Digital Social Hour - Master Focus: The Key to Entrepreneurial Success | Kass & Mike Lazerow DSH #1403

Episode Date: June 14, 2025

🚀 Master Focus is the ultimate superpower for entrepreneurial success! 🚀 In this episode of the Digital Social Hour, Sean Kelly sits down with Cas and Mike, two powerhouse entrepreneurs with a 28-year partnership and a $750M exit under their belts. They share their secrets to staying focused, building thriving businesses, and balancing personal and professional life. Discover why focus is the cheat code every entrepreneur needs, how to pivot successfully when challenges arise, and the importance of surrounding yourself with the right people. Cas and Mike also dive into the art of creating a winning company culture, investing in 100+ startups, and staying ahead in today’s fast-paced world with tools like AI. Whether you’re just starting your entrepreneurial journey or leveling up, this conversation is packed with valuable insights to keep you inspired and on track. 💼💡 🔥 Don’t miss out on the life-changing lessons from two industry veterans who’ve turned their passion and persistence into monumental success. 🎯 Tune in now and get ready to unlock your potential, one focus point at a time! 👉 Watch now and subscribe for more insider secrets. 📺 Hit that subscribe button and join the Digital Social Hour for more eye-opening stories with Sean Kelly! 🚀 CHAPTERS: 00:00 - Intro 00:32 - Working with Your Spouse: Tips for Success 02:30 - Focus: The Key to Achieving Success 05:01 - Therasage: 10% Off Tri-Lite Device 05:49 - Therasage: 10% Off Thera O3 Ozone Module 06:30 - Therasage: 10% Off Thera H2Go 10:00 - Howie and Mike's Stress Levels: Insights 11:17 - Investment Success Rates: What to Expect 13:20 - Targeting Specific Markets in Business 17:35 - Future of Business: Howie and Mike's Excitement 20:00 - Best Age for Parenthood: Insights 22:05 - Is College Worth It? A Discussion 27:28 - Building a Career You Love: Strategies 31:16 - Lead by Example: Effective Leadership 34:17 - Overcoming the Fear of Losing 36:30 - Celebrating Departures: A Positive Culture 38:14 - Putting the 'Cult' in Company Culture 40:10 - Embracing Radical Transparency in Business 42:25 - Going Fully Remote: Pros and Cons 43:23 - Job Hopping: Trends and Impacts 46:05 - Instant Gratification: Understanding the Phenomenon 50:26 - Parenting: The Journey of Having Kids 51:20 - Wrapping Up: Key Takeaways 51:34 - Finding Cass and Mike: Social Media Links 52:06 - Discovering Their Book: Resources APPLY TO BE ON THE PODCAST: https://www.digitalsocialhour.com/application BUSINESS INQUIRIES/SPONSORS: [e-mail] GUEST: Kass & Mike Lazerow https://www.instagram.com/kassandmike/ https://www.instagram.com/kasslazerow/ https://www.instagram.com/lazerow/ https://kassandmike.com/ https://shovelingshit.com/ SPONSORS: THERASAGE: https://therasage.com/ AMNISIA: https://buyamnisia.com/ LISTEN ON: Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759 Sean Kelly Instagram: https://www.instagram.com/seanmikekelly/ The views and opinions expressed by guests on Digital Social Hour are solely those of the individuals appearing on the podcast and do not necessarily reflect the views or opinions of the host, Sean Kelly, or the Digital Social Hour team. While we encourage open and honest conversations, Sean Kelly is not legally responsible for any statements, claims, or opinions made by guests during the show. Listeners are encouraged to form their own opinions and consult professionals for advice where appropriate. Content on this podcast is for entertainment and informational purposes only and should not be considered legal, medical, financial, or professional advice. Digital Social Hour works with participants in sponsored media and stays compliant with Federal Communications Commission (FCC) regulations regarding sponsored media. #ad #businessbrainusa #growthhackingsecrets #businesscoaching #characteristicsofentrepreneurship #motivationalspeech

You do something over and over and over again, good things happen. Find something that you're good at and do it again and again and again. Yeah, it's rare that your passion will make the money that you need to afford your life. Keep the passion, but figure out what your talents are and then surround yourself with people who fill in the gaps and then supplement your life with the things you love. All right, guys, we got Cass and Mike here in Las Vegas. Thanks for having us.

Yeah, let's do this thing. You guys have accomplished a lot. Let's go. You've been working together for 28 years. Yes. You have to remind us. Yeah. Well done though.

28 is big. That's very hard to do while you're dating or now married. But we love each other and we like each other. So we laugh a lot and we fight well. We get over our arguments. We don't take anything personally. I think that really helps in our personal side of things. But like at work, like we're just like,

hey, I didn't like that. Or like, you gotta do this better. Why didn't you do this? And we've taken that home, which has really been effective. Yes, it is very aggressive. So are you. I'm not passive aggressive. What he's saying is I'm aggressive aggressive.

I appreciate it. You're more direct. Yeah, you need that. Yeah, everyone needs that. Just communicate. Yeah, communication's important. How do you not let the business bleed over into the personal though?

That's super aggressive to me. Well, it's hard sometimes. I think our love language is work, right? Like if you look at our book, it's hard sometimes. I think our love language is work, right? Like if you look at our book, it's basically our love story, while it's also a love story to all entrepreneurs. And we met, we were dating while we were working, we started our first company while we were dating, and we both, I think, have the same values and work ethic, and that's our love language. Yeah, because a lot of people say not to mix the two.

