Leap Academy with Ilana Golan - From Near Bankruptcy to a $745M Exit: The Raw Truth Behind Kass & Mike’s Entrepreneurship Journey | E112

Episode Date: June 17, 2025

Kass and Mike Lazerow’s entrepreneurial journey began with a leap of faith and a lot of grit. They started Golf.com with funding from friends and family, only to be acquired by a company that later went bankrupt. Forced to raise capital and revive their business against all odds, they quickly learned that entrepreneurship means facing setbacks every day and building the resilience to keep going when it feels impossible. In this episode, Kass and Mike join Ilana to dive into their new book, Shoveling $h!t, sharing the struggles behind their wins, the fears they confronted, and how they built successful businesses while balancing parenthood, marriage, and health challenges. Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. In this episode, Ilana, Kass, and Mike will discuss: (00:00) Introduction  (00:35) Meeting and Collaborating with GaryVee (03:20) Childhood Challenges and Family Struggles (09:43) Early Ventures and the Birth of Golf.com (13:40) Kass and Mike’s Relationship Journey (18:20) Facing Near Bankruptcy After Acquisition Offers (23:02) Leading with Transparency in Crisis (26:08) Fundraising Success and Tiger Woods's Influence (28:44) Navigating Parenthood While Building a Business (35:33) Prioritizing Health Amid Career Demands (39:38) Breaking Gender Bias in Entrepreneurship (43:57) Building a Thick Skin as an Entrepreneur (47:31) Overcoming Fear and Taking Action Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. Together, Mike and Kass have supported nearly 100 early-stage startup founders and have received multiple awards recognizing their leadership and impact in entrepreneurship and philanthropy. Connect with Kass and Mike: Kass and Mike’s Website: www.kassandmike.com  Kass and Mike’s Email: [e-mail]    Resources Mentioned: Kass and Mike Book, Shoveling $H!t: A Love Story about the Entrepreneur's Messy Path to Success: https://www.amazon.in/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Wow, this show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream roles, jump to entrepreneurship or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success.

So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay? So let's dive in. Great entrepreneurs love suffering and are tuned to pain. You need to be able to have that distress tolerance and it needs to be high so that you can go into the world and figure out who you are and what you're not good at.

Cass and Mike, serial entrepreneurs, best known for golf.com and Buddy Media, which was sold to Salesforce for 745 million. When you are an entrepreneur, there are many failures every single day. So you're really just getting punched in the face all day long. I remember the first time I got rejected by an investor. I took it personally. We had an offer to buy us and then March 2000 we got a call from the president, Brian Stroud,

and he just says, hey listen, I've got bad news. Sequoia pulled out. The market sucks and you're going bankrupt with us. This was a massive blow. When you become an entrepreneur, everyone's getting a front row seat into your failures. But there's nothing we'd rather do. We're trying to offer Chico's to not only help you build a business, but also a life. So what I think entrepreneurs need to know is.

Okay so this episode is going to be so so so fun. I have here Cass and Mike. They are serial entrepreneurs understatement, but they're best known for golf.com. And we're going to talk about Buddy Media, which was sold to Salesforce for $745 million. And since then, they've been helping entrepreneurs. They just wrote this brilliant, brilliant book about their journey shoveling shit. And that is just such a great name. Cassie and Mike, thank you for being here. Thanks for having us.

Thank you so much. It's going to be epic. So we just came back from Gary Vee and you guys just came back from Gary Vee. And we were just there basically for the podcast with him. And he actually forward the book. So I have to take you back in time to how you even met him. Share that story is just such a great story. Gary worked for his dad's company forever. It was a family business, first generation,

started when he was 13. He turned 34 and realized that he had no equity, never made more than $100,000. But he had a show on YouTube called Wine Library TV, which is really the first big show, which got him on like the Conan O'Brien show and all these things. And he showed up at our office. Literally, he showed up. It was a mutual introduction,

but he just came up. I knew kind of who he was. But he said, listen, I have no money. I have a vision for a social media agency. Right now, it does like everything. But at the time, it was just helping companies market. He was marketing his dad's liquor store. And he said, I can't afford an office. Can I use your only conference room? Basically, can I take 33% of your office space? Which is an impossible ask. And so I said, I said, I like your style.

I like the hustle. I'm gonna say yes, but you gotta talk to this lady because she runs all the operations and then you could tell the rest. You know, Gary, he's got this infectious personality. He's just full of enthusiasm. And he just kept going, come on, cash, just say yes. Come on, come on. Truth is, it's hard to say no to him. And we said yes, and then got a front row seat to him building this empire, and really changing the way everybody markets.

And what was nice is that our company culture really matched what he and his brother AJ were doing. So it was fun, we laughed, he is full of joy. There's no different version of him, he's just a joyful person. Yeah, yeah. I wanna put that in perspective because he didn't ask for your office for a couple of days.

No, no, no. He, there was no. So he moved in, he moved in. And he moved at, it's not only him and his. So that's a big ask. They got to 20 people in a tiny conference room, and it was the fire department that kicked them out, not us. I didn't know that.

The fire department came in and they're like, are you running a homeless shelter here? Or like a... All these young kids. And we're like, no, this is dude Gary who keeps getting clients. Oh my God. But look at the relationship that you built from that one yes. Totally. Which was a hard yes.

It's incredible. I mean, it's genuine, it's authentic. It probably defines the word generous. Yeah. But maybe I'll start with you, Mike. I think you mentioned that your parents divorced early. You have your own upbringing. Take us back in time.

