Kass and Mike Lazerow on Why Building Big Requires Feeling Deep

What if the real story behind a $745 million exit wasn’t just the pitch decks, product-market fit, or funding rounds, but the emotional toll it took to get there?

In this episode of Passion Struck, I sit down with serial entrepreneurs Kass and Mike Lazerow for a brutally honest conversation about the unseen side of building big. Their new book, Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success, doesn’t just pull back the curtain—it tears it down.

Kass and Mike built and sold Buddy Media to Salesforce for nearly three-quarters of a billion dollars. They raised three kids. They battled cancer four times. And through it all, they remained partners not just in business, but in life.

But what they share here goes deeper than strategy. It’s about identity, ego, and the emotional labor most entrepreneurs never talk about. Kass opens up about the moment she asked Mike to fire her—and how that decision reshaped not just their roles, but their relationship. Mike reflects on the trap of performative leadership and how success often masks burnout and disconnection.

Together, they challenge the myth of the fearless founder and offer a radically different lens: that scaling something meaningful requires not less feeling, but more. More emotional awareness. More humility. More self-inquiry. And a willingness to be seen in the mess.

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Listen to the episode on Apple Podcasts, Spotify, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Listen Notes, Amazon Music, or on your favorite podcast platform. You can watch the interview on YouTube below.

Essential Lessons from Kass and Mike Lazerow: Grit, Growth, and Genuine Leadership

In this episode of Passion Struck, I sit down with entrepreneurial duo Kass and Mike Lazerow to dive deep into their journey building Golf.com and Buddy Media, culminating in a high-stakes sale to Salesforce. Rather than gloss over their triumphs, we explore the rocky road of early failures and how those setbacks sparked resilience. I ask how hiring the right people transformed their startup, and we discuss why keeping ego in check is crucial when data contradicts your instincts.

We also uncover the intimate dynamics of running a business with your life partner: from creative friction to navigating burnout and raising a family while expanding globally. Along the way, I learn about their transformative mentorships with Gary Vaynerchuk and Marc Benioff, and how honest communication, whether in boardrooms or marriages, became a guiding principle. Finally, Kass and Mike share the “rules” they follow to stay grounded amid constant upheaval, proving that you can build big without losing sight of what ultimately matters.

In This Episode With Kass and Mike Lazerow, You’ll Learn:

• Resilience through Failure: Mike recalls buying back Golf.com after its near-collapse, sleeping in cramped hotel rooms, and relying on total transparency with employees to revive the company.
• Humility in Leadership: Kass emphasizes the importance of “knowing what you don’t know,” sharing why bringing on seasoned executives (like Susan St. Ledger) was pivotal to scaling Buddy Media.
• Balancing Ambition and Burnout: The couple outlines daily strategies, such as non-negotiable workouts and quiet time, to safeguard mental and physical health while chasing aggressive growth targets.
• Founding with Partnership: They describe how their complementary skill sets (Kass’ operational rigor and Mike’s big-picture vision) prevented co-founder stagnation and allowed them to lean into each other’s strengths.
• Power of Authentic Communication: Mike explains why receiving honest feedback, rather than platitudes, has been a career-defining gift, especially when tough conversations surfaced blind spots.
• Why Giving Back Matters: Both highlight how aligning with Marc Benioff’s 1-1-1 model at Salesforce and partnering with empathetic entrepreneurs like Gary Vaynerchuk has reinforced their belief that purpose and profit can coexist.

WHY IS THIS EPISODE WITH KASS AND MIKE LAZEROW A MUST-LISTEN?

Whether you’re launching your first venture or scaling an existing team, this episode delivers no-fluff insights straight from founders who have “been in the trenches.” Kass and Mike Lazerow strip away startup clichés, revealing how resilience, self-awareness, and transparent leadership lessons were forged through real setbacks. Beyond tactical takeaways—like identifying blind spots and assembling the right board—listeners will find inspiration in the genuine partnership that allowed this couple to build multi-million-dollar companies without sacrificing their family, values, or sanity. If you want to understand the messy, human side of entrepreneurship and learn how to navigate it with grit and heart, this conversation is essential listening.

