#815: Chris Hutchins, Deal Master — Helping Tim Burn 15M+ Miles and Points, Flipping Costco Gold Into Five-Star Trips, Flying to Japan for $222, Tech Tools and Tricks, and Avoiding The Optimizer’s Curse

Overview

This episode dives deep into the world of travel hacking, points optimization, and creative arbitrage with Chris Hutchins, host of All The Hacks. Tim Ferriss and Chris explore strategies for maximizing credit card points, leveraging arbitrage opportunities, and avoiding the pitfalls of over-optimization. They also discuss philosophical approaches to money, travel, and happiness.

Notable Quotes

- I really like the arbitrage of anything. My goal has always been to do what everyone else does, but without spending the money. — Chris Hutchins, on his lifelong pursuit of creative hacks.

- Learning the art of spending money as a frugal person is hard, but sometimes you just have to give yourself permission to spend. — Chris Hutchins, reflecting on balancing frugality with enjoying life.

- If you want to understand somebody, talk to them about money and talk to them about sex. — Tim Ferriss, on how financial habits reveal deeper philosophies.

💳 Credit Card Optimization

- Chris Hutchins recommends pairing two types of credit cards for optimal rewards: one that offers elevated points for specific categories (e.g., Amex Business Gold for 4x points on advertising) and another that provides 2x points or 2% cashback on everything else (e.g., Capital One Venture or Fidelity 2% cashback card).

- Avoid canceling old credit cards to preserve your credit history. Instead, downgrade to no-fee versions or keep them active with small recurring charges.

- For those new to travel hacking, sign-up bonuses can yield outsized returns—often 10x or more compared to regular spending.

🛫 Maximizing Travel Points

- Tools like AwardTool.com and PointsYeah.com simplify finding high-value redemptions for flights and hotels. For example, flights to Japan for 37,000 points or business class to Europe for 45,000 points.

- Flexibility is key to maximizing points. Booking speculative flights and setting alerts for upgrades can unlock premium experiences.

- Hutchins shared how he used Hilton points to book a $3,000/night resort for just $600 worth of purchased points—a prime example of leveraging arbitrage.

🏆 Creative Arbitrage Stories

- Pudding Arbitrage: A man earned millions of airline miles by buying thousands of pudding cups for 25¢ each, donating them to shelters, and redeeming the barcodes for rewards.

- Costco Gold: Hutchins bought $300,000 worth of gold bars at Costco, leveraging cashback rewards and market spreads to turn a profit.

- Wedding Barter: Hutchins traded business-class flights to Mauritius for a $13,000 wedding video, showcasing how points can be used creatively beyond travel.

💡 Philosophical Insights on Money and Happiness

- Inspired by Bill Perkins’ book Die With Zero, Hutchins advocates spending money earlier in life to maximize memory dividends—the joy of reliving experiences.

- He emphasizes the importance of prepaying for experiences to reduce decision fatigue and enhance enjoyment, citing his splurge on a Four Seasons Lanai vacation as an example.

- Hutchins warns against the optimizer’s curse, where over-optimization of time or money can lead to anxiety and diminished quality of life.

🤖 The Future of Travel and AI

- AI tools are revolutionizing travel planning, offering personalized itineraries based on weather, preferences, and location. Hutchins predicts AI will further simplify points redemption and uncover hidden deals.

- While AI may level the playing field for travel hacking, Hutchins believes there will always be edge cases for those willing to dig deeper.

This episode is packed with actionable tips, fascinating stories, and thought-provoking perspectives on money, travel, and life.