In short
Mike Lazerow (Buddy Media founder; NYT bestselling author) discusses the personal cost of chasing a massive tech exit, what saved his health, and how entrepreneurs should lead, handle failure, and run difficult conversations. He also explains lessons from building Buddy Media during the early Facebook era and shares his GoGage framework for evaluating startups.
Guest backgrounds
Mike Lazerow is a tech founder and author. He built Buddy Media, a social media software company that scaled to a $745M sale to Salesforce (with Salesforce growing from ~5,000 to ~20,000 people during his tenure). He later wrote Shoveling Shit, A Love Story. He has an artificial heart valve and underwent heart rebuilding; his cardiologist warned him he was going to die. He credits trainer Rico Wesley with helping him recover.
Key claims
Entrepreneurial success can nearly kill you; health and relationships must be scheduled like business priorities. Great leadership requires listening, transparency, and trust. Founders should separate “shame” from “behavior” when failure happens. For layoffs and “running out of money” conversations, “don’t bury the lead,” practice the first line, and lead with empathy.
Notable examples
Buddy Media’s hyper-focus (no side hustles), international travel for sales meetings, a 360-review business coach (Tammy Jersey) revealing he was “off my game,” and Mark Benioff honoring deal terms after Facebook’s IPO stock drop. GoGage evaluates product differentiation, market size/customers, sales & marketing, distribution/operations, and “napkin math” unit economics.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Cost of Success: Health Impacts of Entrepreneurship
1:18 to 3:15
Mike discusses the personal health challenges he faced while building his company.
“We scale it to$745 million and you exit.”
Balancing Business and Personal Life
3:15 to 6:14
Exploring the importance of prioritizing health and relationships in business.
“And what we tried to do in the book is provide some cheat codes, not only to grow your business, but to grow a life that you can live and that is worth living.”
Lessons in Leadership: Learning to Listen
6:14 to 7:45
The importance of self-awareness and listening in effective leadership.
“Because in the area, you had, like Facebook at the time, 100 % penetration.”
Navigating Difficult Conversations as a Founder
7:45 to 13:20
Advice and strategies for founders on having tough conversations with teams.
“It's a really good question because writing the book, I've come to terms with that relationship.”
Navigating Difficult Conversations
14:00 to 17:12
Learn strategies for effectively managing tough discussions in the workplace.
“I've done it like with her a few times, but it's just all about empathy and making sure that how they leave the company or how you deliver the news keeps them as a, an advocate, right?”
The Early Days of Buddy Media
17:13 to 20:02
Discover the motivations and challenges faced during the inception of Buddy Media.
“Don't feel like you have to fill up the conversation with like, you know, words.”
Insights from Facebook's Early Culture
20:03 to 22:22
Explore the vibrant culture and dynamics of Facebook during its formative years.
“So I spent a lot of time walking the floors of their office, which is just exciting.”
Traits of Successful Entrepreneurs
22:23 to 26:05
Understand the common traits that define high-achieving entrepreneurs.
“They would post their thing and be like, I'm not posting on Instagram stories.”
The Journey of Writing a Book
26:06 to 28:00
Get an inside look at the process and challenges of publishing a book.
“didn't mean we're bad people, but entrepreneurs kind of feel that, oh man, it's all wrapped up.”
Creating a Book Marketing Strategy
28:00 to 30:50
Learn about the unconventional marketing strategies for selling books effectively.
“A lot of audio books, a lot of podcasts.”
Show all 42 chapters
Engaging with Entrepreneurs in Central Park
30:50 to 33:05
Discover how direct interaction with potential customers can lead to meaningful opportunities.
“And when you're trying to engage with people in public, they think you're gonna kill them.”
Lessons from a Major Business Deal
33:05 to 37:18
Understand the significance of integrity and relationships in business through a personal story.
“Something you mentioned in the book is that when Facebook IPO'd, your guys' stock went down quite a bit.”
Navigating Post-Exit Identity and Challenges
37:18 to 41:49
Explore the identity struggles faced after a significant exit and finding purpose in new ventures.
“Cass, one of us needed to go back, but it was clearly going to be Cass.”
The Future of Entrepreneurship
41:49 to 42:05
Gain insights into the evolving landscape of entrepreneurship and the tools available for new ventures.
“So I can't see us building the next great venture capital firm.”
The Power of Software for Business
42:05 to 43:31
Explore how software enables business people to solve problems and increase productivity.
“And so business people can eat the world with software.”
Pizza Preferences and Business Insights
43:31 to 45:18
A light-hearted discussion about pizza favorites leading to insights on opening restaurants.
“Yeah, you've talked about it for a while.”
Parenting and Identity After Kids Leave
45:18 to 46:54
Discussing the identity crisis parents face when their children leave for college.
“Whether it's a fitness thing that you're doing, whether it's a book, whether it's, you know.”
The GoGage Framework for Evaluating Companies
46:54 to 49:35
Learn about the GoGage framework and its six elements for assessing business potential.
“is really not for investing, even though it is important for us.”
Investing Challenges with High-Risk Startups
49:35 to 52:08
Insight into the challenges of investing in companies like Uber and the importance of market recognition.
“Like they're just burning tons of money trying to get the software to be amazing, to get amazing people to build it.”
Marketing Blind Spots for Entrepreneurs
52:08 to 56:00
Discuss common marketing pitfalls that entrepreneurs face and the importance of distribution.
“I've seen Mark Pincus do it at Zynga, at Walter, at Scopely do it directly.”
Innovative Marketing Strategies
56:00 to 57:12
Learn about unique marketing tactics that capture audience attention.
Pivoting Business Models
57:12 to 59:39
Explore how to pivot business strategies when initial ideas fail.
“You could shut down the company or you could find something new.”
Scaling in the Food Industry
59:39 to 1:00:44
Understand how to scale a pizza business effectively.
“When you don't get it right, you oftentimes tell yourself stories that you got it right.”
Creative Marketing for Local Businesses
1:00:44 to 1:02:36
Discover creative marketing techniques for local food businesses.
“Let's say there is a pizza shop and they're doing maybe four to$500 ,000 a year.”
The Importance of Marketing
1:02:36 to 1:06:30
Recognize how effective marketing is crucial for business scaling.
“three things that can move the needle, right?”
Social Media and Entrepreneurial Impact
1:06:30 to 1:10:00
Learn how social media can enhance business visibility and engagement.
“get us there we probably won't get there this i mean the irony is this could very well be a failure like we're cool with that but we're not going to fail because we're not putting the time and effort and the focus.”
Embracing Pain in Entrepreneurship
1:10:00 to 1:10:56
Learn how leaning into discomfort can lead to entrepreneurial success.
“asking for the business, going to talk to people.”
The Dynamics of Partnership
1:10:56 to 1:12:22
Explore the benefits of complementary skills in partnerships.
Identifying the Right Business Partners
1:12:22 to 1:13:49
Understand the importance of selecting partners who complement your skills.
“See, my other business partner, Sharif, and my agency, where we make social stuff for brands, Sharif is like the, he's like the operator.”
Creating a Positive Company Culture
1:13:49 to 1:17:10
Discover how to foster a sense of community and individuality in a company.
“So we had a third co-founder, Michael Casper.”
Leadership and Transparency
1:17:10 to 1:19:56
Learn how effective leadership involves transparency and empathy.
“So we're going to move you around so you see everything.”
Fostering Growth and Opportunities
1:19:56 to 1:24:06
Examine strategies to promote employee growth and retention.
“And that's why I've been very vocal of like Oswego over Harvard, right?”
Promoting Internal Growth Through Equity
1:24:06 to 1:25:39
Learn how promoting from within and offering equity can drive business success.
“And Cass has the exact number, but I think like 70 % of all of our promotions were from inside.”
The Importance of Building Relationships in Business
1:25:40 to 1:27:18
Explore the significance of building strong relationships and shared experiences in business.
“The board will approve any individual grant.”
The Early Days of a Startup and Finding Success
1:27:19 to 1:30:16
Discover the challenges and memorable moments of startup life in its infancy.
“I've never made more than 100 ,000 a year.”
Friendship and Collaboration in Creative Careers
1:30:17 to 1:32:30
Understand the role of friendship and collaboration in creative and professional growth.
“So speaking of Conan late night, one of your roommate or your roommate in college was Seth Myers?”
Reflecting on Personal Growth and Support Networks
1:32:31 to 1:36:04
Reflect on the importance of personal support networks and how they shape growth.
“But we're ready and excited to have our own spaces.”
Overcoming Fear and Embracing Life Changes
1:36:05 to 1:38:00
Learn about overcoming fear and embracing life changes for a better outlook.
“And you never know who you're going to need.”
Overcoming Health Challenges
1:38:00 to 1:38:28
Mike shares his experience with health issues and their impact on his outlook.
Fear and Decision Making
1:38:29 to 1:40:41
Discussion on how fear affects decision-making and the importance of overcoming it.
“stressed out i wanted to get to work i didn't like college when you are scared of stuff when you're fearful when you have these thoughts it leads to just bad decisions and a lot of uncertainty, you doubt yourself.”
The Impact of a Key Moment
1:40:42 to 1:41:39
Mike narrates a pivotal moment at a wedding that changed his life trajectory.
Closing Thoughts and Reflection
1:41:40 to 1:42:12
Final reflections on fear and relationships before concluding the episode.
“dates or where it's just like it's something's there i went back to chicago and i had kind of So when I was dating, I'm like, listen, I got to check this out with this other broad.”
Transcript
Automatic transcript. May contain errors.0:00Three years in, my cardiologist said, you're going to die. Not healthy, too much strain on the heart, high blood pressure. What's the point of working, having money, if you die? Meet Mike Lazerow, the tech founder and New York Times bestselling author who sold his company, Buddy Media, to Salesforce for$745 million.
0:18Mike Lazerow:Mike made his fortune by building one of the most successful social media software companies of all time, helping global brands like Nike, HBO, and Budweiser dominate the early Facebook era. Being a successful entrepreneur, though, isn't for the faint of heart. If you're not willing to go into your park and sell your stuff, don't start your company. In today's episode, Mike opens up about the cost of chasing a billion-dollar exit and what it truly means to be an entrepreneur. In order to launch these businesses, you have to have an ego. You are basically asking people to watch you to fail publicly.
0:49That fear of failure is what drives a lot of us. Mike embodies the real spirit of entrepreneurship. He's raw, he's unfiltered, and he's relentless. He shares hard-won lessons on what it takes to build, scale, and sell a company and traits that every founder must have to survive. You don't have to do a whole financial model, but just like on the back of a napkin, like, does it make sense? Because if it doesn't make sense on the back of a napkin, it will never work. Zero chance.
