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:

• Jay’s Twitter
• Jay’s LinkedIn
• 645 Ventures
• Pointhound HQ

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