I know. I just think if you can't work with people you love, who do you work with? People you hate? Like people you can't stand? But you can't have overlapping skills. That's a key here. Well, we don't, but we don't think,

we think that if you are in different lanes, it's much better than if we overlap. And we're in very different lanes. That's true, because sometimes you'll work with a close friend, you have similar skill sets, and then you guys just- Well, you fight or you have like paralysis of decisions. You can't do anything

because you're both micromanaging the process, or you both want your input heard. As opposed to like clear divisions, which is what Mike and I have. We just know each other and we know who has the expertise in that lane. And I was talking to Mike out there, it seems like you guys are grinding

as much as you had in the past. We're working harder than we've ever worked. Which is insane. And we love it. And we love it. Yeah, cause you guys had, you know, $750 million exit and no slowing down. No, no, no, no. It's a lot easier now because our kids are older

and we're healthier. At the end of Buddy Media, which we sold, you know, the sales force, we're close to a billion dollars, we weren't very healthy. I weighed 40 pounds more. I was not the best version of myself. We, with older kids, were able to kind of focus on ourselves a little more, which is hard for entrepreneurs,

as you know, I mean, look at how you're hustling. I'm getting more picky on what I say no to. Cause I'm getting so many opportunities now, but if I said yes to all of them, I wouldn't, I'd be too distracted, I think. It's one of the key cheat codes from the book, is focus. Like focus, how to use it as a superpower, and the entrepreneurs who focus,

who know how to say no and know what to say yes to can do whatever they want. Most entrepreneurs can do anything they want. They just can't do everything. Would you guys say focus was the biggest skill early on that definitely when we started, I think, you know, we decided our last company, we had a business model that changed three times, we pivoted three times. So when you do lots of pivots, and you're trying to find that like customer feedback that works, you have to focus, right? Because it's easy to say, well, maybe they would like this, or maybe they would like that, like you have to go for it. And really good entrepreneurs, they look at like a failed product launch as getting one step closer to like figuring things out. So you gotta focus, that's the number one thing. I know that's Mike's number one cheat code. By far, by far.

And these days that's a hard skill to have. Yes. Yeah, it's hard, but if you focus on the right things, you can literally do anything. And it reminds me of when Facebook went public, they didn't have a mobile strategy. Once they focused on it, the rest is history, right? And so it's not only what are you focused on,

but should you be focused on anything else that is more important? And oftentimes you're tripped up by stuff that you didn't focus on that you should have. And so focus as we've been over a hundred investments and to other entrepreneurs and we support them every day. And the question I ask every time is what are your top three priorities?

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But here's what makes it stand out. It's the only bottle that also structures your water and adds red light to supercharge it. It's sleek, portable and honestly, I don't go anywhere without it. Doesn't know it. But if an entrepreneur's like, you know, we gotta sell, gotta build product,

gotta service it with excellence, gotta build, you know, culture that scales, like then you're like, oh, this person has their stuff together. Yeah, cause a lot of people focus on the wrong things, right, in business especially. Or they don't focus at all. Like we're in a world where you could do anything,

like, and you've inbound through like- And it's scope creep. I mean,'t focus at all. Like we're in a world where you could do anything. And you've inbound through like- And it's scope creep. I mean, all these entrepreneurs, everything's cool. Everything's the newest thing. And they can't really draw a circle around what is it that they're going to build, right? Or what is it that they're trying to come up with,

but focus is the thing. They have to. Yeah, I've never struggled with focus and work ethic. And a lot of people are like way smarter than me, but I feel like those two skills are what got me to a pretty good level. I am definitely not the smartest in the room, but I can outwork anyone.

Cass is smarter. Wait, wait, wait, you can't outwork me. You cannot outwork me. Oh, I love it. You cannot. I used to be able to. I don't work as hard. You lost a step.

I did. You cannot. But Cass to be able to. I don't work as hard. You lost a step. I did. You cannot. But Cass is, yeah, Cass is a monster. That's good. You guys compliment each other well. Yes, very well. I'm in a similar relationship. My wife, my soon to be wife is way smarter than me.

It's a way to go. It is a way to go. That's a way to do it, man. Punch up. You're really smart. You gotta punch up. Yeah. No, it keeps me grounded.

It keeps me, she keeps good people around me. Humble. Yeah. I always love smart women. None of them liked me before the test. That was the problem. But yes, smart, strong women, nothing better. Yeah.

I'm a sappy of sexual actually. Do you know what that is? I have heard of it, but I cannot tell you what it is. Basically it's if you're attracted to intelligence. So in friendships and in dating, that's my number one quality. Like that comes before looks, it comes before everything else.

I love that. Maybe that's what you are also. It definitely wasn't the look. It wasn't the cross eyes. It was definitely the mind. I like that. Yeah, looking at that man. You might need a little diagnosis or not.

Yeah, let's go, good therapy. So you guys have invested in over a hundred companies, you said. That's insane. Is it still actively going on right now? Yes, for sure. We're addicted to entrepreneurs and entrepreneurship and companies and going from zero to one

and then one to a hundred. Not all of them go from one to a hundred. Some of them die, but we think there's nothing more exciting. It's our sport. Yeah. And there's beauty in the struggle. Jay Cole said it. Our son, actually, our oldest son has this tattoo, you know, beauty in the struggle, and there's nothing more we'd rather do. And there's nothing more miserable than being an entrepreneur because,

you know, all the shit that's thrown, you know, you know what it's like your way every single day there's no perfect day I don't think we've ever met an entrepreneur who's like yeah this is easy you're telling me or oh I have enough sleep and I work out every day and everything's great my kids are happy I'm totally thriving that's not what entrepreneurs brought to you by amnesia vodka crafted to leave an impression. Say, and they love it. Yeah, you got two extremes. I just measured my stress levels yesterday and they were off the charts. But at the same time.

Would you do a cortisol measurement? It was a crazy test. He's coming on after you guys if you want to do it. Basically, you speak into his computer and it measures everything. Like technology and AI is just so interesting to me. That's awesome. That's incredible. Yeah, it's insane. I'm and AI is just so interesting to me. How- That's awesome.

Yeah, it's insane. I'm sure my cortisol levels are always high. Yeah, my adrenals were high and everything. All from my voice. Like can you every single organ that was having an issue? That's crazy. Crazy. That's what I'm excited about.

That'd be interesting to see if you could do that and then overlay it to like pernuvo. I took a pernuvo. Right, and then like do full body skin, and then blood work, and then- So I did all these tests. I put it into chat GBT and asked for like a plan on how to fix all my issues within three seconds.

Yeah, that's the best. I mean, before you had to go to five doctors in person. Who would say no. Yeah, they would give you Western medicine. That's a whole nother- It's working, whatever you're doing. You look great. Thank you. You guys too though. Thank you. For 28 years of hard work. Yeah. For 51 give you Western medicine. That's all in whatever you're doing. You look great. Thank you.

