In short
The James Altucher Show - Episode Summary
Episode Title
Shoveling Sh*t: Entrepreneurs’ Secrets to a $700M Exit with Michael & Kass Lazerow
Episode Description James Altucher reconnects with entrepreneurs Michael and Kass Lazerow to discuss their journey from selling Golf.com for $24 million to leading Buddy Media to a $700 million acquisition by Salesforce. The episode explores themes of emotional resilience, the importance of kindness in leadership, and the dynamics of working and living together as a couple in entrepreneurship. The Lazerows share their investment principles through the "Go Gauge," a six-part criteria for evaluating business ideas, while also recounting personal challenges, including betrayal and failure.
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Key Learnings
- Importance of Transparency: Instead of optimism, transparency is highlighted as a crucial tool for founders during crises.
- The Go Gauge: A six-part test that every business idea should pass to be considered fundable. This includes assessing the product, its differentiation, customer base, sales strategy, and financial viability.
- Empathetic Leadership: Strategies for firing employees with empathy while maintaining honesty about performance.
- Dealing with Failure: Insights on how to handle failures in startups and the emotional toll of such experiences.
- Unexpected Business Opportunities: Discusses how sometimes, the best startup strategy could be as simple as starting a pizza shop.
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Timestamped Chapters
- [00:00] Introduction: Bacon, milkshakes, and a first meeting
- [03:00] The Golf.com collapse and family betrayal
- [07:30] The psychology of failure and the will not to quit
- [12:00] Buddy Media’s pivot: from Facebook games to SaaS
- [15:00] Why failure sucks—but trends are your friend
- [21:00] Surviving marriage while surviving a startup
- [26:00] Emotional awareness, therapy, and not “shining the turd”
- [33:00] The $500M pizza truck startup fail
- [38:00] The truth about hiring, firing, and reorganizing
- [44:00] The death of venture capital—and rise of bootstrapping
- [50:00] Investing in pets, ice cream, and par-3 golf
- [54:00] Why Liquid Death is a billion-dollar brand
- [57:00] The Go Gauge: 6 filters for a fundable idea
- [01:02:00] Friendship, failure, and why they finally wrote the book
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Personal Insights from the Discussion
- Emotional Resilience: The Lazerows share their first-hand experiences of betrayal, particularly from family and business partners, emphasizing the emotional challenges faced by entrepreneurs.
- Navigating Relationships: The dynamics of working together as husband and wife amidst the pressures of starting and running a business are explored.
- Learning from Failure: Both Michael and Kass discuss how they have reframed failure as a part of the entrepreneurial journey and how it can lead to eventual success.
- Investment Philosophy: The Lazerows discuss their investment strategies, using examples from their own ventures, establishing that they look for companies that can solve real problems and have a viable market.
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The Go Gauge
Six Criteria for Evaluating Business Ideas
- What is the Product?: Clearly define the product and its purpose.
- Why is it Different?: Identify the unique selling proposition or differentiation in the market.
- Customer Base: Assess the size and accessibility of the customer market.
- Sales and Marketing Strategy: Evaluate how the product will reach customers and how it will be marketed.
- Delivery Models: Consider logistics – how the product reaches the market.
- Financial Viability: Ensure the business model is sound and can be profitable.
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Additional Resources
- Book: [Shoveling Sh*t: A Love Story About the Entrepreneur’s Messy Path to Success](https://www.amazon.com/Shoveling-Story-About-Entrepreneurs-Success/dp/B0DY21NS7W/)
- Liquid Death: [Liquid Death Website](https://liquiddeath.com/)
- Slice: [Slice Life Website](https://slicelife.com/)
- Commonwealth: [Commonwealth Website](https://www.commonwealth.com/)
- Van Leeuwen Ice Cream: [Van Leeuwen Ice Cream Website](https://vanleeuwenicecream.com/)
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Conclusion This episode of The James Altucher Show provides invaluable insights into the entrepreneurial journey, particularly reflecting on the personal struggles and triumphs of Michael and Kass Lazerow. Their experiences and frameworks can serve as crucial guidance for current and aspiring entrepreneurs facing similar challenges in their ventures.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
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1:21Ask a financial professional how Pacific Life can help you today. Pacific Life Insurance Company, Omaha, Nebraska, and in New York. Pacific Life and Annuity, Phoenix, Arizona. Today on the James Altucher Show. Look, you guys, perfect title for your book, Shoveling Shit. Every entrepreneur in the world can relate to it. The CEO called us and says, you know, I just want to let you know, Sequoia has backed out. We have no money to go public. We're going bankrupt and we have no money to pay your payroll. So that is like the biggest punch in the face of just having to shovel. That's all we had to do.
1:59And then I remember a specific call that not only did a family member threaten to sue us, and the family member threatened to kill me. And I'm like, why me? I think every entrepreneur, to some extent, loses family in the process. How do you do anything, right? You do it. I think this is a great point because there are multiple reasons why people start a business, but two of them are, you want to make a lot of money and you really believe that you can provide a value that other people are going to be excited about. That was our first date, James. Our first date was bacon and milkshakes. Milkshakes and pancakes.
2:37We were young and didn't put on pounds like we do now. I know. It's like, all right, let's start there. You got, Mike, you and I met each other in 2006, in this, I would say the summer of 2006, so it's almost 20 years. We're older now, and you and Cass, and hello, Cass. Hi. I used to have you on the podcast. We're all 20 years older, so my metabolism has changed. I used to be able to eat everything. When we met, I had like five pancakes, bacon, and a milkshake. Never worried about gaining pounds. What do you do now? This isn't your average business podcast, and he's not your average host. This is the James Altucher Show.
3:31Well, don't forget you had french fries also. How could I forget? You had all of that. And I'd never, we met at the Red Flame Diner and I knew you were a character, but I'd never seen an order like this. You started with bacon, then you got a milkshake. I'm like, oh, bacon and milkshake. Then the pancakes. And then you said, oh, can I have a side of fries with that? I was like, man, oh man, this is my kind of guy. What was wrong with me though? Like I could never do that now. I would gain 15 pounds instantly. Yeah, I mean, we're older and we actually need to move and we actually need to eat more protein now.
4:05Okay, it's the moving part that I have trouble with. Yeah, I can't eat anything anymore. I could just eat air. That's all I can eat. So look, you guys, perfect title for your book, Shoveling Shit. Every entrepreneur in the world can relate to it and everybody who wants to be an entrepreneur should understand it. And the subtitle is a love story about the entrepreneur's messy path to success. I've seen you on the ups and downs, you know, over these years, obviously I enjoyed the ride with you on buddy media, but until reading this book, I didn't even know how intense it was for you. Talk about like early days, either golf.com, which you sold to AOL for 24 million or buddy media, which you sold to Salesforce.com for, I don't know, 600 or 700 some million.