What shaped you to the entrepreneur that you became? Yeah. So I was from a functional dysfunctional family. Parents divorced when I was six, but it was a very happy childhood for the most part. All of my role models were entrepreneurs. So my best friend was my grandfather, lived till he was 96. He built low income housing in Baltimore and was very involved in the community, Baltimore Hebrew Congregation. So he modeled that and my stepfather managed money and my dad was also a small builder

and had a home inspection business. My mom provided the ethical framework, so she is and she is and she was a lobbyist, public interest lobbyist. She worked on Title IX and basically fighting for everyone but me, everyone but white dudes. So she helped Equal Access and led the campaign against Justice Thomas on the Supreme Court and Leadership Conference on Civil Rights. And so I had this ethical framework and all these entrepreneurs.

And what I loved wasn't that they were making a lot of money because they weren't, they weren't entrepreneurs like we turned out to be, but they had independence and they showed up to my basketball games and they were at family dinner. And I saw other parents of friends and their parents were always working and I'd learned that, oh, that's a job

that they don't have any flexibility. And so I always said that I don't want to sit behind a desk. I want freedom. And that I always said that I don't want to sit behind a desk. I want freedom. And that's what got me into entrepreneurship. And right before your Burmeseva, there was some loss there. Take me there to that moment for a second, because the fear of money is also real with entrepreneurs. And I want to tie it later.

So take me there. I got a front row seat into bankruptcy. My father ran into some business issues through one of his projects. Made a series of bad decisions which led to mental health breakdown, severe depression. I mean, he was in a hospital for six weeks and it left a mark and it left a mark for a few things.

One is I was bitter at the time, right? And it impacted a mark for a few things. One is I was bitter at the time, right? And it impacted our relationship. But I hadn't really thought about the mental health stress that companies put on. And I write in the book about those lessons I learned from him. And I think over time, I've come to accept what happened and realize that it happens to entrepreneurs all the time.

And what's interesting is it's this fear of keeping up with the Joneses, right? Are people gonna judge me? What are they gonna think about me? And at the end of the day, people aren't thinking about you. People don't care that much. And so you're much better off dealing with your issues, even if it means downsizing your life.

There's a ton of shame too. What people don't realize is, and Mike and I say this all the time, is that when you become an entrepreneur, everyone's getting a front row seat into your failures. And when you are an entrepreneur, there are many failures every single day. There's very few wins. The wins have to have perfect synchronicity to actually happen. So you're really just getting punched in the face all day long.

And then when you have big failures, it's not for the faint of heart. And I will want to go there because I think we all feel it. But take me now back in time. You realize you have some dyslexia, I'll match later on. I think I am too. And then you also had your mom and your dad talk to us a little bit. I am the last of four kids in our family, and I have five and a half years between me and my closest sibling and age.

And my mom had zero help. There was no babysitters. My dad was on the road. He was a litigator and was just doing trial law work all the time. I look back, I just don't know how she did it. So four kids under, I don't know, six, seven. And it was crazy. But I kind of had my own upbringing

and then they had theirs. And my dad taught us tennis and basketball and golf at a very young age. He was a basketball player. And so I was on my own a lot. And my mom's favorite phrase was, go outside and play. I was playing with like rocks and twigs.

That's what we did. So I learned to bet on myself. I had no problem spending time with myself. Literally zero problems. I still to this day, would you agree? Yeah, she loves silence. That's her favorite message. I literally, like people say,

like what's my favorite music? It's silence. And I learned to better myself. I also started to figure things out on my own. I was never afraid. I had this confidence of no one else is here to figure it out. So if I can do it, there's nothing to lose here. Take me there for a second, because your dad gave me

this confidence, but your mom showed some anxiety because of this anxiety and depression. So how did that shape you? For whatever reason, and maybe it's birth order and maybe it's because my dad had more time with me because he became managing partner. And that freed up time, like being the founder of the law firm, he was able to spend more time with me, unlike my siblings. I knew my mom was suffering. I knew it. And instead of being sucked into it, I wouldn't let it

get on me. I'm not saying I haven't had severe anxiety myself and dealt with it and 30 years of therapy, but I did not want to be stuck in that kind of system. And for whatever reason, my athletics were a savior to me because what people don't realize is when you play four or five hours of sports, that's massive endorphins. So anxiety doesn't really have a shot to stick around when you're doing that much, which is great.

This is why when you have anxiety, you should get up and move. Right. Physico, yeah, for sure. One of the things that you mentioned is maybe she wasn't as satisfied. No, I don't think she was. And I think that is really related to our audience. I think a lot of our audience here listening, they're like,

I reached a certain point and I ticked all the boxes. I went to the college and I did the kids and I did the thing and I ticked the boxes, but I'm still not college and I did the kids and I did the thing and I ticked the boxes, but I'm still not happy and I don't feel like this is the life. And I think it comes with a lot of anxiety and I will try to tie it. But okay, so back at you, now you're going to college, right? And you're already starting some entrepreneurial endeavors. So take me there for a second.

So I have a very curious brain and creative brain. And so when I see something new that I'm interested in, I disappear. I go down a rabbit hole and I don't come up unless I find whatever is in rabbit holes. I don't know what's in rabbit holes, but I've been looking in rabbit holes my whole life. And the internet was the first time I was just blown away. And I remember the first time I heard about the internet, 93, 94, I went into the computer lab and there was no visual interface, but you could access documents and you could go to some of these early internet and I'm like, oh, this is going to change a lot. And I'm in journalism school and journalism is all

about information, the spread of information. I'm like, oh, this is going to be big for, or not. I didn't know how disastrous potentially it would be for some people in journalism, but I started a business. I'm like, this is the future. I want to be there. Sophomore year, I walk into my advisor's office, Mary Dydinski, who's an incredible woman, the first woman to be the managing

editor of a major Metro Daily, the Chicago Sun Times. Small in stature, but she's a bulldog. And I told her, like, I'm really interested. I want to do this. She's going to do it. And I was like, oh, that's not what I expect to hear from this, like, very hardcore journalist. And we're still in touch with her and we work on some scholarships together. Oh, that's incredible.