You guys too though. Thank you. For 28 years of hard work. Yeah. For 51 years on this earth. She's a little older, so she had a few more years. I'm 54. Okay, let's go.

It's just a fact. It's not editorialized. Whatever. What percentage are you guys shooting out of those hundred investments? Cause you hear these crazy stats with VCs, one out of every 10 or whatever. So we don't believe in that.

We believe like everything we do, we want to do well, and we don't assume some are going out of business. Having said that, you know, we've had, out of those hundred, about 35 exits, there are about 10 of them that are transformative. Those are companies like Scopely, which we seeded, which sold for $5 billion, and companies that haven't exited.

We were seed investor in Liquid Death, seed investor in a lot of the companies that many of your listeners, viewers have heard of. And the reason is we are not just typical VCs, we're entrepreneurs. We roll up our sleeves. That's right. We say to all the entrepreneurs,

give us one thing to do, and we'll do it, and we're done, give us one thing to do and we'll do it. And we're done, give us another thing. And that's how we win the love of entrepreneurs and deal flow. Well done. Those are impressive stats, man. I mean, the winners are awesome. And the good news, I'm not a math major, okay?

I just wanna get that out there right now. I went to journalism school, but you can only lose one time your times your money. So if we invest a million dollars, we can only lose a million, but you can make like a thousand times that, right? On the upside. So I just love the math of like the winners

are so much more powerful. And if you're good, meaning pick the right entrepreneurs in the right markets with differentiated products, then big can be really big. And we've seen it. We have investments where the founders became billionaires, which we love. Damn, that is crazy.

And there's nothing better to see like entrepreneurs like busting their ass for 10 years and reap the rewards. American dream, right? Yeah, it's a global dream. I mean, it's everyone in the world. Oh,, right? Yeah, global dream. I mean, it's everyone in the world. Oh, so you guys are investing everywhere? Oh yeah. We do, but like,

I mean, entrepreneurship is like a global sport now. Yeah. Like you go to Asia, Europe, anywhere. We were in Africa in December, like, you know, everyone wants to start businesses. That's cool. And do you guys target certain markets depending on the trends, like AI right now or anything, or you kind of go by the founders?

I mean I go by the founders. So I bet on the jockeys, right? So, you know Mike gets a ton of deal flow we're known as investors who actually roll up their sleeves and do the work and actually like Execute what we're saying that we will do there's a lot of investors out there who say they're gonna help and then don't do anything. And when Mike throws a deal over, it means that the market's right, the product's differentiated, he knows how it's gonna be going to market,

it's how it's gonna be delivered, and it makes sense, like on the back of a napkin, like the unit economics. So by the time it gets to me, I'm looking to see if the founders are the right ones. Can they actually scale? Do they know what they don't know? That's like the biggest thing.

And do they know how to like form a leadership team around them that fills in all their gaps? So I bet on jockeys. Yeah, the team is everything, right? I bet on races, she bets on Jackies. Races. Well, everyone's kind of like, you bet on the horse or the jockey, right?

And I think the companies that have done well are in the right race, right? So it's about like, and the race meaning like, how big is the market? Like, you want to win a million bucks. Like, you're not going to enter a horse into a tiny race. You're going to go after the Kentucky Derby. And so a big part of what we do is just huge markets. People are like, how did you know Liquid Death was going to be big? The answer is we didn't know, right? Like,

that's a company that really caught lightning in the bottle because Mike Cezar. I hope you guys are enjoying the show. Please don't forget to like and subscribe. It helps the show a lot with the algorithm. Thank you. It was such a good marketer. But what we did know was that water was the building block of life and the largest non-alch market. Right. Right. Like, look, here we're drinking water, right? You need water and we're in a world where kids aren't drinking like they used to. That's right. And so for us, it's about like,

is it a big enough market to build a really big business? And if it's a tiny market, we're probably not interested unless it's a cashflow business that we're buying control of. Yeah. Liquid Death was so impressive to me because like marketing water, that's just really hard. It just seems so silly.

I mean, when he first brought it to me, I was like, I don't know, Mike, are you kidding me? And then I started looking into marketing and how he came up with, Mike Cicero came up with everything. And I was like, this is gonna be huge. I mean, you're starting to see these creator brands like Mr. Beast with Feasibles entering spaces that have been dominated for a hundred years.

Yeah, and shaking them up, which I love. And it's just starting. You combine like, your person as media company, right? Like you, with kind of the ability to build stuff fast. Like we could sit here and launch like nine companies this afternoon. Wow. Literally on the back of like these AI coding platforms,

Lovable and Replit and all these. And so I think the power, and why it's so exciting for you and for your audience is that the power has shifted from the engineer, so skills that very few of us have, we don't, to the marketer, to the communicator, to the business side. And that's really exciting. All of a sudden, technology is not the barrier that it was

Oh, I can't pay two hundred thousand for like a you know full stack engineer Now you don't need it yourself. I'm building stuff at Cast Lake. Why are you wasting your time? Like I want to know these tools well and our son our oldest son is 23 Hey miles if you're out there He just started a company and you know he realizes that if you're out there. He just started a company and he realizes that he just doesn't need a huge team. He and his co-founder can do what they need to do,

like just them, which is incredible. When I think back to Buddy Media, we got up to like 350 people. I would say how many of those do you think were engineers? A hundred? A lot, yeah, raise a hundred million because like we had to build and then sell. Now you just build and sell.

And if you have built-in distribution like you have, you can build stuff really fast and see what sticks. Yeah, a lot less risk these days. Yeah, immediate feedback from your customers, right? So that's huge. Yeah, I'm excited. That's probably the next step for me, because we're getting like 200 million views a month right now

if I could figure out a product or service I align with. Us too, we're focusing more on like how do we launch businesses than just invest because companies aren't going to need the money. You know, we just had dinner South by Southwest with an entrepreneur, young entrepreneur from Poland, who launched an AI company and they got to 100 million of ARR with 30 people.

