Breaking the Feed: Kass and Mike Lazerow on Building, Selling, and Betting Together

BP_The Lazerows_Basecut
Leah: [00:00:00] Mike and Cass, welcome to Breaking Precedent.
Kass: Thank you for having us. Thanks for having us.
Leah: Yes, so excited to chat. I finished your book, [00:00:10] Shoveling Shit just last month. I loved it. I can't wait to talk more about it. Um, before we dive in and start [00:00:20] shoveling, I'd love to open with a little icebreaker. Are you two ready for this?
Leah: It's gonna be a good one. Yes.
Kass: Yes.
Leah: Okay. So you two have [00:00:30] talked about the kitchen table, the place where you bring everything, and you just dump it, and then you rebuild from there. So before we go [00:00:40] anywhere near the amazing companies you've built and invested in, I actually want to in- start inside your marriage.
Leah: I would love for you two to [00:00:50] think back to what the most maybe a, a messy moment in your partnership was. And, and maybe not, not the hardest, but maybe [00:01:00] the messiest. And what was that moment, and what did you do to clean up that mess?
Mike: So they're [00:01:10] usually my messes, so I guess I'll start with that. You know, our messiest moments are when this intersection of, like, personal life and, [00:01:20] you know, business life kind of collide.
Mike: And, you know, typically that's-- for us, it was around kids. And so, you know, as we were [00:01:30] growing our business, all of our businesses, we had young kids. I mean, even going back to Golf.com, you know, we had very young kids, uh, two sons and daughter, who's our [00:01:40] youngest. Two of them have graduated college and are in what's called the real world.
Mike: One's at Northwestern, you know, Vivian, our daughter. And like many [00:01:50] parents, just the shit hits the fan at home. And for us, that seemed to happen around pivotal moments in the company. So [00:02:00] when we sold Buddy Media to Salesforce for close to a billion dollars, we were, you know, our kids were not doing great.
Mike: We, [00:02:10] you know, had, you know, they were struggling in their own different ways, and it was supposed to be one of the best moments of our life. Like, you [00:02:20] know, big sale after, like, doing all these other companies that had exits, but not like this. And we're just talking about, you know, who's taking the kids to the doctor and, you know, what are we gonna do [00:02:30] about this?
Mike: And so, um It was, it's just all in and taxing. You know, and that's what I think about when I think about kind of the tough moments. It's [00:02:40] not really the business stuff. It's like, for us, working is just what we do. Like, we get up and we work, and many entrepreneurs can feel that, right? You get up, you [00:02:50] shovel, and shit hits the fan, and you figure it out, and you keep moving, as you've done, you know, your whole career, right?
Mike: Like, I can't imagine what it took to grow TaskRabbit from, like, [00:03:00] an idea to actually reality. It's kind of a crazy idea at the beginning- ... until it's not.
Leah: Right. Right.
Mike: And, um, and basically we come together and, [00:03:10] um, you know, we're both usually tired at that point, and, you know, I'm not listening as well as maybe I should listen, and not as present as maybe I [00:03:20] should be.
Mike: And that's where a lot of the friction came. The great thing about us is we fight well, and we get through stuff well. Like, you can throw us [00:03:30] in any environment, however tough, and we'll work together to figure it out.
Leah: Yeah. What do you think, Kas? Anything to add to that? How did you clean up his [00:03:40] mess?
Kass: Well, I mean, uh, well, first of all, I think the division of, of labor, so to speak, our different skill sets really helps [00:03:50] us.
Kass: And, um, it definitely helps us in business. I think it's more challenging in the marriage, uh, because you live with that person. [00:04:00] So, like, for instance, like, I like everything organized. I like everything to have, be in a compartment. I like not seeing mess, right? I'm putting everything in my Excel [00:04:10] spreadsheets.
Kass: And, you know, Mike and two of my other kids are artists, and their canvas is the whole apartment. [00:04:20] So I think it's- Yeah ... been interesting to learn, um, how the differences work in the different arenas, both at home and in business. [00:04:30]
Leah: I think you guys would be killer on The Amazing Race. Have you ever thought about-
Leah: doing that?
Kass: You know, it's one of my, it's one of my favorite shows.
Leah: Yeah.
Kass: Um, [00:04:40] I, I think m- I think the hard part would be that, I mean, I think, Mike, you have a good sense of direction, but I think that's always my panic on that show, is that you have to have [00:04:50] someone who- My God ... really understands, like- The direction part, 'cause you're all constantly moving- Like a compass- Yes
Kass: and
Leah: a
Kass: map,
Leah: and you're like- Yeah ... yeah.
Kass: Yeah. That's not gonna be me. That's not me. Yeah,
Leah: okay.
Kass: Okay. [00:05:00] Now, w- w- which, which, you know, tasks to do and the opportunity costs and what to do there, I can help you out there, but-
Leah: Yes ... uh-uh. I love it. I love it. I think you guys would do very well. [00:05:10] Um, okay, I wanna rewind all the way back to the beginning, to the kids you both were before any of these companies existed.
Leah: So Kash, you [00:05:20] said you were always entrepreneurial from as far back as you can remember, and I love this great line about a friend reminding you that you used to sell barrettes at [00:05:30] school- Yes, my friend Bobby ... and you made so much money. I did. So can you tell us a little bit about, you know, where that entrepreneurial spirit came from growing up and [00:05:40] how it manifested?
Kass: I think, okay, so being the fourth child and having, you know, five and a half, six [00:05:50] years, you know, between the closest sibling in age, my brother James, it, it was kinda like I had a different family life, right? They had the three of them, they were all close in age, [00:06:00] and they kinda went off and, you know, they were doing things much different than I was doing because I was younger.
Kass: So I was kind of fending for myself. I think I learned a lot of my [00:06:10] operation skill from my mom because she was just constantly having, you know, four kids running around, how do you do the logistics and getting everything done? And I [00:06:20] learned leadership from my dad. In terms of entrepreneurial, I wanted my siblings' freedom.
Kass: And for whatever reason, [00:06:30] I thought if I could have money, because I remember my mom back in the early days before my dad made managing partner, w- if we [00:06:40] all contributed to a bucket, like a, it was a coffee... What are those coffee tins back then?
Leah: Yeah, like the
Kass: Folgers- We could all go to the [00:06:50] movies ... plastic coffee tin.
Kass: Yes. Yeah. We could all
Leah: go to the-- We could go to the movies. Oh
Kass: my gosh. Wow. But if it wasn't all of us, we all didn't go. Wow. And so there was a lot of resentment from my siblings, even though I was younger, [00:07:00] and I think I just wanted the fairness and equality of being seen, and so I thought this is a way that I could elevate myself.
