SHOVELING SH*T: The Entrepreneur's Messy Path to Success with Mike & Kass Lazerow

0:00I don't even know who invested in us, but I know everyone who said no. You need someone who's not going to drop the ball when you hand off things to them. This is Right About Now with Ryan Alford, a Radcast Network production. We are the number one business show on the planet with over 1 million downloads a month. Taking the BS out of business for over six years and over 400 episodes. You ready to start snapping next and cashing checks? Well, it starts right about now. What's up, guys? Welcome to Write About Now. We're always talking about how to make you get right and in the moment. We could talk about yesterday.

0:39We could talk about last week. We could talk about a month from now. We could talk about the future, but we're here to talk about now. Because you know what? Action is now and present is here. And we need to talk about shoveling some shit. That's why. That's what we do on this show. We talk about what's real. That's what it is. to be an entrepreneur to business person in today. So, you know, I went right to the source. Cass and Mike Lazaro, they are authors of Shoveling Shit. They're entrepreneurs, few brands you've heard of. You know, we'll let them name drop. What's up, guys? Hi, thanks for having us.

1:11It is great to be here. Love the energy and congrats to all your success. Guys, set the table for our audience. They know, they're going to know you now, but they probably know a lot of the things that you guys have touched. You've touched a lot of things as serial entrepreneurs and now authors of an amazing book. But I'm going to let, you know, we're going to make this an actionable learning lesson here of a show. I'm sure they can find your stories all over for the long narrative. But it's important, though, especially as a couple, as a married couple with children, everything you've been through.

1:49I do want you to set the table for them. And I'll let maybe Mike, you choose. You or Cass could go first. Cass, please. take it away. All right. So, you know, we're Cass and Mike, Lazaro, and he and I have been working together, if you can believe this, 28 years together. We started working together when we were just dating. And I had this crazy idea to start golf.com, where avid golfers could come and track their handicaps online and book tee times. And then we started a big company called Buddy Media. And we ran that and grew that. It was the top social media marketing platform for all the top Fortune 500 brands.

2:32We sold that to Salesforce in 2012. And we've been investors and VCs since. And we wrote this book, Ryan, because we want to help entrepreneurs. We want to help them with the cheat codes. We have like 50 plus in this book. And we're really here to connect with your audience and help them to not step in the shit that we have stepped in. Let me just say this. I'm glad you cast a little something called golf.com. Brilliant. Brilliant idea. I read this book and I was reading it. I was like, I wish I had had this 10 years ago. You know, because I'm about 10 years into my, I worked for 15 years for other agencies.

3:15And I was like, damn, I wanted this 10 years ago. I would have saved me a lot of fucking pain. I'm telling you, there is gold in here. Like it's it is phrased and formulated in a way that it's absorbed. Like I'm like, that made sense to me the way you kind of positioned it with the examples combined with the story. So it is the narrative of the entrepreneur's guidebook. You know, that's not as interesting as shoveling shit. I know I'm a creative guy too. I love shoveling. It is. It really it really reads that way. And I sit here amazed. It's the names like golf.com and the things that you guys have worked on and seemingly how I don't want it to just kind of fade off to the side.

4:00Like those are that's a big fucking deal. Like, yeah, you know, like that's a huge. You think, OK, well, I had golf.com. I mean, did you have the URL when you came up with a name? So if you can believe it, back in 1998 when we started the company, the only URL we could get at that time was Golf Serve. So our original company's name was Golf Serve. And then we backed into this asset that we were able to buy. Mike, who is it from that we bought it from? From NBC. Yeah, from NBC that we had just had it dormant. Like, made no sense. $289 ,000. ah i was hoping you're gonna say mike yeah 289 dollars yeah i mean it was it was worth that i believe me as that asset in the in its time for something like this oh i mean that's probably cheap but it's a different world right now it's all about apps and streams and like the front page of a website doesn't matter but when we started there were people at yahoo that created the index of the web, right?

5:06Yeah. People who basically said, Oh, you're interested in golf here, 10 sites you should check out. So it was important back then. Yeah, it was. What was it like running golf.com? We probably learned more from golf.com than we'd learned anywhere because it was both a colossal failure and an epic success. And so we started the company and within a year of doing the company, we got an offer from a Sequoia-backed golf company in Silicon Valley called Chipshot.com. October 99, eat toys, go in public, worth billions of dollars, internet's here, height of the frenzy. I'm like 12 years old. I forget how old I was, I was like, Cass is a little older, or some people say a lot older.