Key Takeaways We Discuss

✔️ Why the idea of “founder as hero” is toxic—and what real leadership looks like
✔️ The moment Kass asked Mike to fire her—and how that reshaped their marriage
✔️ How to build a culture that doesn’t collapse under pressure
✔️ What cancer taught them about slowing down and prioritizing what matters
✔️ The difference between startup survival and startup success
✔️ Why choosing the right partner—in business and life—might be the most important decision you ever make
✔️ How emotional awareness, humility, and vulnerability scale better than ego ever could

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Book Spotlight: Shoveling $h!t

When Kass and Mike dug into their book, Shoveling $h!t: A Love Story About the Entrepreneur’s Messy Path to Success, they didn’t just talk about late nights and boardroom battles—they opened up about juggling marriage, kids, and multi-million-dollar deals. I loved hearing how they treated their relationship as the foundation of everything they built. They shared stories of packing newborns into hotel rooms while raising capital and staying up past midnight to squash creative disagreements before they escalated.

Their book lays out how they set non-negotiable boundaries—like dedicated “quiet time” for two and daily workouts—to make sure they weren’t just co-founders but also co-parents and partners. They talked about the guilt that comes with missing Little League games or date nights, and how they’ve learned to reframe those moments: instead of feeling torn, they focus on teaching their kids resilience by example. For every chapter on scaling Buddy Media or navigating that high-pressure Salesforce acquisition, there’s a counterchapter on how they reminded each other to breathe, unplug, and prioritize family dinners—even when their inboxes were exploding.

If you felt inspired by our conversation about humility, communication, and shared vision, Shoveling $h!t doubles down on those themes with practical “rules” for maintaining sanity as a power couple in a startup world. Whether you’re wondering how to prevent late-night pivots from derailing date night or how to involve kids in your entrepreneurial journey without burning them out, this book is the blueprint. It’s proof that you can build something huge without losing sight of why you started in the first place.

Thanks, Kass and Mike Lazerow

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RESOURCES FROM THE SHOW WITH KASS AND MIKE LAZEROW

Please note that some of the links on this page (books, movies, music, etc.) lead to affiliate programs for which The Passion Struck podcast receives compensation. It’s just one of the ways we keep the lights on around here. Thank you so much for being so supportive!

1. Kass and Mike Lazerow’s Website
2. Kass and Mike Lazerow’s Instagram
3. BUY Kass and Mike Lazerow’s book ‘Shoveling $hit”
4. APA’s recognition of mattering as critical to child mental health
5. Passion Struck Core Value System: https://passionstruck.com/the-passion-struck-core-belief-system/
6. Listen to Passion Struck’s interviews with New York Times bestselling authors Gretchen Rubin and Seth Godin.
7. Check out Passion Struck’s Episode Starter Packs on Spotify or Passion Struck starter packs to get started with the podcast.

Can’t miss my episode with Ethan Mollick on the Impact of AI on Life and Work

Catch my interview with Simone Stolzoff on the Amazing Art of Finding Work-Life Harmony

My interview with Brian Evergreen on How You Humanize Work in the Age of AI

About Today’s Guests, Kass and Mike Lazerow

Kass and Mike Lazerow are serial entrepreneurs, investors, and authors whose partnership, both in business and life, has spanned over two decades. After cofounding Golf.com in 1998 (sold to Time Warner in 2006), they launched Buddy Media, which quickly became the world’s leading social media marketing platform before selling to Salesforce for $745 million in 2012. Since then, they’ve advised and invested in nearly 100 early-stage startups, collaborating with high-growth companies like Scopely and Liquid Death and serving on boards and in mentorship roles alongside visionaries such as Gary Vaynerchuk and Marc Benioff.

Their experiences navigating epic wins, crushing setbacks, and raising a family together are captured in their candid new book, Shoveling $h!t: A Love Story About the Entrepreneur’s Messy Path to Success. Today, Kass and Mike live between New York City and the Hudson Valley with their three grown children and two rescue dogs, continuing to share hard-earned lessons on leadership, resilience, and the importance of giving back.

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