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I recently fell in love with a popular YouTube series called Actors' Table. Since I talk a lot with CEOs, founders, and leaders, a colleague suggested we produce a similar version, but with business leaders. I loved the idea, so we went for it! This was our first episode and I invited five founder-CEOs to discuss their journeys, challenges and lessons learned.
The five featured CEOs were: Sean Riley of Dude Wipes, M1's Brian Barnes, Evan Wray of Mavely, Kristin Olszewski of Nomadica Wine AND Erica Bethe Levin of Globowl. The discussion explored the realities of leadership, entrepreneurship, and striving to create lasting impact.
Here are five highlights from their conversation.
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1. Founder vs. CEO: A Balancing Act
When starting your own company, it's natural to have a desire to be more involved in the day-to-day. Sean Riley described the transition from founder to CEO as a journey from “Michael Jordan to Phil Jackson” — starting as a hands-on player and evolving into a strategic leader. This evolution challenges leaders to trust their teams and let go of the need for control. “You hired them because they're better than you at those things,” said Kristin Olszewski, who shared her past struggles with micromanaging. The consensus was clear: To scale effectively, founders must embrace a broader leadership role, even if that means stepping away from day-to-day operations.
2. Embracing risk and responsibility
Entrepreneurship is a risky business. Brian Barnes, who raised a total of $315 million, spoke about the tremendous pressure of growing a business, especially when competing with giants like JP Morgan and Charles Schwab. “You have to figure out how to use every dollar ten times more efficiently,” he noted. Erica Bethe Levin added a personal perspective, sharing the weight of raising money from friends and family. These stories highlighted the high stakes and emotional toll of managing risk, but also the deep rewards of staying committed to a clear vision.
3. Culture determines success
Company culture emerged as a cornerstone of sustainable growth for all CEOs. Sean Riley pointed out that culture serves as a filter for decisions and talent. “It's always culture fit over talent fit,” he said. The group discussed how a strong culture attracts the right people while driving away those who don't align with the company's values. Evan Wray, who alone sold his company Mavely for $250 millionemphasized this point, even with top performers posing a threat to company culture. “Ten times out of ten, get rid of them, because company culture is the key to scaling a successful business.” Erica reflected on how culture evolves over time, influenced by each team member. “You can't dictate culture – it's shaped by the community you build.”
4. Play your game, not theirs
For large companies, it's hard to stand out and move as fast as a startup. For smaller, disruptive companies, authenticity in branding is non-negotiable. Sean Riley credited Dude Wipes' humorous and relatable marketing as a major factor in its success. “It's about being real and giving people a reason to trust you,” he said. Something that the bigger toilet paper brands are unable to do. Brian Barnes emphasized his approach with the M1 – “People want a product or whatever they're consuming to have an element of craftsmanship.” If these CEOs decided to follow in the footsteps of the conglomerates, they would lose.
5. The power of persistence and curiosity
Resistance and curiosity were recurring themes throughout the discussion. Kristin Olszewski described resilience as “the number one trait for a founder,” while Evan Wray emphasized the importance of curiosity in tackling challenges and finding innovative solutions. Erica Bethe Levin added that maintaining a sense of purpose and integrity is critical in moments of doubt. Together, the panelists agreed that accepting setbacks as opportunities for growth is key to long-term success. After all, entrepreneurship is a rollercoaster. There will be many ups and downs. To be a successful entrepreneur, you must embrace the journey.