Passion Struck with John R. Miles
Kass and Mike Lazerow on Why Building Big Requires Feeling Deep | EP 620
Thu, 05 Jun 2025
In this raw and deeply human episode of Passion Struck, I sit down with Kass and Mike Lazerow—serial entrepreneurs, early investors in Scopely and Liquid Death, and authors of the powerful new book, Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success.We go far beyond startup strategy and dive into what most founders won’t say out loud: the loneliness, the identity loss, the trauma—and the daily choice to love through it all. This isn’t just a business story. It’s a blueprint for building anything real: a company, a relationship, a life—with soul at the center.Click HERE for the full show notesExplore More: The Ignited Life NewsletterIf today’s episode sparked something in you, you’ll love The Ignited Life—our free Substack newsletter created to fuel your growth between episodes.👉 Subscribe now at TheIgnitedLife.net.Catch more of Kass and Mike Lazerow: https://kassandmike.com/If you liked the show, please leave us a review—it only takes a moment and helps us reach more people! Don’t forget to include your Twitter or Instagram handle so we can thank you personally.How to Connect with John:Connect with John on Twitter at @John_RMilesFollow him on Instagram at @John_R_MilesSubscribe to our main YouTube Channel and to our YouTube Clips ChannelFor more insights and resources, visit www.passionstruck.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Chapter 1: What are the key challenges entrepreneurs face?
That's when the ego gets in the way. You start to see them trying to convince themselves that they shouldn't pivot or that something's not working because they tell themselves stories. And those stories are attached to their ego.
Welcome to passion struck. Hi, I'm your host, John R. Miles. And on the show, we decipher the secrets, tips and guidance of the world's most inspiring people and turn their wisdom into practical advice for you and those around you. Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself.
If you're new to the show, I offer advice and answer listener questions on Fridays. We have long-form interviews the rest of the week with guests ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries, and athletes. Now, let's go out there and become PassionStruck. Hey, PassionStruck fam. Welcome to episode 620. I'm your host, John Miles.
This is a space for the curious, the courageous, the ones building lives that aren't just impressive on paper, but aligned in spirit, a community of seekers, builders, and change makers who believe that impact starts with integrity and that meaning isn't something you stumble into. It's something you create on purpose. If you've been here a while, Thank you.
Your presence, your questions, and your willingness to grow out loud. That's what keeps this movement alive. Before we jump in, a quick heads up. Our new substack, The Ignited Life, is growing fast. Every week, I share stories, strategies, and behind-the-scenes tools that go deeper than the podcast. I also give discussion guides and workbooks that go along with each of the episodes.
It's also where I process in real time. through notes that I send out daily, and where our new PassionStruck merchandise line has just dropped. The gear is bold, intentional, and rooted in one core idea. What you wear should reflect what you believe. Think a hoodie that says, Live Like You Matter, a hat that reminds you to own your own spark, and to celebrate we're running a launch giveaway.
Just head to theignitedlife.net and join our ignition room to enter. All right, let's talk about today. We're continuing our new series on The Connected Life, a deep dive into how we build trust, navigate hard conversations, and show up more human in every part of our lives. Last week, I talked to Dr. Andrew Brodsky about the hidden dynamics of virtual communication.
Then on Tuesday in episode 619, the legendary Jon Kabat-Zinn joined me for one of the most powerful conversations I've ever had on the role of presence in modern life. And today we're taking this one even deeper. Because if you've ever looked at someone's success and thought, how do they do it all? this episode is for you.
My guests today are Cass and Mike Lazaro, serial entrepreneurs, early investors in Liquid Death and Scopely, and authors of the brutally honest new book, Shoveling Shit, a love story about the entrepreneur's messy path to success. They have built and sold multiple companies, including Buddy Media, which they sold to Salesforce, for a whopping $745 million. They've worked alongside Gary Vaynerchuk.
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Chapter 2: How does ego impact decision-making in startups?
So great packaging on this book. I wanted to start out with what is the significance of the shovel? Why that metaphor?
Both of us feel, John, that as an entrepreneur, it's not always glamorous and it's not full of glory. There are times often throughout the day that you're going to get punched in the face and you just got to start shoveling your way out of whatever mini crisis or mini failure that you're having. And we liken this whole experience of being an entrepreneur to golf, right?
You pretty much hit really awful shots until you have one really good one that keeps you going. So we thought this metaphor was perfect for an entrepreneur. And that's why we included shovels.
What has been one of my favorite interviews that I've done on the podcast is Sean Foley. Do you know who Sean is?
Yeah.
I knew who he was and I knew who he had coached, but I didn't know the person behind the name and the coaching until I started to really study him. And man, we were going deep into Malcolm X and Buddhist principles and a lot of things. So who was the coach for the Chicago Bulls for so long and then the Lakers? Jackson. Yeah, he's like the Phil Jackson of golf.
I love it.
He's like the Zen master who makes you think about more than just golf.
