mistake in software companies is you focus just on sales and you get a ton of sales. And then all of a sudden you're selling but you're losing customers. So you're swimming against the grain and no one focuses on customer success, right? It's always new logos, new logos.

Any business, any service business, it's easy to file their taxes on April 15th if you're an accountant, but how are you building that relationship to make sure that they come back next year? And so it's not just about getting new clients and new customers. And so when I look at any getting new clients and new customers. And

so when I look at any business, we break it down into unit economics. We just break it down to the most minimum, like what's the minimum unit. So for liquid death, that water company, it's a can, right? Where do we put the water in the can? How do we get it to the distributor who gets it to the retailer and simpler businesses? It's usually really easy. Okay. pizzeria, you need more customers. Like are you doing free lunches for businesses within five blocks of your pizzeria? If you can get them to try your pizza and start that habit, that's a way to kind of get more customers. So don't overthink it. Simpler is better. I'm a journalism

major. I was never trained on business. If it doesn't work on the back of an envelope, it's never going to work in real life. I'd also say that some of the levers that I try to pull with our companies after they've been around a couple years is really doing a deep dive on team. Like who are the players and do you need them? And are they the right people for that role? Like we used to say this all the time. Every time we would do a fundraise, I'd lay off a bunch of people. And people would always be like so surprised,

but it was a way for me to reorganize it and make sure that our mission was still being met with the right people in the right spot. So I was money balling everybody. But I think a lot of waste happens when you get a little bit bigger and fatter and you think, okay, this is how, like a perfect example is this is how many people need to service an account or, or, or beyond customer service or whatever

it is. You've got to start looking at your teams and, and your managers. Do you need managers or do you need doers? And really thinking about how you've organized across. What are some of the biggest mistakes you see? And I know you talk about this in the book, but with hiring and leading teams. So I think with hiring, first and foremost,

people don't do enough, especially as entrepreneurs, they don't do enough thinking before they go to start to hire for the role. And I know that every single entrepreneur knows that they have to move fast and they've got to get the right hire and all that. But you really have to figure out what you're hiring for. Otherwise you're going to go

to like a hardware store for lemonade. Doesn't make any sense, right? You really have to have that defined. And I'm not just saying at a job description level, that's table stakes. After the job description, have you done the second, third, fourth layer of where the company goes in two years or who comes over or who's managing this person you're about to hire? Where eventually is their career path? We always had an org chart. We were four people. We had an

org chart and I had current state, future state, like way off in the future state. And it gave people comfort and it wasn't about like who they were, but it was in a really kind of big department focus, right? And you have to know that before you hire. The second part is you need to be creative with your questions so that you are able to match the culture that you want. Basically, the culture is a reflection of a time in your life that you felt really good in a team environment. It could be a club you joined. It could be obviously a team that you were on or a family trip. And there was some kind of cohesiveness that you enjoyed.

And you're now trying to recreate that. The only way you're gonna get there is not from standard questions. You have to obviously be by the law on what you can ask, but you are trying to get them to answer questions so that you can figure out if the culture is a fit. Because if it's not, if they are not a fit with culture, they will become your worst enemy very quickly

down the road, even if they're a great employee. And what about firing? Because again, I'm still learning this lesson, but I always fire way too slow. So, I mean, look, not everyone agrees with me, but we always hired fast and fired more quickly, right? Or we said faster. It's not easy, but if you can learn the first line

and get it out, which is, today I have some unfortunate news, today is your last day. And you can learn the first line and get it out, which is today, I have some unfortunate news. Today is your last day and you can lead with that. And then remember that your job as a manager or a leader or even the founder is to be empathetic and kind. And if you want to be the best person out there so that you actually have people still rooting for you, even if you fired them, then tell them where they messed up and how you would have hoped they missed it, right? Or fixed it. And so we took it very seriously.

Everybody had, we had such great care in bringing people in, but we had the same amount of care when they went out. That is so helpful just hearing you give the script. And I know your book is filled with a lot of those really tactical things, but it's things like that. They don't teach you in business school. They don't teach you how to have those conversations. And it's only through speaking to other entrepreneurs or doing it wrong

that you start to learn that. So I have to ask, do you also have a script for, and this is me trying to get coaching, when you are giving your employees some feedback on performance not being great, do you have a way you handle that? Yes, well, first of all, the first thing you have to do is make sure that you have a format for giving feedback. This can't be kind of off the cuff, disorganized.

You want to make sure that an employee feels that they're going to have an opportunity to talk through some of this. So we always had yearly reviews, again, for people didn't matter and we had reviews of ourselves. You have to make sure that that's happening because otherwise employees feel an edge. Now if something's happening that you want them to stop, let's just say wrong interactions with a client or something like that.

Yes, you can immediately stop it, but you should also make a note, right, a folder with someone's name on it so you remember these conversations and you remember it. The best way to approach it is to say, listen, and I'll give you this example in a meeting, I know how hard you are working, I see it and I'm really appreciative of it.

What the client needs and what our company needs to give the client is the following and how you're coming across is not meeting that. So you're acknowledging their hard work. The hardest thing about being in difficult conversations is the first line. It's like when actors learn, they just need the first line to help them remember what they're going to say. So if you can get the first line out and I always lead with, I mean, this is pretty obvious, but you always leave with the good so that they can remember that you're on their side,

that you are not doing this to be punitive, you are not doing this to hope that they fail or to be critical of them. It's where you need them to be. So you have to deliver this in an aspirational way. I know you can do this. Here's the behavior where I think you should change. There's also, you know, this concept that I've learned slowly of getting the elephant in the

room and acknowledging kind of the emotions and the feelings of the other person even before you start. So, you know, Natalie, this is not going to be a fun conversation. This is not a conversation that I want to have with you on your podcast. It's not why I was here, but I think it's good for you to hear this and for the organization to move forward. I really hope you listen to what I'm about to say, because this is going to be something that helps us, but it's going to help you moving forward. How you are handling your communication with your team

is creating an environment where people want to leave. And that's not, or whatever it is, right? So it's basically, and I learned this from Cass, because I would basically try to sell stuff to her. I'd's not, or whatever it is, right? So it's basically, and I learned this from Cass cause I would basically try to sell stuff to her. I'd be like, hey, fish is playing Vegas for Halloween. Like it looks like we're free and like, you're going to be doing all this stuff. So, you know, it's cool if I go verse when the kids were

young Cass, you're not going to like what I'm about to say. And I know it's going to create some issues and more work for you at home, but it's really important for me to be able to go blow off the stink with my friends and do it unless there's something that's like really holding back. I'd really like to do this, right? So it's kind of how you communicate by taking the other person's, like how your behavior or how this is going to land on the other person, I think helps a lot.

And it's something that I struggled with so much and I still struggle with, but that first line, you know, like when you lay someone off, like Cass is always says like today is your last day at the company. She doesn't bury the lead, right. And then give the feedback. So it's, you know, that first line is important. I just really think that all founders need to realize the following. People take great care in hiring the right people, but why don't they take great care when they let them go? Now,

granted, there are some really horrible behaviors that happen in companies and those obviously should be done in a very tight legal way, but don't you owe it to them to like tell them how they can be better. Otherwise you're just passing on the same challenges to someone else, right? Some other company. This is such gold. Like I know people listening right now are just eating this up because I think this kind of tactical coaching is really hard to come by of like the specific wording or the framing.

And I really, the both of those scripts and Mike, also what you said about, I used to try and sell this and I think that's the entrepreneurs way it's like, oh, I'll just enroll them in my excitement. And it's like, well, that's probably not going to work this time. And I can think about that my personal life and my professional life. So I really love that. And I also have to ask, cause you mentioned doing things in a legal way. What I love about the book is just how real it is.

Like you're really not sugarcoating a lot of this. And I think that's really important with entrepreneurship is not sugarcoating it. And what I've been trying to do with my content lately too, is bring people a little bit behind the scenes of like, you see the fun stuff, you see the content, but behind the scenes, there's also some not fun stuff that goes on. One of the least fun things for me personally that I deal with is the legal stuff and I've had to get really good at that and I'm getting better at it. But one thing that I know trips me up, but also trips just a lot of founders up

is legal stuff and the fear of messing something up or someone comes at you with a cease and desist or someone comes at you with a cease and desist or someone comes at you with a demand and the fear can come up and you can react from a place of fear versus actually stepping back, looking at your options and really protecting yourself and protecting your business. So how do you think about that? And how has your perspective on that stuff changed as you've gained more experience? Well, I came from a family of lawyers. So I probably didn't have as much fear as most people, as most founders do. So I think that helped me a little bit, but I'm also, Natalie, I'm also a

rule follower until I can get a little wiggle room, but for the most part, I think what we've done really well, and I think we learned a lot from golf.com and then going into buddy media is that the more organized you can get with all of the legal contracts and documents from the very beginning, the better off you are because you have the structure. I know a lot of people are like, Oh, I don't want to spend all this money on, you know, an attorney on that stuff. A lot of the documents right now, and there's so many different companies that, you know, like the AI attorney documents companies out there, Mike knows them all.

Like you don't have to spend a ton, but you should spend to get them right. And that's where founders fall short a lot of the time when things get thrown at you, such as a lawsuit or like you said, like IP infringement or something like that, take it seriously, but step back. Like you said, but you need to be able to deal with these things because this happens in business all of the time. The number one thing we see happening that's that it's a painful process, but it's fixable is if you've picked a name that somebody else is using. That happens all the time.

It's happened so much with all of our different founders. So you're right. You've just got to kind of take it head on and you've got to get your fear out of the way. Yeah. I mean, I definitely learned that the hard way naming my company, boss babe, not going to say much more about that, but there was a big company came after us with that. And we thought there's no way we can take this on. There's no way we can stand up for ourselves

and protect ourselves. And I think you can actually really surprise yourself when you have done the pre-work and you have buttoned yourself up legally and you have made sure you've got your ducks in a row. You probably are better placed to stand up for yourself than you think you are. And I think I'm learning that as time goes on.

And one thing that I'm trying to learn, which is a practice of mine, is like not letting those things keep you up at night. Like really being able to set that to the side and know, do you know what? No matter what comes my way, I know I can deal with it and not letting it spiral you. Have you mastered that yet? I think we're pretty good at not letting things, not letting fear get in the way. And I think this topic's an important one because there's so much fear and so much anxiety that people just ignore it, right?

And we hear it all the time, which is like, oh, the lawyer's just slowing us down, right? In reality, bad legal, or at least ignoring it, is gonna slow you down much more later, right? Than, well, we'll fix it later. Well, maybe, it might be expensive, it might be impossible, right? Or, well, we'll fix it later. Well, maybe it might be expensive, it might be impossible, right? Or we're too early for that. You're never too early to avoid some of these issues with co-founder fallouts or messy IP issues. Or legal is kind

of just like the rain on a rainy day or gravity. It just exists, right? You can respect it or you could just ignore it and hope it goes away, but it just never goes away. Eventually you're going to fall to the ground or you're going to get wet if it's raining out, right? It's a necessary evil. I look forward to the day where just AI handles everything, which is happening for bigger companies.

So Harvey AI and some others. We haven't seen it work for smaller companies as well because legal is kind of a business tool. But look at legal as a play offense, not defense. And I'm not saying sue people, but get ahead of issues so you avoid stuff. I've only been sued once. I'm not going to talk about it because she's a huge famous actress. But we've just done the right thing and we've tried to stay ahead so it doesn't end up in legal issues. I mean, I would also tell you, Natalie, and most people thought I was crazy, including our board, but at our last company, one of the first 15, 18 hires was a general counsel,

because I knew that we were moving at such high speed that if we didn't have someone who could literally herd us in, especially all these amazing salespeople and make sure the contracts were tight, the negotiated terms were better for us, then it was going to be super messy and not repeatable, right, we wouldn't be able to have repeatable revenue. I love that we're having this conversation because it is kind of like the unsexy stuff that behind the scenes is so important.

And actually that's what allows you to build a foundation to be able to scale your business. I invested in a company that I absolutely love. They're called the Small Business Planner. So for anyone listening that's feeling really overwhelmed, they actually, they send you a binder and this was really helpful for me coming from the UK because I learned about UK business. So I was like, what's an LLC? What's a C-Corp? What do I need?

And they send you this binder and it's a physical binder and it tells you, here's your checklist. You have to print out your contracts, print out your incorporation documents. And it's things like that, that I'm like, I wish I had this in the beginning because I was just like in a Google drive, like I'm sure I've got the EIN somewhere.

Like you don't think about this stuff. No, that's so, it's so right. And the more, like, I will say it again, the more art organized you can get. When we sold gov.com to Time Warner, Mike and I had moved from Chicago to DC. And like four weeks after that, I had our second son and it took I think a couple years when we were there and then we sold it but we had documents in Chicago in some like folder that was in some storage unit and we had I mean easier now because it's everything digital but oh my gosh. But we still get

it wrong. Yeah. You know we bought a company and I'm not gonna talk too much about it but we realized we never had, we never incorporated the LLC for the new entity. And you know, we're now looking at potentially selling it and we're going to have to clean it up and it's going to cost so much more to try to clean it up. And so it happens, stay ahead of that. And it really gets to like all these uncomfortable things. Like every entrepreneur loves doing one or two things, right? You may love to code or sell or create content. And then you have all this other stuff, which we call like this pebbles in the sand. They aren't big rock

priorities, but kind of need to file your tax return. You kind of need to do these things and don't get behind on those because any procrastination, any time you're going to save today is gonna be such a headache. You're shooting yourself in the foot down the road. Think I'm definitely learning that now. It's taken some mistakes to get there, but I'm definitely learning that like,

yep, having your ducks in a row really, really helps. Being organized, understanding all of that really, really helps. So bringing it back to the book, I wanna know what made you decide to write this book? What made you say yes to a project like this? I always wanted to write a book. I thought I had it in me.