1:12Mike Lazerow:It's not every day you get to hear from someone who's built and sold a$745 million company. Buckle up. It's an hour and 40 of straight game. Let's go. We built Buddy Media. We scale it to... I'm sorry to Mike Cesario. I didn't mean to. We scale it to$745 million and you exit. What cost came with building and selling that company? So that one was almost my life. I have an artificial heart valve. You may not have known. You may have known. And I had my heart rebuilt. Part of it's artificial. And during the course of doing Buddy Media, I gained 40 pounds. And I wasn't working out. And Cass and I weren't very connected.
1:52Cass is my co-partner. She's the Cass. I'm the Ann Mike. By the way, it's so nice being here alone. I've done everything with cats. Thank you.
2:01Mike Lazerow:You know, we were saying the same thing. It's nice to be away from the girlfriends for a couple days. Yeah, no, it's so great. Don't tell anyone how happy I am. And we sold it. And then Salesforce at the time was 5 ,000 people. It went to 20 ,000 when I was there. Chief strategy officer grew like crazy, two billion in revenue to 10 billion. And so did my body and inflammation. And in, you know, three years in, my cardiologist said, you're going to die. Like, not healthy, too much strain on the heart, high blood pressure, all this stuff. And I remember the day it happened, I called up Rico, a friend who's a trainer who I still work with.
2:43So 11 years later, Rico Wesley saved my life. And I told Mark Benioff that I love the company, which I do. I love Salesforce, still love it. But I need to focus on my life. Like, what's the point of working, having money if you die, right? Three kids, three dogs at the time, same wife. I've only had one wife, knock on wood. And that was, and then I started talking to other entrepreneurs. They're like, yeah, I feel like shit. Like, I'm not working out. My mental health, like mine, wasn't great. And what we tried to do in the book is provide some cheat codes, not only to grow your business, but to grow a life that you can live and that is worth living.
3:24which is what a lot of entrepreneurs, I think, it's just difficult. I mean, look at you guys. Yeah. I mean, it's so hard. No, it's super hard. I think that it's one of the most stressful things, especially when I was at a full-time job, and you're doing both at the same time. Did you ever have to do that, or you never had to do that? I've never had a job. Never had a job. I had a job for five years. I was at the Lakers, and we would do the team thing during the day, and then I'd come home and we'd podcast, and then we would edit videos for our other brands. You have an incredible reputation among that world.
3:53Our head of content, Stephen Ochoa, did it for the Knicks for a while. Yes. You have Stephen working with you. And he loves you. He says hi. Look at that. Come on. That's awesome. There's only a few people. Those are great jobs. And you kind of, it's always on. You get your chops. I'd started a company in college because I was really scared of having a job, like a real job, sitting at a desk. I just knew it wasn't going to work. I cross eyes. I can't focus. And so I started something early internet when there were 20 million people on the internet and then just never looked back.
4:23Mike Lazerow:That's incredible. Do you feel like it would be possible to build Buddy Media as big as you did without sacrificing your health? Or do you think that's just something that comes along with building that big of a business? I think I could have because I prioritize other things. So I've seen over 200 fish shows. I love live music. I have a lot of hobbies, everything from making bracelets. I made these bracelets here to like, whatever. I go down rabbit holes and I just wasn't focus with my time. And by the time, you know, you have kids, we had date nights every Wednesday and Friday and Saturday night, which is a big part of how we kept our relationship intact.
5:04I should have prioritized it and at least prioritize the food part. We were in an enterprise sales world where I'd go out every night and these were like big meals on the company. our average order size is 60 grand at Buddy Media. People paid five grand a month, Unilever and P &G and all these brands. We had a thousand of them. So we got over 50 million of ARR in three years, which was crazy growth. I should have just put on my calendar. We put everything on our calendar, but the most important things for us, like relationships, health, right? That stuff's like, oh, why would I ever schedule that?
5:43Mike Lazerow:I think it's easy to forget about that, but I find I mean, I did, I toured with a DJ group for two years and that's like, you're on the road, you're not sleeping very well. My health at that time was not great. And I noticed that like when you're off, when you're not eating well and your sleep isn't great, you're just not able to bring your best self to work. So I feel like prioritizing the health actually flows into the business. You're able to bring your best self, make better decisions and probably, you know, do better in business yeah it would have i would have burned out if we were if we hadn't sold i definitely would have burned out i would have had to stop salesforce i was working just as hard but it's just different like you don't have the existential like risk so when i could do one more sales meeting i would do it i would hop we had an office in singapore i would hop on a plane to travel 19 hours, direct flight, for one meeting and fly back.
6:40Mike Lazerow:That's crazy. Because in the area, you had, like Facebook at the time, 100 % penetration. So we got a lot of clients who started with us in Southeast Asia and then moved to the US. And we had an office there, but there's nothing like the founder and CEO showing up. What do you think was one of the biggest trade-offs during that period of time? Was it health? was that the number one thing you think was the trade-off? Definitely. Yeah. I mean, we were super focused. You can only do one thing well. So we didn't have side hustles. We didn't have like, we weren't investing. It wasn't until later that we invested a little.
7:15Like our first deal was Tumblr, which looking back is crazy. And then we did Facebook and Buzzfeed and some of those early social apps. But it was just hyper-focus. And this part that I at least remember now that I gave up was the health.
7:31Mike Lazerow:You mentioned in your book that you saw your dad as you were growing up also struggle with like the mental health side of things as he was building his business. Did that ever cross your mind while building Buddy Media or were you just so focused on the growth? It's a really good question because writing the book, I've come to terms with that relationship. So it has not been my strongest relationship. I grew up in a divorced household with my mom and my stepfather I'm very close with. and my dad had some financial issues and some mental health issues that, you know, he landed in the hospital for six weeks and right around my 13th birthday.
8:09And at the time, I didn't give him any benefit of the doubt. I didn't really understand it. And he was having major financial issues, like running out of money on a real estate project and turned upside down and made some bad decisions. I've since like read about it and I was too harsh, I think. I basically wrote him off and didn't really think about it. And it wasn't until I really thought about my own mental health in this book that I connected them. And even though things went really well, like we sold our first, you know, Uwire, I sold that company. We ended up taking the combined company, Public, golf.com,$25 million exit, Buddy Media, billion dollar exit.
8:51And we've been a part of all these other things. Even when things are going well, it takes a toll. And so I couldn't imagine what he was going through. And it was at a time where men weren't allowed to seek mental health. So if you think about the generation, the post, you know, the Vietnam generation, he was a naval officer. He served, he kind of went on to have a home inspection business and building. And I thought he just felt a lot of shame. It was his identity. And we've talked about it. And, you know, part of this is the lessons I learned. It's not my story to tell, but the lessons I learned about not letting these mental health challenges kind of just stack up and then fall over.
9:36And you see that again and again with founder suicide and, you know, just depression. I want to read a passage from the book that we found super interesting as we're going through it. Awesome book, shoveling shit. It just came out two days ago, right? I think there's a hole in my chin. No. Okay. So you had hired Tammy Jersey, who was a business coach. She was like to come into your business and check out how things were, things were going. And this passage says, Tammy confirmed I was broken, or at least very off my game. I felt like a failed dad, an unreliable husband, an absent friend. And now I had confirmation that I wasn't the business leader I hoped or thought I was.
10:13On the outside, I was crushing it. Inside, I was an emotional mess. I wanted to run away from it all. Could you take us back to when Tammy had came into your business and you guys are killing it? I mean, you're making tons of money. You guys are doing awesome. And you have to hear this from like an outside source. What does that mean for you as a leader at that time to course correct and get it headed back in the direction that you knew you wanted it to go? Yeah. So it was one of the most powerful things that I've ever experienced business-wise. I think a lot of us, especially men, aren't very self-aware.
10:45And I was getting in the way of the management team. So I'd go talk to the engineers. I love engineers. And we'd just be jamming like oh wouldn't it be cool wouldn't it be and in their mind it was like oh laz thinks that's cool i'm gonna build it and then my head of technology would be like dude what the fuck like we we changed the roadmap because you spoke to an engineer like you can't do that on the sales side and so cast is an incredible operator it's a very difficult thing how do you tell like your husband co-founder this feedback so she to her credit got a professional tammy and she did a 360 review and she spoke to all of my direct reports and I was both distracting and distracted.
11:31So I wasn't focused. I was not nice in a lot of meetings where we just like, you know, we're not passive aggressive and there's an issue. We get it on the table, not in a mean way, but I wasn't listening. And what came back is everything you don't want in the leader. So someone who's not listening, who's getting in the way, who's changing decisions, who's, you know, basically ensuring everyone's not doing their best work. And I didn't know how to operate because I'd never run a company with 500 people. Like I didn't know how to prioritize my time. I didn't know how to make decisions. And so all of them, I let a lot of my fears, anxiety, doubts spill out.
12:14And the most important thing I did was start to listen. I don't think I listened before then. I would come into meetings. We didn't have a lot of meetings, one a week, because we hate meetings. We're just like, let's get everyone on the same page and then fucking get out of here and do work. And the meeting was me trying to get my way like a drunk baby, right? And since then, it doesn't sound like it on this podcast, but I listen a lot more than I talk. I try to kind of sit in their shoes. And it was just a really powerful experience, which I think about often.
12:47Mike Lazerow:Is listening the number one trait that makes a good leader? It's up there. Yeah. I mean, I think listening, transparency, if you are not trusted by your team, forget about it. There's nothing that you can do to succeed. That relationship between you and your team, you and your investors, you and your customers, it's all about trust, transparency. And so a lot of entrepreneurs don't want to have a hard conversation. They don't want to lay off people. They don't want to kind of own their shit, right? And listening is a part of that. Do you have any advice for founders if they need to have difficult conversations with their employees or their board or just anyone that's working with them?
13:37not only do we have advice we have uh scripts okay great so it's very hard to lay people off for the first time it's very hard to admit you're running out of money right and so it's all about getting you know don't bury the lead right figgy today's your last day we appreciate everything you've done we don't think you're a fit because what we need right now is someone to make shoes for six toed women you've never made shoes apologize for even hiring you so you kind of get like those types of conversations of like i wish i had this convo like six months ago but it's those conversations where like don't shy away yeah and god it's so hard oh nazi that's hard i've you know another story in the book yes this is so funny it's like you know i'm managing sales like i do sales product i'm like the public person i don't know why because Cass is smarter better speaker better looking but I was the one I think she had to stay more kind of with the kids and you know she was the operating the company so she had to be in and so at golf.com our first sales hire I was managing and for whatever reason he just wasn't selling it was early internet I don't think it was his fault so Cassie you got to get rid of this guy like he's cost us 100 grand a year we're running out of money no problem and so I go in and let's just say that he made some incredible arguments and he got a raise and a bigger title and i came out and cast like how to come like it was awesome like it was like he really is with it he made some arguments of like why he hasn't sold which are so amazing and so i think he should be chief revenue officer now and i gave him a little extra money just to keep him motivated and cast is like you're the worst human being i've ever met like literally and from that day forward she takes a lead on all the layoffs.
