Podcast Summary: The Futur with Chris Do – Episode 336: Risk, Failure & Growth: The Truth About Entrepreneurship with Michael & Kass Lazerow

Release Date: March 26, 2025

In Episode 336 of The Futur Podcast, host Chris Do engages in a candid and insightful conversation with entrepreneurs Michael and Kass Lazerow. The episode delves deep into the realities of entrepreneurship, shedding light on the myths, challenges, and essential strategies for growth and resilience in the business world.

1. Introducing Michael & Kass Lazerow

The episode kicks off with Michael and Kass sharing their entrepreneurial journey, highlighting their long-term partnership both in life and business.

Michael Lazerow (00:55):
"We started our first company when we were dating, as all people who are madly in love and newly in love do. And that company was Golf.com..."

Michael recounts their early ventures, including the successful acquisition of Buddy Media by Salesforce for $745 million, emphasizing their complementary roles—Michael focusing on creative, sales, and product development, while Kass manages operations, marketing, and the challenging task of firing employees.

2. Philosophy on Firing Employees

A significant portion of the discussion centers on Kass's unique approach to managing personnel, particularly the delicate process of letting employees go.

Kass Lazerow (03:05):
"My philosophy is that you spend so much time and care trying to recruit somebody for a company that you have to spend the same amount of time when you actually let them go." (03:05)

Kass underscores the importance of handling terminations with kindness and transparency, viewing it as an opportunity for employees to grow and realign their career paths. Michael adds how Kass's approach not only maintains company efficiency but also positively impacts former employees' lives.

3. The Reality of Entrepreneurship: Myths and Sacrifices

Chris Do challenges the glamorized perception of entrepreneurship, urging a more grounded understanding of its demands.

Cass Lazerow (04:04):
"Entrepreneurs who learn to love to shovel are unstoppable... if you can sit in the fear, not try to dismiss it, but still operate in it, those are the entrepreneurs that are unstoppable." (04:04)

Kass debunks common misconceptions, highlighting that entrepreneurship often entails significant personal sacrifices, including strained relationships and missing out on family moments. Michael echoes this sentiment, criticizing the superficial portrayal of entrepreneurs on social media and emphasizing the gritty reality behind the scenes.

4. Dealing with Failure and Pivoting

The conversation delves into the necessity of pivoting and embracing failure as integral to entrepreneurial success.

Michael Lazerow (19:36):
"Sometimes you got to, like, just, you know, you got to suck it up stuff when people are down and out." (19:36)

They discuss their experience with multiple pivots at Buddy Media, illustrating how adaptability and resilience are crucial. Kass adds that the willingness to let go of initial ideas and pivot is a defining trait of successful entrepreneurs.

5. Leadership and Transparency

Effective leadership, characterized by transparency and honest communication, is highlighted as essential for maintaining team loyalty and trust.

Cass Lazerow (22:08):
"If you can lead with a huge amount of transparency... people don't leave because they're so loyal, because you're telling them the truth." (22:08)

Michael and Kass emphasize that unexpected surprises can erode trust, while consistent honesty fosters a committed and stable workforce.

6. Personal Dynamics: Married Entrepreneurs

A heartfelt segment explores the challenges and strategies of maintaining a healthy personal and professional relationship as married business partners.

Michael Lazerow (25:26):
"I'll never do anything with anyone other than Cass. And if I do, please punch me in the face, someone and stop me." (25:26)

They share anecdotes illustrating their differing approaches—Michael's instinctual, risk-taking nature versus Kass's tactical, operational mindset. This dynamic balance allows them to complement each other's strengths and mitigate weaknesses, fostering both personal and business growth.

7. Decision Making: Gut vs. Logic

The duo discusses the interplay between intuition ("gut feeling") and logical analysis in making business decisions.

Michael Lazerow (28:21):
"It's a subconscious processing of data... It is the feeling that I've tapped into, which I call my gut." (28:21)

Kass adds her perspective on evaluating decisions through a logical framework, ensuring that ventures are scalable and sustainable before committing resources.

8. Cheat Codes for Entrepreneurship

As the conversation progresses, Michael and Kass share practical strategies—referred to as "cheat codes"—to navigate the entrepreneurial landscape effectively.

Michael Lazerow (60:18):
"Number one is to me is don't run out of money... the number one way to really bootstrap your business is customers." (60:18)

Cass Lazerow (61:08):
"Focus, focus, focus... use your financial projection as your bible to look at every day." (61:08)

These insights revolve around financial prudence, market research, and maintaining unwavering focus on core business objectives to ensure longevity and success.

9. Marketing Strategies: Conference Marketing

Kass elaborates on their innovative marketing tactics, particularly leveraging conferences to boost brand recognition and lead generation.

Cass Lazerow (66:53):
"We went there and then I would negotiate two, first three for tickets... we'd put our brand on coffee cups." (66:53)

They discuss the effectiveness of creative, low-cost marketing methods—like distributing branded popcorn or coffee cups at large events—to attract attention and foster meaningful conversations with potential clients.

10. Relationships and Parenting as Entrepreneurs

Towards the end, Chris Do steers the conversation towards balancing entrepreneurship with family life, touching upon the mental load often shouldered by partners.

Kass Lazerow (46:35):
"We call him Chris. I actually have a name for him. It's called Vacation Mike." (46:35)

Michael and Kass candidly discuss the emotional and logistical challenges of maintaining familial relationships while pursuing demanding business ventures, emphasizing the importance of open communication and mutual support.

11. Book Launch: "Shoveling Shit: A Love Story"

The episode concludes with a promotion of Michael and Kass's upcoming book, which encapsulates their entrepreneurial experiences and lessons.

Cass Lazerow (58:29):
"It's about the entrepreneur's messy path to success... 50 plus cheat codes in there." (58:29)

Chris Do encourages listeners to anticipate the book's release in June, highlighting it as a resource packed with practical advice for aspiring entrepreneurs.

Notable Quotes with Timestamps

• Cass Lazerow (00:00):
  "Entrepreneurs who learn to love to shovel are unstoppable, period."

• Chris Do (04:29):
  "There's so many things I want to get into in terms of, like, how you stay married and happy working together..."

• Michael Lazerow (17:46):
  "It does hurt. There's no way around that."

• Cass Lazerow (22:08):
  "Being totally transparent with your team... they don't leave because they're loyal."

• Cass Lazerow (06:47):
  "There's this glorification that you're going to have all the time in the world..."

• Michael Lazerow (60:18):
  "Number one is to me is don't run out of money..."

Conclusion

Episode 336 presents an unfiltered look into the entrepreneurial journey, emphasizing resilience, adaptability, and the intricate balance between personal and professional life. Michael and Kass Lazerow offer valuable insights grounded in their extensive experience, making this episode a must-listen for aspiring and seasoned entrepreneurs alike.

For more detailed insights and additional content, visit thefutur.com/podcast.