My good friend and publisher, Naren Aryal, called me up and said, “Hey, you’ve got to check out this guy Mike Lazerow. He and his wife, Kass, wrote a book called Shoveling Shit. We’re publishing it, and it’s gonna be great. You’d love this guy. He’s just like you, only with a lot more money. He’s an entrepreneur, a husband, a father. He’s obsessed with music.”
I said, “Alright, I’m in. Connect us.”
Mike and I booked a call. His team was on it. They sent me a couple of copies of the book, which came with a mini shovel, and yeah, I thought that was hilarious. I read his bio, looked through the media kit, and it was clear, this guy has lived it. He’s built, lost, won, learned. He’s been through the fire.
When we finally got on the call, he was at his house in the Hudson Valley. He had a flat-bill hat on, a Phish t-shirt, and the vibe was just… real. You never know how it’s going to go when you meet someone for the first time, especially over Zoom.
We do these calls live now with our Midlife Male Live crew, so the setup was already rolling. I got him settled, then let the rest of the guys in. We made some small talk, and right away, I could tell this was going to be a good one.
And it was. Mike was incredible. Honest, open, unfiltered. He talked about the chaos and beauty of building companies with your spouse. About loving each other while working together. About Golf.com. About Buddy Media. About all the mess and all the magic that comes with chasing big ideas.
He shared stories about Gary Vaynerchuk and Seth Meyers. He talked about health scares, personal growth, following Phish across the country, what matters to him now, and where most guys our age are missing the mark in business and life. He talked about relationships, about how they evolve when health, age, and money enter the equation. He got into philanthropy and why giving matters more now than it ever did when he was just starting out.
This is the kind of stuff that lights me up. Conversations that come from experience. From reflection. From someone who’s done the hard things, taken the hits, and kept showing up. These are the guys I want to learn from. Guys who are still learning.
And they don’t have to be influencers or celebrities. Honestly, I’d rather hear from someone like Mike than a fifty-something influencer trying to sell you a juice cleanse. At this point in life, authenticity wins every time. Give me someone who’s lived it, who’s still in it, and who wants to talk about the parts that actually matter.
This was one of the most enjoyable conversations I’ve had in a long time. Mike’s someone I want to be friends with. Someone I want to keep listening to and learning from. Someone I hope to support and spend more time with.
Here’s what you should know: Mike Lazerow is a serial entrepreneur, investor, and New York Times bestselling author. Over the past three decades, he and his wife Kass have built and sold multiple companies. Buddy Media went to Salesforce for $745 million in 2012. Golf.com went to Time Warner in 2006. As an investor, Mike has backed over 100 startups, including Scopely, which sold for $5 billion in 2023, and Liquid Death, which you’ve probably seen in every store by now.
In total, the companies Mike has co-founded or funded have generated more than $10 billion in realized returns. These days, he owns and runs a growing portfolio of ventures across healthcare, venture capital, executive recruiting, and sports.
The book he wrote with Kass, Shoveling Shit: A Love Story About an Entrepreneur’s Messy Path to Success, debuted as a bestseller on the New York Times, USA Today, and LA Times lists. And it deserves it.
Enjoy this week’s How I See It conversation with Mike Lazerow.
You can check out the full raw interview for FREE here
On Entrepreneurship:
“There’s beauty in the struggle of entrepreneurship that has really always powered us, and it’s impossible to find balance and that’s okay.”
On Health:
“If you don’t have your health in order going into your 50s, you’re really screwed. Now is the time that we’re doubling down on health span. The focus is on what we have to do today to live a life that we want to live.”
On Fear:
“How do you combat fear? It’s by building your confidence, and when you let the fear go, it just leads to uncertainty, doubt and self-doubt. The fear is never going to go away. The question is: How do you move forward despite the fear?”
On Marriage:
“We’ve had to work on it. When we could afford it, we did standing date nights, Wednesday and Sunday. Communication is key. When we were at our worst is when we weren’t communicating.”
On How to Spend Your 20s:
“Tell your kids to do a lot of stuff in their 20s. Your goal is to figure out what you’re good at, build your network and come out of your 20s really proficient at something.”
On Parenting:
“We try not to solve their problems for them. We don’t shy away from help, but they need to learn to handle things. We also remind them over and over that gratitude and being thankful is really big part of everything.”
On Caring What Other People Think:
“The older I get, the less fucks I give. Like, I literally don’t give a fuck anymore what other people think. We’re doing a lot of stuff that we want to do, just because we want to do it.”
On Learning:
“Every person you meet, you should try to understand who they are, what makes them tick, and build the relationship from there. So at some point, you may ask for a favor, you’re not coming out of the blue.”
On Philanthropy:
“Find something you’re super passionate about, and then you can make a difference. Seeing people who are alive because of the research we funded is the best thing ever.”
On Mental Health:
“A big part of the message of the book, Shoveling Shit, is this idea that there are sacrifices when you want to really do great things. The best way to spend your day is as an entrepreneur where you find your purpose, your passion.”
On Decision Making:
“How do you lead a team to jump out of an airplane? You’re not saying, ‘Don’t be scared.’ You’re saying, ‘Are we prepared? Are we doing the right thing?’ Let’s do it together and nail it.”
On Networking:
“Entrepreneurs hang out with other entrepreneurs. If you can help an entrepreneur, if you can help clear an obstacle, or get them a client or a hire, those are relationships that really matter.”
On Purpose:
“We love entrepreneurs because at the end of the day, there’s no better way to spend your day, but it can suck. There’s misery there,. It’s also an honor to be able to work on your own stuff every day.”
On Continuous Improvement:
“We’ve learned a lot of lessons of what to do, what not to do. We didn’t write the book for venture capital backed founders. We wrote this for every business owner who has to make it today.”
On Guy Friends:
“The biggest blessing as a guy is to have these lifelong, loyal guy friends who make it worthwhile. These are people where there’s nothing they could do to hurt the friendship.”
On Authenticity:
“We’re just the same schmuck we were before we made money. People assume that you’re smarter than you are, whereas you’re just the same person you were before with more money.”
On Preparation:
“If you’re raising money, you don’t want to think about it an hour before. Is your deck ready? Your financials ready? Do you have the story? Showing up prepared in a way that you can bring value really matters.”
In health,
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach.
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