Kass: [00:07:10] And truthfully, I do like a good arts and crafts project, so like making those barrettes was just, it kind of fulfilled two [00:07:20] things.
Leah: I love it. I love it. It's so great. And Mike, you talk about your parents were divorced when you were six, you grew up with your mom and your stepdad, who ran [00:07:30] a money management firm.
Leah: So you said you were surrounded by people who kinda did their own thing. What is the earliest memory you have of [00:07:40] realizing you'd rather do your own thing too than, than work inside someone else's?
Mike: Yeah, so the earliest memories are actually of my dad, who [00:07:50] was a real estate developer, small developer, like single family homes outside of the DC area, you know, a place called Frederick, Maryland, and did kind of individual [00:08:00] homes, some town homes.
Mike: You know, one year won, like, developer of the year. And, you know, I remember on Saturdays going with him to the, like, [00:08:10] his projects. You'd see the construction, you'd see the, the progress. And, um, I also saw him not only kind of win that award, but I saw the [00:08:20] toll that these companies could take on their mental health.
Mike: And, you know, he ran into some business problems and, um, you know, really kind of spiraled and affected, [00:08:30] affected his whole life, and he ended up, you know, severely depressed in, um, you know, in the hospital to deal with, like, depression, and it all came from [00:08:40] kind of financial issues at his development company.
Mike: Um, you know, so I saw the good, the bad, and I also had, you know, my [00:08:50] stepfather, who I lived with, who, you know, always talked about money, and he was a money manager and that he's only had one job his whole life. You know, he's in his 80s now, but, like, he's run his [00:09:00] own money management firm. And, you know, my grandfather, you know, built low-income housing in Baltimore.
Mike: Was very close with him. And [00:09:10] so what I remember is that, you know, there was a freedom that they had to show up to, like, our sporting events and to be home for dinner. And I think as [00:09:20] we dove into the book, I really realized that I got into entrepreneurship and did my own thing, not because of money, even though the money's been great.[00:09:30]
Mike: It's really for freedom. Like, I didn't... I couldn't imagine sitting behind a desk all day and making someone else money. [00:09:40] And so it's just kind of that idea of, like, I wanna control my schedule, I wanna control my life. That was the driver. You would've never started an internet business in [00:09:50] 1994 like I did if you really liked money.
Mike: There were 13 million people- Right ... on the commercial internet and, you know, a few million more on, like, the [00:10:00] university and government, you know, web.
Leah: Yeah. Yeah. It's ama- It, it was an amazing time, and, and you two were certainly early in it. [00:10:10] You, you met at a mutual friend's wedding in the mid-'90s, and you bonded over this, this thing forming called the early internet, right?
Leah: So, so can you tell [00:10:20] me a little bit about what you were both doing at the time? Kash, I think you were at a law firm. Mike, you were running sort of this, like, Web 1.0 business. Um, take me back [00:10:30] there, and then tell me, w- like, was it, um, was there a moment when you two met where you were like, "We could build businesses together, not only, like, [00:10:40] be together, but also..."
Leah: Or did that come later? I'm just so curious.
Kass: Yeah, so I was working at a digital [00:10:50] marketing firm, and I was given the chance, kind of like my first entrepreneurial company, to start the interactive arm of building websites and [00:11:00] things like that. So there was-- And I should say it was actually a traditional agency for law firms, and I was building the digital side.
Kass: And it was great. [00:11:10] It was a lot of freedom that Mike talked about, and I was getting clients and working with them, and I was 25. So when I think about, like, right now, like, 25, that's, like, [00:11:20] ridiculous. Like, that's my kids' age, right? So, um, we-- Mike and I grew up together, meaning that w- our-- like, his [00:11:30] brother and I were all best friends, and all of our friends were in a group, and I knew of Mike.
Kass: I knew of Mike's families and siblings. I went to school with his sister, who is a [00:11:40] few years behind me at the same school. And when we reconnected, um, it was over the entrepreneurial kind of spirit and the freedom that [00:11:50] the internet and the changes, the impact, and the opportunities, and I think, I think we were probably the only two people in our extended friend groups that were [00:12:00] excited about that.
Kass: And so I think that was exciting. In terms of working together, I don't, I don't think we ever made a conscious [00:12:10] decision. I think it was more that when we were at our separate jobs, and I'll let Mike tell you what he was doing, we both asked each other [00:12:20] for each other's advice, and we relied on it. And so when it came time for me, I started golf.com, I couldn't imagine not doing it with him [00:12:30] because he would fill the big gap that I didn't have.
Leah: Awesome. And Mike, what were you up to, and what were you thinking about when you and Cass [00:12:40] reconnected at that wedding?
Mike: Yeah, so we really connected for the first time at the wedding. You know, she happens to be a little older. Um, you know, she doesn't [00:12:50] look it, but it's just a fact. She's, you know, three and a half years older, and so it doesn't matter right now, but when you're in high school, it's like a senior in high school and a freshman, [00:13:00] like, you don't talk to a freshman boy.
Mike: And so the i- like, I kinda knew who she was 'cause she would, like, come over at our house in, like, really short shorts. She was a tennis [00:13:10] player and, um, you know, but short of that, I hadn't really... I don't th- I mean, Cass, correct me if I'm wrong. I don't think we'd actually spoken a word together. [00:13:20] I wasn't very confident around- Well, we
Kass: did at your, your brother's first wedding, and I rem- I remember my girlfriends saying, "He's gonna talk [00:13:30] to you about the internet, so be careful."
Mike: Okay. That's a warning. Well, I guess, I guess we spoke... I don't think it was that great of a conversation, given I don't remember it. [00:13:40] Um, but it, uh, you know, we both were working on this thing called the internet at a time when, you know, you didn't have the modern tech industry. [00:13:50] Um, you know, over the last 20 years, really our career, the last 30, has been, you know, for us, about software and software services, and [00:14:00] that didn't exist.
Mike: Like, there was no cloud computing. You know, Salesforce hadn't launched. You hadn't seen any kind of huge success. You had some consumer brands [00:14:10] like Netscape and Yahoo. I remember when Yahoo went public in the '90s, but this is pre-Google, pre... I mean, way before, you know, iPhone and, you know, all [00:14:20] that stuff.
Mike: And it was just kinda something that, you know, the internet was a subculture that, you know, wasn't the greatest place. You had all these, like, [00:14:30] discussion boards and, um, people were using it for information for the most part. You had early Amazon and some e-commerce. Um, but you wouldn't... [00:14:40] You know, these things are subcultures until they break into the culture, right?
