Shoveling Shit: The Messy Truth of Entrepreneurship

John Jantsch (00:00.821)

Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is Jon Jantsch and my guest, plural, today, Mike and Cass Lazerow Lazaro, the seasoned entrepreneurs and investors best known for co-founding Golf.com and Buddy Media, the latter required by Salesforce for $745 million. They supported nearly 100 early-stage startups, contributing over $10 billion in realized

gains but today we are going to talk about their latest book, Shoveling Shit, a love story about the entrepreneurs messy path to success. So welcome to the show, Mike and Cass.

Kass Lazerow (00:43.033)

Thanks so much for having us, John.

Mike Lazerow (00:44.914)

Thank you.

John Jantsch (00:45.141)

All right, you we have to actually start with the title. The metaphor is, I love being an entrepreneur. It doesn’t sound very fun.

Kass Lazerow (00:55.077)

Well, we kind of looked at it that, you know, what is it that you do every day when you’re an entrepreneur? And, you know, I said this to Mike the other day, it’s about probably 10 failures and one win a day, right? So you’re shoveling nonstop and you get that one win and that’s what keeps you going. It’s kind of like golf to tell you the truth. So.

John Jantsch (01:01.823)

Yeah. Yeah.

John Jantsch (01:12.831)

Yeah.

John Jantsch (01:17.781)

Yeah, that’s right. That’s right. I’ve many of time I’ve stayed on the course because I had one good shot.

Kass Lazerow (01:23.647)

One good shot, that’s right. So we wanted to be the most realistic when it came to a title.

John Jantsch (01:31.089)

Yeah. I think that, I mean, obviously you’re talking about the fact that there are messy aspects of it, but that’s actually how you get through is embracing that, isn’t

Kass Lazerow (01:41.327)

That’s right. That’s right.

John Jantsch (01:44.093)

So how has it been? I don’t know how long you all have been together, but I assume that your entrepreneurial journey has been mostly together. So how is that actually? I, I’m sure you get that question all the time, you know, because I think a lot of people probably can’t imagine working with their spouse. So how, how do you guys make that work? Or I guess first I should say, do you make that work? we lost you Mike.

Kass Lazerow (02:09.477)

We can’t hear you, Mike.

Mike Lazerow (02:12.644)

We make it work because it works. And when I say that it’s because we do very different things, even though we are start the companies together, Cass is an incredible operator, very detail oriented. She thinks in spreadsheets. I am much more of the visionary salesperson, product person. think in screenplays and PowerPoints and more creative medium. And whether you’re married or not, having a co-founder who you compliment, whose strengths

John Jantsch (02:14.505)

Yeah.

John Jantsch (02:19.199)

Yeah.

Mike Lazerow (02:42.864)

aren’t necessarily your strengths and whose weaknesses you can make up for really creates a partnership where you could rely on each other. If we did the exact same thing, I think it would have been a very different story. Let me just tell you, John.

John Jantsch (02:55.965)

Nothing would have gotten done, right? I did a great, a little execution. You know, as I listen to you describe that though, I mean, if we can go into a little bit of couples therapy here, that’s probably the recipe for a good marriage too, isn’t it?

Mike Lazerow (02:58.002)

It would have been harder.

Kass Lazerow (03:10.925)

It definitely has been for us because we divide and conquer. And I think, I will tell you that the times that we get into disagreements are when we are in the same lane. And we figured that out actually writing the book because when we work, we don’t get in disagreements. We might say we don’t agree with a decision, but when we wrote the book and parenting, parenting is very difficult with two people, it was harder.

John Jantsch (03:14.549)

Yeah.

John Jantsch (03:22.783)

Yeah.

Kass Lazerow (03:39.597)

And so we realized that when you can defy it and conquer it and you have that implicit trust that each of you own something and has the expertise to do it, then you’ve got to delegate and let go.

John Jantsch (03:54.399)

So pretty common desire for people out there that start businesses to like create this healthy work life balance, right? You’ve heard that a billion times, I’m sure as I have, you lean into something you call the imbalanced life. And I actually, I’ve never called it that, but actually I think I’m going to agree with your concept because I think that’s really what makes it work. But go ahead and explain how that or elaborate on that concept, guess.

Kass Lazerow (04:10.181)

That’s right.

Kass Lazerow (04:24.005)

So with entrepreneurship, you have no balance because the thought is that you can only do one thing really well at a time. And if you think about your priorities, you’re going to be all in. So it’s the first thing you’re thinking about. It’s the last thing you’re thinking about when you go to sleep. And you’re probably dreaming about the to-dos that you have to do, if you’re even getting sleep. So this concept that everyone always asks us, well, how do you guys do it? What’s the balance?

John Jantsch (04:27.317)

Yeah

Kass Lazerow (04:51.545)

There is no balance. There are times when you’re all into one thing and other things suffer, right? I’m not saying they’re suffering to the point of massive consequences, but they’re not done with the same probably intensity and clarity as what you’re really focused on. So we just don’t believe that there’s a balanced way to go through life when you’re an entrepreneur, because you will have things that you have to make decisions about, and they’re trade-offs.

John Jantsch (05:21.781)

Yeah, and I suspect there’s a great amount of stress that that accumulates with people who feel like they have to have that right but but you’re almost admission to say hey This is gonna suffer this month or this quarter because we got to do this I think it’s probably a healthier way to look at it, isn’t

Kass Lazerow (05:28.901)

Great.

Kass Lazerow (05:33.646)

Yes.

That’s right.

Yeah, and also it kind of lets you off the hook, right? That you have to be perfect in all areas, especially if you’re an entrepreneur who has kids, right? Because relationships suffer when you’re doing something and founding something because you’re all in. And so, you know, we looked at it like when our kids were little, and I’m talking like five, three, and newborn, we knew that they were.

John Jantsch (05:41.737)

Yeah, yeah, yeah.

Kass Lazerow (06:06.297)

they were getting probably 80 % of us, they just weren’t getting the 100 % totally on every single thing.

John Jantsch (06:13.779)

Yeah, they probably survived. So, are they coming to anywhere close to an age where they might join you in some of this? Yeah.

Kass Lazerow (06:15.833)

They did great.

Mike Lazerow (06:16.338)

Thanks.

Mike Lazerow (06:25.434)

Yeah, they already are. you know, we have a son, Miles, who’s launching a business very soon. He’s working on it. And we’ve done a lot of work with their son Cole on our golf team and he’s a business major at Emory. you know, Viv has high executive functioning skills and is an incredible operator. Like her mom, if you’ve ever seen her plan something, you can see that Vivian, our youngest, got a lot from Cass and, you know, really

John Jantsch (06:26.738)

Already are,

John Jantsch (06:45.599)

Nice.

Mike Lazerow (06:54.874)

Everyone’s born an entrepreneur, we think. Many of us go through the normalization process of school and college and we’re told to sit down, shut up, do what everyone else is doing. And then you go out into the world and people say, why are you different? Right? Like, how are you going to create something? You were taught how to memorize dates and history and all this stuff. And so kind of what we want to do with this book is very simple. like, you know, give you the cheek.

cheat codes that we wish we knew at the beginning to help short circuit many of the mistakes that you’re going to make and not only build a successful business, but hopefully a successful life. What’s the value of a business and money if your life is in disarray? And Cass and I have spent a lot of time trying to build a relationship and other relationships.

And it just doesn’t happen by accident. so a lot of those cheat codes about how to do date nights and how to put stuff on your calendar that’s important. It contributes to how to operate within the hurricane of the imbalanced life.

