My guest on Infinite Loops this week knew he wanted to be an entrepreneur from the time he was buying and selling things on eBay.

Jay Reno claims he didn't know what the word 'arbitrage' meant back then, but if you tug on the colourful threads of his career, you'd reveal the kind of tenacity and resourcefulness that allows special founders like him to repeatedly find value in places that have long been deserted by everybody else.

If you listen in on today's episode, it will become apparent why O'Shaughnessy Ventures invested in Jay and his current venture. Jay is the CEO and Founder of Pointhound, which helps people find amazing deals on flights and travel using their credit card points and miles. He's also a partner at 645 ventures.

Among other fun pursuits, he's spent the last ten years building all sorts of cool things; like a same-day grocery delivery service, a craft coffee company, a restaurant and bar reservation app, and a furniture rental service for city dwellers.

We spent our conversation talking about his advice for first-time founders; his learnings from building Pointhound; the whimsical world of credit card point programmes; his thoughts on consumer psychology; and much more!

For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack.

Important Links:

Show Notes:

How To Bring Your Idea To Life
The Virtues of the Y-Combinator Model
Picking the Right Investor
Pointhound & The Points Game
On Consumer Psychology and Trying New Things
Removing the Invisible Barrier
Product Cycles and User Feedback
Slow Down to Speed Up
The Common Pitfalls in Building Consumer Products
The Credit Card Prestige Factor
The Cashback Conundrum
The Future of Pointhound
Jay, The Emperor of The World

Books & Articles Mentioned:

My Inventions: The Autobiography of Nikola Tesla; by Nikola Tesla
Mistakes were Made. (And, Yes, by Me.); by Jim O'Shaughnessy

Day 86: The Real Presence of God (2026)

The Bible in a Year (with Fr. Mike Schmitz)

Intro

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