The Futur with Chris Do

336 - Risk, Failure & Growth: The Truth About Entrepreneurship - With Mike & Kass Lazerow

Mar 26, 2025

Michael Lazerow, a visionary entrepreneur behind Golf.com and Buddy Media, teams up with his wife Kass, an expert in operations and kindness-driven leadership. They share their journey from launching startups to navigating success, emphasizing the myths of entrepreneurship and the necessity of embracing failure. Kass discusses the art of firing with empathy, while both explore the delicate balance between business and family life. Their candid insights offer valuable lessons on trust, transparency, and the importance of genuine relationships in entrepreneurship.

01:22:24

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Episode guests

Michael Lazerow

Kass Lazerow

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Episode notes

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Quick takeaways

Successful entrepreneurs must embrace fear and uncertainty as integral parts of their journey to foster resilience and growth.

Entrepreneurship is often romanticized, but aspiring business owners should be prepared for sacrifices and an imbalanced lifestyle filled with challenges.

The ability to pivot and adapt strategies is crucial for success, as real innovation often emerges from revising initial business ideas based on market feedback.

Deep dives

The Importance of Embracing Fear in Entrepreneurship

Successful entrepreneurs learn to embrace fear rather than dismiss it, acknowledging that managing uncertainty is part of the entrepreneurial journey. The ability to operate effectively amid fear is crucial, as it represents a deep understanding of the challenges inherent in business growth. By accepting the steep learning curve of entrepreneurship, individuals can cultivate resilience and fortitude, becoming formidable in their pursuits. Those who genuinely embrace this concept often find themselves unstoppable in their ventures.

Intro

3min

Unmasking the Myths of Entrepreneurship

6min

Navigating Office Dynamics: Trust, Tension, and Team Spirit

2min

Navigating Entrepreneurial Dynamics

26min

Navigating Communication Challenges

7min

Navigating Family Dynamics and Mental Load

13min

Entrepreneurial Insights and Strategies

21min

Embracing Authenticity in Relationships and Entrepreneurship

3min

In this episode, I sit down with Mike and Kass Lazerow—serial entrepreneurs, business partners, and husband-and-wife duo—to discuss the realities of entrepreneurship, leadership, and working together as a couple. We dive into their journey from launching Golf.com to selling Buddy Media to Salesforce for $745M. Mike shares his instinctive, visionary approach to business, while Kass offers sharp operational expertise, revealing the balance that has fueled their success. We talk about the myths of entrepreneurship, the importance of embracing failure, and how firing people with kindness can change lives. The conversation takes a candid turn as we explore what it means to navigate business, marriage, and parenting while staying aligned. If you've ever struggled with leadership, scaling a business, or balancing work and relationships, this episode is full of valuable insights and honest reflections.

Timestamps:

(00:00) - Introduction

(05:10) - Mike & Kass’s journey from Golf.com to Buddy Media

(11:45) - The biggest myths about entrepreneurship

(18:30) - Learning to embrace fear and uncertainty in business

(25:55) - How Kass approaches firing people with kindness

(32:40) - Navigating marriage and business: The challenges and rewards

(39:15) - The importance of trusting your gut vs. making data-driven decisions

(45:50) - How social media has changed entrepreneurship

(52:30) - The right way to pivot when a business idea isn’t working

(59:05) - Leadership lessons: Why transparency matters

(1:05:40) - The mental load of running a business and parenting