Kass Lazerow: Author of Shoveling Shit

Episode 694

On this episode of The Kara Goldin Show, we’re joined by Kass Lazerow, serial entrepreneur, investor, and co-author of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. Kass has helped build and scale companies like Golf.com and Buddy Media (acquired by Salesforce for $745 million), invested in over 100 startups, and mentored countless founders navigating the chaos of startup life.
During our conversation, Kass shares the raw and real journey of entrepreneurship—what it really takes to build something from scratch, and why embracing the messy, unglamorous parts of the process is what separates those who survive from those who thrive. We talk about building businesses with your partner, learning to fail forward, choosing the right co-founders, and the emotional toll leadership can take when no one’s watching. Kass also dives into lessons from her book, written with her husband and fellow founder Mike Lazerow, and why this “love story” doubles as a survival manual for every aspiring entrepreneur.
Whether you're launching your first startup, scaling your next one, or simply love hearing the truth behind the headlines, this episode is a must-listen. Now on The Kara Goldin Show.

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Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone, and welcome back to the Kara Goldin show. Super, super excited to have my next guest here. She is a powerhouse entrepreneur, also investor Kass laro, who is also and something that we are going to dig into with with a shovel, so to speak. Kass Lazerow is the co author of the upcoming book, which actually it’s not upcoming anymore, because it has just launched this week, called Shoveling Shit, a love story about the entrepreneurs, messy path to success and being an entrepreneur myself, I totally resonated with this on so many levels. You’ve done such an amazing job, Kass, you wrote this book with your husband, Mike, which I absolutely, absolutely love. So a little bit of background on Kass, from launching golf.com to Buddy Media, which sold to Salesforce for over $700 million incredible. Congratulations. Thank you. Thank you. Really, really incredible. So I think that you’ve done so many things right. You’ve had, I’m sure you’ve had those moments where you’ve thought, I don’t know if I’m going to make it. You’ve had to pivot. You’ve had to turn around. Overnight successes are definitely they’re non existent. You talk about it in the book. I think that the importance of the co founder dynamics that you have with your husband are absolutely incredible to hear you talk about that, navigating burnout, all of these things, Shoveling Shit, is a must read for Anyone who hasn’t even thought about becoming an entrepreneur, or maybe wants to figure their friend out or their kid out as they’re like going through these moments in life. So Kass, welcome to the show. Thank

Kass Lazerow 2:52
you so much. What a nice introduction. I appreciate you. Thank you

Kara Goldin 2:55
absolutely so Shoveling Shit, it’s bold, messy, impossible to ignore. When I got the preview copy, I loved your little shovel. So, so cute. Yeah, so how did you get to this title?

Kass Lazerow 3:12
Well, you know, Mike and I have spent the last 30 years kind of building, I would say, our lives together, our careers, our reputation. It was like a very, you know, messy, full of grit experience, and we had some massive success. We had some failures along the road. And what we’ve realized is this next 50 years is really going to be about giving back to the entrepreneurial community. We spend a lot of our time giving our cheat codes that we have learned over the last 30 years from doing it ourselves, not just sitting as investors, but actual entrepreneurs and founders. And when we thought of, you know, what would be a title that represents the entrepreneurial journey, it became pretty clear that it was basically, you are Shoveling Shit all the time. And we thought that was a perfect name that basically explains in a title what you are doing as an entrepreneur. I

Kara Goldin 4:13
think it’s, it’s so clear, you know, I think what’s, what’s interesting is that while you’re Shoveling Shit, you’re not telling anyone that you’re Shoveling Shit right, correct. And so you’re putting on, you know, your best poker face so often. Oh, yeah, definitely. And to try and forget about all of the shoveling that you actually did that morning or you still need to do that night after you get finished with that dinner. So when you think about those days, I’m sure they were challenging to say, to say the least I loved your kind of the the I felt like it was a love story. Story you you know you loved these moments, but it was also survival. I felt like was was going on in the book, too. So why do you think this is so important for people to learn from your own experiences?