15:32I'm conflict adverse. I can do it. I've done it like with her a few times, but it's just all about empathy and making sure that how they leave the company or how you deliver the news keeps them as a, an advocate, right? Like it's a small world. We don't, just cause it didn't work at this job doesn't mean that you're going to be homeless, right? Like there are plenty of other jobs that maybe are better.
15:58Mike Lazerow:Yeah, we had to have a difficult conversation not too long ago. And we're both, we don't like conflict. And so when we sat down. I'm with you, dude. Like, I hate it. We were like looking at each other being like, who's going to say it? Someone's got to bring it up. We were like, great meeting. All right. Like, anything else we should talk about? Like, I don't know. The worst is when like, you know, you have a hard conversation and you just kind of like, you know, shooting the shit. You're kind of trying a way to bring it up. And so what we've learned is just like, don't shine the turn. Just like get it on the table, get the elephant in the room, tell them the reason that you want to have.
16:38And a lot of times I basically started with, listen, there's nothing that I'm about to say that is great. I'm not happy about it. It's going to be a tough conversation, but it's one I want to have. So then they're like, okay, I got focus. I get off my phone and just lay it out, right? And practice. Like if I practice things a few times, especially that first line, and I used to be a drummer and it was all about like, I can't miss when I'm supposed to come in, right? So like get that first, like just get started right and the rest takes care of itself. And less is more. Don't feel like you have to fill up the conversation with like, you know, words.
17:22Silence is a statement. God, it makes so much sense. What do you feel like was a lot of the fuel you were running on in the very beginning of the Buddy Media days with Cass? What do you think was that fuel? Was it, I know a lot of people say a huge motivation for them is like proving people wrong or is it just super ambition that you two were like, we want to build this massive thing together and show it off to the world? So we were now serial entrepreneurs. I had a company in college and we started, which that was the one that went public. We started golf.com together. And so we're now living in New York.
17:58And we sold for$25 million, but we had to buy back golf.com because the company we had originally sold it to went into bankruptcy, all this stuff. So we only owned like, I don't know, 20 % of it. So like after taxes, we made like, I don't know, two or three million bucks, which is more money I ever thought I'd make for the record. growing up in the suburbs of D.C. and just kind of entrepreneurs who aren't in kind of like this tech world. They're real entrepreneurs, right? Like they don't have a safety net. So we moved to New York and we're like, holy shit, fuck, this place is expensive. Our first rent was 11 grand a month.
18:31And I was like, we have two kids. We want to have another. So I'm like, we got to get back on the horse. Like we got to figure. And so I was constantly thinking about ideas. Viv, our third, is born I'm in the waiting room and Mark launches the platform and invites the world's developers to build social apps on top of Facebook. At the time, Facebook was loved. They hadn't ruined democracy yet or our mental health. They didn't own Instagram or WhatsApp, but there's like connecting people on one platform, tag your friends. It was cute. Maybe not so cute anymore. Like we know how it's played out. And I went down the biggest rabbit hole of my life, which I do.
19:14Like I went down the internet rabbit hole. I went down social media. I've gone down crypto. I've gone down AI. Like, and very few times in your life are you given like this generational change. Like if you're an AI developer right now, there are no better ones because it's new, right? Like it's a new thing. So you can dominate if you're 21 years old. And I love that. Like if you want to be a partner of a law firm, it's not going to happen. Like, work 20 years, doctor, all this stuff. But like, in this innovation world, or even with being an entrepreneur in your local town, just do it, right? And so for me, we were powered, to answer your question, we were powered really by the excitement of what happens when the internet goes from a single player to a multiplayer friend environment.
20:00And we were surrounded by the smartest people we knew. Not only Gary, so Gary's first office was in our office it's how we became like family but i look at jonah peretti who was really kind of experimenting with virality at buzzfeed doing the stuff with like the nike sweatshop on the on the nike id shoes right and how do you get stuff viral which is what you guys have really talked a lot about love the last episode people haven't read about or listened to how to do youtube right now um and it was just exciting it was like every day it was new and we talked to brands they'd be like yeah we got to move from tv to like this new stream-based world and we and i talked to like i spent time with zuck and cheryl sandberg and they weren't focused on advertising i remember the last one of the last meetings i had with suck he said yeah just keep doing your brand stuff just keep doing that like whatever that is because we were onboarding companies to their platform and when companies would call up facebook and say hey we need help they'd be like, oh, call Mike.
21:03So I spent a lot of time walking the floors of their office, which is just exciting. What did you notice about those early days of Facebook when you're walking those floors? It was exciting. I mean, it was like, it was all in person. There's no hybrid. It was smart, like the smartest people. They were hiring people that were just smarter. A lot of people I'm still friends with, you know, Kevin Collarin from Slow Ventures and Josh Ron from oceans and um you know look at any company right now and it like goes back to facebook instagram right whether it's like open ai or um you know tiktok even that was a funny story with the instagram when you guys were at south by southwest and gary's like uh they're they're talking about would you ever sell instagram to the founder and he's like no there's not even not even a question and mike was talking to gary and he's like everything has a price yeah yeah and then they ended up selling.
21:57Well, no. And the funny thing is I didn't put this in the book, but at the time, Travis, who was in that room, he was okay with selling. Travis Kalanick, who was launching at South by Southwest at the time, launching Uber in Austin. He's very practical. He went on to build obviously this and Instagram today. Kevin did great. Kevin and Mike made a lot of money, 11 person company sold it for a billion dollars that facebook stock has gone crazy but what's instagram worth today if it's an independent company half a trillion i wonder if uh instagram
22:34Mike Lazerow:gets to the point it is now though if it's not bought by facebook it's also it was so interesting because i feel like during that time period instagram was they were stealing everything i mean snap had stories right and then we'd wake up and it'd have stories and we'd be like I remember there was a period of time actually where every single person said, I will not be posting here. Follow my Snapchat. Do you remember that? Yes. They would post their thing and be like, I'm not posting on Instagram stories. And now look at what it is today. I feel like there's always that initial hesitation of adopting something.
23:06And they were very against stories. I remember that so vividly. It would just be like a black square and it'd say, add my Snapchat. Well, the dirty little secret is that every company was dependent on Facebook for growth. Right. So getting friends to recommend an app or to do something in an app to trigger an app to user notification. And because of that, they had a front row seat to every app. So they could see what apps were taken off at any given time, which was interesting. Yeah, you could see who's spending the most on your platform to acquire somebody.
23:37Mike Lazerow:I'm curious to know, you bring up Travis, you bring up Zuck, you bring up Gary. You've been around some of these incredible entrepreneurs. is there a trait you see in them that's maybe similar in all of these high net worth, very successful entrepreneurs? It's the same trait. I mean, everyone's just a dude or a woman, right? Like they're just regular people. And I think what separates them is hard work, first of all. Like they're willing to do what it takes. I saw firsthand because Gary was in our office how hard he worked to get customers. I remember going, he's like, Laz, we got to go pitch the NHL.
24:15I'm like, okay. So we went, did a joint pitch. They bought it. They did the services. Our software is what was used. And same thing with like, you know, all of those people, you know, Kevin launched as Bourbon. You know, Instagram wasn't Instagram. It was a gamified Foursquare. And it was one of the worst apps you've ever used. I used it. And you would check into a location. You would get points and points were redeemable for like bullshit stuff. Was it for food stuff in the beginning, right? Everything, like restaurants. And one of the things you did is when you checked in, you could take a picture.
24:48He had these incredible filters because he was a photographer. That's what people loved, including myself. I remember those filters. I was like, I just want that. He stripped everything down and he was not going to quit. He was just like, there's no get. Now, hard work isn't enough, right? You have to focus. everyone I've mentioned really hyper-focused. A lot of entrepreneurs, especially today, they try to do everything and they get nothing done, which is huge. And then the third is we don't believe ego is a bad thing. In order to launch these businesses, you have to have an ego. You are basically asking people to watch you to fail publicly, right?
25:36You guys are out on a limb. You guys create tons of content. People vote with their attention every day. That fear of failure is what drives a lot of us. Like, oh, my God, like we raised$100 million at Buddy Media. If this thing goes under, I'm the worst person ever. Not that I'm the worst entrepreneur. You internalize it. It's that shame. There's a difference between like behavior and who you are. And if we had failed at Buddy Media, yeah, maybe we weren't the best entrepreneur or what we thought in our mind. didn't mean we're bad people, but entrepreneurs kind of feel that, oh man, it's all wrapped up.
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26:12Like I'm an awful person if I fail. And I think that that ego is something that has to drive you and you have to keep in check, which is hard. And so there's all these like dichotomies and like, and dialectics and being an entrepreneur of like holding two things that are, it seems at odds with each other. right and what the book's about it's like being an entrepreneur is awful it's suffering it's miserable it's missing your plane having to get a new plane get in at 3 a.m and like all the shit
26:46Mike Lazerow:we do right and there's nothing you'd rather do yeah so it is awful and fucking awesome yeah and the people who are blessed with the opportunity to do it are the people who find their purpose and passion and learn to love it. Learn to love the suffering. Like people are like, why are you working so hard on this book? Like, why are you making all the ass? Why are you doing all the speaking? Why are you doing all the podcasts? Why are you doing all the Instagram lives? It's what we do. Like we shovel. And if we're not going to shovel shit for a book called Shoveling Shit, A Love Story, when do we shovel shit?
27:24It's like the most personal project. And whatever you guys do, you put in all of your effort. the key is to decide whether or not you want it on your plate and so for Cass and me if it's on our plate we're like balls to the wall we're like there's no losing Cass is more motivated by not losing than you know the idea of winning what goes into actually getting a book out to the world so you guys come up with the idea you're like we're gonna do shoveling shit a love story about the entrepreneurship path then what happens all this other work behind the scenes that no one sees yeah So I went down the rabbit hole of books.
27:58I don't read a lot of books. I listen to some. I buy a lot. But usually I'm like, yeah, it's fine. Do you do YouTube at all? Tons. Tons of YouTube. A lot of audio books, a lot of podcasts. I don't sit in traffic. I live in New York City, which is fine. But I don't have a lot of time. So I block time to think and listen, which is a luxury in my life now. And we just interviewed everyone we respect. and everyone from like Will Gadara who wrote one of my favorite books, Unreasonable Hospitality, to Gary obviously, who's been an incredible friend and partner here. And we realized a publisher doesn't matter.
28:39We wanted to own the rights to it. It's our story, right? So we had the opportunity to sell it for like a small little advance, but then they would have owned it. So now we own all the rights. We're doing like audio books in 100 countries and all this stuff. the biggest lesson we learned is that there is no infrastructure to sell books. So when you write a book, you're also the CMO of your book. These publishing companies are not equipped to market in the world. Our publisher actually has learned a lot from what we've done, like the live streams, the how we make ass, the book bundles. We love book bundles.
29:19And what does that mean exactly? Meaning like buy 50 and you get 30 minutes with us. So if you go to shoveling shit.com, like they're still live, I think it's kind of all of these bundles. We just had an epic like New York stock exchange event, like at the exchange. One of the bundles for national shovel day with Gary V celebration of entrepreneurs was dinner with me, cast Gary at fly fish club. It went for nine grand. There are only eight seats, but every nine grand sold 300 books, right? So it's kind of like you have to think about this not as the book, but a platform. And you have to make it worthwhile.
29:58And the most important thing we've seen is that people want access to us because they want to pitch us. They want advice. Just like if you guys wrote a book, they'll want access, right? And so don't write a book unless you're willing to market it. We spent three months writing it, 15 months marketing it. People are like, well, why does it come out in the year and a half? Because we want to sell a fuck ton of books. We got to make ass. Hey, I need you to buy 20 books. Can you give them to your founders if you're a VC? I'd love to speak at your event. I'll speak if you buy 50 books, right? So it's like those types of ass, which are very uncomfortable for us.
30:39But I think will be the difference between us getting out there and not. We don't know yet. it just came out um i love that you guys went to central park though and just you're doing different activations that i haven't seen for a book like i i haven't i didn't know that people would go and do something in central park and people don't yeah you're allowing entrepreneurs to just walk up to you like that is so fun it was so cool like so we went into central park which and part of this is i've always said if you're not willing to go to your local park and sell your product whether you're liquid death whether you're van lewins ice cream i was just with the founder there he bought a truck off of ebay and just started selling his ice cream right if you're not willing to go into your park and sell your stuff like don't start your company and cast didn't love the idea but i was like listen we're setting up a table we're going into central park and we're going to meet entrepreneurs and we're going to talk about their business and sell the book and so i we created a signed free entrepreneur advice and it was cool like recent graduates it's coming up, hey.
31:41And when you're trying to engage with people in public, they think you're gonna kill them. And once they realize you're not gonna kill them in at least New York City, they're friendly. But at first they're just like, I'm gonna do everything to stay away from this homeless person. And we're like dressed like this. Like we're not really dressed, right? And we had great conversations. And one conversation, you know, these young guys were engaging. They're like, oh, what have you done? Like, and we said a few, and then I just made a comment. Yeah, we've had about$10 billion worth of exits. he was like what he's like why are you here i'm like because we got a book to sell and it's 20 bucks each we just have we need a lot of them sold and they're 14 million people who walk through the park so why not get like 0.00001 percent of them to like buy but you have to be creative now did we do that for the video content yes like you saw it did we do it because it was fun for me at least yes and you know cast like we're very different so i'm there like hey who's the entrepreneur people are walking by i'm like you're an entrepreneur and they're like fucking who's this drunk crazy guy and cast would be like you know tone it down a little like but it was fun like i'm just hyped i'm having a good time if you don't do things and have fun and smile like why do them like life is hard enough you brought up that you guys did an event
33:04Mike Lazerow:at the New York Stock Exchange. Something you mentioned in the book is that when Facebook IPO'd, your guys' stock went down quite a bit. But you said that Mark Benioff's, he still honored the initial terms of like the contract. Can you talk about that and how that has affected the way you've moved in business since then? Yeah, really powerful experience. We hadn't signed our deal yet, but the week before I was at Mark Benioff's townhouse negotiating the deal, when Mark Benioff calls, you go. And I basically modeled all of Buddy Media off his book. He has a book about how he grew his business. And so I built the relationship with Salesforce people, Ryan Ete and John Samorjai in their venture business.
33:59And Ryan's like, Mark would just like to meet you. which I kind of know what that means. And so I go to his townhouse and I show him the technology. He loves it. He's very excited. He loves technology. And we basically negotiate the deal. And he's like, I can't go anymore. I'm already overpaying. Don't ask for another dollar. I wasn't working with a banker. It was just two people talking. And it got through my board, obviously, because it was a shit ton of money and life-changing for me. but also like it was the first real exit for Graycroft, which is a big New York firm. So it returned their whole fund.
34:37And a lot of these other venture capitalists who were young, like it like made them look good. Facebook goes public the following week. The stock goes down 50 % in one day and we are dependent on Facebook. And why do you think, why do you think it dropped 50 %?
34:51Mike Lazerow:Were people just so weary of? It was overhyped. Facebook was overhyped at the time? well it was under hype to fast forward but at the time there's so much hype and there is this idea that they don't have a mobile strategy which is so funny right now yeah because it's just mobile and it's a good story about focus because from that day forward mark refused to see any demos that weren't on the phone because don't forget like the iphone came out in 2007 so it's not like at this point is 2011 12 like iphone apps are still new yeah and once they got mobile which is why they bought instagram like they're off to the races and so the reason went down is there's more supply than demand but eventually it went back up but that weekend we were very worried i would have pulled out of the deal probably if i was mark how do you tell your because he was a$16 billion business.
35:54He's now$300 billion. He was paying, you know, on paper$800 million, but it was really a billion-dollar deal all in. So he's giving, like, 5 % of his business to these schmucks in New York just to get Facebook and Instagram and early YouTube and Twitter marketing rate because he wanted the marketing cloud and start there versus, like, traditional advertising. and he called me on, well, first of all, I had, Ron Conway was an investor who's like a legendary investor in Silicon Valley. He called Mark just to like feel him out and Mark knew that I was a little nervous. He called on Sunday night. And the deal was supposed to go through on Monday.
36:38We're supposed to sign. And he goes, listen, I gave you my word. We have a deal. I want you working at this company. I want you to be a partner. I need more entrepreneurs here. We need entrepreneurial spirit. You have nothing to worry about. And I was like, are you sure? Yeah, fuck with me, right? Is this Mark? Like, can you send me a picture? And from that, and the lesson was do the right thing. It was the right thing to do, even though it was hard for him business-wise. We then would go on to see him do tons of like what we call miracles, but the right thing. Like we were having issues with our kids' health.
37:19Cass, one of us needed to go back, but it was clearly going to be Cass. Salesforce doesn't need another operator. And I went to talk to him. I said, listen, one of us has to get back. Cass has to. She had all this stock that was like revesting because he didn't know how to keep us there. So we kind of revested like a third of what we were going to get. And he said, no problem. Like we'll take care of her vesting. She'll earn everything. like as long as you're focused that's all I need. And in the book she said that her cortisol levels were 5x what a normal person was. She had a lot of health issues.
37:54Right around the cell. During that time period where were you guys trying to fix the mental health stuff that you were both dealing with or just like the problems that were coming or did you feel like it was so demanding? We didn't really think about it. Yeah. Because it was just whirlwind and I remember the day we kind and I spoke to the company at a hotel in Soho where our office was, we kind of got this huge ballroom. This is the Buddy Media group or this is Salesforce? Well, this is Buddy Media. And it was like a celebration. We had a company meeting and then a party afterward. And our friend Seth Meyers did this standup bit, which brought the house down.
38:32And Cass and I both felt really numb. Like, yes, we'd done it. And all of a sudden this money was wired into our accounts. but we never really started because of the money. We didn't know how to process like that type of money. And it was over time that we realized, you know, we needed to get better. It wasn't until three or four years later that my cardiologist said what he said, which is like, dude, you're gonna die. Like look at all the markers of death. So you still had to go back into Salesforce, help continue to grow Buddy Media. Oh yeah, I gave him a three-year commitment, which I wanted to do.
39:07I loved Salesforce. You wanted to help Mark and really build this thing. It was like, I mean, it's a startup. Like at the time, it's like number one CRM, number one service, getting into marketing. I'm 34. I don't want to do another company. Pay is good. The people are A players. And I spent three and a half years there until like I just realized I had to, I didn't have to. There are a lot of people like we're very, we recognize that we're very fortunate right born in the u.s our parents weren't wealthy but they had enough money for education it's like upper middle class you know comfortable didn't feel like we were poor educated northwestern like a lot of people don't have the ability to make the decision to go home but like it felt like if we didn't make that if i hadn't made that decision my life could have turned out differently.
40:05Mike Lazerow:Yeah. How did that chapter affect your relationship with Cass? You know, not only as co-founders, but partners and parents. So when I was at Salesforce, I think it was fine. We, and when I say fine, I traveled a lot, but we were still communicating. It was the first time we hadn't worked together. We started a company, we were dating. So this is the first time we're not like working together. what really was hard is after i left salesforce and i had major identity issues i didn't know what to tell people i was cat i have all these hobbies one was like i love painting cast like got me a painting studio as a present like rented it which is hard in new york city to rent a studio and i realized i was bad but i loved it so it's like a hobby stuff you're bad at but that you love, that's hobbies.
41:01Mike Lazerow:Brain has a lot of those. Yeah. I knew that was coming. And so basically we, I was kind of miserable personally. Like I didn't have any direction. We did like 50 investments, some of them great, some of them, most of them shitty. And it wasn't until we came to terms like, what do we do for a living? We shovel ship. And just like Bernice Mountain Dogs need to work, entrepreneurs need to shovel ship. And so what shit do we want to shovel? Start a venture firm, 400 million assets under management. We have a private equity firm. We're buying cash flow businesses. We have what seems like a job shoveling shit a love story trying to sell this.
41:43And we're trying to figure out what we do next. And I think venture capital is broken. So I can't see us building the next great venture capital firm. Why do you think it's broken? Too much money chasing too few deals. and we are going into the golden age of entrepreneurship because of the tools that are available and the ability to solve problems personally and for others that are so easy i mean go to i just went into lovable i'm like build me a social media dashboard okay what's your github account you put it in what's your api keys right like all of a sudden business people can can build software.
42:28And so business people can eat the world with software. And all the other businesses can be more productive. So we're going to open up 10 pizza places. So I read that. I love pizza. Yeah, you love pizza. What's your favorite slice in the city? That's a good question. Slice would probably be Little Italy's eggplant parm slice. And there are a few Little Italy's. We have one on 72nd Street. Pie, probably.
42:58I mean, there's so many. There's so many. We had a good one yesterday. Which one? What was it called?
43:03Mike Lazerow:Oh, I'm blanking on the name. It was a 9-3 on Dave Portner's little pizza app. It was good. And we went and had it with Babin. He was like, this is pretty good pizza. But they're great businesses. Yeah. So you can open up one for$250 ,000. A bad pizza place does a million bucks a year. Wow. 30 % margins. And if you do a bunch of them, you could have a level of management across all of them. and maybe, like, I want to learn how to make better pizza. I have a uni oven, but. I want one so bad. They're the best. You need to get one. You've talked about. If you're creative, they're the best. Yeah, you've talked about it for a while.
