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.

The Business Platinum® Card from American Express OPEN

LIMITED TIME OFFER. Aside from the 100,000 points welcome bonus (available until 8/8/18), Amex recently made huge improvements to the Business Platinum Card, including the fact that you will now earn 50% more points on purchases of $5,000 or more, earn 5x on flights and eligible hotels at Amextravel.com and cardholders will receive a $200 airline fee credit each year.

Apply Now
More Things to Know
  • Limited Time Offer: Earn up to 100,000 Membership Rewards® Points.
  • Earn 50,000 Membership Rewards® points after you spend $10,000 & an extra 50,000 points after you spend an additional $15,000 all on qualifying purchases within your first 3 months of Card Membership. Offer ends 8/8/18.†
  • Get 5X Membership Rewards® points on flights and prepaid hotels on amextravel.com.
  • Get 50% more Membership Rewards® points. That's 1.5 points per dollar, on each eligible purchase of $5,000 or more. You can get up to 1 million additional points per year.
  • 35% Airline Bonus: Use Membership Rewards® Pay with Points for all or part of a flight with your selected qualifying airline, and you can get 35% of the points back, up to 500,000 bonus points per calendar year.
  • You can also receive 35% points back on all First and Business class flights, with all airlines available through American Express Travel.
  • You can enjoy access to The American Express Global Lounge Collection℠ offering access to the most lounges across the globe, when compared with other U.S. credit card offerings. As of 11/2017
  • Terms Apply
  • See Rates & Fees
Intro APR on Purchases
N/A
Regular APR
N/A
Annual Fee
$450
Balance Transfer Fee
See Terms
Recommended Credit
Excellent Credit
Terms and restrictions apply. See rates & fees.

Editorial Disclaimer: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.