John Jantsch (08:03.157)

Yeah, it’s funny. I listened to you talk about the school thing. I didn’t take tests very well because I always wanted to know why or how stuff worked. And you never got rewarded for asking that question. So, I was going to go to the cheat codes. Let’s dial up a few. Maybe I’ll challenge you each to pick your favorite.

Mike Lazerow (08:09.906)

You

Mike Lazerow (08:14.694)

Well, you’re talking to a 1080SAT, so I’m with you.

Kass Lazerow (08:14.765)

No, you didn’t.

Kass Lazerow (08:29.541)

All right, Mike, you start.

Mike Lazerow (08:31.314)

Yeah, so my favorite by far right now is focus and your priorities determine the outcome of your business. This is not something that we knew when we started these businesses way back when I was 18, 19 when I started my first one. But what we’ve seen is that one of the reasons why entrepreneurs do not succeed is that they’re not focused on the right things or they’re focused on too many things.

So the first question I ask any entrepreneur is what are your top three priorities to reach the vision you have? So if you’re an entrepreneur, say, I want to be the number one maker of shoes and whatever it is. Okay. What are the top three things you’re doing to get there? And if they cannot list it off right away without hesitation, that means they don’t know it. Their employees don’t know it. Their investors don’t know it. So they’re never going to be able to get to that vision if they don’t need

if they don’t understand what they need to focus on to get there.

John Jantsch (09:34.355)

All right, focus for me, how about you, Cass?

Kass Lazerow (09:36.983)

Mine’s all about transparency with communication. you really do, if you’re going to lead and you’re to start executing and you’re going to be going, you know, a hundred miles per hour, the only way to keep all the wheels on the bus and your most valuable resources, right? Your most valuable assets in your company, your people that are, that are putting in, you know, time and time again, all of their sweat and tears to help you reach your vision. You’ve got to tell them everything, the good, bad, and ugly.

They can take, you know, bad news. They can’t take surprises. So we’ve always led with just massive transparency, which has really worked for us.

John Jantsch (10:18.911)

So I’m feeling a lot of the businesses I talk to right now. this first quarter of 2025 felt like there was more change and evolution, in how we work than maybe the last five years put together. and I’m, I’m even talking to entrepreneurs are like, I’m just tired, you know, I just don’t want to like learn a whole new game. that I suppose goes pretty much into embracing the grind.

Kass Lazerow (10:29.669)

.

John Jantsch (10:45.658)

as an aspect of yours, what do you tell folks that, that now are just feel like, yeah, okay. I’m embracing their grind, but the target keeps moving all the time.

Mike Lazerow (10:55.526)

I think the number one thing is it’s not just embracing, embracing the grind. It’s actually embracing uncertainty. And so really what’s going on in the world today is what’s gone on for entrepreneurs forever, which is uncertainty, right? You start a company who’s going to be my customers. Where am I going to get all of my stuff to build the product? How am going to market it? Right. And so uncertainty will never go away. Even though I think we’re in peak uncertainty.

Right? One news cycle and all of a sudden it’s, whoa, we’ve like completely done a three, the one 80. Um, if you, as an entrepreneur can learn to not only love to shovel, but really embrace uncertainty as something you shouldn’t fear. You will thrive inside it no matter what’s happening. Right? Like, and many entrepreneurs have to deal with this all the time. And so we’re working with a lot of companies that import a lot of.

supplies and products from all over the world. And to a T, every entrepreneur is like, we’ll figure it out. Right? And they know how to make informed, confident decisions and operate and move forward, even in a world of peak uncertainty. Much different than if you have a job that you’re doing one segregated duty and you’ve never done anything differently. Right? You’re not a utility infielder.

Kass Lazerow (12:19.109)

Mm-hmm.

John Jantsch (12:24.437)

Yeah. fact, you go through enough cycles of this and I suspect you start seeing uncertainty and change as opportunity, right? I mean, because you’ve seen it before,

Kass Lazerow (12:32.409)

That’s right. And we, know, as true entrepreneurs look at, you know, let’s just call it uncertainty or even like a failed product launch as getting one step closer to the thing that’s actually going to work. Right.

