Learning from Business Mistakes: Building a $200M Company with Brian Gottlieb

My guest for Episode #275 of the My Favorite Mistake podcast is Brian Gottlieb, an inspiring entrepreneur and founder who transformed a modest $3,000 startup into a thriving group of multistate companies valued at nearly $200 million.

Episode page with video, transcript, and more

Brian’s companies have earned spots on the Inc. 5000 list for four consecutive years and have been recognized as one of Wisconsin's best workplaces. In addition to being a successful CEO, Brian is a Harvard Business School alum, angel investor, keynote speaker, and author of the new book Beyond the Hammer: A Fresh Approach to Leadership, Culture, and Building High-Performance Teams.

In this episode, we discuss Brian’s journey from working odd jobs to founding his first home improvement company and scaling it to a multi-million dollar business. Brian shares his "favorite mistake"—not pursuing formal education after high school—and how that perceived mistake shaped his entrepreneurial path. We also dive into his approach to leadership, the importance of building a strong culture, and how empowering people can drive success.

Brian also opens up about his time at Harvard Business School and how it helped him evolve as a leader. We discuss the challenges of balancing performance and culture, why hiring for culture fit matters, and how his philosophy of "building people before building a business" has been key to his success. Whether you’re an entrepreneur, business leader, or simply interested in learning from others' mistakes, Brian’s story offers valuable lessons on growth, leadership, and resilience.

Tune in to hear Brian's insights on leadership, the value of mistakes, and the strategies that helped him build a $200M business from scratch.

Questions and Topics:

• What would you say is your favorite mistake?
• How did your decision not to attend college shape your entrepreneurial path?
• Can you tell us more about your experience at Harvard Business School and how it impacted your leadership approach?
• What was your first business, and how did it evolve into a multi-state company?
• How did you manage learning on the job while growing a business from scratch?
• How did you approach building the culture and developing people within your organization?
• What do you think about companies that focus on culture in addition to performance?
• How do you balance hiring for performance versus culture fit, and how do you handle it when someone performs well but doesn’t fit the culture?
• Can you explain the concept of “beyond the hammer” and how it applies to leadership and business growth?
• How do you handle mistakes or performance issues in a way that supports growth and learning?
• What are your thoughts on the “stay interview” concept, and how does it help improve organizational culture?
• How did you empower your team to make decisions and learn from their mistakes?
• What is your perspective on micromanaging versus empowering employees?
• How do you maintain alignment within your company and prevent cultural clashes when bringing in experienced hires?
• How important is long-term thinking in leadership, especially when growing a business?
• What leadership lessons have you learned from Toyota, and how do you apply them in your business?