43:33Mike Lazerow:I just, I love cooking and. Big cooking guy. I, yeah, I think I need to get into making pizzas. I could see you guys doing a cooking show. I feel like we could maybe, I wouldn't be the cook guy. I could be the taster. Yeah, you could be like my little sushi. I could be your B guy. That's your only job. I just taste, I just taste. I just taste. This is really good. This is fantastic. Yeah, cooking with coasters. Come on. I can see that. Like I'm on, I'm dead serious. I bought into it, dude. That is so funny. Especially for a world of like these young men don't know to cook. I have two sons who are going into the world, one a senior in college next year, the other who just graduated.
44:05And you know, like they're not going to get their recipes from Julia Childs. So who are they going to get it from? You guys.
44:11Mike Lazerow:Yeah. Come on. There's a, there's a guy that I went to school with shout out, uh, chef Donnie. He works with Barstool now, but we were in the same fraternity and he's gone on to, create a whole career out of being a chef and crushing it on content. So. Food's the best. I don't know if you know Francis Dillon, who, Francis Ellis from Barstool. He, he eats ridiculous things at his desk. And so he'll just like. Yeah, yeah, yeah, yeah, yeah. Just like the whole lobster. The whole lobster. Lobster, yeah, yeah. And, you know, he's a great dude who's just like, I'm going to buy a whole chicken and crush this chicken.
44:49I'm going to get like a lobster and like, which is, it's an open seating environment. So he tries to get the smelliest food, but like food is like, that's a big cat. Over 50 % of the people know about food. Yeah. I think that I couldn't stop everything. I'd have to do what you're doing with this. Like I wouldn't be able to sit still. I don't think it's just like not, but I don't think in our DNA, I don't think anyone can.
45:13Mike Lazerow:No, I don't think you're supposed to do that. As humans, you need something to be working on. Whether it's a fitness thing that you're doing, whether it's a book, whether it's, you know. The identity thing, though, is interesting. I also feel like you hear that with parents, like stay-at-home parents. Once you're empty nesters, once your kids go off to college and they move out, it's like my whole identity was raising these kids. And now they're not here. They're taking care of themselves. Like, who am I as a person? So that's a huge thing. Yeah. So Cass and I are empty nesters in the fall. And there are two types of people.
45:43There are people who are super excited and people who are scared. we are so excited because what we realize is we can't fire our kids um but we can they can move on at a certain point and um this isn't really the right fit you know yeah well it's cast many times but i fucking want to fire them um but you can't you have to like show up and like you know parent and keep those like boundaries up a lot of our friends who their kids are going like they may love their spouse but they don't like them and so it's all about the kids it's like so if you don't build those relationships now yeah whether you're entrepreneur or whatever you're gonna it's gonna decay and you're gonna not gonna have a great life when what you're working on together the kids when you when you sell them so to speak when you exit i want to
46:38Mike Lazerow:transition to GoGage because you have this great framework that you lay out with six elements that you look for when you're evaluating a company. So can you tell us what GoGage is and what you look for when you're investing in a company? Yes. And the reason why it is so important is really not for investing, even though it is important for us. It's as an entrepreneur, especially one with no money, which we were, your time is your most valuable asset. so spend the time figuring out of is this something worthy of my time so would i invest one dollar of my time into this and that's where it started for us and it just comes down to these six kind of butt simple things which um is what's a product why is it different what's the market size which we use like number of customers like we're in the golf business and we went back and and looked at the deck and we said it was an$80 billion market.
47:36Now we only had a$25 million exit, partly because we didn't own golf courses. So that's 60 billion of the 80 billion. So think about like how many customers and what are they gonna pay? What most entrepreneurs don't think about is sales and marketing. Build it and they will come as not a strategy. That's just hope. That's just diluting yourself. We added one after we invested in this company, liquid death, which we call distribution and operations. It's how do you get your product to your customer? If we had known how hard that was in this business, there's a good chance we wouldn't have done it.
48:15We've never done another one because there's a company that started with water. It took Austrian spring water, put it into a can in Austria, put it on a bus to get to a train, to get to a boat, to get to another bus, to get to another train, to get to... And it was like, oh man, this is not going to work. They figured it out. They onshored their production. To the United States? Yeah. So that distribution thing and operations, we really dive into. And then the last one is, you don't have to do a whole financial model, but just like on the back of a napkin, does it make sense? Because if it doesn't make sense on the back of a napkin, it will never work.
48:58zero chance, like zero chance it's gonna work in the real world if it doesn't work on a piece of paper or spreadsheet. So it doesn't have to be like Goldman Sachs financial analysis, but it's like, okay, what's gonna cost to build it? What are you selling it for? What's leftover? Can you support the organization? And if it's turned upside down, like we've seen so many companies that had negative unit economics and this whole strategy of like, oh, we'll build it, we'll like build the audience and then we'll figure out a way to monetize it. And a lot of those businesses just haven't worked. I have a question with like a company like Uber.
49:37So they go into the red a ton, right? Like they're just burning tons of money trying to get the software to be amazing, to get amazing people to build it. If you were like investing, did you invest in Uber at all? Are you trying to ruin my day? No, no, no, no. Did you invest? Oh, did you like have a chance like Gary? So Gary did it. And I said, I can't. No. Yeah. Okay. I have to leave now.
50:01Mike Lazerow:Oh, man. How does it - Hey, what? If it makes you feel any better, we also didn't invest in Uber. Nice. It was a close second. Yeah, it was a close second. How does that work though when they're trying to pitch people to invest in? They're like, we're going to be in the red for six years. Yeah, so - Like, what does that look like? I'm just curious. So for Uber, I didn't invest because I was just so busy. And I was just like, I can't. Like, I don't know. It may work, may not. but how big is that going to be? Big. And it was the same, it was also at South by Southwest when I stalked Sean Radd about Tinder.
50:31First time I saw Tinder, I was like, whoa, that's going to be big. And so wait, what's the question again? Just like for these companies that are spending, they're needing so much to get off the ground. Like how does that work in the world? Very few companies can make that work. And it takes an incredible founder who is a storyteller, a visionary who could hire people and who could invent the future that doesn't exist. I am not smart enough to do that. I'm not electric enough. I'm not crazy enough. It's much easier to find a market and sell into that market than invent a new market. So for every Uber, there were probably 1 ,500 that didn't make it or 2 ,000 who had similar ideas.
51:18the strategy of losing money losing money losing money and eventually making money just does not work anymore and the reason is because we're at scale with internet technologies we're at scale with ai you could tap into it with zero right like it cost me a million bucks a year to buy a database for golf.com from oracle how much does it you know to use any of these cloud databases even Amazon Web Services, nothing, right? And so find a product that has a market and that if you want to have a venture business will grow and focus on it every day, week, quarter, month, year, right? And over three years, five years, you can build something big.
52:06Trying to invent something is hard. I've seen Mark Pincus do it at Zynga, at Walter, at Scopely do it directly. Mark's one of our investors, and obviously Travis and Airbnb and all these ones. Maybe 10 out of 100 ,000 that tried it. Having said that, anyone who wants to try it, I love you, and I hope it works, and I'll support you. Do these companies need to hit all six on the go gauge for you and Cass to pull the trigger, or have there been ones that have came through the door where you're like, four of six, but this person's crazy, and I'm bought into this person's vision? so the person is not on the go gauge because that's a given okay they have they're great has to be great and we wrote this for entrepreneurs and so it's hard for me to say like you're not an entrepreneur you are we believe everyone's born an entrepreneur and then you go through this normalization process where you lose your creativity and like high school is like sit down shut up memorize this shit right and then you go to get a job they're like why are you different i'm not i just like i went to harvard and i did everything i'm supposed to do and well we don't hire people from harvard because that um and it's all about what have you done and a lot of young people haven't done anything and my biggest advice is like if you want to be an entrepreneur do something do it like whatever it is could be a lemonade stand could be a drop ship business could be flipping vFriends cards.
53:33Mike Lazerow:Is there one element in the GoGage system that you find is a typical blind spot for early founders? Sales and marketing. Because we work with a lot of technical co-founders, just who we are, and they haven't thought about marketing. And if you don't have a strategy to partner with influencers, to get distribution, to become like in the cultural icon of whatever your market is, it's going to be hard for us to get around it. You mentioned distribution. So like, tell me what it took for these guys. That's why we did it with Liquid Death is because we looked at like distribution as just marketing, direct to consumer.
54:16And then we weighed like a six pack and we're like, oh my God, sending these through the mail is hard and expensive. Let's get in stores.
54:23Mike Lazerow:We tried selling merch. Oh yeah, tell them. And we lost so much money on just the shipping because we were like, oh, the hoodies cost a pound. It's out. They actually cost two and a half pounds. It was great. We're going to, we're going to. Like we sent some to the UK. It was like 60 bucks. I'm like, we're just going to eat that. Love you guys. Hope you really. That sounds like our book tour. Like I'm sending books. Yeah. Like 20 BC got$180 book that I sent him. um the i mean the marketing is number one blind spot because you're so in love with the idea you're just like everyone's gonna need this they're just gonna show up and then you launch and it's like crickets i experienced it yesterday i was like we're doing this book signing at barnes and noble we have to market it because i was really nervous like we're gonna be the only author to have zero people and so we showed up there's like a line i'm like yes let's go but it It wasn't by accident, right?
55:19And then the other thing about distribution is you don't have to have it figured out, but you have to know either how you were going to approach it or that you don't know it, like Mike Cesario. And you have to be honest that you know what you don't know. And so he said, listen, I'm not a water guy. Like I worked for VaynerMedia and Netflix, and we knew that he was just an incredible marketer. And he was like, I'm cool with building around me. I just want to do the marketing. and that's what liquid death is known for yeah and the product has to be good like the liquid death product is great yeah it's great you can't beat it we were saying that too with you know drink brands because we've been hunting for like a drink brand sponsor and it's like man it it doesn't get off the shelf if this drink doesn't isn't good like we had gotten potential one that had sent us it was like caffeine but it was terrible and i'm like dude we can't we're gonna put this across from people it's not good like people aren't gonna drink it and then it's weird like you know what is a random drink maybe mike cesario will look at this yeah maybe mike will give it a go he looks at some of my content that's what i'm talking about i love the commercial
56:21Mike Lazerow:man that the super bowl commercial with the kids drinking it so far the one the one they just did with uh kylie kelsey that was a good one they're all good yeah because he thinks in headlines he doesn't market without saying what is going to be written in ad week ad age new york times about this so like fat zach sweat campaign what tastes better the kind of licking sweat off of the comedian fat zach's back or liquid death that came out of someone commenting like this tastes worse than back sweat so he's like let's do a taste test right like it's just brilliant marketing coupled with distribution and if you look at his team he brought in people who've done this from hard mics lemonade to like you know sam adams are real companies you you ended up actually pivoting the revenue model four times for buddy media and i'm so curious we ended up as software as a service as a sas what did those initial conversations look like when you'd walk into cass into her office and be like hey we gotta switch again um well we kind of knew we had to okay so when you launch something and it sucks or no one shows up, you have three things you can do.