Kass Lazerow 5:16
I think being an entrepreneur is not for the faint of heart. So one of the things that we learned, not just through our own experiences, but also, you know, really helping a lot of entrepreneurs. We’ve invested in hundreds of entrepreneurs along the way, but talking to everyone, is that there is this beauty in the struggle, right? So if you want to be an entrepreneur, you have to embrace the struggle. You have to embrace the storm, the chaos, because it is never ending, and as a result of that, you’re going to have to realize that you might have a, you know, a lot of bad days in a row, but there’s nothing else you’d rather do, because it gives you such purpose, such intention, such drive. And it’s, it’s, it’s beautiful in the end, right? It’s this. That’s why we wrote it. It was our love story, because this kind of how we grew up together. But also it is the love story that entrepreneurs have of being in this journey?

Kara Goldin 6:23
Yeah, definitely. So co founders, your husband and you run, have run companies together. What do you think is the most important piece? I think it’s, it’s almost I ran my company with with my husband as well, so I have strong and we’re still married years later. So I I think it’s kind of irrelevant in many ways, to look at that person as your your co founder, as your husband, or not your husband. It really is skill sets, right and yeah, and chemistry and all of those things, but you’re now investing in companies. I feel like I can spot teams, great teams, great leadership, great co founders together. But what do you look for when you think about that?

Kass Lazerow 7:20
I definitely, I mean, Mike and I come from things at a different, you know, angle and perspective. So he’s really looking at business models. He’s looking at, you know, can, can, does the perfect business model? Does this? Is this something that has legs? Is the market big enough? Do they understand what the product is, how it differentiates, how they’re going to get it to market, how they’re actually going to market it, then to their actual customer base. And then, you know, what’s the delivery mechanism. And then at the end, like unit economics, cost, I’m looking at, do the founders know what they don’t know? Right? Do they know what their skill sets are? Do they know how to stay in their lanes? Are they, are they able to delegate and actually have trust that their that their leadership team, their co founder, is going to get things done? So the greatest themes that we have found are those that have no overlap and skill set. So I’m guessing with you and your husband, it’s the same way, and I agree with you that there’s no reason to say, like, you know, in business, that he’s my husband or not, we just happen to have two very distinct skill sets and implicit trust because we continuously deliver on what we say we’re going to do, and that’s also helped our relationship right along the way. It’s been a byproduct of it. We think it’s a superpower we love, I mean, anyone out there, we love entrepreneurs who are married and have figured this out and have no overlapping skill sets. It’s,

Kara Goldin 8:51
it’s so refreshing to hear that. So I remember when we were first raising money for him, and we had some investor that was very interested in supposedly investing in our business, and they wanted to speak to my husband, and they said, listen, we’re very interested in investing in the business, except for one thing, you guys are married, and businesses never work out. And it was funny, because my husband said, so I’ve never really thought about it. I mean, which businesses haven’t worked out? And that where you had to that where you had married founders, right? And they said, well, we can’t really think of any specific ones, but exactly and but I thought it was such a great feedback, and we the moral of the story is, he did, they never did invest. But I’ve always said to founders like that’s not necessarily what the real reason is why they invest.

Kass Lazerow 9:55
I we’ve had similar experiences with fundraising, with golf.com we. Went out to Silicon Valley in a very with a and met, or had a meeting set up with one of the top VC firms out there, very, very well known. And we walk in, and we say our names, and they say, Wait, are you guys related? And Mike says, We’re married. And they say, we don’t work with married people. So Mike closed the laptop. We said, Okay, we’re not changing our status. So goodbye. Yeah, that’s so

Kara Goldin 10:27
funny. Can you talk about how the partnership with Mike evolved through all the chaos of building companies together? How did you two get together and and continue to build on on all things Lazaro, I guess