Absolutely. Since we're talking about golf, Can you take me back to the call that changed everything with the chip shot? What did that moment reveal about the reality of startup life?
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Chapter 3: What does 'shoveling shit' mean for entrepreneurs?
Chapter 4: How did personal experiences shape your entrepreneurial journey?
You pretty much hit really awful shots until you have one really good one that keeps you going. So we thought this metaphor was perfect for an entrepreneur. And that's why we included shovels.
What has been one of my favorite interviews that I've done on the podcast is Sean Foley. Do you know who Sean is?
Yeah.
I knew who he was and I knew who he had coached, but I didn't know the person behind the name and the coaching until I started to really study him. And man, we were going deep into Malcolm X and Buddhist principles and a lot of things. So who was the coach for the Chicago Bulls for so long and then the Lakers? Jackson. Yeah, he's like the Phil Jackson of golf.
I love it.
He's like the Zen master who makes you think about more than just golf.
Absolutely. Since we're talking about golf, Can you take me back to the call that changed everything with the chip shot? What did that moment reveal about the reality of startup life?
So as we started the company, we started golf.com because I had a dream to help recreational golfers track and analyze their game online, be able to get scores on leaderboards of all the tournaments going around and book tee times and really get an official USGA handicap. So we started this in 1998 in the fall And by December 99, during the dot-com boom, we were acquired by Chipshot.com.
And they were going public, so they told us they were Sequoia-backed, and they had all their paperwork ready for filing their S-1 to go public in the spring. In March of 2000, just when everything was crashing in the dot-com era, we got a call from the CEO that told us that Sequoia had backed out, they were out of money, and they were going bankrupt and pulling us back in.
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Chapter 5: What lessons did you learn from failure?
Absolutely. Because what I have learned through the board meetings I've been in, And man, I've got a doozy for you. I joined this company originally as the president. I was a start, it was a software company and the board felt like the CFO and the CEO weren't being truthful to them. And so they brought me in. under the covers of being a president to figure out what was going on.
And I quickly learned that the two of them were using the expense accounts to basically live their life style. They were, they both had bought BMWs off the company, apartments, condos. And then on top of that, we're completely inflating the revenues of the company by about 40%. And having to navigate how you tell the board that
while you're then asked to take over becoming the ceo and trying to work with that ceo and cfo while then the board decides to sue them in the middle of it my lord so i have been through the winner of these things and what i learned from it is what you were just describing is the more transparent you can be the more your board is going to help you and
And there's nothing worse than having a board that has to react at the last minute to try to salvage something that they could have gotten ahead of way far in the future. So what would be along these lines, your biggest bit of advice that you could give a founder or startup on how they should pick their board and how they should treat them?
We look at raising money and managing a board as managing any relationship that's important to you. When you show up to raise money, ideally you have provided some value beforehand. You have a relationship. They know who you are. They have a sense of your credentials, meaning who do you surround yourself? What have you done? Investors don't really care where you went to school.
They care about what you've done and who you've worked with. Obviously, whether you've won or not and so if we look at our most transformative fundraisings and board members, these are people who we built relationships with in many cases over many years.
People like Howard Linzen, early stage investor and Roger Ehrenberg, the SoftBank team who was based in New York at the time, Graycroft, these are firms and individuals who knew us and so by the time we showed up to pitch an investment, They were at least wanted to lean in, not necessarily do the deal.
And way too many founders and really way too many business people look at everything as transactional. So what can they do for me? We always ask, what can we do for you? And that has gotten us so much more in return, I think, than we've ever given, even though we've given a lot. But if you have a give mentality, which you've talked about, the rest takes care of itself.
Well, it absolutely does. And you two now have a ton of experience of being on boards because you've invested in over a hundred companies. So you bring some very valuable insights from that. And one of the things I wanted to ask along those lines is one of the most powerful lines in the book I thought was it's inside their struggles that entrepreneurs often find their reward.
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Chapter 6: How can entrepreneurs prevent burnout?
And whatever that is, it could be like for me, a lot of it is... non-negotiable workouts, and also just quiet time, like no other, no talking, nothing, just quiet time. And burnout's a real thing with entrepreneurs. And it's like Mike said, it's very lonely. It's also, you have to have really thick skin because things happen so much
And there's so much criticism and feedback that's going to be coming your way from people who think they're being helpful, but you have to be able to start to realize that the doubts that you have to be able to put those aside and have the discipline of your brain to say, I'm going to keep focusing on those big rock priorities. And that mental discipline is what
creates the burnout, in my opinion, because you've basically been holding your breath for however many years and you get to some kind of finish line and then you just feel exhausted. So our rule of thumb is prioritize something for yourself at least 45 minutes a day.
And that could be as simple as taking a walk, taking breaks, doing a short workout.
One of our new friends says it's coffee with her dogs in silence. Just that's what it is. It has to be prioritized.