57:35You can keep doing what's not working. You could shut down the company or you could find something new. We like the third. We recommend other people don't do one and two if you have resources. If you don't have resources, maybe you should shut it down, but we don't think that is really something that you should be thinking about. Like you shouldn't be thinking about shutting down until the day after you shut down. Like if you're thinking about shutting down the business, It's like not going, it's not going to end well. And so we launched some stuff, which to, you know, which I blame myself, which were bad.
58:09One was Ace Bucks. This was a currency that sat on top of Facebook that you could earn by playing games and burn through our store. It was like the worst of Venezuela currency, like hyperinflation every day with stuff that sucked to buy. so it's like people like why the biggest lesson is then i'd show up to brands and i'd be like hey you want to use ace bucks like yeah no like that's stupid but we need to figure this out so then we got one step closer which is building custom apps anyone who used the like you know in style hollywood hair makeover app try jennifer anison's hair on your face send it to a friend right or the FedEx you know app where you could send FedEx a birthday message to a friend which would be like a virtual gift right those were great but not scalable and so Cass the operator said listen if we continue this we're just a service company we need to find something else and she told me and the salesperson we were selling a lot of these and that's when we productized it And instead of like these custom apps, we built a platform that offered like saplets.
59:25So saplets were drag and drop, could then like, you know, create apps off of that. And then it was three years, 50 million in recurring revenue in the sale. So when you get it right, you know it. When you don't get it right, you oftentimes tell yourself stories that you got it right. Yeah. Rip off the Band-Aid and pivot.
59:48Mike Lazerow:Do you believe every business in any niche can reach nine figures? No. No? Okay. And I think most won't. I think we're in the best time to build vertical AI apps, and very few will be venture-backed companies, meaning$100 million or more exit. I think most will be, you know, the ones that succeed will be great businesses. They may do$5,$10,$20 million a year in revenue. You know, throw off profit. But a friend of mine has one in the karaoke space that supports his life. He does very little. And I think that's a great way to go. If you want to be a venture-backed company, you just got to raise a lot of money, build, and build out infrastructure, which is not the world we live in today.
1:00:37Why do we want to launch pizza places? Demand's created. People love pizza. sell them fucking pizza so many kids i meet we talk to so many like young people they're like oh all the ideas are taken i'm like dude like this is water in a can like have you seen pop-up bagel have you seen van luyn ice cream like we're still reinventing the building blocks of life water so for you to say there are no ideas like get the fuck out of
1:01:08Mike Lazerow:here yeah like you're not gonna you know succeed i'd love to role play a little bit let's say you bring up pizza, right? Let's say there is a pizza shop and they're doing maybe four to$500 ,000 a year. What does it take to scale a business like a pizza shop from maybe four to 500 ,000 to over a million and then potentially multi-million? The product's great. It's a great product. They don't need help on their product. Yeah. So, I mean, there are two ways. There's like the operations, like how do you like streamline your operations? Are you working with Slice, you know, a leader's company that will help you with that.
1:01:44And the more important way is just creative marketing. And so I'll give away like why we want to do pizza places. You can open up a pizza place and it'll be fine if you offer every company within a mile a free pizza lunch for your people and the ability to like put your menus throughout the office. That's going to generate business, right? So I love the free idea, free entrepreneur advice in Central Park. Sampling has worked forever. Most pizza places don't work for the corporate business, meaning they don't ask for the deal. They don't say, I would love to host your pizza party, right? Most pizza places aren't that busy at lunch.
1:02:28And to do a pizza party at noon, you're making them all at 11 where no one's in there asking for pizza, right? So like that's one idea that just focus on one, two, three things that can move the needle, right? We only did really three things for this book. We made personal, in terms of marketing, personal asks, podcasts, and speaking at events. And yes, we're bringing value at the events, but the end is basically if you buy the book, you'll build the confidence that we built. and you'll have a whole new life, right? Like it's like this whole like inspirational thing of like it's a 50 cheat codes that we wish we'd known and would have fast forward through all of the bullshit stories that are in the book of like us failing.
1:03:15The book is like fail, fail, fail, fail, fail, fail, fail, yay.
1:03:18Mike Lazerow:Yeah. So you would say that marketing is just the number one thing that causes a business to scale. Yeah, people don't know how to market. Yeah. Go talk to like a lawyer. like go talk to like most business the five million businesses created right 20 were created by couples why couples they don't have money for employees right so it's like a family thing it's like gary's business when it started with the wine business his dad it's like hey 13 year old come i need help right and just because you know how to make the shoes doesn't know mean that you could like run the store or sell shoes right get people to show up and i think figure out how to market and i was just talking to a wine i'm not going to name the one but an entrepreneur has a big wine store um on long island and he's just not doing enough events he's not calling law firms and saying let's do like a you know like a wine tasting he's not showing up at all like the taste of events he's not asking for loyalty he doesn't have a rewards program And I don't know, does that double the business?
1:04:33Maybe not. But if you could get 10 % growth every year for seven years, you're doubling your business. Is there something that you notice that founders get wrong when they're trying to scale? When they're like, they're busting at the seams. They know that they need to hire someone. They know they need to bring someone on. What do you notice they make the mistakes on? Because you've mentored so many founders. so the good news about scaling like we don't want you to scale up until you're literally bursting at the seams so we don't want like this whole thing like oh raise the money you're gonna need in two years like like no like don't hire another salesperson until every one of your salespeople are like over quota back to back right every single person they're like and then it's like oh we're leaving money on the table so we need to bring people on so the biggest mistake on scaling is scaling too fast so many entrepreneurs like i hire all these people and it's like i just have expenses yeah and this you know the entrepreneur i was talking about earlier like had moved into like beautiful store and hired associates and hired biz dev people to get out there and they just weren't doing it right he just layered expenses and not revenue um and going forward i just think that you should be able to measure everything and that's what like ai data lets you do you know we own cash flow businesses one's a an executive search firm primarily in the medical space but also does non-profit and a producer's output so an executive recruiter their output is directly related to how many outbound calls they did so when someone says i had a bad month i'm like okay let's look at your calls you had a bad month because you didn't build the pipeline not because the market's soft and so usually they're inputs that you can measure like we haven't looked at like the numbers for the book because there's nothing we can really do in terms of the list like usa today lists we're just doing what the inputs we think are going to get us there we probably won't get there this i mean the irony is this could very well be a failure like we're cool with that but we're not going to fail because we're not putting the time and effort and the focus.
1:06:46Mike Lazerow:I would argue though, it doesn't matter how many you sell. In my opinion, I understand that you're going after like the legacy play, but I think in my mind, right? Like the way we list, we think about the podcast is like, if we can just help one person, incredible. I feel like if, if even just one person reads the book and take something from it, like that's a, that's a huge win. And already you've sold so many copies that are going to impact people. I mean, people are going to listen to this, put it into their business, buy a copy of the book. Like, I mean, that's priceless. Hopefully. And if you do, let me know.
1:07:18And we have the Founders Farm community, which we meet every two weeks. And we're like entrepreneurs helping each other out, like with stuff. And now like selling to each other. We have entrepreneurs, like one guy who makes like signs. He's like sold four signs. And so it's a, you need to have goals that matter. Do we really care about the number we sell? Like, no, it's not like a business. You don't make money selling books. but why do it if people don't read it? So for us, it's like, you know, for us, the next 50 years is about impact and money to a certain extent. We're capitalists. We like making money.
1:07:58It's just like what we do. But the impact is directly related to how many people know about it. Yeah, that's fair. Which is why I think that you've done an awesome job of getting on social. Like, that's so cool to see. You don't have to do that. We don't. Which I respect a ton. And it's, I mean, I think it's the, it is the way that you're going to sell more of the books. I appreciate that. And I also would encourage everyone listening to like get over their fear of doing social. Gary for many years was like, you've got to get back to it. Like you have a point of view, you engage with people in ways that people like you're like vulnerable.
1:08:37I don't know if it's like my cross eyes or bad, bad heart or whatever, but it's like, we went silent for 10 years and we worked really hard the last 18 months we should have never gone silent we should have continued to stay out there so if you're listening to this and thinking like oh i don't want to be in camera i'm not good in camera cas hated it for the first 20 videos now
1:08:58Mike Lazerow:she doesn't even think about it she's great on camera which is she's great i love her yeah i'd love oh i'd love her obviously but i love her on camera i love her because she's good on camera No, I love her on camera, but the first 20, like go back and look at our first videos, we were too overproduced. She was wearing too much makeup. I would like comb my hair. It would look so stupid. I've never done that. I wear a hat or like to mess that. And eventually it's like, let's just like be who we are. Like it is what it is. And people like it great if they don't, whatever. Costa and I were talking.
1:09:32I came into Costa's room when we were prepping for both of the interviews, like your interview and gary's interview and i'm like i'm not going to new york if i don't post every fucking day until we go i'm not gonna have gary say what are you guys doing on facebook i'm like i'm gonna have our account be posted on facebook he's like all right what do you guys have well it's interesting because we we did the central park thing the day before we did gary's podcast and we kind of did that because we know it would make him proud we we knew that like asking for the business, going to talk to people. And the first thing he did was like, wait, were you guys in Central Park?
1:10:10Were those your kids? Because we don't want to put all the kids' faces on. So it was just a bunch of 20-year-old kids. No, those are real. This wasn't staged. He's like, oh, my God, that's shit I would do. So get out of your comfort. Lean into the pain. Too often we lean into the comfort. like oh that's a little uncomfortable i'm gonna go like watch netflix whatever right as an entrepreneur the pain is where it's at like if you're having pain around there there are others and maybe you solve that pain or if it's painful maybe there's a reason and if you do it others won't and you'll get noticed right so it's that pain is like we kind of like maybe a little too much like we've this week has just been like nuts and cast is like you're not working hard enough i'm like what like what else can i do calendar stacked yeah i'm like she's like you have 10 o 'clock like we're not watching netflix like go like go like make a few more like text a few more people grind it yeah but that's like when we're in it it's like and i appreciate that it's not like it's not hurting nagging it's like yeah you're right let's go like there's always another call to make do you feel like you two push one another yeah 100 yeah and not only push like in a very direct way like that the idea of letting down cast and not doing what i say i'm gonna do is one of my big stressors so we're hosting pre-prom for our daughter tomorrow night and even though i don't drink i'm in charge of alcohol and like i'm stressed out if i don't get this right like alcohol with like senior prom like they're only about to have one drink at our house we're trying to keep it responsible they're going to college so we got to get we got to desensitize it like that is like a stressful thing of like not that it's vivi our daughter it's like oh man i got delivered for cast yeah if you have a partner that you've like you guys are very different right and if you have different skill sets different like strengths and then can trust each other to do what you say you're going to do like it's magic like you guys are married yeah how's it like to work with your husband it's been great honestly i think uh we just do different things and it's the reason why i think the show is able to happen he does all the cooking you do all the laundry exactly he cooks the meals and i clean the pots yeah yeah and it's the best when you're like if i had to operate a company and remember all the details i wouldn't do i wouldn't do this.