I kind of think in terms of like book titles. And so I had all these like book titles, which actually became the chapters of the book, like perception is reality, putting the cult in your culture, leaders shovel first, things like that. And I had all the lessons that Mike and I had been giving and still do on a daily basis to entrepreneurs who ask us for their advice or help. And we just thought this would be a great way

to amplify all the messages and we could get it out once and then get it to as many entrepreneurs as possible. It's not been easy writing a book. We were in the same lane for the first time, as I said earlier, so that was difficult. Although it only did take us three months, but editing the process of like the creation of the cover and things like that, that was much harder than I thought and picking the right title and stuff like that. I'm curious as you were writing it, was there one particular lesson in there or a chapter in there where you're writing

it and you're like, I wish I would take my own advice more often or like you really realize you learned this because you've made that mistake too much. I know that for myself being in the book writing process, there's been parts of it that are so therapeutic. So I'm like, wow, yeah, this is what I think and I probably should do this more. Like it's just been so interesting. Yeah, for me, it was a lot of the stuff I hadn't dealt with from my childhood. You know, I have a father who was a different entrepreneur, but he was an entrepreneur. And he ran

into some financial issues. And the financial issues caused him to do some stuff, which I know he regrets, you know, including not wanting to live. And he was majorly depressed and ended up in a mental hospital for many weeks. This happened to be a few months before my 13th birthday. So it was kind of an important time. I never fully took stock of what he was going through and the impact of financial pressures on the entrepreneur and the shame, especially at a time when men did not have the license

to go seek out mental health. And for me, what was interesting is the book process let me come to terms with that and forgive him, really for the first time. I've been carrying this with me for 40 years almost. And none of us have overnight success, no matter what you see on Instagram. You know, the Lamborghini you see that guy's living in his parents basement. Like it's

just not real, right? And if they really have wealth, it took many, many, many years to build for us 30 years. You know, we had little wins, but we didn't sell a business for a billion dollars until we were in their thirties. And so the process of writing the book let us learn more about ourselves, improve our life, but also we think we'll give impact and we'll create impact for people who aren't confident like we weren't. We were full of fear and doubt and uncertainty. And as we became more confident, we're like, we got this. What else can happen?

We've seen everything, right? And I think that's what the book is. It's if you too can develop confidence, can get better making decisions with uncertain data in this hurricane of just bad news. If you cannot be led by fear, you too can build a business that outstrips you, that lives way beyond your life,

impact that's way beyond what you're doing, and build a life that is really fulfilling, however you choose to define that. And we'd love seeing our entrepreneurs that we invest in become much smarter, much wealthier than we are. And that's, it's just an awesome thing to see them succeed. And that's what the book does. Hopefully we want to look back in 20 years,

be like, wow, I picked up your book, I hired better. I made the right decisions. I pivoted. And without that, maybe I wouldn't have done it. Like that's really rewarding to us. Thank you so much for sharing that. That's really, really powerful. And it's funny.

I think entrepreneurship can be the most intense ride of personal development and personal growth, because it can encourage you to look at so many different things that you maybe haven't looked at or be that forcing function to do the work, to become more self-aware, all of those things. I love bringing that element into it. There's one other thing you said too, which I think is really powerful, which I think you don't see in the world of Instagram and content is building wealth takes a long time.

You know, I think we're all used to the three second scroll and seeing all of these fancy flashy lifestyles and believing it and buying into the highlight wheel and you know, we know that's not the truth and that's not what it looks like on the outside. Generally isn't what it is on the inside. And from the two of you that obviously have built an incredible, incredible legacy, really, you know, you've built a lot of wealth and you've seen a lot of things.

