The Entrepreneurial Rollercoaster of insurtech and Beyond with Jeffery Arnold

In this engaging episode of Industry Voice, host Jeff Shi sits down with serial entrepreneur and best-selling author Jeff Arnold. The conversation delves deep into Arnold’s dynamic journey through insurance, insurtech, private equity, and even professional sports ownership. Jeff shares how he went from stand-up comedy in North Hollywood to building and exiting multiple tech and insurance ventures, including RightSure, Lender Bridge, and Lender's Portal.

With ten books under his belt—five of them Amazon #1 bestsellers—Jeff reflects on how he transformed academic struggles into thought leadership through discipline and creativity. He opens up about his foray into semi-pro soccer team ownership, the real ROI of sports investments, and his current mission: giving back to the industry through mentorship and board roles in various insurtech and AI startups.

This episode is packed with authentic insights, entrepreneurial lessons, and inspiration for founders, investors, and insurance professionals looking to leave their mark on the industry. Whether you're curious about the evolution of insurtech, scaling agencies with AI, or writing your first book, this episode offers a wealth of takeaways.

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