Well, thank you for sharing that. And I wanted to go back to this journey because I understand the whole thing started in a hospital room where Cass, you were giving birth, I think to your third child. And I know you have a child named Miles. So I love that. You love that name spelled differently. But so you're, you had just had a C-section, you're recovering and
You think Mike is going to bring you some cuisine to help you get over the surgery. And instead, he has another passion that he wants to talk about. How did that all play out?
Well, I was used to his ideas coming out at any time or any place. That is something that I've always been used to with Mike. And that starts from the minute he wakes up to the minute he goes to sleep. He will say, I have an idea. I had thought maybe it just wouldn't have come out while I was in the recovery room with our third child, but he, I'll let Mike tell it.
He was, saw this big announcement from Facebook and he could, he just couldn't help himself.
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Chapter 7: What role does transparency play in business success?
I'm not gonna say on such a great program, but three months later, she was sitting in an office at the corner of 60th and Columbus building desks and Buddy Media was off and running.
I just wanted to use this point of how did your path intersect with Gary Vaynerchuk, who wrote your forward, because I understand as you were starting in the midst of starting this company, he was also starting VaynerMedia and you were co-habiting for a period of time, if I understand the journey correctly.
exactly right and we're talking earlier about giving and we love entrepreneurs and we get a call from this guy who i knew because he had a wine show i don't drink wine but it was like one of the first youtube shows on wine And he basically said, I've been working for my dad since I was like 13. I've never made more than 100 grand. I'm 34 years old.
I have a concept for a new type of ad agency that helps companies market the way I've marketed at my wine company, Wine Library. The problem is I don't have any money for an office. Can I use your only conference room as my office? Now we're in like a thousand square foot max. He's asking for 250 square feet and the only like private room.
I say yes immediately, but I say, yeah, you got to talk to this lady over here. Who's my partner in all things. And I thought Cass was going to say no to Gary. Those of you who know Gary know that you can't say no to Gary. And he has a gift of gab unlike anyone else. He's great with people. And Cass said yes, and he has been one of our closest friends. And I would say mutual mentors.
We come to each other whenever we need really help. So we own a pickleball team together. We are investors in V friends. We did want empathy, wine, his wine company together. I'm a very large collector of V friends. He was involved with buddy media. Obviously we worked on clients together and everything in life. The more you give, the more you get.
And we had no idea that he would build a 3000 person, half a billion dollar empire. a half billion dollar revenue empire out of that little conference room. But there's no better entrepreneur that I know. And the main reason I say that is unlike Cass and myself, we raised money from venture capitalists to build software and then sell it.
Gary self funds all of his businesses and he uses revenue to grow the businesses, which is really the best way to fund businesses.
No, it absolutely is. And I want to ask you another question about Vee Friends, but I love, here you are right here. I have, for those of you who are listening, I have a copy of Gary Vee's Meet Me in the Middle children's book, which I interviewed him about. But what got you guys, besides Gary being very difficult to say no to, one of these days he's going to wear down the jets enough to buy them.
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Chapter 8: How do relationships and networking impact entrepreneurship?
Anyone who's had a baby knows that baby does whatever it can to get what it needs. Now, whatever it can in that case is crying, but talk about advocating for him or herself. They come out advocating, right? and weaponizing their voices to get what they want. And then they go through this industrial normalization complex, right?
They go to school and they're told to sit down and shut up and memorize these things and be like every kid. And then you add social media where I'm not as good enough in my mind as everyone else. And no matter what age you are, and you have this toxic brew that creates kids that are both ill prepared for the world and lack confidence and don't think that they're enough in and of themselves.
We spoke about ego earlier, and there's no doubt that entrepreneurs have ego and they need ego, right? That's the rocket fuel. for them to be able to have the unshakable confidence, the vision, the charisma to do what they do. But pregnant in that ego is the wrecking ball for the company and for your life, right?
Inside that ego is also why we ignore feedback, refuse to pivot, hire the wrong people, build a toxic culture, micromanage people. Like, don't get me started, right? And so...
kids are now coming into the world with very little confidence they don't have that ego which is necessary to say i don't need external validation to do what i want to do i am enough i have everything i need inside me and that is creating issues across the board as we spend a lot of our time with young people we love it it keeps us young
Thanks for sharing that. And my kids are about the same age as yours. I have a son who is 26 and a daughter who's a senior in college. So I get this and I'm also close to my nieces and nephews. So I'm hearing the struggles that they're going through as Gen Alphas, which I thought the Gen Zs were going to be the end of this, but the parents
I guess the way I like to phrase it is if a child needs to feel like they matter and that they feel significant and that their values matter to the world, it gets most reinforced by the parents. But if the parents are checked out and they're disengaged and they're not feeling all of that, it's almost impossible for them to give it to the kids. And so you've got this loop now that's happening.
that we as a society just can't seem to break out of. And that's where a lot of my focus is going.
And also the focus of a lot of parents that are helicoptering and just doing everything for them. I think the other part of the confidence issue is we don't let kids fail safely when we have 18 years to let them pretty much fail safely, right? If not 22.
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