In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Andrew Bennett, a self-described "person number six" at Provide, now Head of Small Business at Fifth Third Bank. The conversation covers betting on your best friends, knowing when to blow up what you've built, and what actually makes an exit work.

Andrew's path to fintech ran through minor league baseball diamonds and college dugouts. He spent most of his twenties coaching before packing his life into two suitcases and flying one-way to San Francisco to join two childhood friends building a small business lending startup. What followed was a decade of pivots, near-death moments, and ultimately an acquisition that he calls the best of both worlds.

About Our Guest Andrew Bennett is Head of Small Business at Fifth Third Bank, where he leads the evolved business originally built at Provide, originally a healthcare-focused fintech lender. Before fintech, Andrew spent years coaching baseball at the high school and college level, a background he credits with teaching him more about building teams than he expected.

In this episode, we cover:

• How a baseball coaching career became unlikely preparation for building a company
• Why focus and not product was the real unlock for Provide's early survival
• The cultural cost of pivoting when your team is split between two visions
• Why your acquisition insight matters as much as your product insight
• The mindset shift from startup operator to leader inside a large organization
• What small business owners and venture-backed founders actually have in common

Listen now for a founder-adjacent story full of hard pivots, shared delusion, and the kind of luck that only shows up after years of hard work.

About Round Two

Round Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts.

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