And how long did that take? That didn't happen. Tell them how long it took. It took like 12 minutes, cause this guy was like 13 years old. Like it took nothing. And I was both jealous. I'm like, dude, you're young, handsome, rich,

and you don't have to manage all these employees, but also super fired up because he was using AI tools that others had built to build his AI tooling in the voice space, like AI voice space. And you're just gonna see great companies built by dreamers. And people are always, oh, all the ideas are taken. There's nothing else to do. Well, look at Liquid Death.

Right. Like look at any of these newer companies. Like, you know, look at Pop-Up Bagels, which is a new bagel like craze. I love how you say bagel. Bagel. Bagel. I say bagel.

Bagel, can you say bagel? Whatever it's called. But like, he innovated on the most simple bread product. Right? So anyone who says- That's the one in New York, right? Yeah. I think I saw a story about that one. It's going national now. We need them out here. The bagels suck out here. Yeah, well- That's the one in New York, right? I think I saw a story about that one. It's going national now.

We need them out here. The bagels suck out here. Yeah, well. I wish they sucked in New York, cause I love them and they just like go right here. I grew up on bagels, man, in Jersey. I miss them. Bagels and pizza.

We have them every day. We love pizza. You get the Taylor ham or just plain. Yeah, I mean, I'm a big plain fan or cinnamon and raisin. I know that's like very like- Basic. Controversial. I like everything, I like stinky.

Throw some salmon on it, just so people know I'm coming from a mile away. Tomato, onion, capers, and salmon. Can you imagine that? It's after you get married. You gotta play cool while you're not. And safe. Yeah, 25 years in, I'm just stinking it out.

Yeah. I feel that. A little hot and juicy. Have you been there? No. No? I don't even know what that is. You'll be staking for two days. Okay. Okay.

It's the seafood boil. Oh yeah. No, not, yeah. It does a strip club. No, no, no. I don't go out there. No. So you mentioned the daughter and I know you mentioned the son. What do you guys think the best age is these days to have kids? To out there. No. So you mentioned the daughter and I know you mentioned the son. What do you guys think the best age is these days

to have kids? To have kids, okay. So, well, most people think we were young when we had them. We had, I was 30 and he was 27. So I feel like he was young. I actually think that the earlier you can have them, the better. I think the recovery of your body is just,

especially for the female side is just, it's a lot. It's a lot and the toll of the stress of literally keeping another human being alive is probably best done when you're youngest. Now I know that that- That's if you want them. Like if you want kids- Well, duh.

Then I think- I mean- So if you want kids, have them right away.. Well, duh. Then I think. I mean. So if you want kids, have them right away. His question was, when do you think the optimal time is? The optimal time is when you want them. Oh my God, no. A lot of people I've found. Here we go.

Either get talked into it by their significant other. Or they're both a little wishy washy, right? So if you want to have them, have them right away, but it's okay not having kids. Like kids are just big investments. Well that's true, there's zero ROI on kids. You can't fire them. We like companies, we like companies

that you could fire people, like if they're not working out. Your kids you can't fire. That's true. The ROI I think happens when they get old, like past 20. Way older, yeah. And then they have- We think. We think.

And then they have grandkids. I think the ROI is about grandkids, but that's a big, that's a long investment. Think about that. That could be 30 years before you get- Yeah. The return on investment is very low. You look at the stats on how much parents spend

on their kids every year, it's pretty crazy. Oh yeah. So I was saying this to my friend the other day. We set up those, I can't remember what they're called, the accounts for college funds, right? And now that our daughter, so that'll be the third kid, right, is going to college, that money is ready. It's like we're going to have income now

because I can just spend that money now on her, you know, in her college. I'm loving it. No more expenses. Viv. Let's go. Speaking of college. So did all three of your kids go to college? Yes. One graduates this year. We have a junior Emory and one starting at Northwestern in the fall. Nice. You guys are believer in that system still? It's a good question. Yeah, I don't.

We believe in it for the right kids. We don't think it's as necessary as it was in the past. So there's no shame involved. Companies are hiring people who didn't graduate. We don't care. We hired people who didn't graduate. Oh yeah. I'm not telling you,

if you went to Harvard Business School, we're not hiring you. Really? No, no, no, no, that's your thing. You didn't get into Harvard. Ah, he, no, no, no, no. Really? No, no, no, no, that's your thing. You didn't get into Harvard. Oh, he's better. I just find them entitled. Okay, but still, but still, did you apply to Harvard?

Yes. Yeah, I got rejected. Okay, so, yeah, so let me answer the question. I think there was no alternative, I think, to college for the three kids. I think our oldest needed to go because it was an exercise of getting through something, college for the three kids. I think our oldest needed to go because it was an exercise of getting through something,

having a goal, sticking with it long enough, even if you're miserable, right? Do I think he actually learned a lot in school with like what he studied? No, I don't. Middle guy, I think he probably hasn't enjoyed classes, but I think he's loved the living, being an adult, learning how to adult.

I think our daughter who wants to study like cancer and science, she's gonna need those classes. And I think she's gonna love it. But no, I don't think everyone needs to go. I just don't think there's an alternative with a safety net for a majority of people if you don't go. We're also among the luckiest people in the world. Let him hear that. You get what I'm saying? I'm processing that, yeah. Because like, if you say, okay, fine, no one goes, there's gonna be a lot of

people with no structure and nothing to do and they're gonna fall apart. Yeah, I could see that. Yeah, my thing I guess is the tuition aspect too. It puts a lot of people in debt. Stupid, one of our friends' kids got into U Miami, it's like $78,000 a year. That is insane. Well, that's, my point was gonna be like,

we're the luckiest people in the world. Yes. Right? Our parents were middle class, they could afford education. Born on third base. Yeah, so we're very cognizant of who we were born into and our kids are even more fortunate. Hopefully they're listening.