Mike: Like, they're... People have been working on AI for 20 years, but it wasn't until really [00:14:50] ChatGPT launched a few years ago that people are like, "Oh, this is like AI," right? And so the people you meet at the time, um, you know, become [00:15:00] very important because they're part of your community. And, you know, the people, you know, who I remember from the time are, you know, Mark Cuban, and Marc Andreessen, who was working on the browser, and, [00:15:10] you know, obviously Cass and, you know, all these other entrepreneurs who've gone on to do other things like we have.
Mike: But it all started because we went down this rabbit hole and [00:15:20] believed in something before others did, which is kind of a h- a hallmark of our career. We kind of not only see things a little, a little earlier, [00:15:30] but we believe that they're gonna be bigger, um, before they're big, and that's the key to most of the successful entrepreneurs is they see things and they're [00:15:40] willing to do stuff that seem impossible, but turn out to be directionally correct, whether it's like launching a golf business like Golf.com or [00:15:50] social marketing like Buddy Media or putting people on Mars like SpaceX.
Mike: It's all a version of, like, getting there a little early and, you know, focusing. [00:16:00]
Leah: Yeah. So let's talk about Golf.com because it is a wild, wild story. And you two are [00:16:10] newlyweds at the time, and you go through this kind of, like, crazy, we sold it, we think we've hit it big, and then you get this phone [00:16:20] call. So Cass, will you walk us through kind of what happened with Golf.com and how you decided to move forward from there?[00:16:30]
Kass: Yeah, so it was pretty exciting. It was the height of the internet, and everybody, every company in the world, they were going [00:16:40] public. Like, I remember watching, like, toys.com, and it was just exciting. And we were really working hard. Uh, [00:16:50] and a company approached us, and they loved the content that we were doing.
Kass: At the time, our goal was to provide USGA handicaps online and help golfers [00:17:00] book their tee times, and really, we were trying to speak to that recreational golfer that we were. And they, this company named chipshot.com approached us, and they [00:17:10] said, "Look, like, we wanna acquire you, and what would it take?" And they offered some cash, and then [00:17:20] they, our board kind of voted let's do all equity because they were f- going to file and go public the following spring.
Kass: So we closed the deal. [00:17:30] We negotiated the deal on our honeymoon in October 1990, 1999, and we closed the deal December 23rd, '99. And by that, like, ear- [00:17:40] late March, early April, we got a phone call from the president that said they had run out of money because Sequoia decided not to [00:17:50] back them anymore, 'cause the bubble was happening, and they had nothing to pay us, and we had already given over all our bank accounts and [00:18:00] everything, and we had nothing.
Kass: We had no access to anything. Payroll was done by them, and we were pretty devastated.
Leah: And you had put your life savings into [00:18:10] this company. Yes. This is your first year of marriage. Yes. Mike, what did it actually feel like to lose everything that early with the person you [00:18:20] just married and, and not let it affect your whole life and your whole marriage?
Leah: Like, it feels, like, pretty, [00:18:30] pretty, like, intense to go through.
Mike: It was definitely intense 'cause at the time, you know, I had started a company at, you know, Northwestern when I was there called University Wire, which [00:18:40] was a student news service, and we'd merged it with a company called Student Advantage, and around this time, we'd taken it public.
Mike: Actually, a little before what [00:18:50] we're, the time we're talking about. So Kash started golf.com- I have this company which is now a public company, which is now like, you know, worth over a billion dollars, which at that [00:19:00] time was a lot. Now it's like, you know, we have trillionaires and stuff. But at the time, like a billion-dollar company was a decent-sized company.
Mike: [00:19:10] And right around the time that I was looking to move over to help Kash, we started to feel this kind of, [00:19:20] um, you know, just the internet markets were starting to soften. And I remember the feeling, this is way before the [00:19:30] crash of 2020, and one of the things that really hit us was like this idea that Sequoia wasn't gonna, as Kash said, like support this business, which was a [00:19:40] high-flying business, you know, doing a lot of revenue even though the margins weren't great.
Mike: Um, and so it was a double whammy. Not only did we have to buy back Golf.com when ChipShot went [00:19:50] under, um, but I had millions of dollars of stock of this, you know, public company, which I-- on paper I was very rich, [00:20:00] um, you know, much like more money than I ever thought I would make. You know, forget that I'm 24 at the time, so I was really young.
Mike: And so [00:20:10] all of a sudden, like ChipShot goes mahola, and the stock Student Advantage goes from like $30 to like less than one in April, [00:20:20] all in the same time period. So that was painful, but we also didn't have a... We were living in Chicago, didn't have a ton of expenses. We did have [00:20:30] one child, Miles, at the time.
Mike: Um Or was it-- I think it was like a year before we were having... we had Miles. So it was kind of we were thinking [00:20:40] about having a kid. We just got married in '99. Um, and we did kind of what we've always done, which is like, okay, we could [00:20:50] complain about it, or we could start shoveling. So when we named the book Shoveling Shit, it's not like a funny term.
Mike: It's this idea of [00:21:00] like it's shoveling shit, a love story. It's this idea of entrepreneurs. They fall in love with the shoveling and the journey. It happens to [00:21:10] be our love story as well. That's why we kind of called it a love story as well. But we did what we always do. We started shoveling, and what did that mean?
Mike: It meant hit the road, try to raise money. You [00:21:20] know, we needed not only money to buy it back, which we got it basically for free. We gave them a little money. Um, but we had employees we hadn't paid, so we told them that, "Hey, as soon as we [00:21:30] raise money, we're gonna, like, make good on that." And we got... You know, it's one of those times in our career that not only do we shovel, but, like, a lot of people [00:21:40] shovel and don't-- and aren't successful, right?
Mike: Just 'cause you, like, work hard doesn't mean that you're gonna have an outsized outcome. We started shoveling at a time when there was this kid named [00:21:50] Tiger Woods who decides to, like, run away with the Masters. Like, literally, like, this Black kid who-- and I only say that 'cause no one had ever looked like him at the [00:22:00] Masters.
Mike: You know, Augusta, Georgia, they didn't have any Black members, and Tiger was as big of a celebrity after he won as, like, Taylor Swift is [00:22:10] today. People don't realize how big he was. We happen to own golf.com at this point So all of a sudden, all these advertisers want to, [00:22:20] you know, put their name all over Tiger and tell the world that they're one of Tiger's sponsors.
Mike: We happen to own, pre-Google, the number one real estate in [00:22:30] the golf business, and so we're able to get it to, you know, a few million dollars of revenue, and then sell it for $25 million to Time Warner, which eventually [00:22:40] brought us to New York. But I bring that up because it's like not only working hard, not only working smart, but it's always about getting a little lucky, which is what we did with Tiger.
Mike: We, uh, [00:22:50] we could have never written that into a business plan, that there's gonna be this kind of generational talent that walks away with, like, these tournaments.