And what happened was I just got going, and what I tell all entrepreneurs is, if you want to get going, there's only one way to start, and that is to start. And your first business oftentimes isn't your biggest, sometimes it is, it oftentimes fails, but that experience, especially that I'm thinking through, like, you know, we have a kid who's graduating this weekend

from college and he's launching a business, and we're thrilled because it's the only way to learn how to do this. So if he wants to be an entrepreneur. Squap your knees. You just gotta do it. Now we think that they're Chico's, that's why we wrote the book,

just some of the stuff that we got wrong, but you gotta get dirty, that's the only way. Then somehow you learn about your idea with golf. some of the stuff that we got wrong, but you got to get dirty. That's the only way. Yeah. Then somehow you learn about your idea with golf. So you start with that, but then you change to golf. So I talk to us a little bit about that. Yeah. So coming out of college, I tried the management consulting route.

It wasn't my favorite. I was stuck on a government project that was just really painful. It was 1994, and software was coming out to build these things called websites. So someone just said, here's a manual, can you just read it? I'm not a coder, but I did, and started building that company's website. And I happened to mention it to my father's good friend, Jay Jaffe, and say, you know, you work with law firms, they're a marketing agency, you should build websites for them.

I bet you could build a lot. Literally the next day, he's like, come work for me, I'll double your salary, and we'll figure this out. So I got my real first taste of starting my own branch of a company, a little bit of a safety net there. And then by the time I moved to be with him in Chicago in 1997, we were playing golf all the time. Every weekend we were playing golf on these public course golf courses that were cheap, primarily because we couldn't afford anything. And I really

wanted an easier way as a golfer to track my game and get a handicap because it really wasn't set up for equity in golf for recreational golfers versus private country club golfers. So Mike had the idea, well, wait a second, let's create all that golf content and syndicate it to all the big websites. And this is back in 1998 where eyeballs mattered, right? Websites really, really mattered. And so I started it.

I brought on Mike Casper, who's our other founder. And then he left his job, which was after he got acquired from Student Advantage and came and worked with us. Amazing. How did you guys meet? So we knew each other growing up. We knew of each other. So Cass, I don't want to spill the beans, but she's a little older,

friends of my older brother. And you know, when you're like 15 and 11, 12. I'm 15 and he's the annoying 11 year old. You can't like really build a relationship. But I kind of knew who she was. We went to a wedding in 1996 and we were seated next to each other and I thought things were going okay. And just in our banner and then after

the bride and groom had their first dance, even though I was like riddled with fear, sweaty, I walk over, hey would you like to dance? You were really sweaty. I was nervous because she's like hot in a red dress, she's older, she went to an Ivy League school, she's also like doing internet stuff. So I'm like, and it was the best five words of my life, like we danced with me and we had a great night and then the next weekend I went to DC

and we had an even better weekend and it was just right. And I wasn't, a few things, I wasn't looking, nor was I good with what they called like the women. The women being, yeah. I wasn't good at dating. With women that actually exist. I wasn't good at dating. Dating would be better if you did that.

It was for these apps. And so it was like nerve wracking to walk up to someone at a bar and be like, hey, what's your name? And I was never good at it. So when Cass liked me, I'm like, done, let's go. Let's get married. Which you emailed her with a lot of romance. Oh, I was nervous about that.

He did. We were about to launch the company. It was this Sunday before we were about to launch golf.com. And I was downstairs. We lived above our apartment because we couldn't afford the business to have a space. So we were figuring it out. And he says, it's March Madness, and I remember this.

He takes our dog, Cookie, upstairs, and he goes, I'm just gonna watch. I'm gonna take a little break. I'm like, okay, well, I have some emails to go through. But he's like, okay, good, I'll see you upstairs. And I had 40 emails, so I started at the bottom. Right. But his was at the top. So, I waited probably 20 minutes, but

my other co-founder, he would be like over there, like looking at me. I'm like, hey, stop looking at me. You're being weird. And like just keep going back to my email in order, like, okay, delete, delete. And then was like, oh no. And then ran upstairs. I had other stuff planned. It was like a romantic night and we went to a few of the Italian restaurants.

So it wasn't all digital. Will you marry me? It was very simply like an email, will you marry me? You didn't really ever say it until- Well, the email was, our relationship started on email because we were dating long distance, and I think it should continue. I want to cry, I'm gonna try not to cry.

Please don't, easy crier. And yeah, will you marry me? And like 15 days later, it seemed she finally came upstairs. It wasn't 15 days, it was a good 20 minutes. I'm saying it felt, it felt 15 days. That wasn't like something that I liked. I know, because you click on that send and you're like,

why is he not responding basically? Well, I couldn't figure out why. I'm checking to go out. And his wife also worked with us and she kept turning around going, and I'm like, okay, why is everybody weird? Why are you smiling things out? Well, the weirder part was that we had started a business while we were dating. So looking back, there's no doubt there's no one I'd rather start a business with, but we were dating for like a year when we started the first business.

It's weird. I wouldn't recommend that in general because I don't think we'd talked about a lot of the stuff that we recommend co-founders talk about. Just talk about, right. We somehow got lucky. And we grew together. recommend co-founders talk about. Just talk about, right. We somehow got lucky. I think we organically knew our work ethics, because I think we both saw that we don't drop the ball on things.

If we say we're going to do something, we do it. If we have to stay at work late, we're not just going to punch out. There was some overlap in terms of all of those values that we both held very close to us. And we liked hard work. And we both felt like we wanted to own something. We need to talk about it afterwards because my husband will listen to this episode. But you know, if we're going to try to start a company together, there's going to be a divorce in one week.

