This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
How well do you know the TPG story?
The fundamentals are fascinating: Brian Kelly, aka The Points Guy, got started in the points and miles game when he was just 10 years old helping out as his dad’s travel agent. Fast forward to his mid-twenties and he found himself working as a buyer at Lord & Taylor. Not happy with the career path and the pay, TPG headed for investment banking — but that still didn’t fulfill him. After a few years in HR at Morgan Stanley and raking in the points for all his work-related travel, TPG started an award-booking service that would one day become ThePointsGuy.com.
Early on, TPG would consult with clients for the low cost of $50 to help book award tickets. But after some time and switching from consulting to blogging, things started to take off. And when he was recognized at a cocktail party as “The Points Guy,” he knew he had to “make the jump.”
That’s where the When To Jump podcast comes in, a program started by Mike Lewis in which he interviews public figures, academics, executives, and everyday people about their experiences taking the plunge. When to Jump is a community dedicated to exploring a question many of us think about: When is the right time to go do what you really want to be doing?
Lewis interviewed TPG about his experience getting into award travel — and what prompted him to make that crucial decision of leaving a safe and lucrative career in finance to running a points-and-miles blog full time. The full podcast, 30 minutes long, can be played below.
You’ll hear some fun stories of a young and broke TPG hustling his way through New York City (including posing as a wine expert) to his rise as one of the top bloggers in the biz.
When To Jump will be releasing the book, When to Jump: If The Job You Have Isn’t The Life You Want in early 2018. It will contain more about TPG’s story and other top influencers, like Sheryl Sandberg and Arianna Huffington, and when they decided to make the jump.
Know before you go.
News and deals straight to your inbox every day.
NEW INCREASED OFFER: 60,000 points! With great travel benefits, 2x points on travel & dining and a 60,000 point sign up bonus worth up to $1,200 in value, the Chase Sapphire Preferred is a great card for those looking to get into the points and miles game. Here are the top 5 reasons it should be in your wallet, or read our definitive review for more details.
- Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
- Chase Sapphire Preferred named "Best Credit Card for Flexible Travel Redemption" - Kiplinger's Personal Finance, June 2018
- 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
- No foreign transaction fees
- 1:1 point transfer to leading airline and hotel loyalty programs
- Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 60,000 points are worth $750 toward travel
- No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards