"When you start 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 earlier struggles with micromanagement. The consensus was clear: To scale effectively, founders must embrace a broader leadership role, even if it means stepping away from day-to-day operations."
"Entrepreneurship is a risky business. Brian Barnes, who raised a total of $315 million, spoke about the immense pressure of scaling 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 responsibility that weighs on the shoulders of those who lead their companies, especially when failures could impact many more lives than one's own."
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