Kass Lazerow 10:42
so Mike became and I think I was for him, too, but I’ll talk about my perspective. Mike became someone that I would come home from work, when I worked at a company right before we started golf.com and I would bounce ideas off of him. And he was the person who, when we first started dating, was interested in the internet, understood, like web 1.0 when you called it back then, in the, you know, the middle 90s. And it just was a partnership of of, like thought leadership. He just was really reliable with his perspectives. And I always went back to him, because he was the one that was most knowledgeable, and he started to rely on me in terms of, like, what does it mean to operate? What does it mean to lead teams? How do you communicate effectively, things like that, and really, a lot of multitasking in terms of operations. And so when I started golf.com I was like, I need you here working, you know, with me. And so he eventually left his job, and we did that, and it was beautiful, because we kind of just started to like separate. It was people say, Oh, my God, how do you work with your husband? 24/7, well, we work together, but it’s not like I ever I wasn’t in meetings with him all day. I think that would actually be very annoying to be in a meeting with anybody full time. But what was beautiful is that, and we had this with our leadership team, if you start to pick the same kind of if you use the same formula, you have this implicit trust because they are someone who shows up for you in your regular life, your personal life, and now they’re showing up for you in the same way in business. So that trust allows you to have much more bandwidth to do other things or to get your job done. And it’s, it’s a great it’s a great feeling when you have that trust.

Kara Goldin 12:34
So your book Shoveling Shit, this your first book, and it’s quite, quite good. What’s one myth about startup life that you were really hoping to break by writing this book? I think,

Kass Lazerow 12:50
I think for me, there’s the biggest one is that it’s going to be all glory, right? It’s going to be all great. I would say to any mom out there who’s an entrepreneur, the mompreneurs that you might not miss a basketball game or a recital, but there’s going to be a lot of other things you’re going to miss in the middle and in the small moments, and so you got to be prepared for that, because being an entrepreneur is about a lot of sacrifice. I’m not saying it doesn’t come with amazing perks, but this myth that you can do anything you want, you can work however many hours, it’s actually the opposite. And I’m sure you understand that it’s 24/7, your mind doesn’t turn off. If you’re lucky enough to have teams around you, you are thinking about their well being, and you are responsible for them in their livelihood. So it’s a it’s a big job. Yeah,

Kara Goldin 13:45
definitely. And I think you also talk about the struggle with the guilt and family time, friend time, employees not being enough, not spending enough time. How do you manage that emotional roller coaster. What? What is your suggestion for anybody who is whether I really think it’s not just founders, but also leaders in general, what suggestions would you have for that

Kass Lazerow 14:15
easy for me to say this in hindsight, I think, but I think if you do not schedule time for yourself, I think it’s particularly important for parents who are founders, to have 45 minutes. I’ve I’ve learned this over the last 20 years, that if I can do 45 minutes with doing something that no one else has asked of me, it can’t be for someone else or in service of someone else. It has to be something that’s for me. And it could be working out, it could be meditating, could be reading, it could be doing whatever you want, micro, focusing on, I don’t know, needlepoint, whatever you want, but you need to put it on the calendar, and that’s something that Mike and I did not do well. For those those years, and it really caused massive burnout. And I remember the day I walked out of our office after Salesforce had bought Buddy Media, and it took me a good year and a half to get my nervous system like better, because I was so used to being at the beck and call of to do’s and tasks that I really hadn’t ever sat with myself just going, Okay, what am I gonna do today? So I think it’s important that you schedule everything. If it’s not on your calendar, it’s not gonna happen. And even if that’s a 10 minute walk, I mean, just put it on the calendar.

Kara Goldin 15:40
Yeah, definitely. So when you were going through, I mean, you’ve built incredible businesses and exited these businesses, but what was your biggest shit shoveling moment, and how did you climb out of that and and live to tell