Leah: Well, it... I mean, like, you bring [00:23:00] something up kind of interesting, Mike, right? Luck and timing. I mean, you could never have predicted that Sequoia was gonna pull out and leave you all, like, [00:23:10] high and dry, right?
Leah: And then, again, you could never have predicted that Tiger was gonna come on the scene and, and help propel this company forward. So I mean, man, it's like so much [00:23:20] of entrepreneurship is, like, what is happening at the time. And like you said, being able to almost tell the future or see the future or take a risk that you [00:23:30] think the future is gonna hold.
Leah: I mean, that's the name of the game, right?
Mike: So much of... Like, so much of this is luck, making your own luck, whether you're an entrepreneur, whether you're an [00:23:40] investor, whether you're an executive. You know, I look at our biggest deals on, like, the venture side, and I happened to have lunch with these two Harvard [00:23:50] dropouts who basically said, you know, "We're gonna beat Nvidia And I was like, "Dude, you guys don't...
Mike: haven't even been like bar mitzvahed yet. Like, [00:24:00] what's going on here?" Um, but they were like really confident, and fast-forward like three years, like that company, Etched, is like just raised like, you know, [00:24:10] they've raised 800 million. They have a billion dollars of orders, and like, you know, whether or not they kind of topple Nvidia, who knows?
Mike: But there's a place for their like, [00:24:20] you know, for their chips, and their stack, and their supercomputers in this infrastructure world. That was like... I'm not a chip investor. That was such a lucky [00:24:30] lunch that I said yes to. They wanted to have lunch with me. I was like, "What? Like, do I really wanna have lunch with these, like, semiconductor kids in a world where I don't do semiconductor," right?
Mike: So [00:24:40] like every part of our career has had these, like, moments of like just, how did that happen? Like, I've no- now you could say you put yourself in the [00:24:50] position or, like, you know, you create your own luck, but like a lot of this is just like pure luck.
Leah: Yeah. It's total combination. So, so let's, let's jump to Buddy [00:25:00] Media because in 2007, Mike, you came up with this idea.
Leah: Kash, you had just given birth to your third child, and by your own telling in the book, you were nursing a [00:25:10] newborn while you were building desks in the new Buddy Media office. So Kash, what did that feel like starting from the ground up again? And to [00:25:20] you, like, what was the cost to saying, "Yes, let's go do this at this moment"?
Kass: Well, it felt overwhelming.
Leah: [00:25:30] Mm-hmm.
Kass: It felt like we were sprinting, and I was kind of above water, and there was also this excitement. I could [00:25:40] see it and hear it in Mike's voice, and he just kept saying, like, "This is gonna be big." Like, "I know this is gonna play out. I know we can ride [00:25:50] this wave. I know we can figure it out."
Kass: And he get, he does get excited about a lot of deals, and most entrepreneurs he loves, but there was a [00:26:00] difference in the excitement. And so I w- I wanted to be supportive of that, and because I know I can operate in that uncertainty, and it [00:26:10] doesn't ... In, in work, it doesn't really bother me that way because I, I know he'll figure it out.
Kass: Um, and the sacrifices [00:26:20] were us saying, like, "If I do this with you, I..." One of us, probably me, it, "We are going to sacrifice [00:26:30] being there in all the moments with our kids, not missing the important, you know, milestones, but the everyday stuff we will be missing in the [00:26:40] beginning. And do we wanna do this?" And we both said, "If we can do this for the next five to seven years, we'll figure out a way for me to get [00:26:50] out and get back to them."
Kass: And that was our bet, and we did have that conversation, which is crazy, 'cause we were young.
Leah: Yeah. Well, that's, I mean, I think, very thoughtful, [00:27:00] too, and, and the foresight to, to plan that out. And I mean, Mike, you've been candid for years that, you know, you sort of got the credit with Ernst & Young [00:27:10] Entrepreneur Year of the Award, uh, Fortune 40 Under 40, and you two were equal partners, you know?
Leah: Side by side, you know, working through Buddy [00:27:20] Media, scaling it. And, and part of the reason you wrote the book was to give some transparency and visibility, right, to Cass's contribution. [00:27:30] Why did you feel like, Mike, it was so important to, to really name that and show that?
Mike: Yeah, so I mean, I didn't really wanna write a [00:27:40] book, so it was Cass's idea.
Mike: She, she had it on her bucket list. I was like, you know, I was a journalism major at Northwestern. I knew that I would have to do a lot of the writing. Luckily, Cass does a lot of [00:27:50] the thinking and had remembered a lot of the cheat codes. It's basically like the 50 cheat codes we wish we knew when we started out.
Mike: And, you know, once we started writing, what [00:28:00] became apparent is this, like, I was... One of us had to stay home At the time we started Buddy Media, I wouldn't say I was the most [00:28:10] outgoing, and I definitely wasn't comfortable on stages. By the time we were done, like, you know, I'd spoken on every like tech stage.
Mike: I'd... [00:28:20] You know, I was at every event. You know, I was out selling. We had offices in Singapore and London and throughout the US, and hundreds of employees and, you know, we got to [00:28:30] fifty billion of ARR in like three years from starting to sell the product, which at the time was a lot. Now it's kind of like these kids are getting there in like thirteen minutes.[00:28:40]
Mike: Um, and I just realized that, yeah, I may have done a little more in terms of the public stuff, but Cass was more strategic. She managed the people. She made sure [00:28:50] we hired well, we fired well. Um, and so the beauty of the best co-founders is you work together, but you don't work together. [00:29:00] You do very different things, and the stuff that I was forced to do was more public.
Mike: I was forced to go out and speak on stages and [00:29:10] sell, and we had offices all over the country that I was the one going in and training the sales team. And, um, and eventually, because it was my name as [00:29:20] CEO, I'm the one who was selected as Ernst & Young Entrepreneur of the Year. I was forty under forty. I was all these things, like won like every award you could at the time because we were a really hot company.[00:29:30]
Mike: And as we were writing the book, it was just important for me to tell the story of the success because it is safe to say, without Cass [00:29:40] Every company that we've done would've been a failure. I've done one company without Kash, and it was a huge failure. [00:29:50] I did it with a friend. I talk about it in the book.
Mike: Um, it's still around, but, um, yeah, it was... It's been a failure to date. You know, no revenue or very little revenue, and [00:30:00] no product market fit. And the book is this look at this imbalanced life, not only between founders, but also between, like, [00:30:10] your work and your personal life. And I wanted to highlight that, like, the life we've built wouldn't have happened, obviously, without Kash, but more [00:30:20] importantly, I would've hired the wrong people.
Mike: I wouldn't have fired them. I wouldn't have focused the way I focus without a great operator partner.
