Unlocking Free Flights Through Credit Card Points: An Entrepreneur's Journey

This chapter features the CEO of a travel points assistance company sharing insights from their entrepreneurial journey, including lessons from past ventures. The discussion highlights the innovative service Point Hound, aimed at helping users maximize their credit card points for free flights.

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#425 What if your credit card points could take you farther — literally? In this episode, host Brien Gearin sits down with Jay Reno, founder and CEO of Pointhound, a company revolutionizing how we use credit card points to book flights. Jay shares his entrepreneurial journey, from launching a VC-backed furniture rental startup to building Pointhound after discovering the hidden value in points most people waste. He explains how his search engine helps travelers find the best flight deals using points — sometimes turning 100,000 points into a $6,000 business class ticket. You’ll learn how to choose the right cards, optimize your everyday spending, and avoid the biggest mistakes people make when redeeming rewards. If you’ve got points sitting around, this episode could change how you travel forever!

What we discuss with Jay:

+ Why most people waste credit card points

+ How Pointhound finds 10x flight value

+ Best cards for transferable points

+ Manual MVP before building tech

+ How Jay earned 20M+ points at Feather

+ Using points for business class flights

+ Personalized flight deal emails

+ How Pointhound makes money

+ $200B in unused points annually

+ Plans to scale to 100M+ users

Thank you, Jay!