Bending Rules - Mark Josephson, former CEO of Bitly and later founder of Castiron, discusses the trade-offs in hiring an outside CEO versus navigating the journey as a founding CEO

Intro: One challenge in growing a company, especially as a first-time entrepreneur, is answering the question, “Am I the right person for the CEO job at this time?” I’d say that in the VC world, there’s a bias toward having a founder continue in the capacity of CEO. But what if that founder isn’t gaining investment traction or lacks industry expertise? In my first start-up, when I was twenty-six, the ultimate answer to that question was “no.” It took me two years to figure that out, and I have zero regrets about having brought on a CEO, which ultimately put the company on a different trajectory, culminating in a successful exit. To this end, it was fun to have Mark Josephson join the podcast this past week. Mark was brought in as a "CEO for hire" twice: first at Bitly, where he successfully grew the team and achieved an exit to Spectrum in 2017, and before that, he helped Seevast reach over $100M in revenue in 2006. He subsequently built and sold Outside.in to AOL in 2011. Even with those successful outcomes, Mark had to scratch his “founder” itch and started Castiron as founding CEO, a company that was acquired in 2024. Mark shares the difference between being hired as a CEO and being empowered to lead versus the connection that team members have with founding CEOs, where the leadership inspiration often comes from within that founder, creating an implicit trust. Regardless of one’s approach, Mark demonstrates that it can work in either capacity. I encourage founders to look inward and then create a team formula they believe will give them the best probability for success, egos aside. Our discussion can be found below. 1: 00 -- Bending Rules kicking off year 2 3:59 -- Hired twice as CEO for start-up/early stage companies 8:09 -- How to find those early mentors 15:56 -- Transition from employee to entrepreneur 23:43 -- Difference in CEO roles if founder versus hired gun 30:48 -- Empowered to lead versus power w/in to lead 43:22 -- Challenges along the way and near death experiences (for the companies that is) 49:01 -- Traits of a successful entrepreneur 54:54 -- Can you find balance as an entrepreneur?