4:52What's like an example that stands out if someone says entrepreneurship is about shoveling shit? What's a personal example that stands out? I think the best example is with golf.com. So we started the company in September 98. And by December 99, we were acquired by a Sequoia-backed company in California named ChipShot.com. They made custom knockoff clubs. and they thought that our content, our golf content that we syndicated across to thousands of different sites would be a perfect fit. And this was the height of the internet boom. Our board, investors, everyone said, okay, let's do this. And we did an all stock deal in the due diligence.
5:37They were going public in the spring in April of 2000. Obviously the end of the IPO market was essentially March 30th, 2000. Exactly. and by March they called us the CEO called us and says you know I just want to let you know Sequoia has backed out. We have no money to go public. We're going bankrupt and we have no money to pay your payroll. So that is like the biggest punch in the face of just having to shovel. That's all we had to do. We had to shovel our way out of there and we did it through transparency with our employees. And then Mike and I and our other co-founder just hit the road and started trying to fundraise.
6:21But okay, that's the story. But then there's underneath that, like you casually mentioned in the book, oh, even one family member threatened to sue you, but you blew that off. But the reality is when people are calling you, threatening to sue family member or not, or when Don Valentine, the biggest VC in the industry at that time, basically withdraws, his funding at the last minute. This is really emotionally painful. Like, did you cry? I think I would have cried. I mean, well, first of all, we didn't blow off the family and we're trying to sue us. We had to deal with that. And that was probably more painful to me than actually having the rug pulled out from under us with chip shot, because you just kind of don't understand, you can't compute why someone wouldn't be supporting you.
7:13That's family. So that was really, really tough. And I remember going home each day and just being so upset with Mike that this person was doing this. But for the chip shot thing, my reaction, I mean, my true feelings, and I'm being totally honest, I was angry. I was so angry and I kept replaying it in my brain. Like, what did I miss in due diligence? And obviously hindsight's everything. But now Mike and I talk a lot to entrepreneurs about when they're fundraising, like pick your head up a little bit to see what's happening in the market. We should have been smarter that things were not going well.
7:54But it was so sudden. Like, don't forget, it was that, I think it was that first day of April that the Nasdaq fell like 20%. Like it was very sudden what was happening. Yeah, but there were other signs. What were the other signs? Mike, I mean, I would say we heard other companies that they were no longer going public. We saw other companies' funding stop. And I think we were just a little too naive back then. Yeah, I mean, it's not only that we were naive. If we take ourselves back, we were riddled with fear. And I went to journalism school, started a company at journalism school, which was an okay result.
8:32Golf.com, when we sold it, it was going great. And I was scared that we were losers. I was like, everyone's going to think we're the worst business people ever. We're 23, 24. And the idea that I had to tell everyone that we failed, that we lost this money, I remember the feeling there was a pit in my stomach. And then I remember a specific call that not only did a family member threaten to sue us, we were on a call and the family member threatened to kill me. And I'm like, why me? Like, why not Cass? Like, she's like kind of responsible as well. And we had so many emotions that were driven. If he said, I need to kill at least one of you, would you have given up Cass as?
9:21I mean, let's just say if she had volunteered, I wouldn't have said no. I had worked hard to stay alive. I had like a bad heart. I had like two surgeries. It had been a battle just to stay on this earth. You know, Cass missed like, you know, everything comes easy. Just answer the question, Mike. Answer the question. He wouldn't have said no. Listen, I would have volunteered knowing that Cass would have said no. Let me take this one. I'll be like, okay. Ah, chess. He's playing mental chess there. But I agree with you, though, that the family member thing, I mean, I'm saying in the book, you kind of dismissed it with one line.
9:57Yeah. And then because it wasn't really the point of the story. Yeah. But I think every entrepreneur to some extent loses family in the process. I've lost close family members in the entrepreneurial process. It's almost like someone dies and the family can't stick together because entrepreneurship is a whole life of its own that comes in between things and money is so emotional. And I think that is extremely painful. And that's just one of the things every single entrepreneur listening to this is going to have to deal with. Yeah. And you have to realize that it's, you know, we didn't know investors.
10:31And so we wanted to build this thing before we sold it. The best business is one that you could fund it off of customers. Yeah. And we turned to the family and it was at a time when the internet wasn't popular. This idea of startups and making money and all this, like it just didn't exist. I think the risk that is in these businesses wasn't fully comprehended by people who made money in real estate and law and real businesses like cash flow. And, you know, what's interesting is you've been on a tear, like how to write a book, how to start a podcast. I've listened to several times because they're like top of mind.
11:10How do you do anything, right? You do it. For us, the best thing that came out of golf.com is we just got started. and I would tell any entrepreneur out there, how do you start a business? You start a business, start doing it. Yeah, I think this is really important advice for a lot of reasons. One is if you tell people, oh, I've got this idea and they all say, hey, that's a great idea. Then you got the same dopamine as if you actually did it. So your brain's now like, oh, well, I need to just watch TV now. I already did it. So doing it really is important. Like I could tell people all day long what my ideas for my next book is, nothing matters until I write the book.
11:49Yeah, it's about the reps, you know, getting the reps. The other thing is, though, that's really important is, and I know we've all learned the hard way, but when something like that happens, when funding falls through, when acquisitions fall through, when deals fall through, I kind of reflexively now, but I didn't when I was younger, I kind of reflexively now say, okay, there has to be an opportunity hidden in there. There's some opportunity I'm missing because this bad thing happened. And look, you picked a part, upgolf.com and totally redid it and created a great company. But do you think this is general advice that's good?
12:23So I think that the best entrepreneurs look at failure as one step closer to success. Every entrepreneur I know has had to pivot both personally and in business. And you start with something written down on a piece of paper and a spreadsheet, and then you get punched in the face. And then you're like, oh, that didn't work. And you remember Buddy Media, right? We launched with Ace Bucks. You were the only person who played our word game. Loved it. You thought I was cheating. Because you're so good at it. But I love the game. And so that was a game that the whole purpose of the game, which we took freemium games, hooked it up to a loyalty program.
13:02But we launched as a currency that was worse than the Venezuelan currency like we didn't realize that you can't just kind of insert money into the money supply without a way to like take it out and so um that was a colossal failure we didn't give up we basically said let's do something else custom apps that worked but it wasn't scalable we got to do something else software okay and then took us three years to get to 50 million of sales off of that business. And so failure to us is just another part of the game. If you have the resources to pivot, so money, and you have the will to throw things out, which is very hard.