What have you learned about money and wealth that you wish you could tell your 20 year old self? I think if I had to do it, I never really thought money would change anything. I think it, to me, it provides just comfort or convenience, right? I've always been afraid of not having my own money. So I think more of that has been chasing that kind of fear that the whole money thing, it's strange. You have it, you don't have it. And then you do, you know, with golf.com, everyone thinks, Oh my God, you made 25 million. No, no, we didn't. We only owned like a sliver. Mike and I made $3 million combined before

taxes. And if you take the total amount, let's just call it 1.8 million divided by two, it's 900,000 over seven years. That's not all. We didn't get paid for those seven years when we were doing gov.com because back then. So I think what I would like to tell people going forward is that you need to get your win, even if you don't have your financial gain, and that will propel you forward into whatever success you want. And what I learned about money is a lot of people come out of the woodwork when you have it and a lot of people treat you very differently when you have it.

And it's not always the greatest feeling. And I would just add that I love money. I'm a capitalist. I also didn't get into it just for the money. You know, my dad went bankrupt. I wanted to be independent. I wanted freedom. I didn't want to be chained to a desk. The money in today's society, it causes us to do a lot of bad things. And the biggest negativity that we're seeing is just to keep up with the Joneses. It used to be like you had the people in the neighborhood, but now it's like, you know, it's, oh, I got to like show that I'm like at this level. And it's just toxic.

What money buys is freedom. It buys your time back. It buys, you know, unfortunately with our healthcare system, healthcare is becoming a luxury product. So it buys healthcare and it buys a level of security and you'll never see us post private planes and Lamborghinis. And it just creates such awful feelings among the people who are watching, whether it's true or not, right? Which we could post all that stuff, but why? If you, God wants you to be rich, if you read whatever you read,

the Bible, Torah, whatever, and there's a requirement to do something with the wealth to benefit others. So it's OK to make a lot of money. But are you doing anything to help your community start there, right? Before you go to like curing malaria like Bill Gates. And I think that's what we've always thought of like, oh, it's like the best drug ever is like giving it away. Our efforts of cycle for survival to fund like, you know, in total, we've helped raise $412 million to fund cancer research. That's cool, right? Like that feels euphoric. And the day

we cure cancer is going to be like, that's awesome. Like we're, we're a little tiny part of this, right? And that's what we kind of get off on is like helping. And that's why like all the profits from the book are going to cycle for survival, it's why every company had a social good component to it. But you know money will amplify your great characteristics and your awful ones. I think the way you've put that is incredible and I fully agree it buys choice and I think that's a really beautiful thing and I think that's why I'm so passionate about talking about money to women,

especially is it buys choice and it buys security and independence. And I think that's incredibly important and especially for women. But what's also really interesting is I'm lucky enough to speak to so many really successful founders, like you guys on this podcast had someone on just before you too. And I always hear the same thing is like most of the time you get into business for the freedom and the choice and the independence and you've got that drive and at some point it really changes from this intrinsic to very extrinsic. How can I give this away? How can I make such a big impact? And I

feel like those are the entrepreneurs that are really going the distance and are still, when they could have retired 20 years ago, still putting out incredible work into the world because they're so motivated by ways in which they can make the world better. And I just think that's such an inspiring message for the entrepreneurs listening, who are maybe in the earlier stages,

who can't even fathom getting to that point. It seems to be the place that almost all really successful entrepreneurs get to, which is just so reassuring, I'm glad. You know, we're at, you know, make money. That's what you're supposed to do as an entrepreneur. And realize that once you do, you're still the same schmuck you ever were,

and you now have an added responsibility of making people's lives better. I love that so much. Thank you both so, so much for this episode. I have got so many notes written here. I was like constantly with my pen. This has been amazing and I just really appreciate how real and tactical you both are. I think that's what I love the most about the book is it's one of the most real books

that I have picked up in a really, really long time and I have recommended it. I've bought so many copies for friends. It's the best place for people to go grab copy Amazon and it's shoveling shit. Yes. It's shoveling shit. A love story about the entrepreneurs messy path to success. I love it. I absolutely love it.

It is so helpful. I think it's like a little toolkit every entrepreneur needs to have and be able to refer back to. Um, so everyone listening, I will also include the links in the show notes. So shoveling shit on Amazon and where else can everyone find you? You can find us at Cas and Mike on Instagram, TikTok. You can also go to info at casandmike.com.

Amazing. Thank you both so, so much. Thank you too. Thanks for having us. We appreciate you. Thank you.. Thanks for having us. We appreciate you. Thank you. Appreciate it. Wait, wait, wait, before you go, I would love to send you my seven figure CEO operating system completely free as a gift. All you've got to do is leave us a review on this podcast because it really supports the growth of this show. This is my digital masterclass where

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