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Recently I fell in love with a popular series on YouTube called Actors Round Table. Since I talk over with CEOs, founders, and executives a lot, a co-worker suggested we create a similar version, but with business executives. I actually liked the idea, so we did it! This was our first episode where I invited five founders and CEOs to speak about their journeys, challenges and lessons learned.
The five CEOs honored are: Sean Riley of Dude Wipes, Brian Barnes from M1, Evan Wray from MavelyKristin Olszewski from Nomadica Wine and Erica Bethe Levin from Globowl. The discussion touched on the realities of leadership, entrepreneurship and the pursuit of lasting impact.
Here are five key takeaways from their conversation.
1. Founder vs. CEO: Balancing
When you begin your individual business, it’s natural to wish to be more involved in on a regular basis life. Sean Riley described the transition from founder to CEO as a journey from “Michael Jordan to Phil Jackson” – starting from a hands-on player to a strategic leader. This evolution challenges leaders to trust their teams and let go of the need to manage. “You hired them because they’re better at it than you are,” said Kristin Olszewski, who shared her previous struggles with micromanagement. The consensus was clear: To scale successfully, founders have to take on a broader leadership role, even if which means moving away from day-to-day operations.
2. Taking risks and responsibilities
Entrepreneurship is a dangerous business. Brian Barnes, who has raised a total of $315 million, talked about the enormous pressure to scale the 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 burden of raising money from friends and family. These stories highlighted the high stakes and emotional toll of risk management, but also the enormous advantages of staying true to a clear vision.
3. Culture defines success
Company culture has grow to be the cornerstone of sustainable growth for all CEOs. Sean Riley emphasized that culture serves as a filter for decisions and talent. “Culture fit is always more important than talent fit,” he said. The group discussed how a strong culture attracts the right people while removing those that do not align with the company’s values. Evan Wray who just he sold his company to Mavely for $250 millionemphasized this issue, even with top performers who pose a threat to the company’s culture. “Ten times out of ten, remove them because company culture is the key to business success.” Erica wondered how culture evolves over time with each team member’s influence. “You can’t impose culture – it’s shaped by the community you build.”
4. Play YOUR game, not theirs
It’s hard for large corporations to face out and move as quickly as a startup. For smaller, disruptive corporations, brand authenticity is non-negotiable. Sean Riley credited Dude Wipes’ humorous and accessible 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 larger toilet paper brands cannot do. Brian Barnes emphasized his approach with M1: “People want there to be an element of craftsmanship in the product or anything they consume.” If these CEOs decided to follow the conglomerates’ lead, they might lose.
5. The power of resilience and curiosity
The themes that recurred during the discussion were resilience and curiosity. Kristin Olszewski described resilience as the “number one trait of a founder,” and Evan Wray emphasized the importance of curiosity in meeting challenges and finding revolutionary solutions. Erica Bethe Levin added that in moments of doubt, maintaining a sense of purpose and integrity is crucial. The panelists collectively agreed that using failures as opportunities for growth is the key to long-term success. After all, entrepreneurship is a roller coaster. There can be many ups and downs. To be a successful entrepreneur, you have to just accept this ride.