13:45Well, also like, again, like you started off, Facebook was this new, but really great social media platform, obviously. And you started off with these games that were really fun. And I enjoyed. And look, Mark Pincus was an investor. He started Zynga, which was built off of Facebook games. So you had kind of reason to believe this was going to be a great business. But what you ended up doing actually was building up expertise and building apps. And this is a great lesson, which you sort of address in the book, but it's great when times are hard to turn into a service business. So you built up this expertise building game products, but then you became a service business building custom apps for Fortune 500 companies.
14:27And then you basically pivoted from that to being software as a service so that they could use your apps to market themselves on Facebook, which was a brand new advertising industry. Now Facebook's the biggest advertising platform in the world next to Google. Yeah. So the best thing that we did is stay close to customers. We would go and we'd talk about Acebox. We didn't talk about custom app development. And what we kept hearing is that they needed help, the brands. We're talking about GM and P &G and Unilever, they needed help to figure out how to market in a world where people aren't watching TV, they're just glued to their feeds.
15:01And we launched that solution of publishing content, advertising that and building experiences. And so I hate failure. I'm not one of these people who's like, I think Elon Musk, who said failure is an option. If things aren't failing, you're not innovating enough. It's like, no, failure sucks. You would never start something. It's the worst. You're not going to launch something hoping that it's going to fail. However, doing anything meaningful usually takes a lot of reps. And that's the story of our career. The other part of our career is trends. Trends are your friends. And if you can get ahead of big trends, like I think you've done many times in your career, good things happen.
15:45I think that's right. Because I mean, let's say the components of a great business, and I'm just going to be very superficial here, is a great idea with product market fit, but also a great team so that you leverage each other's expertise. But also the trend is your friend. Like if you're at the bottom of an exponentially growing industry, there's a lot of tailwinds behind you, pushing you along. So you were at the beginning of, just like the internet had website development agencies and that was a huge industry in the 90s. You were at the beginning of social media marketing agencies. You were the first, I would say.
16:22Yeah, definitely. I mean, we were out there trying to figure out what social marketing was and how that impacted Fortune 500 brands. And I think we did a good job at taking our failures, meaning none of the business models that worked previously and realizing what our customers actually wanted. They needed help marketing to their customers on Facebook and then eventually, you know, what was Twitter and things like that. So it made sense to us, at least to keep going at it. Like in 2008, when the entire financial world fell apart and, you know, I know you had money raised. I remember you insightfully raised right before that period, some money.
17:06So you had mitigated your risk correctly, maybe because of your experience with golf.com. But how did you then realize, okay, this is the pivot. We're going to basically serve these Fortune 500 brands and tell them how to market on Facebook and write software to help the market. Did they have the budgets to market on Facebook? What was your sales process like then? Yeah, so there was no strategy that we could have learned at business school or through like McKinsey. It's basically staying close to customers. And we kept hearing the same thing over and over again, which is we need help to launch our content and experiences on what it was early Facebook and then Twitter and YouTube and all these other things.
17:47And we just had an open line of communication to say, would this be of interest? Would this be of interest? Would this be of interest? And it really was Unilever that broke it wide open. They basically came to us with a problem, which was we have 100 brands that do business in 120 languages all over the world. And we have this global platform that if someone shows up from you know Venezuela speaking Spanish we need a different experience than if they show up speaking French in Paris or you know English in US or UK and so we built it for Debbie Weinstein who's now at Google but was our client and we would be in product meetings be like what would Debbie think and then when someone said I don't know I literally would pick up the phone and I'd be like hey Debbie do you have a second she'd say no I'm like well I need a second you know what do you think about this she's like yeah i'd buy that shit and like that became the business too many entrepreneurs are just constipated perfectionists they sit around waiting for like the perfect product the perfect time to launch and that shit don't exist like no you don't know and also i think let's say you had that call with debbie weinstein and she says yeah i need this let's say at that point you had no money that's still an enormous opportunity because you could just say yes and then do what she said.
19:09Because none of it was rocket science, right? You would just figure it out from there. And even if someone listening to this at home saying, well, I'm 21 years old, I don't have access to investors, you could still just do it. There's nothing that's hard. Unless someone says, oh, okay, I need a rocket ship. You can't do that. But you can do like, oh, okay, I'm going to build a menu so you could pick how you want to advertise on Facebook. Yeah, it comes down to just like we said in the beginning, it's the reps. Just jump. just start doing, right? And take that customer feedback like we did from Debbie and then improve the product along the way.
19:44Yeah, and again, it's like with golf.com, you had the worst situation possible. Your business fell apart to essentially, you could have basically walked away from it and nobody would have said that was an unreasonable outcome. But you basically had some asset value there. You rebuilt the business from scratch. which I guess you scraped together some money and you were ultimately able to sell for a reasonable$24 million. And of which, because you had all these investors, you say in the book, it's not a secret, your take was$3 million. And then of course, from there, you leveraged upwards. I think that golf.com is a great story, which is the worst possible thing happened in the worst economy.
20:26Like the dot-com economy did not recover for at least three years. I would argue five years from that moment. And yet you were able to build up and five years later, sell the business. That's right. Yep. And it's also never crossed, you know, never crossed our mind to quit. Like I had, you're growing up, I had a Vince Lombardi quote, like on my wall, which is winners never quit and quitters never win. And I just thought he was a cool coach. I didn't know how like apropos that was for the life of an entrepreneur. and if your first thought is we got to quit, like really tune into that because maybe what you're doing is too small of a market or in your gut you really don't have anything.
21:09But if you really believe in what you're doing, it's always too early to quit. I think this is a great point because there are multiple reasons why people start a business, but two of them are you want to make a lot of money and you really believe that you can provide a value that other people are going to be excited about. And if it's the latter, like you just want to make a lot of money, you actually don't know when to quit or not. Yeah. Because you need religion to, I think, not quit when things are going down. Like you said, let's say you build a website. Let's say you built a social media dating website.
21:46I'm just making this up back in those days. And nobody was going to it. You probably should quit unless you really believe in what's happening. Like if there's no users, Maybe you made something bad, but you just won't know. You probably should quit. In that case, Vince Lombardi's wrong, right? Well, I think there's a lot wrong about that, but it's a mentality that is right. And when I say a lot wrong with it, there are times when you should not raise money. There are times when you should not invest your time. As a young entrepreneur who had no money, our most valuable asset was time. And that's what a lot of your listeners, their most valuable asset, they may not have hundreds of millions of dollars, but they have hundreds of millions of minutes, right?
22:28And so don't waste that time doing stuff that's not going to produce the life you want. And at the same time, like there's this culture that we have that like quit while you're ahead, which we just believe that once you get ahead, that's when you step on the gas. Like that's not when you quit, that's when you step on the neck of competition and that's when the fun starts. But entrepreneurs need to really have that grit and resilience. And I think that's what being an entrepreneur is. It's like getting punched in the face every day, getting data points from those punches, and then having some optimism that you'll figure this out because it's just going to happen day after day.
23:10And like you guys said, it's very hard. Like nobody wants to fail. Failing sucks. And at the bottom, yes, maybe your thoughts are, okay, there's an opportunity here. Like there always is. But also your thoughts are, this sucks. This is failure. You have both feelings at the same time. I did not want to lose. Like I looked at everything as winning and losing because, you know, I was a trained athlete and I could not believe that I was going to get a big L, but not from me. It wasn't like, I'm okay if I lose, if I lose the match. But the fact that Chip Shot had pulled that out and they weren't honest with us, that really, really bummed me out.
23:55Take a quick break. If you like this episode, I'd really, really appreciate it. It means so much to me. Please share it with your friends and subscribe to the podcast. Email me at alcatra at gmail.com and tell me why you subscribed. Thanks.
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24:49And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small and medium businesses say using LinkedIn helps them find high-quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. Post your job for free at linkedin.com slash altature. That's linkedin.com slash altature to post your job for free. Terms and conditions apply. We're spending more than ever. I hate my job. The price of everything has gone up. AI is threatening my job. It's crisis after crisis.
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25:49and i want to in a few minutes speed up to current day but back then you're 23 24 years old you're really experiencing failure like the likely outcome at that moment was you were going to go out of business and whatever, it's almost like it feels like a death of sorts. How did you guys survive relationship-wise? Could you leave the work at home and go out for dinner and a movie? Or what was happening personally? The good thing is that we had each other. I mean, there's good things and bad things. The bad thing is all of our eggs were in one basket. So like one financial basket that we had literally zero money.
26:30So the amount of money that Mike and I had saved as very early on in our career was like, I don't know,$25 ,000,$30 ,000. That's what we invested into the company. And that was gone, right? Like that was taken away from us. So that was the bad news. But the good news is, is we both knew what we were going through. So we were the best support system that we could have. It wasn't like one of us was having this horrific experience and the other one was like, hey, what's for dinner? It was like, okay, how much do we have left in the bank? And should we eat ramen tonight? It was scary, but I felt this sense of calm because we were both in it together.
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27:10But I feel like, honestly, a lot of marriages would not survive that. Like you would take it out on each other. You would cut your losses in every way and just start from fresh or you just wouldn't be able to get along anymore. You'd be scared. One person would say, look, Mike, you should get a job. The other person would be like, no, no, we got to start this business and move to a smaller apartment. Like these are real critical things. I mean, so it wasn't easy because we were now, we started golf.com when we were dating. I would not recommend that, although it's not impossible, but Hey, you want to go out on a date?
27:45And then like less than a year later, like let's start a company together. We then just, we got married in October of 99, right before everything fell apart. We're trying to get our feet as a married couple and as business partners and as business people, right? Because we're learning business together as we're trying to learn marriage, thinking about starting a family. And Cass, you may have forgotten this, but there was a woman who really saved me named Nancy Randleman, who's a therapist in Chicago. Yeah. Because I was as unaware of how I was impacting Cass of any person I'd ever met. And so I was both not present, I was shining the turd, meaning like if things weren't going well, it's like, oh, it's going great.
28:31Don't worry about it. I was dismissing her feelings. I wasn't being vulnerable. I was like a young dude, right? I was 25 when we got married. And so I didn't know anything about myself, most importantly. And I would encourage everyone, seek out people to educate you about your weaknesses, to give you constructive feedback, and then take action based on that. And I remember sitting in Nancy Randleman's office by Wrigley Field after I got like parking spot, which was hard on Cubs games and crying because I was not only an awful business person because we were failing, but I was an awful husband.
29:09And Cass kept saying like, stop shining the turd. Like, I need you to be present. I need you to listen to me. And that's been a 30 year journey of self-awareness. But like Cass, at that moment, were you thinking, hey, this is on shaky ground. This might not work out. I don't think the business was why I would have ever had doubts about Mike and me. I think it would have been more about how we communicated, right? So the business, for some reason, and maybe it's because I had blinders on, like I knew Mike was the person who complimented my business strengths like perfectly. and I think being a newly married couple, you know, everything gets amplified when you work together, right?
29:54Because we weren't like just seeing each other at the end of a workday, we were seeing each other 100%. So we were trying to figure that all out all at once, like Mike said, but my doubts were about how we were going to figure out how to get to a better place. It was never about like, oh my God, this business has ruined our relationship. What Mike was saying, though, of like, you know, not really communicating, always maybe being too overly optimistic and you knew he wasn't being forthright. Like, did you ever question whether that would repair itself? yes i mean you always question it and also remember it's easy for me to look back now with 28 years behind us and kind of have more faith but when you're building something and it's only been one or two years or at the time when we got married three years like everything is doubtful right like you have doubts about like oh my god is he ever going to tell me the truth or is he ever going to be present like he said and i'm sure i provided a lot of you know behaviors that caused him doubts.
30:59I don't think back then my doubts were as big as everybody might think they should be. I don't know why, but I think that the bond that we had created over the three years of dating and then getting married strengthened us. And I think Mike knows very well now that I am relentless. Like I am like a bulldog. And when I know that he can improve on something, I want him to improve. And so I think that's how I treat myself. And so I don't think I ever looked at like, oh my God, this marriage is not going to work. I'm going to be like, I'm going to run him into the ground if he doesn't listen to me because I know he can get there.
31:45And were there any points during this time that you had fun, like go out to a movie, go out to a party and just go dancing. Yeah, totally. We had great friends. Like all of Mike's best friends from college, they all were there. And we had belly laughs upon belly laughs, playing beer pong. We would go to shows. That's when I actually liked music back then. Seth was doing ImprovOlympic at the time and waiting tables. So Seth Meyers, I was living with when I met Cass. Yeah, we graduated Northwestern together. He's godfather of our daughter. Yeah, I didn't know that until I read the book. Yeah, and so he was working at the Twisted Lizard, which was an epic Mexican joint.
32:26So good. In Lincoln Park, which we loved. And we would then go see him on Monday nights at ImprovOlympic doing his improv stuff. He wasn't, at the time, good enough for Second City, so he got rejected. Pickups and pickups. Don't forget that one. He had a one-man show. And so we did have some fun. And that fund was replaced by kids a few years later because you can't really do these companies and parent and go out every night. But what's interesting is at the time, when you're in any relationship, you don't have the confidence. And so although right now Cass says that she never doubted some of this stuff, to me, my experience was if I don't get this together, I'm going to lose the love of my life and the best business partner I could ever ask for.
33:12And I couldn't help myself. like a lot of guys and you know so it felt very existential to me like if i don't get myself help and figure this out like you know fast forward and i don't think there's much i can do for cas is like what's called she's pot committed right like we're getting serious 30 years later um and so we've settled into a nice system of communication and trust and fun and you know we We not only love each other, but we like each other. We're going to be empty nesters in the fall, and we're so excited about free time together. But the early days, it was not easy, and I think a lot of entrepreneurs that we're talking to felt the same way.
33:59By the way, I think the reason I dive into a lot of this stuff is I don't think people realize how critically important this is for success. I mean, of course, there are a lot of successful people who have divorces and multiple dramas in their lives and so on. But like, take when you sold golf.com and you guys personally made$3 million. $3 million in New York City and being entrepreneurs, people think that's easy street, but it's not. Like, particularly if you're going to now reinvest that$3 million into starting a new business, you kind of have to, if you get a divorce, your money's gone, first off.
34:35And you're starting from scratch. Like, it's over. Well, don't forget taxes. taxes took half of that right taxes legal kids yeah you kind of have to know how to like leverage that initial dollars into future success which is of course you did take risks i mean you started off buying you know the ace bucks brand and games and and you took risk and so on i just point this out is that this is a very important part everyone has a different story with this but your story is very inspirational on the marriage side. I want to ask, there's one kind of anecdote you talk about in the book, which I thought was fascinating.
35:12Zoom, S-U-M-E, a company you weren't involved in, but they basically were like, I don't know, like a mobile food truck for pizza, something like that. And they raised$500 million. So, you know, this is a chapter that we're talking about kind of different ways to approach markets. And we believe in very large markets and giving customers what they want. People were surprised we did Liquid Death. Well, there's the building block of life. I wanted to ask you about it. Liquid Death is like the best company on the planet. So put a fork in that for a second because I want to ask about that. But Zoom, tell me.
35:48Yeah, and so we love pizza. Who doesn't love pizza? But we also love it as a business. You have companies that you can launch a pizza place for about$250 ,000 in New York City if you are just moderately successful. Average pizza, you'll do a million dollars of revenue at 30 % margin. So you're basically making your money back in year one. And if you market, and we have an idea to market, we're going to open up pizza places. Cass hasn't agreed to it, but we are going to do it. You can then do, hey, your first pizza party for your office is free on us, right? Because a pizza doesn't cost anything.
36:24Now, if you want to approach the pizza space, there are a lot of ways to do it. open up a pizza parlor, right? That's what we're going to do. Number two is you can provide picks and shovels to pizza places. That's what our friend Alir, who started a company called Slice does, and he sells a lot of picks and shovels to independent pizza makers to help them compete with Domino's and all the delivery guys. What's the picks and shovels in the pizza business? You need boxes. You need a point of sale system. You need ingredients. You need all this stuff, which they provide bulk buying for and make it easy, the most important thing they do is they will provide your delivery services.
37:03Because if you're a mom and pop pizza shop, you may not want to go to eBay and buy a truck and deliver pizza. You are better off working with Seamless and all the different sites and tap into their distribution and Slice helps you optimize all of that. And he's built a very big business. He's well on his way to becoming a billionaire. We love Alir. We think he's one of the great entrepreneurs, not only here, but where he was born in Macedonia. And he did something that he knows because his family was in the pizza business and he knows how difficult it is to run a pizzeria and especially a modern one.
37:44The third way to compete in pizza is you create a new product and try to change behavior. So this company, what we're talking about, Zoom, they raised$500 million. So it's half a billion dollars to create a truck that the pizza would cook on the way to your house. So when you got it, it was fresher, okay? They couldn't figure out how to get the pizza to not slide out of the oven when they drove. And literally they should have just put half a billion dollars into a pizza oven and then moved on, right? Lost every cent in this stupid fucking company. So if you can attack a market with a product and service that makes sense and it's a big market, you can create a business.
38:32You don't need to reinvent the world. And that's what that section is about. I love this concept of there's multiple ways to slice a trend, say. So with pizza, you could start a pizza parlor. By the way, you could take a more financial engineering point of view. You can do a roll-up of pizza parlors. You could buy a bunch of pizza parlors in a category or across the country or whatever, and then get synergies that way and go public and so on. Kind of like a Papa John's did. Or you could do this picks and shovels, whether it's software or, hey, we're basically pizza company in a box. Like you started a pizza place.
39:10We'll just handle all your stuff. Just sign up for us. It's a subscription. will get you boxes, sauces, software, the whole thing. And then the new product idea is hard. What I will give the Zoom, and it's spelled Z-U-M-E, what I'll give them credit for is they raised$500 million. And so this reminds me also of April 2000. So at that time, I had just raised$30 million for a company that made wireless software apps. So we were a little ahead of our time. We were talking to everybody about going public, but then of course, like you guys, the IPO market fell apart. and my big regret, I still had$30 million cash in the bank.
39:47I should have just bought a chain of gas stations and just been profitable until this internet thing came back because I knew it would. And I think people lose track of the fact that money has value, that if you raise it so easily, it doesn't mean it doesn't have value. Like you should always respect the money, you should respect profits, you should respect services that provide value and you don't necessarily need to respect what you told investors if you think you have a better idea to stay in business? Like, i.e., buying a chain of gas stations would have worked out better than what would have happened ultimately to me in that business.
40:22Well, we basically are sharing that idea in the book. And so we, you know, these cheat codes that we put together over 50, it's not for venture capital businesses. This is for companies that are pizzerias, salons, service businesses. and it's back to basics. It's, you know, how do you pick a co-founder? How do you create company culture? How do you moneyball people in the right position? Yeah, and so I like the moneyball chapter, which is basically, you know, it's kind of like what John Doerr says, measure what matters. You have to measure, as boring as it is, you have to measure your financial metrics to know where you should double down, where you should back off, where you need to hire, where you need to fire, where you need to get customers and so on, which is basically what you did throughout the business of Buddy Media.
41:10That's right. We were in an event today, and Mike and I shared that one of the great little cheat codes is every time you raise money, lay off people. It's a perfect time to lay off people. It's a time to figure out how to reorganize your life and make sure that everyone there matters as you move forward. It's not the time to sit and within seconds hire people. first see if everyone's doing their job. How do you fire people? I have a hard time doing that. You have to be really direct, James. You have to start off and just say the one phrase that I always say is, unfortunately, today will be your last day.
41:50Just get that out. You have to be kind and you have to have empathy. And if you really want to be a good leader and a good person, you have to then teach them what they failed to do. You have to be willing to have an uncomfortable conversation They might be upset, angry, tears, and really help them for their next job. What if they keep arguing with you? Like, what if they say, no, but I did that. But no, I'm willing to do that. Like, give me one more chance. I can call people back faster. Thank you so much. I appreciate what you're saying. But today will be your last day. Yeah. And I see you're the one doing this.