Leah: Mm-hmm, mm-hmm. Well, it is a [00:30:30] beautiful love story, the book, and you ended up selling Buddy Media to Salesforce for $745 million. No small [00:30:40] feat there. Um, but here's the precedent I most wanna sit with, because as I was reading the book and I was reading about this massive outcome and all, all the shit that you [00:30:50] shoveled to get there, you would think that the aftermath would be this massive just celebration, but it kinda fell flatter than that.
Leah: Can [00:31:00] you talk about what you two were feeling at that moment when you sold the company?
Kass: I can start by saying that I think I felt [00:31:10] I was trying to feel relief, and I was having a tough time, like, breathing out because... [00:31:20] And you probably know this very well. When you are leading company, you are leading people, and the people, you are their livelihood.
Kass: What you do on a daily basis [00:31:30] impacts how they live, how they make decisions for their families, and it, it became a very big responsibility for me and Mike. And [00:31:40] so I think I was feeling relief, and it was, like, kinda slowly letting the air out for me that everyone was going to be [00:31:50] okay, and more than that, that everyone was going to do well because we believed that we should give a piece of our company to every single [00:32:00] person.
Kass: So that's, that's what I was feeling. In terms of, like, like, did we realize, like, how much money we made or how much money we made [00:32:10] other people, that didn't... That took a long time to kinda hit.
Leah: Yeah. And Mike, how were you feeling? 'Cause there's a lot going on at home as well, you've already said. So how [00:32:20] did it hit you, that moment when you had achieved that massive goal?
Mike: Yeah, so I mean, we obviously were proud, and [00:32:30] it was a happy moment. But we also, deep down, at least I can talk about myself, I'm not gonna talk for Cass, um, [00:32:40] didn't feel great, and I didn't feel great about relationships in my life. Cass and I were at each other's throats because I was, like, all over the world, and we weren't connected the [00:32:50] way I think, um, we are connected when we're at our best.
Mike: I was 30, 40 pounds overweight, which was an issue for me 'cause I have an artificial heart valve. And, [00:33:00] like, the one thing my cardiologist says is, like, "Stay in shape. You don't wanna put extra kind of... You don't wanna cause the heart and the valve to work extra hard." [00:33:10] Um, and you know, I just didn't feel great about a lot of stuff.
Mike: I remember talking to the cardiologist, and he's like... And he knew about the, the sale. He's like, "Well, [00:33:20] what's... You know, why does it matter, like, you make all this money if you're gonna die young?" And that kinda stuck with me. And then I, I remember I went out, we went out to dinner with our really good [00:33:30] friend Gary Vaynerchuk and his wife Lizzie.
Mike: And Gary had, you know, hired, this is a little after we sold, um, you know, he'd [00:33:40] hired this guy Mike to, like, literally travel with him and, like, be his health coach, which is a little extreme, but that's what Gary... He is extreme. That's the way he is. Um, [00:33:50] and he... And I remember him turning, he's like, "Dude, you... If you don't do this, you're gone."
Mike: Like, and you know, I have no self-control. I'll eat, eat whatever's in front of me. I wasn't lifting [00:34:00] weights like Cass has me doing now. Um- And so I was out of shape, like mentally exhausted, relationships were in shatter, but I had a little [00:34:10] more money in the bank. And so after four years at Salesforce, which was a great four years, but it was more of the...
Mike: Like, I worked just as hard. Like, there [00:34:20] was no work- there was no just phoning it in as like chief strategy officer at Salesforce at the time. Um, you know, I basically went to Marc Benioff. I said, "I, [00:34:30] I just gotta get healthy." Um, and he said, "I get it. No problem." Like, you know, he's always been great to us. Um, and, uh, [00:34:40] you know, since then, really that was 2014, haven't missed a, uh, workout with Rico, who's my trainer, and I try to eat well during the week, and [00:34:50] then not worry about it on the weekends.
Mike: And, you know, just try to like, you know, take it easy if I can sometimes.
Leah: Yeah, that's a good balance. Shout out to [00:35:00] Rico. I need, I need a Rico- Yeah, he's the best ... in my life right now. Yeah,
Mike: we all do.
Leah: Yeah, we all do. We all do. Um, and you mentioned Gary Vee. He wrote an awesome forward for the book for [00:35:10] you all.
Leah: Um, and you've talked about how the book, it's not just a tech book. It's, right, for the 5.5 million people who start businesses every year, the restaurants, the salons, [00:35:20] the service companies. Why was it so important to both of you to strip the glamour out of the founder story and actually focus on the [00:35:30] shoveling part of it?
Kass: I think it's because, you know, and Mike says this a lot, you meet a founder and the first thing out of their mouth is, [00:35:40] "Everything's great. I'm so psyched." You know, "Everything's going well." You know, "It's straight up," right? Like, "We're doing so well." But the truth [00:35:50] is, when you start a company, when you run a company, when you run teams, it's exhausting.
Kass: You are getting punched in the face every, every hour, [00:36:00] and there's nothing you'd rather do. And so I think because we like helping other entrepreneurs and because we're such [00:36:10] fans of other entrepreneurs, it was important for us to name that this-- there's this beauty in the struggle, [00:36:20] and we wanted them, all the entrepreneurs not to feel alone, because it can be very lonely and you do f- kind of feel at times crazy how [00:36:30] much you can be struggling and still love what you're doing
Leah: Yep.
Leah: Yep. Absolutely. That totally, totally resonates from all sides. [00:36:40] So, um, you know, like me, who was an entrepreneur, moved over to the other sate- side of the table, you both are now, for well over a decade, [00:36:50] focused on investing in companies, helping entrepreneurs. Mike, you said flat out that you don't like the term VC, which I can understand.
Leah: You'd rather be an [00:37:00] entrepreneur partner. I love that. Um, can you talk a little bit about why you wanted to move to the venture side, to [00:37:10] the investing side, and what you love most about it?
Mike: Yeah. So it was a gradual evolution. You know, we started doing deals even [00:37:20] before we sold. You know, they were smaller.
Mike: They were like 25, 50,000, $100,000 checks. Um, and the reason is we just loved entrepreneurs, and we had access to [00:37:30] just great entrepreneurs, so, you know, we're very early and, you know, a lot of companies, and some turned out to be multi-billion dollar businesses. And so [00:37:40] as we kind of... As I transitioned out of Salesforce, took a year off, and we really talked about how do we wanna spend our time, it [00:37:50] became apparent that going from zero to one is just hard, and we'd done it like seven, eight times, and we had kids [00:38:00] who, you know, needed us a little more.
Mike: Like, you know, bigger kids, bigger problems. You know, at the beginning, just keep your kids alive. Like, no one's... At one years old, it [00:38:10] doesn't matter who feeds them, but it really matters when they're like 14, um, that there's, you know, they're not gonna listen to you, but they're gonna mirror the [00:38:20] behavior that, you know, you do.