1:12:44I wouldn't be an operator. See, my other business partner, Sharif, and my agency, where we make social stuff for brands, Sharif is like the, he's like the operator. I'm like the ideas guy. I come up with the ideas. He's in the spreadsheets. He's sending all these invoices out, producing our shoots that we're doing for these brands. I'm like, I could never do your job. I could not do this. And I'll edit the spot sometime. I'll oversee the creative stuff. and it's like having someone that does everything that I can't do or like can't do well has changed everything because the first business I ever did in college failed and we were two videographers it was so stupid and we thought in my head the young guy I mean was like double double the money like we're gonna make double the money we do the same thing like we can actually kill this we're both doing well by ourselves and it just crashed and burned he was like a sales guy yeah we needed a salesperson and it just crashed and burned.
1:13:37And I didn't realize it until probably six months after. I'm like, why did this not work? What was wrong with this idea? And it's part of the journey, though. Now I know. Now I know what I'm looking for. At golf.com, we needed an engineer. So we had a third co-founder, Michael Casper. Great guy, still a friend. And so you pick partners who complement you. And my biggest mistake, Shape Matrix, we never really had the conversations. And it was really like ego on my side that led to a failed business that we talk about in the book.
1:14:12Mike Lazerow:I'd love to hype up Cass because she's not here. How pivotal has she been in your guys' success? And what do you feel like makes her such a great entrepreneur? So I think she's 57 % related to the success, like responsible. I am maybe 30 and then there are other people. And this hit me Monday night. We had 300 people, 190 entrepreneurs at the New York Stock Exchange. They hosted celebration of entrepreneurs presented by Stiefel Bank. And I'm very cheap, so we sold a sponsorship. and after the event people felt so seen and loved and what did she do okay you showed up and if you're an entrepreneur you got a gold name tag if not you're silver it didn't have your title it happened it said like what your best like project or trait was so one of our friends, a New York Times author, or award-winning.
1:15:21He would never put on New York Times bestselling author, but Cass, for every one of these people, got their unique thing, right? You then had, if you're an entrepreneur, you got a shovel that was gold versus silver if you weren't, right? Gold shovels, you could go to these carnival games, and she got this inflatable poop that you have to throw through these holes and you would win prizes. Now, when you go to these corporate events, most people think like the prizes are like whatever, a backpack from these. From the bank. Yeah, backpack. There was like a$1 ,000 Nobu gift card. Oh, wow. There were massages.
1:16:05There were full spa days. There were 150 gifts because we knew that not all the entrepreneurs would do it. And when people walked out, there were Krispy Kreme donuts. god i love some crispy green now she never had a bat mitzvah she's italian roman catholic growing up this was her way of like programming something for all these entrepreneurs to celebrate them to say i see you right one of our friends runs a stationary company that's gotten pretty big you could do like monogram stationary she shows up and she's an entrepreneur right she gets a she'd never thought of herself as an entrepreneur. And I said to her after, I'm like, that event, the warmth, how everyone saw themselves, how they were seen was the first thing we'd done in a while that felt like a buddy media event where employees would come and they'd get the same treatment, right?
1:16:56And with Cass, it's not just what you do, it's how you feel. And she's really tuned in to how people are feeling and how to create this environment which leads to like her cult-like culture like she's all about like let's create a cult that is for good like a positive cult and you only do that through these like rituals and symbols and making people feel like oh you're looking into my soul like you know who i am you see me and people like it's interesting about companies is people love being a part of something bigger and they want to be unique so i want to be a part of this and feel like i'm just like everyone else but i want people to see that i have like a mohawk and that i am expressing myself so to be the same and unique and i think that's what cast is really good at at the company you feel part of this like community, but we know what your goals are.
1:17:56Oh, you want to start a business? So we're going to move you around so you see everything. You want to be a CEO? Okay, let's go. Let's start on the management track. Your goal is to go from a developer to a developer of engineers. You now have a three-person team after you prove that you've done your job. And her saying was, do the job you want and the do the job you have in the one you want to show that there's like you're growing and like that type of stuff in a company has been lost in hybrid work and frankly management styles that have lost a lot of the humanity and cast is the best at that what have you observed from how cast manages people what can people take and put into their companies that really helped you guys be successful so transparency transparency is number one and she forced me to hear i was never i'm always like let's shine the turd i don't want the turd on the table like i don't like bad news so you know yeah i i'd say hey we got this huge customer and cast would be like yeah but we missed our numbers by 50 like like i don't care right so that transparency with yourself and your company they know when things are going well and not well and um so that's number one number two is that empathy part like listen like she's so good at listening to all of the management team because you get to a point where hundreds of employees you don't do it for everyone but your leading is showing others how to lead like if you're a screamer at home your kids are going to scream at their kids right no matter what you say they don't listen to anything you say but they mimic everything you do we know that like now that our kids are like fully baked you know 18 is the youngest and the lessons that i've learned from cass is basically it's okay to be human at work like she was breastfeeding viv at work like she is okay with bad news it's just she's not okay with people lying and not being transparent and it's just something that has been harder for me but for her it's you know she's a leader she's a born leader what were the first few hires like
1:20:18Mike Lazerow:the first key hires that you guys made for buddy media and we talked to gary a little bit about hiring and i asked him about hiring like you know a players versus b or c players and he was just like that's funny i'd rather have a b player that's just fucking down for the cause do you feel like the same way or do you feel like the same exact way okay but what he's saying about b player is credentials yeah you can't survive in vayner media vayner x in his orbit if you're awesome so it was like a gut shot when dustin left right but i know dustin so well seven years he was like the main videographer for all gary's stuff but he also wanted to grow and move on which is totally understandable i don't think you would say on his resume when he started seven years ago that he's an a player right but he was so committed to learning to the beginner's mind to doing anything that needed done.
1:21:17And that's why I've been very vocal of like Oswego over Harvard, right? Like Fresno state over Yale, college athletes over overly educated college kids, right? Like military over management consulting. Like these are people who know how to work as a team. They know how to communicate they know how to commit and when someone who has been the captain of the northwestern field hockey team comes to us and she's like i want a job yes you want a national championship like without any fanfare no one knows this you led a team you practice like crazy you're in the gym at 6 a.m and so when you say you want to work here and if you do half of what you did there here Yes.
1:22:12And I think that's what Gary's saying. Their performance is A+++. Who they are on paper is like a C. How would you keep people coming back hungry? Because I feel like a big thing that I've noticed from people who are in jobs is it gets really stagnant. You do the same thing. You're not growing. And it just kind of makes people stop because they're like, what am I doing working so hard if I'm not moving up? Or maybe there's a role that opens up. Hire someone from another place. You're like, I'm here. I'm working super hard. Or they think they're working super hard. How do you kind of keep that fire in the culture that you guys had within that company?
1:22:52So not everyone wants to grow. Yeah. Like some people are like, I have family. I want to work nine to five. I do this. And that's cool. And would you find that out early? Would you kind of try to figure out people's initiatives and be like, do you want to leave? Or do you want to make a business one day? Sometimes. Okay. Sometimes you don't know because everyone's a great salesperson when they're interviewing, right? So it's like they'll say what they want, but, you know, Cass is very good. And for the first 100 people, they all interviewed with Cass. Then it's kind of she can't do it.
1:23:27What's interesting is, like, people have a growth mentality or they don't. a lot of young people who we hired, who've now gone on to far exceed us. I look at Miles Klieger, who was a client. He then joined as a salesperson, then a sales manager. He grew braze to a$5 billion business, right? Or Wayne Slavin at Sure Insurance. They had never done this. You recognize that. You recognize that these are people who are on a mission. and you basically do what you can to like help them grow knowing that they're gonna escape your orbit at some point which is totally cool like when someone said i want to go start a company great can we invest how can we help the you have to have conversations that map out their journey if employees feel that they're pigeonholed and that there's no room for growth, then they're just not going to stay.
1:24:32And Cass has the exact number, but I think like 70 % of all of our promotions were from inside. That's awesome. Wow. Even like the biggest one, which is Jeff Ragovin joined as a salesperson, became chief revenue officer, did such a good job. We named him a co-founder. We couldn't imagine our business without him. Why did you feel like, I feel like a lot of people with their business are like, 100%, this is what it is. This is ours. You guys had given away percentage of it. Obviously, you had to raise money. You had to raise$100 million for Buddy Media. How do you kind of decide when you and Cass are starting it, what percentage should we keep versus what percentage do we have to give away to actually make this thing what we think it can be?
1:25:12Yeah. So give equity if people are going to value equity. Everyone in our company had equity. I tell other founders that if someone doesn't want equity, they're not going to value it. It's too valuable. Don't give it away. Number two is there is kind of a formula for this. So if you're a venture-backed company or if you're a growth company, tech company, you're going to start with 10%, 15 % in an option pool. All that means is they've been approved by shareholders. They've been authorized to give away. The board will approve any individual grant. Typically C levels are at the 1 % range and then it goes down from there.
1:25:51We love equity because it's the best way to do like financial incentives that align everyone and it also feels the best. Like Abby Lauterbach started with us right out of NYU. She's now senior sales executive at LinkedIn at 26 years old, like she makes kind of life-changing money, right? Like, do you know how great that feels? Yeah.
1:26:15Mike Lazerow:I don't know how good I could imagine. I mean, for the person, not for her. She may not even think about it. I mean, like to see her grow. And to know that it's like, she's set. And I'll know that for the rest of my life. And you know, you had like, I don't know if you saw like Dave's Hot Chicken sold yesterday. There were like 20 millionaires. Three dudes started with like a little tiny stand in a plastic table. Like if you make money with people you love, it's fucking awesome. And if you lose money with people you love, whatever, you're all in it together, right? It's not like there's no guarantees, but some of our most fond memories are like telling people what's happening and what it means for them after they shoveled so much shit to make us look good.
1:27:04Like we got all the credit. They did all the work. Not all of it, but maybe 90 % of it. Gary just calls you and he's like, hey, I want to start this company. So Gary says, I mean, he had a pitch and his pitch is I'm 34. I've worked for my dad since I was 13. I've never made more than 100 ,000 a year. I have no money. I have a concept for an agency that will do for other brands. That's what I did with this wine library, which was my dad's store. Dad's first generation doesn't believe in giving away equity. Didn't have a fight, but he was just like, respected it. I don't have money for an office, but can I use your conference room?