42:27Mike can't do this. Mike's not doing it. I did it once. And the guy I went to fire got a raise and a bigger title because he did what you just said, James, and he made a very convincing argument. I know. It's hard. Basically, if you're a salesperson, you can be easily sold. And I'm like a salesperson at heart and I'm easily sold. So you have to know this about yourself. Like when I'm looking at a deal, for instance, I'll go into the deal with a friend of mine and I already know I'm not going to like this deal. I will tell my friend, they're going to convince me to invest money in this deal. After the meeting, you have to tell me what I just said because I'm going to forget it.
43:05And that technique has worked for me. It saved me money.
43:24I'm just curious. Why did you invest in Buddy Media? We didn't have a plan that made sense. We didn't know each other that well. You somehow said yes. And I remember thinking like, really? Like, did you really say yes? Like, do you really want to do this? Like, that seems crazy. I'll tell you exactly why. And by the way, I then wrote about it in a book in 2008, well before you guys were successful. I wrote about it in the Financial Times, almost assuming you were going to be a success for all the reasons why I said yes. For one thing, when we met that first time, you wanted to give me advice or even be the CEO of a company I had just started called Stockpicker.
44:00And you gave me all these ideas. And I've told you the story, but you gave me all these ideas. And I stole every single one of them without, of course, hiring you as CEO, or I didn't need to take any investment or anything. And you were cool with it. And all the ideas were great. They all worked. And the other thing is I loved the concept of gaming on Facebook. I had a lot of faith in you as an entrepreneur, just from our meeting and from the reasons I said. But I'll tell you a really important thing, and this motivates the way I invest to this day. Peter Thiel and Mark Pincus were investing. So if someone smarter than me is investing, like as you point out in the book, Peter Thiel was on the board of Facebook and you were setting up a Facebook marketing company.
44:41Mark Pincus was the leader of all Facebook games and had a billion dollar company doing that. So they clearly knew the Facebook ecosystem and they were putting money with you. So I think to myself, what am I going to do? If I ran into Peter Thiel, am I going to say, whoa, whoa, Peter, are you an idiot? How could you invest in, you invested in Facebook. That seems pretty good, but how could you invest it? But like, no, of course he's going to be smarter than me in this. And so to this day, I only really invest if someone smarter than me is also side by side with me. So like if Warren Buffett, I'm just going to make an example.
45:16If he invests in IBM at a hundred and now IBM is at 80, I'm not going to say Warren Buffett's an idiot. I'm going to say, oh, I can maybe buy shares of IBM at a discount to where Warren Buffett bought them. And that's essentially what was happening here. Probably wouldn't have invested in a later round, but in the round that Peter Thiel was going in, I'm in. Well, it's interesting because why I love stock pickers so much was you put that in motion in the public markets. Yes. I was religious about this idea. Yeah. You're scraping kind of all the filings from the leading investors and basically say, hey, do you want to invest like all these hedge funds and all these great investors here it is and it was the beginning of like the big data movement online where you could like create not proprietary but unique data sources and monetize them and i thought that what you were doing was just gonna be hugely successful i didn't know how close you are with kramer and you know how the deal would get done like you sold it right afterwards yeah i sold i basically started and sold it within four months something like that Which is amazing.
46:19But perhaps I, you know, jumped the gun so fast. I'm a seller of businesses. I have never done like what you did. I mean, okay, I've built businesses too over years, but I'm more interested in building and selling and then having the next idea. But of course, that is ultimately what you did now. And you've been running a VC fund where you invest in good ideas. I wanted to figure out, like you mentioned earlier, trends are your friends, essentially. What are the trends you see right now for entrepreneurs? I think actually it's a fairly difficult time for entrepreneurs because let's just say AI is a big trend, but it's very unclear what's going to become quickly commoditized in the AI world.
46:57And this is just one example. I'm saying AI, but there's other examples. Yeah, so it's never been a better time than now to start a company, both because of opportunity and lack of competition for your time. So if you think you're going to go to law school and become a partner at Simpson, Thatcher, any of these firms, it's just not happening. So these firms are going to deal with AI. They have too many partners already. The only way to make it an illegal business or accounting is if you're a business development person who brings in business. And so we're all entrepreneurs. You can admit that to yourself today and get up from your desk and start a business.
47:38or you could ignore that and be left behind because you will be replaced at some point, either by another human or by a machine. And so it's never been easier to launch a business and never harder to launch a venture business. We moderated a dinner last night and these are all AI entrepreneurs building what's called vertical applications. So they're not building the language models like ChatGPT and Claude. they're building applications on top of them like we did on Facebook. And there was one who does like AI interviewing for staffing firms. And I'm like, okay, that's cool. How many competitors do you have?
48:21He's like 38 known competitors who've been funded. The reason they have 38 competitors is because it's not rocket science to build an AI interviewing app. No matter how many features you put into it, it's just not rocket science. Anybody can do it. and not only not rocket science, the AI will guide you through how to build it. So please go to Lovable or any of the AI platforms and just build an app for your family and it'll show you how to set up GitHub, how to connect everything to it. And it's super easy. Now, he also has over a million dollars of annual recurring revenue. And I said, listen, the bad news is I don't think that you're going to get funding as a venture business.
49:01The good news is I think you can build a$10 million business that throws off$7 million a year and you could have the best life you've ever imagined. And so we're having a, it's a crisis of venture capital. Venture capital is dead as we know it. I say that as a venture capitalist today. Entrepreneurship has never been brighter. And pick a problem that exists that you know and solve it. And that's the easiest way. And if the problem is there's no good pizza places on your block, start a pizza place. If the problem is you have nowhere to get a haircut, start a place to cut hair. Now you're telling me.
49:41Yeah. So, I mean, I just think that like, and I'm reminded of this every day because, you know, this morning we met an entrepreneur who we love named Ben Van Leeuwen at an event. He came up after us and, you know, he didn't know how much I knew about his business because I've studied it. Like, he had very little money. he bought a truck off of eBay to sell ice cream in Brooklyn. And he just took like water sugar, milk, sugar, flavoring, whatever it is, it goes into ice cream. And he developed a cult following today. Fast forward, he has 70 stores, very profitable. And he has a life that's just amazing.
50:21I know that store. They're the best ice cream. Yeah. Yeah. And so the other one is pop-up bagels, right? You think you can't reinvent a business. Some guy comes around and invents a bagel that blows your mind off. And it's like, wow, he just did that. But it's hard to ideate. Like it's easy to say, oh my gosh, every problem has been solved. Everything else is niche or too small. What's a big problem that you've seen recently that you would invest in? We like healthcare a lot. I think that one of the things that Mike and I are very excited about is how AI can help with all the different research out there that is clinical and trial research.
