Cait Brumme, CEO of MassChallenge, joins Jack for a sharp conversation on what founders actually need beyond funding: grit, customer proximity, the right network, and the ability to commercialize in hard markets. Drawing on her background across impact investing and Harvard Business School, Cait breaks down why MassChallenge is built to help early-stage companies get to real traction, not just better pitch decks. The episode dives into hiring, leadership, and the balancing act every founder faces between conviction and adaptation. Jack and Cait also get into the future of AI, where it can create massive upside, where it can quietly erode human connection, and why the smartest builders will stay grounded in reality while everyone else chases noise. It’s a strong episode on building durable businesses, solving meaningful problems, and keeping the human edge in a world moving faster by the day.

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Host: Jack Moran

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