1:27:45At first I thought he was just like, oh, for a meeting or something. I'm like, sure. He's like, oh no, for the office. Like, can I take it? And he moved in, AJ, Marcus, and a bunch of goofballs. Wow. And the only reason he left, we didn't kick him out. He had way too many people. We had a surprise visit. It was a very old building because it was the only one we could afford. And the fire department came. And they looked in there. They're like, is this like, are these like Iraqi refugees? Like what? This is like a homeless camp. Is this like a bunch of young people not dressed well, just on laptops.
1:28:21They look like a sweatshop. Oh, my God. And the fire department says, I'm going to come back tomorrow. And if this is here, you guys are all in trouble. Wow. I'm like, okay. You're kind of new office. I think it took like a week. Wow. Yeah, we loved having him here. I loved it. Cass, he'd walk into Cass's office. He's like, Cass, Cass is really good at ping pong. Like really good. She played professional tennis. She's incredible pickleball. Cass, Cass, Cass, we got to play ping pong. Cass is like, I'm on the call. and he'd just be like come on now now like we gotta go i only have 10 minutes and so it was fun it was like really like we think about those days and like going to south by and like selling together like it was just fun like yeah it was just a lot of hope a lot of energy yeah we had an event he's starting to get his name we're like hey we need we're doing this thing hill country barbecue like we don't money for a speaker we need you to get on stage just do something and he's like i got it like no problem no pitch no prep i still i still can't believe he's the best speaker yeah he doesn't have slides right he'll just freeball the speech it's
1:29:27Mike Lazerow:incredible it's insane how did you guys meet in the first place he social media was small and we had an employee of ours who was very close with him and the employee had reached out and he kind and thought the business looked cool. And then he wrote me. Oh, wow. And I knew about him because he had just gone on Conan O 'Brien's show. Sniffed his armpits, that one? Sniffed his armpits and ate dirt on TV. He said he sniffed it to get his odor palette up. He was on some shit. Yeah, and Conan O 'Brien was like, this guy. This guy's crazy. And he was a little, I mean, Gary was so awesome and so grounded.
1:30:09But when he wants to be crazy, he can. And he's like, I'm shooting my shot. I'm going to go on Conan and the world's going to know. You're going to know it. Damn.
1:30:18Mike Lazerow:Wait, okay. So speaking of Conan late night, one of your roommate or your roommate in college was Seth Myers? Yeah. Still, you know, one of my best friends, Vivi's godfather. Was that a, was that like a random pairing? So it wasn't random in the sense. Oh yes, it was random. You know, we were freshman year, we show up and our rooms were right next to each other. neither of us loved our roommate and we hung out a lot we had a lot of fun his roommate played the trombone in the marching band and I played his trombone on our hall I would just walk down our hall until one day his roommate came back seeing me and I was like I had like the northwestern like hat like I dressed and not he didn't he'd never granted me permission and I think that put over the top they needed a breakup and i kind of wanted to break up and so we eventually you know rushed the same fraternity and we weren't we had a lot of fun we weren't what they call like cool like we made ourselves laugh like we're kind of dorky he loved the red socks i remember red socks lost and he locked himself in his room for a day sitting in the dark on the floor i'm like this guy he's still like that with the steelers um and you know then we lived together when we graduated he was a very successful waiter at the twisted lizard in chicago great mexican place i don't know if it exists i was working for you know my company you wire and then i met cass a year later cass would stay in our apartment that apartment was three bedrooms and a closet, I had the closet.
1:32:04I had no windows or air, and I loved flannel sheets. So Cass is like, this isn't working, we have to move. You gotta move out, let's move in together. She moved from DC, we moved in. And so my last roommate technically before Cass was Seth Meyers. That feels like the time period we're both in right now. Like you should see our spot. But it's the best, I loved it. I've loved it, I've loved every minute of it. It's like, it's a studio, we live in a studio. But we're ready and excited to have our own spaces. And I can't wait to build out an office. Yeah.
1:32:37Mike Lazerow:I literally just moved out a couple days ago in with my girlfriend. We're about to be office guys. We cannot wait to do offices. I loved it. I mean, I loved that time. It wasn't just Seth. It was Brian and Derek. Brian was management consultant. He was never there. Derek sold insurance. Now he runs Arthur J. Gallagher's commercial insurance company, which is like a public. He's like a real person. and we call him the insurance commander. So if you ever need to be saved by insurance, call Derek. Give him a ring. I don't know if he does like personal, but if you need anything insurance, call Derek Vandervoort.
1:33:09Okay. And we support each other. Like what's cool is like we've seen, I've seen Seth go from waiter to one to two person show, hiccups and pickups, to being rejected by Second City, to going to Amsterdam, to be in Boom Chicago, where they discovered him. I've seen him try to act on SNL. He's an awful actor. He's great if he's Seth Meyers, but if he tries to do anything else. But he's really a writer, and so I was very nervous when I asked him to read the book early. Not because I want him to read it, but I want him to promote it. He has like 5 million followers. And he liked it, and he agreed to provide me a recommendation, and then what was cool is two days ago, he actually publicly posted, which it's hard to ask.
1:33:56your like it's really we just have a relationship yeah so i it's hard for us to ask for stuff and so the fact he did that like those are friends like you know those are your real friends
1:34:10Mike Lazerow:yesterday we had a moment we got together with tyler babin and we were on the roof of their office you can see this like we're in the middle of new york you see the empire state building we're eating pizza and I remember like must have been four years ago that we met Babin and I just remember like sitting there and like having this moment like how cool is this that like so much has changed since we first met and we're kind of just catching up you know and we're we just feel like we're doing it and it was awesome have you had those types of moments with somebody like a Seth or a Gary where you guys are you know eating pizza or something and you're just kind of reminiscing on, wow, I can't believe we're here?
1:34:52Yes. I mean, all the time. And the reason is because the people you surround yourself with now are the same people you're going to go back to for advice and hang out with and create together. So did I know when Gary showed up that we would have a wine business, Empathy Wines together? We co-own a pickleball team, the New Jersey Fives. I'm an investor in the V Friends company, right he made money off buddy media he supports us he's sold i would say without gary this book no chance of being a success he did a three-hour live stream it's hard to get him for a 10-minute podcast yeah i sat in his office and and i teared up and of course cas is like there he goes again mike's crying do you have to tell like the world and it like hit me hard that here we went from like our little conference room he's now welcoming us to this full floor hudson yards doing a three hour thing i can't believe you guys went for three hours it was so fun and then what's cool is like at on monday harlan cohen who does help me harlan he really helps college kids with like dating and roommate advice and i helped him i was like i syndicated him through my news service introduced him he just reminded me this to peterson that publishes his books we've been working together since i was 21 and now he's like new york times bestseller and like a huge following and you know your friends and the people you help are the people in your life and i just can't emphasize enough that you cannot be transactional like you have to show up saying how can i help like i showed up today like okay what are the stories how do i make this interesting like i don't try not to talk about the book because like fucking no one cares like i care about the book buy the book on amazon but that's not what makes it interesting right and so you have to show up giving give give give give give that's the only way stuff that will eventually start coming back and i look at people like dj ski that i mentored i have vcs who were like their first fund who are now like super rich and successful um i don't really i have a lot who are failures i still love them but not as much but there's not as fun that's poor people um no it's uh you know it's just life is who you surround yourself with and you never know.
1:37:30And you never know who you're going to need. Like, you know, I've had some medical stuff that if it weren't for some friends, it's like, oh man, like that doesn't go well. If you could go back and talk to your 18 year old self before you built UI, before you went on to start Buddy Media, Shape Matrix and all these awesome things and write this incredible book sitting in front of me, what would you tell yourself before you went the journey i wish i had learned the kind of destructive power of fear like i was very fearful like i had ulcers like in high school um when i almost died i came out of that surgery like with my heart my new valve and my new heart and my mom at least says i was a new person i was like chill great outlook i was just and i remember being happy i'm like fuck i'm alive like that's cool and before that that was a little later at 18 i was just like i was in a hurry i was stressed out i wanted to get to work i didn't like college when you are scared of stuff when you're fearful when you have these thoughts it leads to just bad decisions and a lot of uncertainty, you doubt yourself.
1:38:50And at the end of the day, most of the stuff we fear, like isn't, it's just like the boogeyman, right? Other than sharks, I'm very afraid of sharks. Sharks are your buddy. They don't wanna get you. I know, but it's not like an intellectual thing. It's like just a fear. It's like something, I can't help it, but getting eaten by a shark is not great. And I also don't like dementia. I'm a little scared of that. um that's like the worst thing that getting by a shark would be quick so it's probably not as bad as dementia shark ain't gonna get you they want to be your buddy that's what people say but i feel
1:39:26Mike Lazerow:like i'm delicious you just gotta stay on the boat or stay in this on the sand you know yeah people say that to go in the water which i've started doing um and we used to have a place in turks and caicos and the only reason is clear water i'm like at least if i get eaten i'll see it coming but i think the fear part is just so disastrous and i even think about the most important like there's one moment there's a most important moment of my life like would have spiraled in a whole different direction and i'm at a wedding and i see cass she's like she was a tennis player like long legs like this red dress i'm like fuck like hot she went to ivy league school i got rejected by five ivies she's like working she's interested in the internet i'm told by friends and i was sweating my ass off i'm like there's no way i'm asking that broad why did i say broad in my slacks to dance and i walked over like sweaty and she felt my hand and it was like i'm like will you dance with me and she said yes i'm kind of like tearing up here like imagine like this schmuck's life if that doesn't happen and everyone has something that if they just get over that fear maybe like and you know what happens when you aren't on your phone you look up and talk to people like good stuff right it's called networking young people are like what's networking so i can get off your phone and just talk to people anyone um and that moment I was so riddled with fear but for some I still don't know why and then the next weekend she's like why don't you come to DC I'm in Chicago I'm like oh I can't do that even though I haven't told anyone but we kind of hooked up that night that first night sorry Cass you're not here um and uh in a very innocent way it was very lovely um but yeah she's like come to DC and I was like really nervous but then i didn't have money i remember looking southwest had a 45 flight into baltimore i'm like it's a sign 45 bucks that's like less than like my beer tab at like barley corns in chicago and it was just an awesome weekend like i mean you know you probably had dates or where it's just like it's something's there i went back to chicago and i had kind of So when I was dating, I'm like, listen, I got to check this out with this other broad.
1:42:02And fear, like I was so riddled. So that's my only thing that I wish I knew more of. I love it, Mike. Thank you so much for coming on the show. Ladies and gentlemen, this has been episode 161. Go get yourself a copy of Shoveling Shit live on Amazon. It'll be the first link in the description. Drop us a comment. Leave us a like. hit that subscribe button we'll see you guys all next week peace
From the publisher
The 10 Minute Personal Brand Kickstart (FREE): https://the505podcast.courses/personalbrandkickstart What’s up, Rock Nation! Today we sit down with Mike Lazerow, the founder of Buddy Media, a billion-dollar startup he sold to Salesforce, and the author ...