51:03And we just think health companies, it's just a huge market right now. Do you agree, Mike? Yeah. I mean, I think every part of healthcare needs to be re-imagined. I think only way we can balance the budget is really getting healthcare costs in order. By the way, Wilbur Ross just told me this yesterday. Wilbur Ross, former Secretary of Commerce, basically said people underestimate how much of a surplus in the economy this could create if healthcare costs are brought under control. Yeah, 20 % of it is administrative costs. And you have on one side all these software companies that are helping hospitals and patients try to figure out what should they be doing.
51:46and then on the other side if you look at kind of how you read like any sort of radiology report like a lot of its machines on the other side you have software companies helping insurance companies figure out how not to pay for stuff and it's like this battle between like payers and providers if you just got rid of the paper in the system it's going to give doctors time back and get you know costs out of the system but i think that's just like the tip of the iceberg how we educate our kids, how we spend our money, how we invest our money. Sports is going through a revolution right now. Co-owners of a few smaller sports teams that are just entertainment properties that have been very profitable.
52:29Okay, so let's take basketball. This is kind of a franchise situation where basketball has been growing nonstop for the past 50 years. So if you buy a piece of a basketball team now, you're going to sell it for a profit five years from now, almost certainly. Same thing for many other popular sports. Maybe there's new sports like pickleball, who knows? But that's out of the reach of the average person. So let's just brainstorm. So solving a problem, what about fractionalizing sports team ownership? And is that something that's possible? Yes, it's happening. It's a company called Commonwealth that basically started as a crypto company and you buy shares in different properties.
53:09They've now won a Kentucky Derby with their horse. So thousands of people own a part of this horse. And two years ago, they won the Derby. Now, you know, that's now going to go to funding golfers and tennis players who need money to practice. And I imagine it's going to be fractional ownership of teams, but the vast majority of teams are not the major kind of NFL, NBA, MLB teams. A lot of the entertainment properties in sports are minor league baseball. We own a pickleball team with Gary Vaynerchuk. We own a high stakes par three golf team that competes for big money under the lights, just par three.
53:53We just won in a tournament too, by the way. And that was a six figure acquisition, right? And now they're getting TV deals and people like the format. They had concerts at night and it's a party atmosphere. It's entertainment. And okay, so what else? I I agree with that on sports and with your perspective on AI. Like what else are you guys in? We love the pet space. Really? Pets are the new kids. I'm all in on my pets. I love them. They're my favorite children. And we love the pet space. I think there's a lot of noise in it right now, but I think people spend enormous amounts of money on their pets.
54:33So we love it. Yeah. And one of the, like, when you look at the pet space, I'm not talking about just doing like products, but like, you know, I've always wanted to launch like an AI pet psychic, like upload a photo or video of your pet, get an instant reading of like the pet, their energy, their thoughts, their future, and just charge like 10 bucks per reading, right? That's really funny. You should try it, by the way. That would take literally one day to create. Believe me. As soon as this book is done, I'm going to be launching a business every day. But I had another business, you know, what was it called?
55:09mama money back, which is like, you just hire detail savvy moms who use AI and the phone to fight for health claim money you're owed. That's a great idea. Mike's been watching me over the last 30 years fight the insurance companies on claims. And it doesn't matter what insurance carrier it is. I know all of the codes and I know what they're going to do. And I know how they pass you off. And I know that whole process. And I've taught a lot of other of our moms to do the same thing. And I was like, gosh, we should just make an army of moms that get money back for people and just take a like small portion.
55:50That's a great idea. There's already legal slash AI sites that fight your traffic tickets. Why not take all your knowledge, put it into an AI combined with the AI already knows all the rules of every company and state. Like you can make an AI that does this. Yeah, totally. That's interesting. There's so many like ideas. Why do you invest in, I love liquid death just because the idea is one of those things where like, damn, why didn't I think of that? Like just put water in a beer can and call it liquid death. Like, is there more to their success than that? I'm sure there is, but why did you invest?
56:22I can tell you when Mike brought it to me, James, I was like, are you fucking kidding me? This is water in a can. and I went to sleep. He's like, just sleep on it. And I woke up the next day. I'm like, wait a second. And we knew Mike Cesario, right? He worked with Gary V for a long time. And just looking at the marketing, because I like thinking about how products make people feel. I was like, this is going to be incredible. This is going to be like American Girl doll, but on steroids. Yeah. And I was all in. It's completely cool is the only word I could think of. It's made not drinking cool everywhere you go.
57:03I love that. People are putting liquid dead tattoos all over themselves. I mean, think about that. Yeah, that's incredible. I don't know where the company stands right now, but I'm assuming that investment is doing well. Yeah, I mean, we're registered investment advisors. We can't talk too much about results, but what's publicly been reported is it's now a unicorn and it sells a lot of water. what we like about all... So we have something in a book called The Go Gauge, which is like we boiled down to all startups to six concepts. Oh, yeah. Thank you for bringing this up. And we use Liquid Death as kind of an example.
57:43And one of the big parts of that is how many customers are there going to be? Not just market size, but like how many actual customers will buy this? Like the golf industry, everyone says it's 80 billion, but unless you loan a golf course, you're not really going to tap into that revenue rate. And we looked at it, we're like, man, the largest non-alcohol market is water. And do we really like Fiji and all these things out of a plastic bottle? Right. And so I saw this can, which is, you know, this is their grapefruit one I'm holding up to the camera, what they call grapefruit. And I saw the white can and I'm like, that's cool.
58:22And then we used to be, we're still in the music festival business, That year before it launched, I took it to Bonnaroo in Tennessee, which we were part owners of before we sold it to Live Nation. And people were taking the cans and after they drink it, they would refill it with water because they loved the can. Wow. And I remember thinking, wow, this is happening. And you had all these hot chicks and young people. And I was just like, man, oh man, this is cool. So walk me through the Go gauge about when is a business a good idea? And you could use Liquid Death. you could use other example, like what's, what are the six things and how do you check the box?
58:58And you have to check the box on all of them. I mean, we think it's better if you do, but I think a lot of businesses don't necessarily see all of them at the beginning, but it's very simple. It's what's the product. You need to be able to say like, what it is in a second. And so for Liquid Death, it was, you know, a health product, water, marketed like a product that's bad for you that is trying to get plastic out of the ocean. So it was on a mission. It's in an aluminum can. Then it's, why is it different? So, okay, like it's got to be different to be like a business. And so for Liquid Death, it was kind of how it marketed and how it made people feel much different than Fiji and the other ones.
59:44People don't get like Fiji tattoos. We thought this was a brand that people would love. and then it's a customer and we love the wellness space and so the third one is like how many customers are there and this is first of all water is a you know 60 billion dollar a year market you have you know beer drinking at an all-time low you have wellness picking up we thought this was just a great wellness product then it comes down to sales and marketing which is the number four, which is just how people are going to find out about it. Liquid Death was started by a creative director, Mike Cesario, who worked at Netflix and Vayner Media.