And I think the cost sets a lot of people back and when I look at like four years of like doing something, so do something where you can show up and say, here's what I've done. Because that's what we care about. We don't care about like where you went to school, what you said, like what have you done, right? So even if you like, if you're working at McDonald's,

if you go to like Oswego, figure out your story. I think you've done this really well. Like what is that story that you're gonna put out to the world and it has to be based on something tangible you've done. So if you're just gonna like not focus for four years, you're better off going to college. I'd like to also see the acceptance of trade schools,

you know, in the US. I think that's gonna be a nice safety net. I can see that happening. Those jobs are coming back right now because my generation's super lazy. Yeah, well, so I don't wanna like totally agree, but I agree. Well, when it comes to like using our hands and stuff,

like if you asked a 25 year old to change a tire, they would not know how. Most of them wouldn't know. But it's not taught anymore. So I like the idea of trade schools. I like what Mike says in terms of like, what does your resume say? Talk about what you've done.

Talk about what you've worked on, right? And I just think that you have to have that kind of structure. I think most people will need that. Yeah. I look at it also from the point of view of like, how you're allocating the money. So like, would I rather spend 50K a year on college

or a mentor like Gary Vee or someone? But can everyone get that mentor? Yeah, that's true. So like, I keep thinking like, it's easy to say that. I mean, let me give you this story. So when we started Buddy Media, one of the interns that we had, Gotti, right? He came from Northwestern, right?

And journalism school, and he was a freshman, and he did so well at our company that summer, Mike turned to him and said, don't go back to college. And I literally, we had like a screaming match about this because I said, you can't say that, he's gonna go back to his mother, A, and first of all, you're gonna get a phone call. And second, like this kid needed structure, right?

He needed that foundation. He needed that. Yes, he did. We'll never know. Because he went back. He went back, yes, he did. Yes, he did. Most people need the structure.

I'm not saying that it's worth the money or the four years. I would love for college to be a little bit more efficient and mindful of time and actually what you're doing. I'm not a big fan of like all the required classes. Oh, I hated those. That's why I dropped out. I mean, it's just so stupid. I'm not a fan of like, oh, you have to take a language.

Like, didn't we do that all in high school? Yeah. Like didn't we have that forced on us in high school? Spanish class, yeah. Yeah, like why do you have to pick it up in college? Why can't you pick what you want to study? Yeah, well, you went to journalism school, you said? And a master's. I did journalism.

You mastered in it? Got a master's. So they had an accelerated program, so I got a master's in journalism, which I have not used at all. That's not true. You're an incredible writer. Okay. Thank you. Thank you, Cass. You're welcome, hon. That was pretty nice of you.

I started a company at Northwestern because the internet was happening. So, I'm 50, this is 1994, the internet, you know, the commercial internet was happening. You know, we're talking about like Marc Andreessen and Mosaic and Netscape and Yahoo was now around. And so I'd launched a company in college and spent most of my college career,

at least in junior and spent most of my college career, at least in junior and senior year, like working on my company, which at the time very few people did. Now everyone has a company in college, it seems, including our son. And that just set me on a path that if you can go to college

and focus on something you love and just continue to put in the time, I think what we've realized, and you're like an incredible example of this, you do something over and over and over again, good things happen. You get good at it, you get known for it, and you build a network and you can see opportunities

that other people can't see. So a lot of people are jumping around every year, every two years, or trying different things. We don't think you have to be passionate about it. I know that you are passionate about what you do as we are, but find something that you're good at and do it again and again and again, and you'll have a life you like.

I like that. And then supplement, kids always talk about like, oh, but I've got to only do follow your passion, right? Figure out what, you know, all that kind of stuff. It's rare that your passion will make the money that you need to afford your life. I think that's rare. And so instead of having that mindset, keep the passion,

but figure out what your talents are and then surround yourself with people who fill in the gaps and then supplement your life with the things you love. If it all of a sudden intersects synchronicity, great. But if not, you gotta know what pays the bills. If you wanna have an independent life in which you're functioning and have a balance of something that you do that you love, that's another way to do it.

You gotta be realistic, yeah. I mean, when I started this, I sucked at it and I, it was uncomfortable. Right, but you're doing the hard stuff. Yeah. We know how you feel. I mean, we're re-engaging with content and just in the last year, it's like, man, we really sucked.

We still suck. We still suck. In five years, like keep this tape, in five years, we're gonna be awesome. Oh, I bet. Because we do it every day and it's kind of a practice now and it's getting more comfortable.

We listen to people who are, we started, we had zero, we reached what, 1.3 million people last month. That's impressive. Well done. So it's just keep doing it. And our kids, what's great is your kids don't listen to anything you say.

You could tell them, don't do that, do that, just like out of their head. But they pay attention to everything you do. So they are watching. And they're in your priorities. And so how you treat people, how hard you work, your relationship. If you're a screamer, they're gonna be a screamer.

If you kind of eat like crap, they're gonna eat like crap. We noticed the the biggest thing like Mike and I were talking about what he just said the other day You know, we obviously, you know, we weren't healthy during our last company in the last like 12 years we've really concentrated on health and longevity and Really hitting the gym again and now all three kids work out Wow And when we tried to get them 12 years ago, like, hey, come work out, they didn't want to have anything to do with us. They didn't take you serious.

And it's like, it doesn't matter what you say, it's what you do. And now they all work out. Lead by example, right? Yes. And Cass has the lifts more leg weight than anyone in the family. Really?

That's not true. More than me. What's your leg press? No, no, no. Leg press is not, no. Really? That's not true. More than me. Well, what's your leg press? No, no, no. A lot. Leg press is not, no, we were doing dead lifts. We're doing the dead lifts. Dang, you guys are dead lifting?

Yeah. I hate it, but she was an athlete. She has me doing it, but she's a monster in the gym. It's good, it's good for you. You have to work on legs. You would have skipped legs. It's the worst three minutes of my day. You gotta do legs twice a week.

Most people just do it once or nothing. I do it twice a week because I'm trying to increase my vertical jump right now. I got a basketball game tonight. Ooh, what position? Well, I used to be center, but six, six ain't center height anymore these days. Oh my gosh.

These kids are freaks. They're like seven feet minimum. And they can all jump. Well, can you shoot then? I can't, I need to develop that. So what's your skill then? My game is fast break layups. Okay. Yeah, cause I was a track runner. Oh, so you're fast. I'm fast develop that. So what's your skill then? My game is fast break layups. Okay. Yeah, cause I was a track runner.

Oh, so you're fast. I'm fast, yeah. Ran the 800 meter. Wow. I mean, six six fast is valuable in basketball. Yeah. But yeah, I'm probably like a powerful these days. I can't be a center anymore.