Mike: And so we... Yeah, like a lot of entrepreneurs, they end up as investors 'cause we just get tired, and we love entrepreneurs. [00:38:30] We love the action. We think we can help, and it's been a great run, uh, and we think that, um, you know, we bring the [00:38:40] entrepreneurial mindset to our founders and, you know, some listen, some don't.
Mike: It's their prerogative. Like, it's their company. We don't wanna run it Um, [00:38:50] but, you know, partnering with great investors will probably make us more money than we did as entrepreneurs, and we did pretty well. [00:39:00] Um, and these are entrepreneurs of all stripes from, you know, very young to not so young, men and women, um, you know, New [00:39:10] York, LA, you know, Chicago, all over the country.
Mike: We just love... We've done 100 deals, you know, so we just love-- You don't do that unless you love [00:39:20] entrepreneurs.
Leah: Yeah, and across a lot of different categories as well. I mean, I was looking through, it's like everything from Liquid Death to, to Braze to, like you said, the [00:39:30] semiconductor company. I mean, it's just, like, such a wide range.
Leah: Can you talk a little bit about this framework, this Go Gauge framework? Because obviously you [00:39:40] can apply it across categories, across businesses, and that's sort of the lens that you learned that you're now bringing to investing as [00:39:50] well. So can you talk through that a little bit?
Mike: Yeah. So the Go Gauge is something that we really use to green light ideas as an entrepreneur, [00:40:00] and what we realized is that the same framework that we use can be used on the investing side.
Mike: And so we outline kind of in the [00:40:10] book kind of how we think about it, and it's not, I don't think, your typical business school or even like, you know, BC, like tip-- like traditional BC [00:40:20] framework. It's just what's worked for us, which is basically like, what's the product? You should be able to explain it in a sentence.
Mike: Why is it different? Everything we do, if it's not [00:40:30] different, it's gonna be hard for us to get behind, um, even if it's a CPG company like Liquid Death. It was very different because it was direct to consumer and marketed like a [00:40:40] wellness product-- marketed like a beer, even though it was a wellness product, and using social marketing, all these things.
Mike: And then it comes down to, um, you know, what's the [00:40:50] size of the market, which we look at how many customers and what do they pay. Like, we're very like, um, you know, we just break it down to the most simple, like how many [00:41:00] people are-- can buy this and what do they pay? Um, and we'll talk about margins, everything in a second.
Mike: Um, we're very sales and marketing focused, [00:41:10] so yeah, it's a huge market, but how are you gonna reach that market? So all of our companies, the... And as we've become more [00:41:20] mature. We've... And as technology's matured, we realize the only thing that matters is demand generation and attention. Like, if you have a, if you [00:41:30] have a baby Jesus product and no one knows about it, doesn't matter, right?
Mike: And so we really dig in there. And then because of Liquid Death, uh, [00:41:40] you know, the fifth one is kind of this whole operations angle, which is like, how are you gonna, you know, how are you gonna build the product? How are you gonna get it to [00:41:50] customers? Which is a big part of, like, the chip story, right? I'm like, how are these Harvard dropouts gonna make it?
Mike: Like, it helped that TSMC, the largest manufacturer of chips in the world, like, [00:42:00] was behind them very early on. And then the sixth, and then I'll shut up, is, you know, just in the back of the envelope, do the unit economics make sense? [00:42:10] So you could justify a lot of things in a spreadsheet, but if you're going to sell it for X, what are the costs [00:42:20] to create it, right, and market it?
Mike: So it's cost of goods sold, and then what's left over for, like, the company's operations, [00:42:30] legal, you know, general accounting, all that stuff. Um, and it's very s- like, for us, like, as a journalism major, it's just been very simple unit [00:42:40] economics focus, um, verse, you know, if this was private equity and we're doing financial engineering of [00:42:50] companies, maybe we take a different approach.
Mike: But venture and most investing is basically, um, you know, fits well into these six buckets. [00:43:00] Now, I haven't talked about the team. You know, we think that there are certain things that are like table stakes. Like, we're not gonna work with assholes. We're not gonna, like... You know, if we don't wanna [00:43:10] be with this person in the trenches for years and years and years, like, we'll never do the deal.
Mike: So we have dinner with everyone who we invest in. We get to know them. Um, I [00:43:20] mean, like core investments. Like, we do, like, crazy little investments every now and then, which we don't, but the really core important investments, you know, the people is [00:43:30] like table stakes. Um, those six things are what we really use.
Mike: And entrepreneurs who are listening to this, save yourself time and [00:43:40] energy by going through the go gauge with your business, and if you can't realistically You know, put, convince [00:43:50] yourself, you're not gonna convince anyone else, including customers.
Leah: Right. Right. Yeah, no, I love the framework. I love the framework.
Leah: And, you know, when you look at kind of the [00:44:00] traditional venture playbook and kinda the precedents set in venture, they are, don't co-found a company with your spouse, don't mix love and money, don't have [00:44:10] three kids in the middle of building it all. But you two did all of this on purpose. You wrote the book about it.
Leah: Um, can you summarize, like, what is the actual argument [00:44:20] you're making in this book, particularly for people that may not feel like, "This isn't the right time. I may not have everything, you know, perfect. I may not have my life together"? I mean, Cass, what [00:44:30] would you say to those people?
Kass: I would say that there is no perfect time to start a company, and that the messy middle, that [00:44:40] chaos, needs to be part of the journey, and that there's not gonna be a lot of balance.
Kass: There's gonna be a lot of integration. And just [00:44:50] because you give something 100%, doesn't mean the other areas go down to zero. And so you just have to [00:45:00] remember that, especially as a, as a female, as a mom, that just because you give 100% at work doesn't mean that you're giving [00:45:10] nothing to your family, right?
Kass: And we have to be a little bit less harder on ourselves, but that messiness, that chaos, is what you need to [00:45:20] embrace because it will be like that your entire journey. There's not one entrepreneur out there that was like, "This is the greatest thing that's ever happened. Every single day has been easy.[00:45:30]
Kass: Everyone's having a great time. Everyone's showing up for work." That just doesn't happen. It is full of struggle, and there's a beauty in it. [00:45:40]
Leah: Yeah. I totally, totally agree. There's never a good time for any of it. Right. I'm curious what you two think about AI right now and how... I [00:45:50] mean, it's rewriting the cost to start a company.
Leah: It's giving people more access to build, non-technical people, the vibe code ideas, right? [00:46:00] But in a world, you know, where AI is kind of taking over some of these commoditized skills, what do you think becomes [00:46:10] more valuable as humans? I mean, particularly as you think about, you know, these messy middles, these messy parts, are there areas that you think, you know, [00:46:20] humans just, we have to stay in the loop, and this is gonna become, you know, the most valuable thing we can contribute to a company?