5:52um and we didn't know much and these guys are like we want to buy your business and then merge it with our golf club manufacturing business and sequoia had like backed google and all these big companies and then april 2000 came around and the whole market crashed and we got a call actually right before that saying oh by the way we're out of business we can't pay any of your people and you can buy it back but you know there's nothing we can do for you and we just had to shovel shit i remember that call really i mean that call is like in my not only my mind it's like in each cell like i was like what does happen is this reality like and we're pot we're totally in so when you work with your spouse there's no like oh my spouse has a great job like we'll be fine.

6:47It's like, oh no, we're like having one kid, health insurance, zero income now and no money. We hadn't really made any money at the time. And don't forget Mike that ship shot had already transferred in those like two and a half months, they had transferred the bank account. So we had no access to anything. Yeah. So that was like, Cass is fucking the best. Like I'm like freaking out in the corner. She's like, we got this. She got all the employees. She was super transparent. You know, she runs the companies. I do like sales and biz dev and raise money. And we, it's been three years, three months trying to raise money to kind of buy it back and relaunch it.

7:26And somehow Cass ensured that none of the employees left, which was miraculous. Talk to me about the raising money thing you talk about in the book, by the way, the handbook for an entrepreneur. It's, you know, it's a muscle that you have to develop and you get better at it the more you do it. So there's a lot of fear that you build up, Right. Like, oh, my God, I don't ask this person for money. Oh, my God. At the end of the day, you know, it really is about your own fear because all they're going to say is yes or no. Right. It's like they say no, just move on. And that's something I think for me, Mike's much better than I am.

8:01But for me, I think I just realized, oh, like the worst thing could happen is they just say no. Right. That's it. So I think that what you've done, Ryan, what like a friend who we're talking about, Gary Vee and others, that's raising money, right? You don't go to investors. You go to customers. You win the business. You generate the revenue to then generate the profits to plow back in the business to grow. And so our heroes are the people not that have the safety of venture capital, right? But it is those entrepreneurs, like a lot of your listeners, who don't have the safety net, who are running restaurants, who are running service companies, who are running agencies.

8:43And they need the revenue to survive. And that's how you fundraise. And if you do a good enough job on the customer side, then maybe you have the ability to raise money to do an acquisition or to take some money off the table or to do, to make some moves, right? Yep. We've always been in businesses up until now that requires building software and a lot of upfront costs. And frankly, it's just easier for us than I think what you and a lot of others have done, which is hard. I appreciate you saying that it is hard, but at the same time though, like there's brilliance in both sides, I think, you know, like depending on what works for you, Like, cause I'm, I ask even for my own self, I mean, cause I'm developing something now that's tech heavy and you know, it's like, and I've never had a partner and I'm like, or I've never had a dollar from anyone.

9:39I have no debt in the bank. So protect that. Yeah. And it's, it's not easy and it's not. Don't pee poo that. Like that's very rare and awesome. Investors are great. some of our best friends, but you're bringing a partner on board. And so unless you're ready to communicate and report and listen, it's, you know, it's work. It's a relationship. I do think it's fascinating for you guys being a husband and wife, founders of companies and investors together. You talk about in the book, if you are going to have a partner and a founder, those skill sets that work well, like you fill a gap. Like I have a certain number of skills.

10:25You need to work with another person or group that fills the holes you have. And it sounds like that work, maybe that's why it has worked. I know it's been work, but for you two, because like you said, Mike, you know, you've got the operator and then the sales and marketing and, you know, maybe idea guide. I don't want to say you don't have ideas cast, but I'm just shortening. The split is totally there and you're dead. Yeah, you nailed it. Yeah, you nailed it because that's exactly what you need. When you have co-founders, you really do need to figure out how to balance out the skills. And if you overlap, there's going to be just absolute micromanagement and paralysis of decisions.

11:05So the best thing you can do is have a co-founder or more than one co-founder that had different skills. And that's when things really gel and you build this like implicit trust and you can move very fast. That's been the hardest thing for me. I've become a chameleon in some areas, but I know where the gaps are. And as an entrepreneur, and I think as people listening can relate if you, cause it's like, trust is the word cast as the perfect word, because I don't, I don't have a hard time trusting people. Like I trust my employees. I'm not a micromanager, But when you don't have to think about your weaknesses because you know it's getting – it's like having a good wife or a good partner or get anything.