And who do you play against? Is like a- Lifetime league. It's big in New York actually. Oh yeah, lifetime league. Yeah, I'm a member there. Real big in New York. They come here for the national basketball tournament

every year. Yeah. You guys got into pickleball at all? I tried it twice. I have the right frame for it because I'm long and skinny. Yeah. So I think I'd be good if I took a serious. Are you guys pretty avid pickleball players?

I am. Yeah. You play doubles, mixed doubles. I will not play mixed doubles with him. We can work together, but we can't compete together. I'm not what they call an athlete. No, no, no, that's not true. He's pretty good. He wasn't. He's pretty good. The issue that I have is Mike's way of showing his competitiveness is not how I show it and need it on the court. So I'm

extremely competitive. I grew up playing tennis. I played in college. I played after college. And I need him to want to win. And there's a switch that I can't turn off. And Mike sometimes thinks that this is just for fun. And for me, it's not. It's pickleball. You don't take it serious.

I do with her, but if she sees an act, she'll step on it. On the court. On the court. On the court. Like a weakness, you'll exploit it. Yes, for sure. For me, I like having fun playing sports. As do our kids. I mean, our boys are incredible.

And I never competed at the level she did. She was a two-sport college athlete. Finally admit that, thank you. Wow. D1, Mike. It's golf and tennis, it's not real sports. Tennis is a tough sport. Dude, what are you saying?

They're not team sports, they're not team sports. It's. I'm gonna get a lot of hate for that one. But I will tell you. And that's untrue. It's why she's so good at business, because she doesn't lose. And I think our.

Why not like losing? I love that. Our kind of drive comes from like more of fear of losing than like the glory of winning. Like we never thought about, oh, we're gonna make all this money, we're gonna have an independent life. fear of losing than like the glory of winning. Like we never thought about, oh, we're gonna make all this money, we're gonna have an independent life.

It was like, if we fail, we're like, everyone's gonna think we're losers. Interesting. And rejection is always. For you, I'm much more about just paying. You never really got rejected as much as I did. Which is true, you got into schools because of tennis. You got jobs.

We're getting personal here. No, I got rejected from four out of the into schools because of tennis. You got jobs. We're getting personal here. No, I got rejected from four out of the five schools I applied to. You shouldn't have applied to them. That's my whole thing. But I love that I did, because those rejection letters, I have a stack of 60 of them on my desk.

And they've been on my desk every day of my life. That's your motivation. With jobs. Jobs and all the colleges. Yeah, there's no rejection letters from chicks. Like, what else would it be? No, but all of a sudden you said 60. I was like, you didn't apply to 60 colleges.

No, the jobs. I applied to a lot of internships in college. I always wanted to work, and all these newspapers were like, no thanks. Wow. And I went back and I looked at the hiring managers on the letters, and they're all like, most of them are losers.

Hey. Which I like. Mike, stop. I went back and I looked and they're like, oh yeah, they're so happy. So you hold some resentment towards those that wrong. It's not resentment, but like. It sounds fuel.

It sounds like. We had like, so I don't remember all of our investors, but I remember every VC who said no to us. Wow. Everyone. And I see them at a lot of events. And we know the ones too who looked at us and were like,

oh, we're not, we're not going to invest in a couple. Yeah, like there's some who said like us and were like, oh, we're not gonna invest in a couple. Like there's some who said like, and big ones, like brand name ones. There's one who pulled a term sheet. We got a term sheet, we're so happy. They're like, oh, we talked to the partnership and we have to take it back, which is bad.

If you're an investor who gives a term sheet to a founder and the founder, I mean, it's the best day of their life. It's closed at that point. Yeah, and then to hear a few days later that it's the best day of their life. It's closed at that point. Yeah. And then to hear a few days later that it's like, oh, psych, right? I was joking. Yeah.

I see that guy everywhere. I'm so happy. Cause like it cost them, it was early. It costs them 81 times their money on Buddy Media. Cause it was the early round. I know. And Mike also. But I love that. I know. And Mike also. But I love that.

I love that. He also will follow that guy around and just stand by him. Yeah, I'll be super happy. I'm not that petty, but I think getting bullied early on for me definitely motivated me. It's just my motivation. And I'm super friendly to all of them. I don't have a mean bone in my body,

unless someone really. Rejected you? No, no, rejected me. I'm a nice to all of them. I don't necessarily cheer for them in my body unless someone really. Rejected you? No, not rejected me. I'm a nice all of them. I don't necessarily like cheer for them. I'll tell you one thing. Because they weren't cheering for me. I'll tell you one thing that you changed for me,

which was interesting is Mike would never allow if someone in our company decided to leave, which was very rare, he would never allow a party for them. He's like, why are we celebrating them leaving? It's just the wrong way to look at it. And you celebrate people on the way in. Interesting. If they're going to another company.

I know. Like if they were like for some reason, but there was this culture, I don't know if it still exists, that like when people leave a company, you have like going away lunch. I heard about that, yeah. And I was just like, no fucking way.

Like we celebrate people the day they start and every other day, but once they're not on our team, I wish them well and I hope they do great, but they're just not on the team, right? It's like, you know, once- Business. Yeah, like when someone leaves your basketball team, you're like, great. Like you're not on the team.

I also talk to you and I hope you do well. You see them as an enemy now? Not really an enemy, cause I don't see, it just kind of, you're not my people. Like from a team perspective. Having said that, we've had like a lot of people leave to start their own companies, which we love. Which we love.

But I will say it had us change our focus a lot because most people think, okay, like we should do all this like bonding stuff and everything like that. And we took it very seriously how we hired them, the interview process, getting to know them and making a big deal their first year. If you could make it with us a year, that was a big deal.

So we actually didn't have a lot of people who left other than to start companies, which was- Well, Cass, I mean, one of the cheat codes from the book is all about how to put the cult in culture, because it's still work, you're not gonna love work, but if you can create an environment where people are laughing and they're recommending their friends

and they're doing work they think is valuable, like to them personally, you have a really positive experience at work and you have a company that's powered by that. And so Cass, who is an incredible manager and HR director, was able to create rituals and symbols and traditions at a company that you would see in kind of like a cult or a religion,

which I think kept people bonded to each other. And not just through like goofy things, but through philanthropy and giving back and going into the community and every company event would have some sort of social good part, making sandwiches, donating toys, I remember over the holiday cycle for survival, you know, we've helped raise 400 million for cancer research.