And we're just like, no way. But you're starting golf.com, and again, you're right in the best trend possible. The internet. Everything is booming. Yeah. Talk to us a little bit about that. So we launched the company in September 1998. By December 23, 1999, we had an offer

to buy us, which was an all stock deal, which we thought was great. It was like a $10 million, $20 million all stock deal with a company. From a Silicon Valley darling, kind of. Sequoia backed, company named Chipshot.com, who told us and we saw in due diligence, they were going public in the spring. And just like every other company like E-Toys, right, worth billions, we thought this was great.

Our board voted for it, our investors were happy, and we spent the next three months trying to convince Chipshot why we shouldn't move there, which actually, if you think about it, like, thank God we didn't move all the way out to Sunny Vail, California. Let's wait with the story for a second, because your initial investors from Golf.com were basically friends and family, which could also get very scary and make Christmases very awkward. Talk to us a little bit about the initial raising capital. Well, most entrepreneurs need to go to friends and family to get that first chunk.

People always say, well, okay, we're going to start the business, we're going to raise money. No, actually, you've got gotta have a proof of concept. You've actually gotta do some stuff on your own, like open a bank account and put money in there and pay some people. If you don't have it yourself, you're going to be asking friends and family.

And so you have to be prepared that, and you have to prepare them, that you are going to lose their money. Because this is called venture for a reason, right? Did you know that at this point? Because again, like now I know it. I don't know if when I started, I knew the risk of going to family.

We definitely knew it. I think you and I would say to... We knew the risk and we would do anything to make it work. When you believe in something, there's nothing you won't do. Gary was very surprised that we set up a table two days ago in Central Park to sell the book, which we did. We were offering free entrepreneur advice, and I just think that you have to be willing

to do everything. If you're not willing to go into your park and sell your stuff to your local community, we happen to live walking distance to Central Park, so we're lucky that there are 14 million people there every day, but also, if you aren't gonna ask people who love you to support you, do you really believe in what you're doing?

It's not an easy ask. It's not like you're sitting there going, hey, you wanna make some money. That's not it. We are starting something, there's an opportunity, but you have to assume you are going to lose your money. We didn't know investors also. Like most entrepreneurs, when you start out,

you don't know these. You don't know, exactly. And venture capital is a very small subsection of entrepreneurship. This book is written for pizzeria owners and salon owners, the real entrepreneurs who have to fund their business off their bank account and customer revenue. So now you're back to the story. So you have, again, all these investors, which are friends and family, which I think is really

important because there is a lot of fear also and anxiety of making that not work, right? Even though it's real. Right. And everyone was psyched. Everybody's psyched. This is our company was psyched. Behind the scenes, we were basically, like I said, trying not to have them move us all out there. And then March 2000 hits and we get a call from the president, Brian Straub, and he just says, Hey, listen, I've got bad news. We were on a speakerphone because there were no Zooms or FaceTime. And he's like, look, Sequoia pulled out, the market sucks, and we're going bankrupt and you're

going bankrupt with us and we can't pay your payroll. And we were just like, wait, what? And say it again. And all I kept hearing was we don't have any money for you because when you get acquired, your bank accounts are locked, they're done. So they were paying all these employees and I think our biggest panic was, oh my God, what does this mean? And then of course you start going through your head, okay, my dad lost money, my brothers lost money,

his family lost money. We lost everything. We lost all of it. We put in all our money. We put in 30 grand that we had saved over seven years each. So it's messy. Talk to me about that day and right after, because I think one of the things that people need

to hear the real truth, right? Because on social media, it always looks- Rosy. Very rosy, because again, every single great leader has a history they're not sharing on social, right? Or in general, that's not what they talk about. Yeah, I mean, this was a massive blow.

This was, we are dead. How do you sleep? How do you wake up? How do you continue despite the blow? First and foremost, I think, and we did this right, Mike and I said, along with our other co-founder, we need to be truthful right away to the employees. There can be no sugarcoating to this,

and we learned that the hard way because, you know, you go out there, they know something's going on, right? Like, people can sense it. And we went out there, we were honest, and we said, we have no payroll. We can't pay ourselves, we can't pay you all, but we're going to start this thing over. We believe in it. And not one employee left. So what I think entrepreneurs need to know is there should be no distance between you and your team in terms of knowledge, the good, the bad, and the ugly. They can't handle surprises.

They can handle change. They can handle bad news. But when you hold stuff back because you think they're going to react some way, it just makes it worse. We just had this conversation with Gary. It's so funny. The difference between transparency

and freaking everybody out. I think the way I always lead is by saying, I believe this will freak you out. It is freaking me out. And I am going to sit here in it with you and we're gonna come up with a plan and move forward. When you name things, they have less power, right? And that became the way we move forward.

It's transparent. Now people ask us all the time, well, how transparent? Do you tell people salaries? No, I don't tell people salaries. But I'm not hiding anything. The truth, okay. So at that point, you're basically in survival mode.

Yes. And the only way is to raise enough capital to pay salaries, I assume. Yes, took three months. Which is pretty incredible for the year 2000. I mean, things were... That is insane. Things were like literally, there were carcasses of businesses on the ground everywhere we went.

So to be able to raise capital in such a short time and for the investors to know that this is kind of going into also debt to some extent, that's not simple. No. So is that because of your belief? Is that because of the story? Is that because you already? The biggest lesson was name the problem,

take responsibility as a leader and communicate a plan. Like what are you gonna do about it? She said, we just sat around the employees saying, oh, woe be we, like woe is me. And so our plans, we said is we're hitting the road and we're not coming back until we get our money. Like literally. And we didn't have money, so we're flying like Southwest.