John Jantsch (12:46.429)

Yeah. So, since you mentioned failure, were there any significant learning experiences for you along the road that really kind of inform maybe some of the cheats in the book?

Kass Lazerow (13:02.405)

No doubt, like the number one, I think, experience for Mike and me was our experience at golf.com. When in 1999, December 23rd, we were bought, we were acquired by chipshot.com. They were a Sequoia-backed company going public in April of 2000. And we took an all stock deal because our entire board voted for that.

And we thought we in a year and a half had made it big. We were going to be, you know, millionaires, you know, times a hundred is the height of the dot com like bubble. And by March 2000, the CEO of chipshot.com called us and said they were going bankrupt that Sequoia pulled out and we were going into bankruptcy with them. So.

It taught us a lot. It taught me about due diligence and what did I miss. It taught me about transparency because we had to tell every single employee that we didn’t even control the bank accounts. And what was amazing is because we’d always led with transparency for three months while we went out and raised money and started the company over, they all stayed. Not one employee left. And I think it taught, I think that’s where like, I would say like I really tapped into my competitive nature.

I hate losing more than I love winning. And so we just learned a lot. What about you, Mike?

John Jantsch (14:25.653)

Yeah.

Mike Lazerow (14:32.54)

So that one’s a huge one. And as Cass talks about it, the company was started by three Harvard graduates, or maybe dropouts, I forget if they, but very young. We were all very young. And they went on to do great things. So we all learned so much from this failure of how to fund a company, how to make sure you don’t run out of money, how to hire responsibly, how to attack a market, unit economics of products, which is one of the issues. How do you?

Kass Lazerow (14:56.857)

not shining the turd, right?

John Jantsch (14:58.514)

you

Mike Lazerow (14:58.844)

Yeah. so, you know, one of them, know, Rajiv Goel started Pubmatic. Nick Mehta started Gainsight, which is a huge, you know, software company right now. Amr Goel has had a great career. So those are the three founders. I also started a company without CAS and it showed me the importance of having a co-founder who you can trust, who you have different skill sets and we just couldn’t work well together. And the company to date has been

you know, a huge failure. And I write about that in the book. I take responsibility for not going through the motions of understanding how we were going to work together. What are our values? Are they shared? Is the work ethic the same? Is our vision for the company the same? And that’s a really hard thing. Like if you start a company with someone who you, for whatever reason, can’t work with, it’s hard to rebound from that.

John Jantsch (15:54.794)

Yeah.

So speaking of pivots, I know you look at a lot of companies, a lot of to invest in and things. there times when you, like, are there certain indicators that say, you know, this company should pivot or is it just for another opportunity or is it just because no market fit? Is there something that you look for in suggesting somebody really changed their, maybe their whole purpose?

Mike Lazerow (16:27.868)

So as an investor, you know, well, first of all, as entrepreneurs, we’ve pivoted eight, nine, 10 times. And so that always comes from a combination of metrics and gut feel. So when you set out to do something, how are you going to know it’s successful? Identify those metrics, but really deep down in your belly, you know, when things aren’t going as expected. And unfortunately, as human beings, we have a tendency to do more of the stuff that doesn’t work.

and it’s not working, then change to do the stuff that is working. And I remember Mark Benioff, we were in a meeting after we sold, he said, just do more of what’s working and less of what’s not. And it hit me like, man, that is deep, right? Cause he’s pointed out that we were doing some stuff that just wasn’t working. Okay. It’s a new company. And so, you know, we’ve, as an investor, it’s very hard for the investor to force a pivot.

John Jantsch (17:06.45)

Right.