Wow. And so that part of the culture of like, how do you do good together is like a really big cheat code in the book. It also helps too, because whatever you start with as a founder, the chances are you're not going to end up with whatever you thought you were going founder, the chances are you're not gonna end up with whatever you thought you were gonna do. You're gonna pivot. And we had that happen what, three or four times

at Buddy Media, our last company. But if you've actually spent the time making sure the teams are working, right? And providing great leadership, which to us means like radical transparency, we would share financials, we would share all the good, all the bad. Oh yeah, yeah, yeah, I mean our investors hated it but never leaked. We treated the employees like they're the board. Yeah. Like we owe you to tell you like what's going on just so you know how

your work levels up to the company. Yeah, so that they can all be aligned and... And that's part of the focus that you talked about. Like they knew what the number one area of focus was, which is really helpful because there's a conversation that happens at a lot of software companies and other companies. You know, the person building the product has a whole, you know, roadmap.

The person selling it is like, oh, I need this for this customer. We're not gonna be able to get this customer until we build it. The product seems like, okay, we have a for this customer. We're not gonna be able to get this customer until we build it. The product team is like, okay, we have a full roadmap. What do you want me not to do? Right? Well, I need all that, but I need this as well.

When you focus and you say, listen, number one is getting new customers on board. Number two is product. You then can like look at both of the team members, say, listen, you both have valid points, but we're gonna build this because getting new customers on board is the number one focus for the business.

You can make decisions as a team. So you go back to your areas of focus to make decisions and people don't feel like you're just choosing sides as a leader. Yeah. You know, we ran the companies as kind of, I think, benevolent dictators. Like we listened, but it was like our decision, right?

A lot of companies these days are run as like democracies. Crowdsourcing their shifts. Which is hard. With a board and everything. Yeah, just and like, hey, employees, let us know what you think. Let me send out a survey, like yeah. I hate someone else's service.

Yeah, where it's like leaders lead and you know a leader when they're leading and most people who aren't leaders Want to know that someone has their hand on the steering wheel? Yeah And let's also forget that because we shared all the information and because we were relentless with being transparent When we did have to pivot no one jumped ship Right because a lot of people are gonna be like, oh my God, I have no idea what we're doing now. Right?

They'll freak out and they'll be like, screw this, let's all go. Right? One person leaves, two, then it becomes a mass exodus. That didn't happen when we had to pivot. And I think that's because, again, we committed to making sure that we were focused and then we shared that focus 100% in every conversation.

Hey, remember, you're doing this because these are our top three goals. Hey, remember, it would be all teams, one-on-one, department meetings, by the water cooler, you name it. Yes, it is harder as well being remote. I hear this all the time, but I don't buy it. As leaders, you gotta go where the hubs are

and you gotta meet with the people. You guys went fully remote? We didn't, because we sold the company before COVID. And if you remember, it's like 2019, no one did video calls. Like that whole Zoom thing, like we used to use like Skype way back when, but it was not a thing.

Like you wouldn't hop on a work call and a t-shirt from your house, like a video. And you wouldn't, yeah. We're not believers in remote work. We think that if you're doing something that's important, being together, bouncing off each other, that electricity is important. The energy is big.

I'm big on that too. Yeah, and just getting to like, great companies you can feel it. Like you walk into an office, you're like, wow, I could feel it. I don't do any pods remote, all in person. Which I love. And it's just, we're in a world that everything's so easy,

instant gratification, like taking the time to put down the phones to interface with your coworkers or colleagues or new friends, like it's where it's at. Yeah, well done, that's phenomenal culture because job hopping is a common trend these days with my generation. Yep. Every two years.

I blame a lot of them. Why do you think that is, by the way? That's a good question. I think it's a lot of things, but I don't know. Detention span dropping. I don't blame it on your generation, though. Yeah. I don't, we're not that much older than you,

but I think companies have taken people for granted and they haven't evolved with the digital society I think companies have taken people for granted and they haven't evolved with the digital society we're in. And so. What does that mean? I mean, that sounds very vague. So hiring managers don't get back to people who apply. Well, the ghosting is just horrible. A lot of ghosting.

So companies ghost. Then people start at companies and there's no constant feedback, number two. Number three is the best thing you can do for employees is show them that you see a path for them. A path for growth. So the first thing I would ask any new employees, what are your goals?

Not here in life. Do you wanna start your own company? If so, I wanna know that. Do you want to work for GE? Do you want to travel the company? If so, like I wanna know that. Do you want to like work for GE? Do you want to kind of travel the world and just get super rich? Just tell me what you want. We're talking about like small companies.

We're talking about like starting companies. Like this isn't what you do if you wanted to go and work for a corporation. But most companies ignore this. I agree. Most companies look at these young people as just cogs. We see it with our kids. They also don't, they don't believe that everybody counts, right?

So it's not that, like Mike called us benevolent dictators. I actually believed that everyone's opinion counted. It didn't mean that I actually was like, oh, I'm gonna sway my vote, but I am gonna listen to everyone despite age, where you've come from what your background is I think that's important again It goes back to the energy because if everyone's aligned with the mission and you're in the same

You know headspace and you know how you're rowing right the pace, you know that you're in this boat together Good stuff happens. I Agree, but no happens. I agree. But no, I definitely agree with you too. It's interesting, because my grandparents had the same job their whole life. Yeah. And that was common for that era.

I mean, I go back to like what you said, you think your generation jumps a lot. Is it that they're just not happy with the perks or they get bored? There is a lot of comparison in my generation. So they'll see their friends making more money on social media or whatever, and they feel like they need to keep leveling up.