1:00:25And his whole thing was, I want to do stuff that my customers at the agency wouldn't let me do. And stuff like, you know, he started a country club that only way to get in is you sold your soul to the company, right? that he did a, someone commented online that this stuff tastes worse than back sweat. He went out and hired a comedian named Fat Zach and had people lick Zach's back after the sauna and compare it to a sip of liquid death. And 10 out of 10 Americans thought that liquid death tasted better than Zach's back sweat. It's brilliant marketing. What was the, like, obviously this idea rests completely, at least initially on marketing.
1:01:10What was his initial marketing that you think set it on fire or convinced you that this marketing will work? I mean, the thing that got me is he had a can and on the can, it said something like, inside this can is a proprietary technology that when you drink it, it reaches down your throat, it grabs thirst and it strangles it to death. And then the thirst hops out of your body and it stomps on the thirst to make sure that it murders your thirst forever. right and it was like such a a cheeky thing now we funded it in 2019 it launched in really march of 2020 which coincided with the pandemic we did not think that collab between a water product called death water and the pandemic was a great collaboration but we were able to get through that and the rest is history.
1:02:05So the last two that I'll talk about is just kind of delivery. How are you going to get the product to customers? And then we don't do big business plans for new companies. We just look at the financial model. We say, does this model pass the smell test on a napkin? Well, let's talk about number five for a second. And again, I want to mention our focus on liquid debt. But to sell a bottle of water in a store, you have to get shelf space. And that's very difficult. Coca-Cola has a lot of shelf space in every store. And even Whole Foods, it's done regionally. So you have to go region by region. And there's already a lot of healthy protein drinks, energy drinks.
1:02:45It's hard to get shelf space. And that's the key. As software entrepreneurs, we had a GoGauge before Liquid Death that had five things in it. We added delivery because it's been so difficult at Liquid Death. And if we knew, frankly, if we knew about the CPG space, what we know today, we may have never done the deal because they were making, they were taking Austrian spring water, putting it in a can in Austria, putting it on a truck to get to a train, to get to a boat, to get to another truck, to get to a train, to get to a wholesaler that then sells it to distributors and then retail. So it's been a battle, but now that we are mature and we've onboarded or at least brought into the country all the manufacturing, it's now doing incredibly well.
1:03:39Well, look, I loved the concept of the GoGage. I meant to bring that up earlier in the show, but we were having so much fun talking about other stuff. I'm glad we brought it up, though. And look, I've known you guys for a long time. I've made money because of you guys. Thank you very much. I'm always loyal to anybody who makes me money. And I like to think that, you know, we don't see each other, obviously, a lot, but I'd like to think that we've been friends over this time. Yes. And, you know, your book was great. Shoveling Shit, a love story about The Entrepreneur's Messy Path to Success. And I'm glad you guys wrote a book because I know, at least, Mike, I know you've been ishing to write a book for like almost all of these 20 years.
1:04:18Cass, I'm assuming you're the same. I'm so glad you wrote this book. And it's a good read. It's not like a boring book about entrepreneurship or business. You have stories, great suggestions, great advice. I can confidently recommend this to any young entrepreneur or seasoned entrepreneur. And I remember my one time we talked, you wanted to write a book. I think this was like 2013 or 2014. You wanted to write a book about the concept of being weird, about a book about weird people. I still think to this day, that is a great idea. Being weird. No, I love that book. And we started it and we did a lot of research because we happen to have a lot of weird friends and friends who have done all sorts of things from Gary to, you know, a friend in the porn business.
1:05:02And, you know, we also know how hard it is to write a book and we wish we had listened to your series on how to write a book. Anyone listening to this interested in a book has to go back. James gives the world an incredible how to both how to come up with the ideas, how to write it. And if we were to do another book, that is our model. So thank you. And, you know, we love you. We love what you put into the world. And frankly, we're proud of you. I mean, you've built such an incredible following by just giving to the world. You just give these ideas. Well, thank you. I appreciate it. And look, I hope eventually we all get together and I hope this book does well and come back on the podcast anytime.
1:05:44I really love having you guys on. So thanks once again. and Mike Lazarell, Cass Lazarell, Shoveling Shit, a love story about the entrepreneur's messy path to success. So many other great stories in there. You got to read the book to see it all though. Thank you. Appreciate you.
From the publisher
Episode Description:
James reconnects with entrepreneurs Michael and Kass Lazerow, whose journey spans selling Golf.com for $24 million, launching and pivoting Buddy Media into a $700 million Salesforce acquisition, and now investing in breakout brands like Liquid Death. This episode isn’t about startup clichés—it’s about emotional resilience, firing with kindness, how marriage can (barely) survive co-founding, and how to spot a trend before the world does.
They break down their “Go Gauge,” the six-part test they use before investing in a company. They talk about the trauma of being betrayed by family. And they reveal the surprisingly simple cheat codes they’ve used to keep building—and keep loving each other—across decades of risk. Whether you're building a business, looking for one good idea, or wondering what failure really feels like behind closed doors—this episode will give you a few new answers.
What You’ll Learn:
- Why transparency—not optimism—is a founder’s best crisis tool
- The six traits every idea needs to pass their “Go Gauge”
- How to fire someone with empathy and still tell them the truth
- What to do when your startup fails and the investors vanish
- Why the best startup strategy might be launching a pizza shop
Timestamped Chapters:
- [00:00] Bacon, milkshakes, and a first meeting
- [03:00] The Golf.com collapse and family betrayal
- [07:30] The psychology of failure and the will not to quit
- [12:00] Buddy Media’s pivot: from Facebook games to SaaS
- [15:00] Why failure sucks—but trends are your friend
- [21:00] Surviving marriage while surviving a startup
- [26:00] Emotional awareness, therapy, and not “shining the turd”
- [33:00] The $500M pizza truck startup fail
- [38:00] The truth about hiring, firing, and reorganizing
- [44:00] The death of venture capital—and rise of bootstrapping
- [50:00] Investing in pets, ice cream, and par-3 golf
- [54:00] Why Liquid Death is a billion-dollar brand
- [57:00] The Go Gauge: 6 filters for a fundable idea
- [01:02:00] Friendship, failure, and why they finally wrote the book
Additional Resources:
- 📘 Shoveling Sh*t: A Love Story About the Entrepreneur’s Messy Path to Success by Michael and Kass Lazerow
- 💧 Liquid Death – The canned water startup redefining beverage branding
- 🧾 Slice – Supporting independent pizza shops with tech
- 🐎 Commonwealth – Fractional ownership of racehorses and athletes
- 🍦 Van Leeuwen Ice Cream – The indie creamery with 70+ locations
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