11:45Like it got your back. You don't have to think about it because thought takes energy, takes – it's distraction. It's the mental bandwidth that it takes up in your brain going, is this person really doing their job? And then that takes you away from doing what you're great at. Yeah. And has that worked for you? Oh, yeah. It seems like it's got to be your super strengths as being able to count on it. We call it our superpower because when I say I'm going to do something for Mike, he doesn't have to worry when, you know, he says he's going to do something, he delivers. So when you have that and you're starting a company and then you're running it and then you start to get like super fast and you hit the gas and you're scaling, that's what you need.

12:31You need someone who's not going to drop the ball when you hand off things to them. Now, as investors, how do you evaluate your investments? How do you, I mean, are these just, they just get put in front of you and you go, oh, we like this, but don't like that one? It seems like that. I mean, looking at our investments, we've done space, we've done liquid debt, which is water in a can. We've done game companies. We've done music festivals. We actually spent a lot of time thinking about that because we did the first 75 deals off our own balance sheet. And then we started a firm, which just meant accepting some outside capital as well.

13:10And how you make decisions about investments is how you make money. I mean, that's the make or break. And what we realize is how we make decisions as investors is how every entrepreneur should look at their business. And so we put together what we call the go gauge, but it's a very simple six questions, idiot proof. The six things are very simple and it's what's a product? Why is it different? And what's interesting for you. And I know a lot of your marketing background is not that different than how you come up with kind of great marketing ideas, right? What's a product? Why is it different? Who's going to buy it?

13:47Not what the market size is, but who specifically is going to buy it and how many of those people, right? We're in the golf business. We didn't own a golf course, So we're not getting tea time revenue to really hone into like who's going to buy it. And then it comes down to where we think we've outperformed, which is sales and marketing. How do you get people to find out about the product distribution and operations? How are you going to get the product to people? Which, you know, for this company, Liquid Debt, we had no idea how hard that was going to be. we're putting the water in the can in Austria, shipping it by boat to the U.S.

14:25just to get it to distributors, to wholesalers, to get it to distributors, to get it to retail, to hopefully get it to a customer. H2O, no. So have we done another deal? Have we done another liquid deal? No, because they're very hard. And the last one is just, does a financial model make sense? Not Not from a Goldman Sachs analyst perspective, but from brass tacks, unit economics. You're selling it for Y. Can you make it for less than Y? What is the net profit that you're going to make off of the product, the margin? And then what do you need to support the company? And especially early on, things pivot so much.

15:07You talk to customers, they punch you in the face. And you've got to change. So we just want to make sure we start with something that makes sense on the spreadsheet and then pivot from there. I like that. That sounds practical, but with a blend of intuition and belief, which I think that's kind of got to be it. Right. It's like, yeah, the numbers got to look good and you have all this stuff, but you got to believe in it. Right. So what I just said is like the table stakes. And then if we get through that, they meet Cass. and the entrepreneur. And it's impressive in a great way. You know, every entrepreneur, even when we say no, let's just say gets a lot from their conversation with Cass.

15:52We hated when investors would take a meeting and then they ghost us. They're like, they don't even, and I know every one of their names because those are the people I remember. I don't even know who invested in us, but I know everyone who said no, like every round. Oh my God. You and I are cut from the same cloth, brother. Everyone who says no, like I have a, and I have all my rejection letters right here from college. I have like, I have a hundred jobs that I was rejected from, but regardless for me, it comes down to, do I want to have dinner with this person once a week? Like, is this someone I want to hang out with?

16:22Because you look at like Scopely took 10 years to go from that initial money we gave to a$5 billion exit, right? You look at Mike Cesario, liquid death. He's in it six years. We've been working together. We love each other. We love hanging out, right? We love jamming on the business. We love working on problems. So for us, it's do we love the entrepreneur? And is it the right entrepreneur for this company? Just because it makes sense on paper, it could be the wrong entrepreneur. I'm not going to build a space product on the wrong guy. And also coming back to what you said, Ryan, which is, does the entrepreneur or do the co-founders know what they don't know so that they're filling in the gaps, those holes you talked about earlier with the right people around them in their leadership team.