We're staying with three of us. We're doing overnights everywhere. Three of us are staying in motel rooms with bulletproof glass at the front and with Cass's Aunt Boo rest in peace in New York City. 900 square foot apartment where we're on a Murphy bed and he's in the living room and Mike Casper's on the couch. And like many fundraisers, we just got lucky. And when I say

lucky, we were in Chicago, we didn't know a lot of investors, we didn't find our money in Silicon Valley or New York, even though that's where we went. We met one of the few venture capitalists, Keith Bank, who happened to be on a mission to play the top 100 courses, loved golf. He still does. Golf is his life. And he introduced us to a lawyer, Bill Weaver at Sacknoff & Weaver. Rest in peace. Who also has passed, but he had golf friends at Medina and he was a member of Medina Country Club, which is as prestigious as you could get. High end, yeah. Like very prestigious kind of one of those clubs, right?

Right. I didn't tell them Jewish. I can't like, I gotta be buttoned up, right? And he welcomed us and he got all his golf buddies and we were in this, I remember this ornate ballroom, the most designed ballroom you could ever see. It was like the Versailles ballroom. And we just said this is what we're doing. And by the end of the lunch, we had a million dollars. And like, I remember Bill being like, all right, who's in? Raise your hand. Yeah, Bill just like drove it.

And I literally was like, wait, what? Like, is this really, are we voting with hands? And Bill, like his only thing, he's like, I'm gonna help you raise money, just use my law firm. That was it. Incredible. And we're like, yes. We're like, yes, Bill, we will do that. And we came back and told the employees, we didn't lose one employee. And I think what's important for people listening is,

first of all, a lot of it is that you found these common grounds and interests, right? Because again, there's a little bit of if they understand the mission, you basically attract them to want to invest. But you also again, all the coolest opportunities are always in this hidden market. It's all connections. It's all right, like it's who knows who and that open incredible doors. And it wasn't that we knew these people. Keith Bank was a cold call. Let's also say this though, golf was hot. Yeah, so the other thing that we got lucky on,

because timing is everything, is trends are your friends. And we've seen it over and over again. Not just the internet, but we bought golf.com back, and there's this kid, Tiger Woods, who wins the Masters. So like, all of a sudden you have like, imagine Taylor Swift winning like golf tournaments. That's what it was like globally. You just say Tiger and every kid in China, every kid in Europe. So that's why I feel like Bill and his friends, also Bill was incredible with

technology and really in the front in terms of understanding how technology would impact the world. He really was a pioneer in terms, especially in a law firm. And between that and really loving golf, I think, you know, we hit a little bit of a jackpot there. If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career and life to the next level. I have the perfect solution for you. We have a program that helps you fast-track and leap your reputation and career, become the best version of yourself, get the dream role you deserve, move up to leadership, jump

to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes. Now back to the show. Now at this point, you're then growing golf.com, but you're also getting married, three kids, that is a lot. Yes. How do you navigate all of it? You know, there's no perfect time to get married,

there's no perfect time to have kids. We knew we didn't want to miss out on certain things, like children, and we just jumped because just like, there's no perfect time to take a vacation, right? A little bit more of a commitment. Just a little bit. But we had our first two children while we worked at Gov.com. And it was a lot of work.

It was a lot of work in between changing diapers. There was a lot of, I would say, parenting that wasn't the best. Well, the first year of any new parent is a blur, right? To add to that, entrepreneurship and trying to build a company together, my husband and I would bite each other. So how do you, how did you cope?

Like I think one of the big things was like, you never thought like when we would go down, literally it was the size of this room where we worked, and we'd put the kids to bed and we'd come back down. I remember we could work really late back then. We're old now. We're like, oh, so we're tired. But you thought, and I thought, if we had stuff to do, you'd get it done.

Yeah, everything, you just do it. And entrepreneurs can always do another call. There's always more work, but you know it has to get done, right? And so we just believe that you can do anything, you can't do everything. And so I look at that time and we did two things. We did the company golf.com and the kids.

And we did the same thing with Buddy Media. Viv was born right, the day I got the idea for buddy media and I really like that it keeps us out of trouble You know what you're doing every day. You're fired up to get up You have a reason for the company to succeed. I didn't really think about money But I did think about how do we make this a success so we can pay for education, right? We could pay for college. We could provide them a life. We were born on third base in my mind.

We grew up in the suburbs, parents could afford education. I didn't feel rich, but there was nothing I needed. And there are two ways to be rich. You make a lot of money or you need nothing. And we were like right in the middle, right? I don't think they made a ton of money, but we didn't need much. And so I think the best time to have kids

is when you're running these businesses, you're just gonna lose some friend relationships. You're not gonna be able to work out as much as you want. You're not gonna be able to travel. You can't just throw that in there. I was like. They're trade-offs. Don't say they're trade-offs. You're not going to be able to travel. You can't just throw that in there. It's like- They're trade-offs. All things are trade-offs.

There's consequences and trade-offs. So talk to me about the consequences, because I think one of the most important pieces is that you can have it all just not at the same time. Yes. So how do you become OK with the things that you don't have? At least every single mom who's an entrepreneur that I speak to, I say the same thing.

Easy for me to look back, but if I could go back in time and say to myself one thing, it would be, give yourself some grace that when you're 80 or 70% doing everything right for the kid and you're 100% focusing on the company, that's still great. They're still gonna be okay. So you have to have some release of that guilt because you're just never gonna be able to be perfect.

You can only do one thing great at a time. And I think the guilt is everything, right? Because I think this is where we're not hurting necessarily the kids. It's more of our never be present in anything. That's why it was helpful for us. I never said, oh my god, neither of us are present.

It was kind of like, well, he knows exactly what's happening with me. It's so hard to sit and play right now. I had a built-in support system who knew exactly what I was doing or not doing for that matter. Let's talk a little bit about you're growing this business now by the media, you're trying to navigate marriage, kids, a ton of hard work. Does it ever come to a place maybe there or in Gov.com where oh God, I don't know if I can do this. This is too much is definitely for me.

