Live from SXSW: Mike and Kass Lazerow’s ‘messy’ path to success

Key takeaways

Success in entrepreneurship often comes from navigating unexpected challenges and learning from failures.
Transparency and clear communication between co-founders are critical for the success of both their personal and professional relationships.
Company culture and employee appreciation play a crucial role in building a successful business.
Strategic decision-making, including assessing alignment of values, can significantly impact the success of acquisitions.
Understanding the importance of team dynamics and investing wisely is crucial for aspiring entrepreneurs.

Summary

The Messy Journey of Entrepreneurship

In this episode, Jeff Berman talks to Cass and Mike Lazerow about their entrepreneurial journey, emphasizing how the path to success is often filled with unexpected challenges and learning experiences. They discuss their experience co-founding Buddy Media, the social media marketing platform that ultimately sold to Salesforce for $745 million. The Lazerows highlight the importance of resilience in entrepreneurship, especially when faced with significant setbacks, such as the near-collapse of their early business venture, golf.com, during the dot-com bubble.

Navigating Co-founder Dynamics

Cass and Mike discuss the unique dynamic of being both business partners and spouses. They delve into the complexities of making decisions together, managing roles within the company, and maintaining balance in both their personal and professional lives. They share anecdotes from their time at Buddy Media, illustrating how their relationship helped them navigate high-pressure situations while stressing the necessity of clear communication and division of responsibilities to keep both their marriage and business thriving.

Lessons Learned and Shared

The conversation centers around the valuable lessons Cass and Mike have distilled into their upcoming book, "Shoveling Sh!t: A Love Story About the Entrepreneur's Messy Path to Success." The Lazerows emphasize the significance of transparency and accountability in business, sharing personal stories about challenges they faced while building their companies. They also touch on the importance of company culture and resiliency, encouraging future entrepreneurs to embrace mistakes and learn from them.

Strategic Decisions and Acquisitions

The Lazerows recount their strategic decision to sell Buddy Media to Salesforce despite receiving a higher offer from Google. They describe the due diligence process and how they assessed which acquisition would align best with their company values and vision for the future. Mike illustrates the importance of identifying shared morals and philanthropic goals between companies, underscoring how these factors influenced their decision to choose Salesforce over the higher bid.

Industry Insights and Investment

Towards the end of the episode, the Lazerows share insights on their investment philosophy as they have successfully transitioned from entrepreneurs to investors, having invested in over 100 companies. They discuss what qualities they look for in potential investments, emphasizing the importance of the team, market potential, and the need for entrepreneurs to understand their gaps in knowledge and skill sets.

Show notes

Serial entrepreneurs and investors Mike and Kass Lazerow are best known for co-founding Buddy Media, the social media marketing platform that sold to Salesforce for $745 million. Host Jeff Berman joined the Lazerows on stage at the 2025 SXSW conference to discuss their extraordinary career journey as co-founders and spouses. They’ve distilled their most meaningful business lessons into a new book: Shoveling $h!t: A Love Story About the Entrepreneur's Messy Path to Success.

Book details: https://shovelingshit.com/

Note: Kass Lazerow is on the board of WaitWhat — the company that makes this podcast.

Read a transcript of this episode: https://mastersofscale.com

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