17:08So I'm always looking for that. I'm looking for humble, high kind of entrepreneurs and ones that know, say, look, this is not my expertise, but here's the person who does it. I love, I'm going to get back to the book, Leaders Shovel First. Yes. This is a big one. And I have a subsection within this, and I have my shovel. I had a page folded, but my shovel was what I used to actually keep the page, the bookmarked. So I'm telling you, guys, buy it for the shovel, stay for the book. You know, like. I love that. We're selling shovels. Yeah, yes.

17:53So it sounds obvious, but I'm going to let you guys. I mean, it's core, right? If you're going to get the team, they got to see you shovel. Not only do you need to do it first, it reminded me of kind of the analogy of like CEO and official mopper of the office, you know, kind of like, am I making the right connection? I mean, that's what I took away from it. It's kind of like. I mean, we're talking startup world here. So if you want to get a group of people to jump and take a risk and work for you when you have nothing but like air, right, as promises, like, hey, we're going to make this a big company.

18:32And you really are just selling them a story, right? You're selling them an outcome. You're selling them a feeling they get when they come into the office. Then you also have to make sure that you show up every day and you're no better than they are, right? you're a good leader you're going to handle you're going to make the tough decisions and you're going to be 100 transparent and you're going to lead by example and that can be you know putting together mailing lists like we used to do in the old days like everyone's stuff in envelopes or in our golf.com days we'd ring a bell and everyone would start packing golf balls into packets or it's basically saying like we're going to give back to this community and we want everyone to be a part of what we're doing because it's really incredible.

19:20So it's all about leaders shoveling first. It's also a very different vision, I think, for leadership than maybe some younger entrepreneurs have. Too many of our companies that we work with, the founders treat them like democracies. And I don't know if everyone's noticing what kind of pressure testing democracy as a model for government. Let me just tell you, it does not work at companies. Your job is to be the boss, not the buddy. You're a benevolent dictator. You make the decisions. People want to be led with compassion, with clarity, with transparency, not by a dick. Just tone it down, listen to your people, but make decisions, communicate why, align everyone's interests correctly with financial incentives, and the rest take care of itself.

20:13If you're working for a company that has a leader that isn't leading, that's just makes decisions based on the last person she spoke to, or he spoke to, those are not going to feel like very empowered employees. And so it's really kind of look at yourself as, you know, a very nice dictator. You have the most, you have the most to gain, but you have the most to lose. Yeah. Like if it goes out of business, you know, it's on you. if you run out of money and you're not going to be worrying about, oh, I listened to this person and tried to make a decision that kind of threaded the needle between what everyone wanted.

20:55And that gets so many companies turned around. I want to spend a moment here because I'll say this, I have failed more than I can count. I am not the best leader on the planet at all times, But I'll tell you the one mistake I haven't made in my 10-year journey. I'm not everybody's buddy. Like, I'm not best friends with any. Like, I like my employees, and I want good people, and I want there to be camaraderie and all that. That's the one thing I think I've figured out early on. It's just this is just not going to be my best friend. You know, like, it just does not work that way. And that's number one.

21:36So I related heavily to that, Mike. And number two, we do live in this world where this generation and pre-COVID and post-COVID, I've struggled a bit with the employees that worked well under me pre-COVID and the ones post-COVID. My wife's like, you used to be so good with employees. Now everybody doesn't like you. And I'm like, no, I haven't changed. But there's this sort of coddling and, you know, again, there's some fine lines here providing the benefits of work and making it feel comfortable and all that. And some of the amount of coddling, it's a fucking job, you know, like I don't know when that switch.

22:19I agree with you. I want self-respective on that. Y 'all know what I'm trying to say. You and I are going to be friends on this. And I think, listen, I think, you know, COVID really did impact a lot of people and it really changed how people work. It also changed people's perspectives. And I think somewhere along the way, probably, you know, result of, you know, helicopter parenting. Right. You know, all of us wanting more for our kids, but not letting them fail. Right. You need to have really good, you have to have kids that can fail, right, in safe ways so that they understand that they are resilient and can overcome failure.

23:03So you have that, then you get, you know, COVID and then you have technology. And I think you're getting this, this collision of all of these traits and producing people who, you know, they kind of want to work, but they don't want to work that hard. Right. And they need a lot of encouragement. and that's on top of like the previous generation that needed a lot of validation, right? That they were the greatest things in the world because somehow in our country, we give out trophies for second, third, and 50th place. Don't get me started on that one. Well, Cass, second place is okay. Like that's silver medal in the Olympics.