I mean, every day we're having those conversations. We're having these conversations even about what we're doing right now, which is selling the book. It's like, oh my gosh, is this ever going to end? There's so much you can put on your plate as an entrepreneur. And we both don't want it to end. And we don't want to not put in the maximum effort. But it's going to be a bestseller anyway. So why are you putting so much time and effort? Because I mean, the thing is like when we commit to stuff, we're all in.

I think that. And I think a lot of entrepreneurs- It's like a personality thing, right? Yeah. Like why do anything if it's going to be suboptimal? Why write a book if no one's going to read it at the end of the day? And so I think when we're going through these companies, every day is, oh, we're as miserable as we possibly could be at work,

and there's nothing we'd rather do. So that's why shoveling shit a love story, because it's not about like, oh, look at us, we're working so hard, our life is miserable. It's like, no, this is where we find our purpose. This is where we find the passion. And this is how we build a life that's worth living, which was always important to us.

And our kids are like, well, you could have been billionaires. We see how you work, right? But I'm like, were we around? Did we go to your school stuff? And for the most part, we made trade-offs. Could we have made more money? Maybe, but we were crafting a life that included date nights on Wednesday and Saturday nights,

and being able to take a trip a year, and having close personal relationships outside of just us. We're trying to offer cheat codes that not only help you build a business, but also a life. And as we looked at the book, that was the stuff that I thought was most important, because when I started out, let's just say, I wasn't self-aware, I didn't know my strengths

and weaknesses, I didn't know what I wanted in life, and it took us to be very proactive and cast, I think, as the operator, kind of compassionate feedback to get to where we are today. And so we share a lot of that in here. And I love the book. I think I shared with both of you separately and together because I think it hits home. For me as an entrepreneur, I'm sure it hits home for other leaders as well.

But for me as an entrepreneur, it does feel like you're essentially shoveling shit all the time, right? And it's like, but take me there, because Mike, at some point you're flying and you're away a lot and then your health deteriorates, because again, these things are real. I can see it myself, like I'm not where I used to be. So I mean, it's like, how do you? So we prioritized a few things,

company, kids, our relationship. What I didn't prioritize was my health. So I weighed 40 pounds more when we sold Salesforce, traveling all over the world. We had offices in Singapore. Social media was global. So we had global customers. And we're talking about nine of the top 10 global marketers. So we had London office and we had someone in France, we had someone in Australia.

And so I'm like on a plane, client dinners, not working out and then we sold to Salesforce. And I used to drink, I don't drink anymore because it just doesn't do it for me. Was there a moment when you said enough is enough? COVID is when it really happened, but I'd already cut back a lot because it just didn't agree with me.

And it wasn't a moral thing or an ethical thing. I love cannabis, I love other stuff. It's just that to me just doesn't do it. I'd wake up feeling not great. I also have an artificial heart valve and my health has always been top of my mind, I guess. And so it got to the point at Buddy Media and my health has always been top of my mind, I guess. And so it got to the point of buddy media and then Salesforce where I work even harder.

Salesforce, there's no slowing down. And we wanted to grow and the company did, went from 6,000 to 20 while we were there in the four years and 2 billion to 10 billion in revenue. And my cardiologist said, you're gonna die if you don't get in shape. You're putting too much pressure on your heart valve, which it's like any machine, but it's gonna stress it out.

And I had dinner, it was September 2014, we had dinner with Gary and he looked great. And he'd hired someone as a trainer to travel with them. And at that dinner, I forget then it was a sushi place, I'm like, I gotta do that. And he even said, he's like, he's like, you're fat. Like you're like not gonna live. Like you look, and I'm like, you're right. And so 2014, I started prioritizing that.

It's easier. Before that, what did you think? Did you see all of that happening? Oh, we both, I was 35 pounds heavier. I had an undiagnosed severe thyroid issue. I was in pain. I was getting migraines daily. And literally like chasing migraine pain, but trying to prevent it with different medicines.

We both saw it. We saw it. And we weren't connected like we... Like when we're at our best, we're like yin-yang. We know what's going on. When I'm on a plane, a 19-hour plane ride to Singapore, which I would do like every quarter, we weren't talking. We weren't doing date nights.

And so, you know, it just felt very lonely and very like, this can't continue. Because then you get to that point, you're like, you show up to the very like, this can't continue. Because then you get to that point and you're like, you show up to the gym and you can't do anything. Because you're too tired. And then you eat with clients and you start shaming yourself.

But it's like, okay, we're at like Jean George restaurant trying to wine and dine. I can't get like the veggie menu, right? And so we're in a culture right now that celebrates wellness more. But at the time, if you remember, enterprise software was sold over steaks and wine. Oh, it was not health. Oh, totally.

And so now it's kind of, you know, a lot of the people we work with, like, let's go for a walk or let's go to a class or let's go play pickleball. That didn't exist as much back then. And if you didn't drink back then, it was very, very awkward. Yeah. Very, very awkward. In eight, like, drinking eight. And I remember as a woman, I would go to these bars and people would expect you to drink. It was actually almost like a test, right?

Like, they would kind of like push the drinks at you. And I'm like, I'm not going to get drunk near you. So like, that's not going to happen. So I was just like toss it or something like I would find my way. But speaking of as sorry, a woman, I do have to go there for a second. Like I think there's a lot of advantages that we have, but there's also a first impression disadvantage. Like if they don't know exactly who you are, the first impression sometimes is harder. I can tell you, when we were running golf.com, talk about a really tough industry for a woman.

I mean, it is 100% male dominated. If you just look back at what were the advertisers. Oh trust me, I was in the Air Force. Yeah, I know. I hear you. What were the advertisers at the US Women's Open, and it was tampons and shampoo or something. This was a very hard industry.