Mike Lazerow (17:24.988)

But you could ask questions. You know, the questions are, why are customer metrics not meeting your expectations? Why is there no one using the product? Do you think there is another psychographic of people who you think would be more attracted to the product and have you tried to reach them? Right, so you ask a series of questions which force the entrepreneur to think to themselves. It’s not about,

them reporting to you, but it’s about them getting their own thoughts in line, usually written down, and if they can’t convince themselves, they’re never going to be able to convince anyone else.

John Jantsch (18:07.711)

Yeah. I know I personally respond a lot better to somebody asking me questions than telling me what to do because that definitely makes me figure it out. I think a lot of people are sort of resistant to just being told what to do.

Mike Lazerow (18:21.606)

We respect entrepreneurs too much.

Kass Lazerow (18:26.639)

But I think entrepreneurs also have to go back to their measurements of success, right? So if they really have goals that they’ve written down, and certainly if they’ve told their board and investors, those are the goals for the first year, what they need to do is go back to how they define success with each data point, right? So you say, like, okay, I’m gonna have 15 customers. If you have three, that’s a good data point.

to kind of understand what’s happening. And then you have to open that up. You have to put aside your ego and your pride and say, okay, what’s really going on here?

John Jantsch (19:06.805)

So you guys have your hands and have had your hands in a lot of things. You’ve been wildly financially successful, but beyond that, is there any kind of, have you thought legacy? What you want to kind of leave and accomplish in the entrepreneurial world? Obviously the book is something that we’ll live on, but I’m curious if you give that much thought.

Mike Lazerow (19:31.982)

Do you want to take that?

Kass Lazerow (19:33.347)

You go first.

Mike Lazerow (19:35.164)

Yeah, so the last 50 years have been very much about earning. For us, that meant earning degrees because we went to college and reputation and money and all this stuff. The next 50 years for us is about scaling our impact. And that’s on two fronts. One is how do we help entrepreneurs build businesses and lives even bigger and better than what we built? So we do not think that what we did is unusual.

Anyone can do it with the right focus and the right effort and the right funding. And that’s what the book’s about, but it’s what our speaking is about, our founders farm community, it’s all that. We’ve always integrated philanthropy into everything we’ve done. Not only because we wanted to, but it’s great for culture and there’s nothing better to make you feel better, but also an organization bring it together. so Cycle for Survival, which we were the first.

corporate team and we’re still very involved and on the leadership committee for we’ve raised over 400 million, 100 % goes to cure cancer, cancer research. And we’ve made huge strides, but too many people we know are still being impacted by cancer. So if we can, at the end of the day, if we could help companies and help founders reach their potential and if cancer is cured, we think our life was worth living.

Kass Lazerow (21:01.101)

And I’ll add one thing. I think if we can continue to be generous in our time and giving back to others, I think that would be great.

John Jantsch (21:13.513)

That’s a great note to end it on. appreciate you taking a moment to stop by the Duct Tape Marketing Podcast. Is there anywhere you’d particularly like to invite people to find out more about your work? Obviously, I know the book will be available everywhere, but anywhere you want to invite people to connect with you?

Kass Lazerow (21:29.827)

Mike, do you wanna go?

Mike Lazerow (21:31.354)

Yeah, www.shovelingshit.com. You know, we embrace the shit, but it’s not just about the shit. It’s Shoveling Shit, a love story. So our love for entrepreneurs are hopefully very evident when you go to shovelingshit.com.

John Jantsch (21:50.005)

So I’m curious, did you have to buy that URL or was that available?

Kass Lazerow (21:53.219)

You, guess what, John, it was available, if you can believe that. It was amazing. We knew it was the correct name.

John Jantsch (21:56.819)

What? That is amazing.

Mike Lazerow (21:58.95)

That’s when we knew that it was right.

John Jantsch (22:04.35)

That’s hysterical. Awesome. Well, again, I appreciate you stopping by the show and hopefully we’ll run into you one of these days out there on the road.

Kass Lazerow (22:11.269)

I would love it. Thanks, John.

Mike Lazerow (22:11.954)

Thank you, appreciate it.