Live from SXSW: Mike and Kass Lazerow’s ‘messy’ path to success
Mar 20, 2025
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Mike and Kass Lazerow, co-founders of Buddy Media and seasoned entrepreneurs, discuss their remarkable journey as partners in business and marriage. They share their tumultuous experience during the dot-com boom, including a near-collapse due to a botched acquisition and the strains of financial stress. The pair also delve into the importance of adaptability in entrepreneurship, effective board relationships, and employee engagement initiatives. Their insights reveal that success is often messy, blending personal and professional resilience.
Mike and Kass Lazerow emphasize that resilience and adaptability in entrepreneurship are essential for overcoming challenges and achieving success.
The importance of fostering a strong and inclusive company culture is crucial for enhancing teamwork and overall organizational success.
Deep dives
Innovative CRM Solutions
Atio represents a new wave in customer relationship management systems by adapting to the unique workflows of each business rather than requiring businesses to adjust to its framework. Its AI capabilities allow it to automate routine tasks, such as organizing contacts and syncing calendars, thus minimizing manual data entry. This automated approach not only streamlines operations but also empowers teams to prioritize scaling their business rather than getting bogged down in administrative tasks. The introduction of such innovative solutions highlights the shift in how technology is becoming increasingly aligned with operational needs.
Life Lessons from Entrepreneurship
Cass and Mike Lazaro share the raw and honest experiences that shaped their entrepreneurial journey, particularly the challenges faced when starting their first company, golf.com. After being sold, they were blindsided when the acquiring company declared bankruptcy, leaving them devastated and responsible for their employees' livelihoods. The Lazaro's resilience shone through as they decided to start over, emphasizing a crucial lesson for entrepreneurs: the ability to persevere and adapt in the face of adversity is vital. Their story offers a potent reminder that the path to success is often fraught with obstacles that require both grit and creative problem-solving.
Importance of Company Culture
The Lazaro couple places significant importance on developing a strong company culture that fosters teamwork and collaboration. Drawing from past experiences, Cass emphasizes the elimination of cliques and negative behaviors within the workplace, aiming to create an environment where every employee feels valued. Initiatives such as scavenger hunts and unique celebrations of success are used to bond teams and enhance morale. This focus on creating a supportive and inclusive culture is presented as a critical factor in not just employee satisfaction but overall organizational success.
Navigating Growth and Investment
As the founders of Buddy Media, Cass and Mike Lazaro navigated significant growth and investment opportunities that ultimately led to the company’s acquisition by Salesforce. They faced the daunting choice between accepting a lucrative offer from Google or aligning with Salesforce, opting for the latter due to shared values and vision. This decision exemplifies not only the necessity of strategic thinking in high-stakes situations but also prioritizes organizational ethos over mere financial gain. Their investment philosophy has evolved into looking for entrepreneurs who demonstrate resilience and the capacity for growth through challenges, creating a framework for evaluating future business opportunities.
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.