I think there's not a lot of patience in my generation. Oh, so there's no earnings. So it's immediate gratification. I don't like this. Oh, all the time. Even myself, I find myself wanting instant gratification when I make a post, if I don't hit a certain amount of comments,

I'm like, damn, like what's going on? So I find myself in that. And a lot of kids think like that. That's hard. That's a hard way to... But I think that like what you just said is like part of your craft, which is why I love kind of content these days. I went to journalism school, you would publish in the Chicago Tribune,

and you're like, there's no connection with the reader. There's no feedback. Right? And so I think that like paying attention to the metrics that matter is what propels you forward in any business. And you know, unfortunately, we're in a world that it used to be we didn't value like old people as a society. And now I don't think that a lot of companies value the young people because it's never

been a better time to be young. And people, every young person I talked to, I was talking to a 10 year old the other night, we had dinner at a friend's house, I'm learning about apps, I'm learning about kind of culture, I'm learning about like all of this stuff, which is under the radar. And how they communicate. And so that is what companies should be using in their-

And not be fearful of it too. Yeah, and I think that like, we're seeing the death of the old manager. Right. Or the career manager. The career manager and you know in a few years all the managers will look like kind of us in some way,

right, and I think that that's great. Like we are the first generation that had email in college. You know so everyone younger than us is just digital. You barely did. Well we didn't have email, we had email but no. So everyone younger than us is this digital. Well, we didn't have email. We had email, but no one emailed us. Well, that's the difference, right? Yeah, now people email you.

It's like, why have they had email? I do find it funny that I had to teach the boys, especially, and our daughter, but the boys that like, hey, when they're applying to internships, work is done over email, not tech. And so please check your email. Yeah. I prefer text.

Oh, I mean, I get it, but you can't do long, you know, you can't, you can't move a product forward in a text slack. You can do it in Slack. But Mike, Mike had this thing where you wanted to get the whole family on Slack. Yeah. How'd that go? Not well. We're it in Slack. But Mike had this thing where he wanted to get the whole family on Slack. How'd that go? Not well. We're not in Slack. I just, I lose a lot of stuff.

Insurance cards, I'm like, just get it all on Slack. Let's all just work on Slack. Yeah, it's hard getting the fam in one little chat. We have some fun ones though. Ours is called Fab 8, cause we had three dogs. It's like chat. Like chat is where we live our life. Like I think all of us.

And you know, we want people to text us when we have a relationship. Like if it's an email, we get buried. I have people who are like mad at me for not returning email. I'm like, I have a thousand emails. For you, I get back to you. I try to, but it's just very hard because if you are going to do great work, Oh, here it's just very hard because if you are gonna do great work,

Oh, here we go. you just can't sit in front of your computer, right? Like answering emails is doing other people's work. And so I open my email when I want to. Or it's pushing the work to the right person. Listen, I'm not the most responsive to something, including my wife, I guess. I've seen this approach.

I think Damon John talked about it. You can become a slave to your email inbox. I was a slave. Checking it every 10 minutes. So maybe I've gone too far to the other side, but we'll talk about it later. I check at least twice a day. Just twice?

Yeah, cause sometimes it's important. Wait, that's it? Is that not a lot? No, that's not a lot at all. I feel like that's a good amount. Interesting. Really? Twice a day? How often do you check yours? I would say five. No, that's not a lot of all. I feel like that's a good amount. Interesting. Really? Twice a day?

How often do you check yours? I would say five. No way, you do it more than that. Wow, five. Well, no, you might get the notifications, you don't care about them. I mean, so I think we scan. So we've inbound from like a hundred companies,

we have all their stuff. 25 times. So I'm scanning, and I'm also constantly saying, hey, if you really need me, it's an emergency, text me. Yeah. Because I can't guarantee. Well, you guys have hundreds of companies.

I only have this. Yeah, yeah, yeah. Yeah, that makes sense. But it's, you know, everyone's gotta figure out how they can work in a way that like, lets them do their best work. Yeah. Right, like I have a very distracted mind.

You could never wear an Apple watch. Yeah. Like I get distracted easily. You have ADHD? Yes, among other things. And so for me, it's very hard, like all these notifications disrupt my flow. I'm all about flow.

How do I get into this rhythm of doing what I think is important work to me? No, I live on do not disturb. I think I'm on that mode all day. And it's the best thing for your brain. Probably. It lets you do your work. Yeah, well, I just- Do you want kids? I do. Yeah, so- That's why I asked that question partially. It's just my own. Well, I would have them when you're young and do this and work hard because I think the best thing is that you get the time back when they're older. Bigger kids, bigger problems.

Yeah, I was thinking 30. Yeah. For 28 right now. Yeah. Great. 29, 30. Let grind now when they're little, everybody can love them. It doesn't grind when they're big.

Right after, after they need you, they get to that tricky, like 12 to 18 is just, you got to be around them. You're gonna be a great dad. Thank you. You know how to listen, you know, to communicate, like, you you got to be around them. Yeah, you're gonna be a great dad Thank you know how to listen, you know to communicate like and you can be cool. You're gonna be present And that's what it's about. I love it and you're still gonna mess up That's what we also your life and you're gonna feel like a loser Like worse parent ever every day. Yeah, I know it's challenging. Yeah

Well guys, it's been awesome. Anything else you want to close off with? No, I just appreciate you having us on. I appreciate you having the book there. Yeah, check it out. We'll link it below. Yeah. No, I just thank you. I appreciate it. It's been fun talking with you.

Yeah, and everyone reach out. I mean, we're... We're here to help. Don't email him, though. Don't email him. I mean, listen, email until we respond. It may not be right away, but all of our info is castandmike.com or shovelingshit.com. And the only reason we put this out was to help you build your confidence as an

entrepreneur from the mistakes we made. So here's our 50 cheat codes that we think will like help you avoid issues. You'll probably make all the same mistakes, even though we'll tell you like what to do. But hopefully you avoid some of the pitfalls. I love it. We'll check it out guys. We'll put the, uh, is it on audible too?

It will be June 3rd. It comes out and then, uh, we'll be in a hundred different countries on audible. And obviously you like analog. That'd be Amazon. It's a lot of it. Yeah. I'm an audio book guy, so I'll definitely give it a listen. Thanks guys.

Thank you. Appreciate it. Yeah, I'm an audiobook guy, so definitely able to listen. Thanks guys.