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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.

American Express® Gold Card

With some great bonus categories, the American Express Gold Card has a lot going for it. The card offers 4x points at US restaurants, at US supermarkets (up to $25,000; then 1x), and 3x points on flights booked directly with airlines or through amextravel.com. It is currently offering a welcome bonus of 35,000 bonus points after you spend $2,000 in the first three months.

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  • Earn 35,000 Membership Rewards® Points after you spend $2,000 on eligible purchases with your new Card within the first 3 months.
  • Earn 4X Membership Rewards® points at U.S. restaurants. Earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per year in purchases, then 1X).
  • Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • Earn up to $10 in statement credits monthly when you pay with The Gold Card at Grubhub, Seamless, The Cheesecake Factory, Shake Shack, and Ruth's Chris Steak House. This is an annual savings of up to $120. Enrollment required.
  • $100 Airline Fee Credit: up to $100 in statement credits per calendar year for incidental fees at one selected qualifying airline.
  • Choose to carry a balance with interest on eligible charges of $100 or more.
  • No Foreign Transaction Fees.
  • Annual Fee is $250.
  • Terms apply.
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