Kass Lazerow 16:05
so I think there’s two in my career that I’ve learned the most from. And I and I will say the two different I learned different things. One was my grit and tenacity. So when we started golf.com It was september of 1998 in starting to be the heyday of the internet, right web, 1.0 and we ended up selling it to a company called chip shot.com in December of 99 december 23 I remember it with the with the promise that that company, which was Sequoia backed, was going public in April of 2000 and in March, we received a phone call from the president who said they were bankrupt, and they were pulling us into bankruptcy. And this was, this was just I I’ve never been in so much shock. But what was interesting is, I think because I’m a I was a former athlete, and I was so competitive, I was angry. I wasn’t angry that this, like they were telling me this. I was angry that I was going to have a loss. And I think that fueled me and the grit and tenacity where I was just like, Okay, we are going to tell every employee we have no money to pay them. Because we didn’t, we didn’t, we didn’t control our bank accounts anymore, so we had nothing. And we were just married in October of 99 so we were not paying ourselves. We were both making zero, which I think is another myth that people think you’ll make a ton of money, you know, being an entrepreneur, no. And we got back on the road. We told our team, we understand if you have to leave, but here’s what we’re gonna do. Not one person left, and we were around the country. We had a third co founder. We all slept in the same hotel rooms, and it showed me that in adversity, that I could rise and not give up like, hope that I could turn things around. And I think it was my first big lesson in shoveling that that it wasn’t like, even if you get to an outcome, you’re still going to be shoveling. And I think that was like a Oh, like an aha moment for me, like, oh, okay, so this never, like, even though you have this like, light at the end of the tunnel, you’re still gonna have this like, oh shit moment. And the second time I learned something was when we pivoted our business model, which was entirely different, like a huge like turnaround, to a SaaS model at Buddy Media. And I sat in the board room and with Mike and all the other board members, and Mike had brought up this idea. Mike has, I don’t know, 30 ideas a day he tells me about, but this idea, he had conviction behind. He had mentioned it a couple times to me, but now I was hearing him, and I know the voice, that means we’re doing this. And I remember I panicked, because really, the work was going to be on me and the and the engineering team, but I was going to have to go out, rearrange teams, fire and let go people. And I had this, oh, my god, I can’t do this moment. And I took a deep breath, I walked outside, and I had to have like a meeting with myself to say, okay, we can do this because the shoveling that it takes to pivot and still stay focused and have that loyalty and trust from teams is a lot.

Kara Goldin 19:30
Yeah, definitely, B to C, companies versus B to B. You’ve had experience in both. What would you say is the tougher to build for

Kass Lazerow 19:42
me. I think, you know, B to C. I think the direct to consumer was just really hard with the golf space. It was, you know, we were looking for recreational golfers. We thought the market was great, you know, e toys at that time, was worth billion. And had gone public, but we had a small marketplace, right? Like, even though golfers are huge in terms of their disposable income, we were going after the ones that were the avid golfers. So I think that is very hard marketing, because you really have to get people to feel right. I look at our best investment right now of liquid death. It was in terms of most exciting business, you know, B to C, and they get it, but it’s a lot of work to go after. You know, consumers. I think having recurring revenue while you sleep, coming in the door with our big enterprise deals with Buddy Media was a lot easier, harder sales pitch. I was never a salesperson, so I will leave that up to Mike and our other co founder, Jeff, but, but I like going to sleep knowing that money’s still coming in the door. Yeah.

Kara Goldin 20:51
So interesting. So when you think about your first business, you’re also looking at lots of deals today, that potentially you’re going to become involved in, invest in, what is a piece of advice you wish you had heard before launching your first company. You talk about this in the book too, but I’d love to hear your perspective on that.

Kass Lazerow 21:18
I think what’s essential after you kind of go through the steps of understanding what it is that you’re selling, like, what’s your product or service, you know, how is it any different? What’s the size of the market? How are you going to market this and go to market? How are you going to deliver this to your consumers and target audiences? I think it’s customer feedback. I think what we did really, really well with Buddy Media versus golf.com even though two different business models was that we took on some flagship customers, like big brands, even though they didn’t pay a lot to get the feedback that we needed to find product market fit. And I think if, if founders could realize that and be less rigid about their first business model, right? What you start with, you’re never going to end up with. It’s just really, really rare. So if you can figure that out and get to that faster, it’s a huge benefit, right? So take on customer feedback, give the product away for free or for nothing, so that you have someone who becomes your brand advocate and says, Oh my God, these guys are doing it great, and do it in exchange for those references, right? So we had a lot of clients like that in the beginning, which were just crucial to our success, because they gave us the product roadmap that we needed.