Mike: Yeah, I mean, our-- [00:46:30] You know, we're big believers in AI. Um, obviously, as investors, we have-- we've done very few deals that are just pure AI companies, [00:46:40] but everything that we're excited about is AI-enabled. And so we think AI-enabled services and just companies that use AI [00:46:50] as their operating system will outperform everyone else.
Mike: And so, you know, if you look at kind of what, you know, General Catalyst is doing with hospitals, literally [00:47:00] a VC firm buying hospitals and putting in kind of an operating system, what we're doing, we own a executive staffing firm called The Moraine Group, which has been around for [00:47:10] twenty-five years. That is an AI company.
Mike: It's a company that's using AI to kind of do what it does best, which is help companies build [00:47:20] teams. And so, you know, why we're so excited is we are techies at the core, but everything we're focused on going forward [00:47:30] really is in tech. It's traditional companies that's enabling... They can do more faster, more efficiently with AI.[00:47:40]
Mike: And anyone listening who is not, like, building, playing around, tinkering is just gonna be left behind because you've too many people [00:47:50] who, you know, read about AI and think they know it, but the only way to really learn it is just to do it. And I'm not talking about just, like, going to [00:48:00] ChatGPT, but, like, what are two-- what are things that...
Mike: What's one thing that you're doing every day that in your heart you know you shouldn't do every [00:48:10] day? Like, you could automate it. And so I've automated my inbox, my, you know, messaging, my, um, really everything I can, [00:48:20] and I've been able to learn the tools which I'm now, like, sharing with a lot of our companies.
Mike: Um, and all of a sudden, the CEO, the founder can be the number [00:48:30] one programmer at a company.
Leah: Yeah. I think that's hugely powerful. I mean, I, I had a background in engineering, which gave me the ability to kind of build out my [00:48:40] prototype early on and show it to people. But a lot of people have amazing ideas but aren't engineers.
Leah: So I think it's pretty exciting that, you know, founders and [00:48:50] non-technical people can contribute and, and it's like a new way of communicating, you know, in a product conversation as well.
Mike: It's incredible. I [00:49:00] mean, say what you want. Is it good for humanity? Bad? Like, get over it, 'cause it's here
Leah: It's here. We're living it.
Leah: We're in the middle of it. Yeah
Mike: So it's gonna be used, [00:49:10] you know, like all technology. It's not good or bad, it just is a tool. It's gonna be used, you know, incredibly efficiently by the bad guys. [00:49:20] It'll be used by the good guys. It'll be used by your competition. It'll be used by your employees. And so just get to know it, and don't be [00:49:30] scared to jump in.
Mike: The good news is you don't have to go end to end with your AI strategy. Just start with something And then build from [00:49:40] there, whether it's you as an individual or a company.
Leah: Yeah. No, I love that. I think, um, you know, it feels like you two aren't [00:49:50] afraid to take a different path, and I love that about your story.
Leah: And as you look at now being on the venture side, the investing side, you know, going into [00:50:00] these early-stage companies, are there rules that you see that this industry has followed, you know, for decades that you just feel like, "These are [00:50:10] bad rules," like, "We're gonna do it differently"? Is there something that stands out to you that you in this role would do differently?
Kass: I think right off the [00:50:20] bat, the one thing that I would say is this rule that, you know, big VCs don't back married people. Um, I- we [00:50:30] think that it can be a superpower, so I would love for that to go out the window and really have people look [00:50:40] at the skillsets and how complementary they are as opposed to duplicative.
Kass: So that would be the one thing. And, and stop worrying about labels. [00:50:50] Just, just look at the skillsets. Are these the right people? You know, do they fill in each other's gaps, and can they get stuff done quicker because of that?
Leah: Yeah. [00:51:00] No, I love that, and you see co-founder breakups all the time. I mean, for people that are not married
Leah: Right? It's like-
Kass: Right ... it happens all the time And it's the [00:51:10] same story. It doesn't matter, right? Yes. It, it, it's the same story. You get founder paralysis when there's two engineers or there's two product people. Mm-hmm. Yep. Um, you, you know, have different [00:51:20] skillsets, but one's working harder than the other.
Kass: One's working not as much. And it's definitely, I definitely think when you have more than one founder, it's important that you fill [00:51:30] in your gaps, your blind spots. And instead of just making these arbitrary rules about what will or will not happen in the future, you gotta look more at the skills. [00:51:40]
Leah: Yep.
Leah: Totally. Well, I love that you titled the book Shoveling Shit and not, you know, the $745 million exit [00:51:50] or how we made it. And I just love that you deliberately focused on the messy parts and the truth, the authentic truth, right, [00:52:00] about what it is to build a business. What do you think changes in business culture if we actually celebrated the shoveling piece instead [00:52:10] of, you know, these massive outcomes that everybody loves talking about?
Kass: I, I know Mike has probably a couple really good answers, but I think, um, more [00:52:20] empathy to founders from their investors, um, less taking up the founder's airtime and space, uh, [00:52:30] with their opinions, especially those founders who have... You know, I'm sorry, those investors who have never run a company and started a company before.
Kass: I think that's big. Mike, what do you think? [00:52:40]
Mike: No, I mean, I don't really have much to add there. You know, what I would say, based on one of the past questions that you asked, is like, I do think [00:52:50] venture capital is dead in many ways. Um, you know, we've had a run from like really, I would say like two... like twenty [00:53:00] ten to like maybe twenty twenty-two, which is a great run.
Mike: Um, but most of the companies that exited just... [00:53:10] those won't exist. Like the buyers won't exist. Like y- you've had a lot of like software services that have been around. And [00:53:20] so, you know, how this ties to the question about culture is the only thing you can do, and I keep telling entrepreneurs this, the only thing you could focus on [00:53:30] is like your team, your culture, your customers, and only raise money if you can really [00:53:40] deploy it in a way and get a step change result.
Mike: Um, I spoke to a company earlier this week that's gotten to twelve million in sales. They haven't raised money. [00:53:50] They have a great young team, and they're like pitching me. I'm like, "You guys, like you have a great business. Why are you talking to a schmuck like me? Like just go talk to customers. Continue [00:54:00] to...
Mike: You know, they're profitable." Like you, you've been told or you read on TechCrunch and all these things that like you have to raise money, but like investors [00:54:10] just bring a whole mess of issues if you don't need the money. You gotta report to them, you gotta talk to them, you have to have like proper governance.
