Mechanics of Money

How to Turn Business Spending Into Free Business Class Flights | Colin Stroud

Sam Silverman | Silverman Capital Season 1 Episode 22

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0:00 | 28:53

You're sitting on a pile of credit card points and no real idea what they're worth. What if the same balance that gets you a $600 hotel room could get you an $1,800-a-night suite instead? And what if the reason you can never find award availability has nothing to do with your points at all?

Sam sits down with Colin Stroud, founder of Go Somewhere, a credit card rewards consultancy for high-spending business owners and people sitting on large point balances. Colin got into points out of necessity: he'd taken a low-paying job, had a wife and a baby, and realized the only vacation his family could afford was a $400 Airbnb in the woods in rural Ohio. He went down the rabbit hole from a boring corporate desk, started booking trips for friends, and turned it into a full-time business in 2023. He's since helped 500+ families take trips they assumed were out of reach, from transatlantic business class for a family of nine to $30k+ luxury Caribbean stays during peak dates.

In this conversation:

  • How Colin went from no travel budget to consulting on points full time
  • Why flexible bank points beat co-branded airline and hotel cards for most travelers
  • The $6,000 flight to Italy Sam booked for 70,000 points, and what that works out to per dollar spent
  • How to match a card strategy to where your business actually spends, even when your categories earn no bonus
  • Why airline status is close to worthless if you were already going to fly up front
  • Which hotel statuses you can buy and which you can't: Marriott Ambassador vs. Hilton vs. Hyatt
  • The $30,000 Christmas week in St. Kitts a client got for points and nothing out of pocket
  • Marriott's fifth-night-free rule and why points only redeem well at the top end
  • The $10-a-month tool that hunts premium cabin deals for you in plain English
  • Repositioning flights: paying $200 to reach a hub and unlocking thousands in award value
  • The planning reframe that turns "there's never availability" into a $1,700-a-night room for 30,000 points

Topics covered: credit card points, travel rewards, points and miles, business class, award travel, flexible points, transfer partners, airline status, hotel status, Marriott, Hyatt, Amex, Chase, Capital One, seats.aero, luxury travel, business owners, high spenders, travel hacking

Guest: Colin Stroud, Founder, Go Somewhere | https://www.gosomewhere.world

Newsletter: https://www.mechanicsofmoney.co
Website: https://silvermancapital.com

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