Kara Goldin 22:43
Yeah, definitely, when you think about male entrepreneurs versus female entrepreneurs, I’m so curious. You’ve been in very male dominated spaces with golf and also with tech. What advice do you give to female entrepreneurs who are kind of living in this male dominated space that you’ve sort of learned over time.

Kass Lazerow 23:08
So what I tell a lot of them is, ignore the noise. It’s just noise. I think female entrepreneurs are incredible because of their multitasking ability. For the most part, they can do 50 things at once. And the biggest thing I always say is there’s gonna be a lot of noise, there’s gonna be a lot of differences, let’s just say, on how we are treated when it comes to fundraising, when it comes to leading, and you just gotta punch up, punch up. Play bigger. Go for it, and as much as you can it’s gonna suck. You gotta have a good support system of friends who you can vent this to. But I think female entrepreneurs are, we love investing in them, like there’s, there’s probably not a female entrepreneur that I don’t like

Kara Goldin 24:05
that’s I love it, so it’s great you had your book is full of truth bombs, one tough love lesson after the other two. What’s your favorite tough I guess it probably wasn’t your favorite at the time, but hardest lesson that really kind of hit you personally, that that you think back on, I guess fondly, because you learned a lot through that lesson. Yeah, sounds like that’s that’s definitely something that that you pay attention to, which I think is important to learn from those lessons. But what is, what was one tough love lesson that really hit the hardest for you

Kass Lazerow 24:48
when we ended up going into bankruptcy with golf.com and then Mike and I, and our other founder, Mike Casper, went on the road to raise the money, and we did. We ended up. Raising another million and a half, which was great. We came back and we had a new board, and this wasn’t just like friends and family board. These were two sharks, Matt sorovich and Jeremy Minnich, and we got on our first board call, and I’m running it. And so he says, How are sales? I’m like, Yeah, you know, they’re, they’re okay. Mike, why don’t? Why don’t you tell you know, Matt, how’s it going? And Matt, I mean, and Mike, you know he, he didn’t sugar coat it, but he wasn’t, he wasn’t completely factual it, you know, when what I would say is I learned, I think both of us learned, that day you need to be factual, and nobody cares about, you know, mistakes. You know, investors, employees. We can take bad news. We just can’t take surprises. So when Mike had said, Yeah, you know, they’re okay, we’re doing this and this, I hear master of it slam his hand on the table over this conference call and say, Don’t shine the turd. And I mean, he screamed it at us, and I just will never forget it. And from that moment on, we really embraced that. We treated our employees like they were investors, so they knew everything about us, everything in terms of, like, the financial stability of the company, our wins, our losses, what we all were going through, and we also did the same to investors, so there was never any surprises. And that’s what entrepreneurs need to understand, because that’s how you build a very loyal employee base, but also how you have investors who stick with with you and try to help you when you need it

Kara Goldin 26:42
absolutely well. So much to be this is just such a great book Shoveling Shit. Everyone needs to get a copy of this for sure and start reading. It’s been fun to have you on the podcast, but also just really fun to to meet you and thank you and and hear all about the brutally honest thinking behind it. I really, seriously, really, really appreciated it, and I love how you stayed so grounded in your values and your vision. And I think through storytelling, that’s how we do get through the messes, right? And definitely, I can’t wait to hear more of them. I’m sure you couldn’t fit them all into the book, so it’ll be fun to to hear many more of those. And, and, thank you, everybody for for for listening and and thanks Kass for coming on really. Thank you for having me Shoveling Shit. Definitely pick up a copy. Thanks again,

Kass Lazerow 27:48
thanks again. I appreciate you. Thanks Kara. Thanks again

Kara Goldin 27:52
for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast, just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book undaunted, where I share more about my journey, including founding and building hint we are here every Monday, Wednesday and Friday. Thanks for listening, and goodbye for now. You.

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