Mike: You're gonna have an audit at some point if you get like [00:54:20] big enough. And I think entrepreneurs that just put their head down and build, they can build bigger businesses than we ever could because, you [00:54:30] know, like when we started out, we have to spend three million dollars with Oracle or a million dollars a year with Oracle, like just to have a database to power live scoring for [00:54:40] golf.com, that's twenty-two cents-
Leah: Yeah
Mike: through one of the cloud providers, right? Yeah, it's insane. Now we have to have ten engineers, right? Now you can [00:54:50] hire one, and it's a thousand X engineer, right? And so focus on the business, the customers, the culture, [00:55:00] and only talk to schmucks who have money if you actually need the money. And most companies like either don't need the money or there's [00:55:10] no chance of being a venture, you know, company with a venture kind of profile, like hundred percent plus and getting [00:55:20] to billions of dollars of revenue, um, which is okay.
Mike: And the ones that are true venture companies Are really gonna [00:55:30] require so much capital that the venture capital industry can't meet the demand, right? Like-
Leah: Yeah. So interesting ... like, you know, it's- You're right. It's gonna be this, like, [00:55:40] barbell that happens. Yeah.
Mike: And we're... I mean, we haven't talked about this publicly, but we're not raising another, like, traditional, like, [00:55:50] venture fund because of this.
Mike: Like, a lot of venture capital firms, you know, it takes 10 years to know if it's gonna be a success. [00:56:00] They hire all these people. They need the fees to pay all their people, and you just get on this, like, you know, the treadmill of, like, you gotta raise every [00:56:10] three years these funds. But if you ask a lot of the LPs, the, the investors in these funds, they just haven't seen the [00:56:20] returns since 2022, and it's only gonna get more competitive.
Mike: And the idea that, like, you're gonna invest in a company that happens to invest in the next Anthropic, [00:56:30] like, just isn't a strategy for professional money managers.
Leah: Yeah. Yeah, it is a crazy time in venture right now, and it's certainly shifting, and [00:56:40] AI is changing everything there, too, and, and you're right.
Leah: I mean, the outcomes, there hasn't been liquidity. You know, LPs are not happy with it as an asset [00:56:50] class. So it's... I think we're right in the middle of this transformation happening right now, so it is fascinating. Living it myself, [00:57:00] too.
Mike: Yeah, we all are. I mean, listen- We
Leah: all are ...
Mike: we have 100 companies. We want-
Leah: Yeah
Mike: you know... Listen, some of them will go public, some of them will sell- Yep ... a lot of them won't. [00:57:10]
Leah: Yeah.
Mike: Right. So we'll figure... I mean, there are continuation funds. Like, there's a whole cottage industry now around, like, the lack of liquidity, which never existed in this market [00:57:20] because we were flush with liquidity.
Leah: Yeah. So if we fast-forward, let's say, 20 years from now, when someone [00:57:30] tells the Cas and Mike story, what is one precedent you want them to say you broke that maybe almost no one [00:57:40] else was willing to take on?
Kass: Mike, you start.
Mike: Yeah, I mean, I think [00:57:50] the... Listen, you nailed it earlier. We didn't write an optimistic book, but it's very, [00:58:00] um, it's a very positive book. But, like, entrepreneurs don't need more optimism. Like, if you're a pessimistic entrepreneur, you're [00:58:10] probably not gonna do that well because going from zero to one, it just confirms your pessimism.
Mike: Everyone says no, and you're like, "Why did I do this [00:58:20] anyway? I knew it was gonna suck," right? But we're, like, really optimistic, and I think the message that I wanna kind of convey [00:58:30] is that, yes, it's gonna be hard. It's gonna be, like, messy, but this... inside this world of entrepreneurship is where you're gonna find your [00:58:40] passion, your purpose.
Mike: Um, and I think if we, in twenty years, if we've helped... Like, it's-- we've been really excited that it was, like, [00:58:50] instant bestseller and it's still selling and, like, a lot of people seem to have read it. Um, and if... But, you know, I'd love a whole generation of entrepreneurs saying, like, [00:59:00] "I Didn't make the mistakes that you made because I was aware of what, you know, some of those mistakes were.
Mike: And, [00:59:10] uh, and it's our way of just giving back. I don't think, I mean, businesses have been around for 10,000 years. Um, we knew AI was [00:59:20] coming, so we didn't really focus on too many strategies that AI was gonna crush. It's why we wrote so much about culture and, [00:59:30] you know, this imbalanced life, and team, and sales, which I think AI's only gonna [00:59:40] accelerate.
Mike: Um, so I'm not really answering your question, but we wanna be known to help.
Leah: You are, because, you know, it's funny, as you were talking, I [00:59:50] was remembering when I was just getting started as a founder, and there were two books that I read that actually gave me the confidence to start my company. They were Founders at [01:00:00] Work by Jessica Livingston.
Leah: Stories, you know, of those founders like LinkedIn and Six Apart- Yeah ... and, you know, back in the day. And then it was this other book [01:00:10] called Raising Venture Capital for the Serious Entrepreneur okay? And it was, like, a H- Harvard Business School, someone who [01:00:20] wrote it. It's on my bookshelf. I don't know. It explained the whole venture ecosystem to me, which I had no idea about.
Leah: So I think what you just said, like, actually played out for me because [01:00:30] people, entrepreneurs are gonna read this book today, and 20 years from now, they're gonna point to it and say, "This is what gave me the confidence to start." I love it. Cass, what about you? [01:00:40] What about you?
Kass: I, I definitely think Mike nailed it that w- we didn't write, like, a hopeful book, and we didn't write a guide to how to do a [01:00:50] company and how to start it.
Kass: It was just could, could, could all the entrepreneurs following us not make some of the same mistakes? So I think [01:01:00] that was not a typical, uh, book that you see out there. I also will go back to just because someone says no because of some label they've put on [01:01:10] you, like Mike and I were dating Um, and then when we were married, I think we broke that precedent that we were like, "Okay, well..."
Kass: Then we packed up our [01:01:20] bag after they told us, "We don't invest in married couples," and we just left. And we broke it, and we succeeded. And I think that [01:01:30] everyone, especially women, need to stop worrying about some of those labels and prejudices and just go around the door. Go [01:01:40] around it.
Leah: Yeah. I love it. Break down that door.
Leah: Leave it open for the person behind you.
Kass: Exactly.
Leah: Well, you two have certainly opened so many doors [01:01:50] for others, and you're leaving them open, and you're making them wider, and you've done so much to help founders in the industry. So I loved this conversation. Thank you so much for being a [01:02:00] part of it, and I definitely recommend people check out the book.
Leah: We'll link to it in the show notes and everything as well. Shoveling Shit: A Love Story About- Thank you ... the [01:02:10] Entrepreneur's Messy Path to Success.
Kass: Thank
Mike: you. Thank you