I think it was easier at Buddy Media. I think Mike also looked at me and always has as an equal, and so there was just no way around that. We had difficult investors who would sometimes try to make me less than, and that's just what happens with women. So walk me there for a second. Was there specific moments when you're like, how do I change this? I think change people's perception is hard to do.

I think my dad had always taught my sister and I to be equal to my brothers, and ironically less so my mom, which was very odd to me. I remember being young and being like, why does my mom think I should serve my brothers? But my dad's teaching me how to box so that I can punch my brothers. This is very interesting. But I think part of growing up with a tough family is you have thick skin. And I found it very funny.

I find it more frustrating as I get older that I'm still living in a society that devalues women and things like that. But you just got to keep moving forward and you got to have advocates around you. And I had a lot of great advocates. I think what you're doing here also is breaking those ceilings, right? Like I think sometimes I share it even with my staff, even in the podcast, when we reach out to, again, a lot of leaders, like a lot of women don't say yes.

That's interesting to me. And it's like so interesting because we have Richard Branson, we have, you know, we have like't say yes. That's interesting to me. And it's like so interesting because we have Richard Branson. Right. Your guests are like epic. That's so wild to me. And most women say no. That's crazy.

Or they just ignore us. I mean, I'll give you an example. We've experienced, you know, one of the most frustrating parts of running buddy media was often women on women. Being hazing. Like violence. Not violence, like hazing. Like literally hazing. What I mean by emotional, like mean girl stuff.

And I remember Cass would just go after it. Like if I see this again or fire people on the spot. I would fire them on the spot. I was not going to be in a community of people who are working this hard to have one kind of mean girl experience. But I will say this, we, Mike, Mike actually bought it and then for us a golf franchise, the New York Bluebirds.

And we happened to in this last... So I bought it without telling her. I knew she wouldn't like it. And so I was like, wait, what? So in any event, we ended up winning one of the big tournaments with this incredible team. And we're co-owners, right, with everything. of the big tournaments with this incredible team. We're co-owners with everything. And Cass does all the work.

We had to find the players. We had to find the head of player relations. We had to get all the uniforms, come up with the brand, market it and all that stuff. They kept trying to hand the trophy to Mike, and Mike kept just handing it back to me. It's just so funny. And then when we were celebrating, Mike's like, you hold it up. So you have to have advocates around you, but it still exists.

It's infuriating. It is. And I usually don't go there, but I think it is important, especially as you work together. Like, I'm sure there were places that you walked in the room and you're just not, like you must be like that. When we started golf.com, I was, I think, president or something. And you guys were VPs, I don't know why that was. Who you started the company.

Yeah, I know, but like I don't care about titles, but I'd go into the room and no matter what my title said, they looked at him and our co-founder. Yeah. So let's talk for a second about thick skin. You mentioned the word thick skin. And I think that's really, really important because I think in entrepreneurship, you're gonna hear a lot of hate.

There's gonna be things from, I don't know, lawsuits and things. I mean, think shoveling shit. Things piling your way. How do you create that thick skin? You create it by doing it. So the first time you do anything, I remember the first time I got rejected by an investor,

I took it personally. And then the hundredth time you're like, whatever, like I guess that person doesn't like making money. They must not be a capitalist if they didn't invest in me. And the only way to develop a thick skin is to do the stuff that's hard. And what's interesting is you have to lean into the pain because that's where everything is.

Your customer pain is what you're trying to solve. Oftentimes a pain that you have is where great businesses are powered by. And people are like, find out what you're passionate about, do what you're passionate about. It's like, no, do what you think makes sense from a business, which are we think six specific things. Very rarely is it in a passion.

And frankly, when we did golf.com, we ended up hating golf and not playing for 10 years. So whatever you think you're passionate about, do it for a living and you will be anti-passionate about it. You will hate it. And so I just think great entrepreneurs love suffering and are tuned to like pain. They know when their employees are in pain

and when customers aren't happy and when, and I just think live in that, live in the discomfort because that's where you grow and that's where good businesses come from. I want to lean something that you said because I think it's really important for the listeners. We do believe in a zone of genius. Like I do believe there are sweet spots

where your unique experiences and skills and connections and everything or whatever shaped you, that can be a really good spot. But what I love what you just said, and I think is important, sometimes people start a business because they're in love with a certain thing, idea. I like to coach, I like to whatever, to teach. But when you're going to start a business, 95% of the time, you're not going to coach. You're going to do sales, you're going to do marketing, you're going to do whatever,

you know, show bullshit, right? Because I think people are coming from the passion, but what they actually going to do is 90% of all the rest and the passion is not going to be there. So I think that's just an important distinction. Great entrepreneurs can do anything. We talked about Gary, right? And he has an agency. He has a trading card business. He has like We talked about Gary, right? And he has an agency, he has a trading card business.

He has like all of these things, right? But running a business is running a business. We've started buying businesses, cashflow businesses. And we run our playbook, which is giving back and all these things. Like first thing we did with our healthcare staffing firm is we started the kind of this matching program, which is a profit sharing program. And employees, it's a 25 year old company, they never felt

a piece of like all the profits, right? And then alignment happens and then good things happen. And whether it's like a healthcare staffing firm or a car wash or pizzeria, it doesn't matter. It doesn't matter. Treat people with respect, align incentives, make sure people can grow within the organization. We constantly were saying, what do you wanna do? Like you wanna start a company. You're not here as your last job,

and what you're doing at this company is not your last job. So we wanna understand your path. So we have a growth path for you. Which makes sense. But talk to me about money fear. I grew up watching a dysfunctional relationship between my parents and my mom, literally fearing she had no money, which is odd because they were married for 42 years before they divorced. But it was like, I am not going to have somebody else's money. That was exactly what my mantra was all the time in my head. I will make my own

money. I will be self-sufficient. I will not lean on anyone else. So that's what we did. And now I think we lean on each other. But I think that's it. You know, I had a question for you in the Air Force. Don't you feel like that prepared you because you had to suffer so much? Oh, yeah. And I feel like when I was an athlete, that training, that six hours of training a day, that's just what prepared me. And that's why I... Athletes and military, the two best places for like, entrepreneurs to train.

