Navigating Communication Challenges

This chapter shares a personal story highlighting the importance of clear communication in both business and personal relationships. It explores how addressing difficult conversations and self-awareness can strengthen partnerships and foster mutual respect.

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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