Passion Struck with John R. Miles: Episode 620 – Kass and Mike Lazerow on Why Building Big Requires Feeling Deep

Release Date: June 5, 2025

In Episode 620 of Passion Struck with John R. Miles, hosts John R. Miles welcomes Kass and Mike Lazerow, seasoned entrepreneurs and authors of the candid book Shoveling A Love Story. This episode delves deep into the gritty realities of building and scaling businesses, the interplay between personal relationships and professional partnerships, and the essential mental shifts required to sustain passion without falling into burnout.

1. Introduction to Kass and Mike Lazerow

John R. Miles begins by introducing Kass and Mike Lazerow, highlighting their impressive entrepreneurial journey, which includes building and selling multiple companies like Buddy Media, acquired by Salesforce for $745 million. Beyond their business acumen, Kass and Mike's partnership extends into their personal lives as spouses and parents of three, offering a unique perspective on balancing love and business.

2. The Shovel Metaphor in Entrepreneurship

The conversation kicks off with the significance of the shovel metaphor featured in their book. Kass explains, “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” (07:16). This metaphor encapsulates the relentless effort required in entrepreneurship, likening it to the perseverance needed in golf—persisting through bad shots until a good one propels you forward.

3. Navigating Failure: The Golf.com Acquisition

A pivotal moment in their journey was the acquisition of Golf.com by ChipShot during the dot-com boom. Kass recounts the abrupt reversal when Sequoia pulled out, leading to the company's near-collapse. “[...] being an entrepreneur is a test of your grit and your ability to endure suffering” (08:42). This experience underscored the importance of resilience and the harsh realities of startup life, teaching them invaluable lessons about due diligence and the fragility of business ventures.

4. Managing Ego in Founders

John raises the critical issue of ego among startup founders, asking Kass and Mike how they handle it. Kass responds, “I think the ego happens a lot. It comes forward, and I think a lot of founders get blinded by their ego and pride” (14:38). They discuss how ego can prevent necessary pivots and honest assessments of a company's performance, emphasizing the need for self-awareness to navigate challenges effectively.

5. Building and Maintaining Relationships

The dialogue shifts to the importance of relationships in business growth. Kass shares their strategic approach to building relationships with investors and board members, highlighting transparency and giving value as cornerstone principles. “[...] if you have a give mentality, which you've talked about, the rest takes care of itself” (18:17). This philosophy not only facilitated their successful fundraising but also fostered long-term, mutually beneficial partnerships.

6. Overcoming Burnout and Prioritizing Well-being

Addressing the inevitable issue of burnout, Kass and Mike provide practical strategies to maintain personal well-being amidst entrepreneurial chaos. Kass advises, “you have to prioritize your health so that you actually can function right” (23:24), suggesting routines like non-negotiable workouts and dedicated quiet time. They stress that burnout is not a failure but rather feedback, urging entrepreneurs to listen and adjust accordingly.

7. The Intersection of Personal Life and Business

A touching anecdote reveals the intertwining of Kass and Mike's personal and professional lives. Kass recalls bringing up a business idea during her C-section recovery, leading to the inception of Buddy Media (25:46). This story illustrates how deeply personal experiences and relationships can drive business innovation and growth, reinforcing their belief in purpose-driven entrepreneurship.

8. Collaborating with Gary Vaynerchuk and Embracing Intellectual Property

The episode highlights their collaboration with Gary Vaynerchuk, whose forward-thinking VeeFriends concept resonates with Kass and Mike's emphasis on empathy and community-building. Kass states, “intellectual property is one of the most powerful businesses and forces in the world” (30:59), appreciating how Gary harnesses IP to foster positive communities and drive impactful business models.

9. Balancing Co-founder Relationships and Business Growth

Kass and Mike discuss the dynamics of their partnership, emphasizing complementary strengths—Kass as the operations-oriented voice of reason and Mike as the visionary ideator. Kass mentions, “It's like Yang and Yin. It was just the glue” (48:09). They advocate for founders to partner with those who offer different skills to prevent decision paralysis and foster balanced leadership.

10. Lessons Learned and Advice for Aspiring Founders

Wrapping up, Kass and Mike share invaluable advice for budding entrepreneurs:

• Self-awareness: Understanding personal and business blind spots is crucial.
• Strategic Hiring: Prioritize cultural fit and the ability to wear multiple hats in early stages.
• Embracing Failure: View setbacks as learning opportunities rather than defeats.
• Prioritizing Health: Ensure that personal well-being is maintained to support sustained business efforts.

John encapsulates the essence of their discussion with poignant takeaways:

• Ego is a wrecking ball.
• Self-awareness is a survival skill.
• Burnout isn't failure, it's feedback.
• Prioritize your well-being like your life depends on it because it does.
• Success isn't built in spreadsheets, it's built in the trenches.

Conclusion

Episode 620 of Passion Struck offers a raw and honest exploration of the entrepreneurial journey, emphasizing that true success is molded in the midst of challenges and personal sacrifices. Kass and Mike Lazerow's insights serve as a beacon for those striving to build meaningful businesses without losing sight of personal integrity and well-being.

For those inspired by this episode, Kass and Mike's book, Shoveling A Love Story, is available on Amazon. To dive deeper into their experiences and gain further practical advice, visit passionstruck.com and consider joining their community of seekers, builders, and change-makers.

Note: Timestamps correspond to points in the transcript where key discussions and quotes occur.