23:44Let's not get crazy about this. Second and third, I'm not saying you're happy with it, but let's still give like bronze medals just after that. I didn't talk. I'm not talking about the Olympics, but Cass is the most competitive person you'll ever meet. Oh, I like Cass. Okay. You know, but, but I, I hear it. I hear what you're saying. I hear it. I felt your pain as well. And, um, there's this kind of like, yeah, I'll do, I'll do what I can between these hours. And, you know, we got to get back to wanting to show up and rise to occasions, that kind of mindset. I, I, it's a struggle. I mean, it's real.

24:22And I have some good people now and I love them and they do a good job. And, and not even my current, I've, I've downscaled. I'm lean right now, baby. I'm leaning mean and fucking dangerous. But, you know, I've watched it, man. And that's why I was, you know, relating to these parts of the book where I'm just like, yeah. And I got to read You couldn't attend every one of four kids' games and practices like you do without having a team that is epic. I know your businesses and they're very service and operations intensive. So the shit don't shovel itself at your businesses. Absolutely not. There's no AI that's just going to push a button and boop.

25:11I wish, Mike, but no, you're right. You're right. And so knowing how there are entrepreneurs who can't leave their desk and that's not an entrepreneur, that's a job. Yes. You should be able to empower people, pay them well, communicate clearly the focus of the organization, what we're trying to accomplish, where we're going, what's most important. Give them the resources they need to do their job. And if they do it, that goes on the promotion list when you need to hire someone who's above them, right? So, we have people who started as babysitters for us who ended up as senior people. One who's a senior executive at LinkedIn, Abby Lauderback.

25:57And we believe that people do well, care about their future. Too many entrepreneurs think it's all about money. employees want to know that you care about them. And that means that you're thinking about what's next for them. What's the next step in your organization or outside the organization. And if you do that, they feel like they're seen. Yeah, it's good. Good points, Mike. And true. And I do. I've had a lot of good people. It's just that I felt that change though. Like the last It's like, because I've gone through, let me call out a space spade. 18 months ago, I kind of was just fried. Like I'd been, I'd done the ad agency business and, you know, for others and myself, look, service business for 20 years straight, you know, it weighs on you.

26:47Like every conversation was weighing on me. Like, you know, because, you know, in the service business, you only hear about what's bad. You know, like I only get the answer, the how can I save the business calls, you know, or how are we going to land this plane calls? And I was just fried. So I kind of I kind of indirectly stepped out of the business thinking it could kind of run itself. Oh, yeah, that didn't work. I mean, when you think of I mean, hopefully it's OK. I ask the question, but when you think of everything you've learned in the 10 years, like what are the cheat codes for you that you wish you'd known?

27:24All these cheat codes are just stuff we learned the hard way, right? Yeah. Like, especially this one, Caswell admit, I'm not a born leader. I was an awful leader. I would wander the office. I would tell the engineers, Hey, wouldn't it be cool? Like I would do everything you shouldn't do. Um, but are there any cheat codes that you've picked up that you think that are like, gold for you now? I mean, mine became more self-awareness as a leader and learning that is a different self-awareness than employee Ryan, you know, like even at the highest level. I mean, I was a CMO and been, you know, the highest of big time agency, like it's, but still it's a different self-awareness you have to have with your leader combined with I am a I can be myopic and here let me let me explain I'm very flawed person like we all are I know my flaws I know them well no one knows them more than me but I'm very fucking driven very driven I can't imagine someone not being driven like I am and I used to think everybody was that way like they we all had our different flavors of ice cream, but we started at a baseline that everybody's this way, right?

28:44This is the human nature. This is humanity. We are Americans. We're all driven to like, just do incredible things or not subtle for average or whatever. And I just, I, even as an entrepreneur, I thought I worked my first four years thinking everybody was that way. So I just assumed that was the baseline. And then they had skills in specific things, but it was never in question that part. And learning that that is not true. Especially what you have. Yeah. Expectation. Unrealistic expectations. Yeah. Yeah. Is the number one thing. Yeah. I mean, I think what saved our marriage and our companies was kind of my self awareness journey.