I do agree with it. And I think at the end of the day, it's so funny because my son is now signing up for college or whatever. And I'm like, I don't really care where you go, because all I care about is that you have resilience grit and the first, you know, your first chance at internship. That's all that matters. It's funny. Our oldest is graduating this Saturday. And what we're celebrating is that he got through something that he hated. I love that. That's it. He hated the whole four years. He didn't like studying. He didn't like the classes.

He made some friends. But I said, this is what you need to be in the world. You need to be able to have that distress tolerance, and it needs to be high so that you can go into the world and figure out who you are and know your strengths and know your weaknesses. That's so true. And I was like, you know what, if you want to take a gap here, take a gap here. If you want to work, you want to work. You know what I think about education. I think it's really, really important, but I think it's time to disrupt it. It's broken right now. People have to realize no decision's final. You could be in med school and say, I hate this

and go become an entrepreneur. You could be a stay at home mom, which is the hardest job or stay at home dad, the hardest job. Like we would have failed miserably. And make a decision that, you know, say I need to like get out there and interact with people. And I think that that idea people get stuck.

And I think your mom, she was highly educated, one of the first women to be accepted in the Chicago Business School, made a decision or was told, societal that she'd be a stay at home mom. And I think- That's my mom too. And I think that- It crushed her.

It crushed her. As she down, there was an anger and resentment toward your dad. And it's not that the kids aren't enough, it's that she had more to offer. There's more to offer to the world, and the regret creeps in. And her voice, she had a lot to share. She could have shared a lot more. And a lot of kids would probably be better off, I'm not saying you, if the parents weren't

around. Right. Like, if they were working. But they actually chased their dreams. So for people who are listening, except for obviously reading your book, except for the people listening, and they want more for themselves,

they want the impact, they're trying to figure out what's next and maybe they're afraid to take that step, but they really do believe they're meant for more. They just don't know what that more is. What would you say to them? We say this all the time. It's not about where you went to school. It's not about your GPA.

It's literally do something. Take the step to show that you led a project, and here's how you helped people, or you hired a team to go finish this. Or, like in my case, I was given this chance to run an interactive arm of an agency. That was a lot that I had to figure out. You can't get stuck and paralyze saying, I know I have more to offer,

but I don't know where to start. Your job is to figure out your talents. What are you good at? Figure out what you're not good at, and then find people around you that fill in those gaps so that you can go out in the world and say, okay, I'm going to apply this now to this kind of job. I didn't like that, but I learned something and

now I'm going to sharpen my skills over here. And then eventually if you say, I can be an entrepreneur, great. Be humble enough to say you are not going to be the smartest one in the room. Right, that's strong. So that's like really good practical advice. No, he's got to call it with something that's totally different. No, it's not totally different, but I think what's holding a lot of people back who I speak to is fear.

There's something that isn't even like based on anything real, but they're scared of something. And oftentimes- What will people say? What if they fail? I mean, there's resilient things. But it's oftentimes it's stuff they can't verbalize, but it's what it's my mom gonna feel.

Like for me, like my mom wanted me to be a political journalist. She still does. And she's like, why wasn't I like celebrated in the book? Cause like you really weren't like, you didn't want me to be an entrepreneur. Like what was I gonna say, right? Like I got my ethics from you.

Oh my gosh. And oftentimes it's just, I'm not gonna say irrational fear, but fear that will never go away, but you have to jump with the fear. Like when you jumped out of airplanes, which when you went like, you know, you had to jump full of fear, but you still have to jump. You did your prep, you knew that your parachute

was gonna come out, you knew you were gonna land, you trained for it, and people need to jump. And they have a parachute that they don't know, you know, they don't always recognize. Now when you don't jump is when you have like a huge mortgage and three kids and you have real responsibilities. You gotta be an adult, right? Decisions have consequences. But the other thing is that you told on top of that is by doing you are and Gary says

this all the time, you're doing the reps. So you know, like Mike said, you're gonna have fear. How do you get over the fear? By jumping once, then jumping twice, then jumping three times, and then the fourth time it's not as bad because you know it's gonna happen now, right? And you're developing, you're doing the reps. And you're gonna love starting over. Like Gary is like, everyone else is probably asking you like why are you working so hard? But he's like, I know you guys like starting from zero and building something. And learning. And proving yourself.

And you know, I told him how many books we sold. He's like, yeah, it's not a surprise. Like you guys have been out there, literally in Central Park, asking random people, tourists, to like go to Amazon and buy the book. And so I think when you get over the fear, get over the uncertainty, the self-doubt, all that stuff, you develop a confidence that lets you start fresh no matter what. Whether you lose all your money, whether you have to change careers,

whether you have a new experience. And that confidence is what we want to give people in this book. We didn't have it figured out. Like there are a lot of moms that we speak to or like it's the first time someone has given me the ability to be nice to myself. So perfection and balance just don't exist.

They don't exist. Take imperfect steps every day and done is better than perfect. And then you get started. Hey, Mike Cass, thank you so much. Thank you for having us. This is amazing. No, this is great.

First of many, hopefully, congrats on the business. We may have to sign up because we're reinventing ourselves. You're going to partner on something for sure. Yes, kind of. Thank you. Thank you again. Thank you. I hope you enjoyed this as much as I did. If you did, please share it with friends. Now, also, if you're feeling stuck or simply want more from your own career, watch this

30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilana Golanchov.