Picture this:
A 12-year-old boy, one of four kids, sits at his computer in the early 1990’s, planning a family vacation.
Using travel points from his dad’s consulting work, he books a trip for his entire family of six to the Caymen Islands.
His fascination with travel points only intensifies as he grows older.
In college, he becomes known as the guy who can turn a handful of points into luxurious trips. Classmates and friends seek his advice.
After graduation, he accepts a job with a $65,000 annual salary. During evenings and weekends, he builds a travel blog as a side hustle. He assumes he’ll share what he knows, offer a little coaching, and maybe make a few hundred extra dollars.
Fast-forward, and this kid is now the mastermind behind The Points Guy, a global brand with 140 employees.
His name is Brian Kelly, and we met up recently to talk about how he turned a small side hustle into a multi-million-dollar company.
Here’s what that meeting looked like:
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Obviously, I’m challenging him to a basketball shoot-off the next time we meet.
Our interview is on YouTube. If you haven’t watched it yet, I’d highly recommend you check it out — whether or not you’re interested in travel.
He talks about how his income skyrocketed from a few hundred dollars to over a million in six months. He describes sitting at a hotel in Madrid, seeing a payment come in for $394,000, an amount that felt surreal.
He was a twentysomething with a salary of $65,000, and somehow his little weekend pet project was producing seven figures. He felt imposter syndrome. Success felt fleeting, confusing.
His reflections about how he grappled with this shift — internally and externally — holds lessons for everyone.
Not everyone will experience a massive windfall. But we all have moments when we feel pushed beyond our limits. Moments when we’re facing the unknown, swimming outside of our usual depth. Out of bounds.
When there’s no roadmap. No checklist. No script. No dress rehearsal. And we’re navigating this uncharted landscape while carrying enormous self-doubt.
His story of how he handled that situation carries lessons that resonate across situations. Take a listen if you haven’t heard it yet.
Have you ever thought:
- “I’m bad at money.”
- “I’m not tech-savvy / not handy / not organized.”
- “I suck at math.”
- “I’m not, like, a business-y type of person.”
- “I’m a spender. I’m bad at saving money.”
- “I’m terrible at investing.”
- “I’m not good at making money.”
What’s the common thread?
These are fixed mindsets. These statements reflect an idea that your skills and situation are innate and unchangeable.
You have it or you don’t.
You’re smart or you’re not.
You’re born with it, or you’re S.O.L.
But there’s another mindset — growth mindset — that embraces the opposite perspective.
Growth mindset believes that talent, skills and abilities are potentials. These can develop.
We all have a mixture of fixed mindset and growth mindset ideas within us. These ideas live along a continuum, and our beliefs traverse that continuum based on our environment, our social circle, our information diet, and our mood.
Mindset is momentary. We have a mindset “set point” where we chronically hang out, but as soon as we interact with others, our mindset starts to shift along the spectrum.
The more we need to prove ourselves or perform — for example, at work, school, on a sports field or stage — the more our mindset shifts.
Whether it teeters closer to fixed vs. growth, in those moments, depends on the people around us.
Stanford psychologist Dr. Mary Murphy described the research underpinning these insights in a recent interview.
Watch it on YouTube to learn how to tilt yourself towards a growth mindset.
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After earning his MBA in accounting and finance, Jason Tartick took a job in the banking industry.
He spent a decade as a banker, the guy with the rubber stamp that says “approve” or “deny.”
Jason’s life took a turn when he rose to fame on Season 14 of The Bachelorette, which led to appearances on The Bachelor, Dancing with the Stars, Live with Kelly and Ryan, and Good Morning America.
He decided to use this national spotlight to drive attention towards financial literacy, particularly focusing on relationships and money — a fitting intersection for a banker-turned-reality-TV star.
Although he’s in an unusual position — People Magazine writes articles about his breakups and new flings — Jason’s advice is geared towards couples outside of the paparazzi’s glare.
He joined me in last week’s episode to discuss critical questions that couples should ask each other, such as “What’s your debt-to-income ratio?” This answer sheds light on each persons’ attitude towards debt.
He also shared this horror story during our interview:
One newlywed couple had different credit scores. Hers was excellent. His was poor. They decided to buy a home together.
The husband suggested that his wife apply for the loan, which was granted only in her name. However, since they were married, he wanted to add his name to the deed.
As soon as he did so, the IRS confiscated the house. He owed hundreds of thousands in back taxes, which he never disclosed to his wife.
The couple divorced, and his now ex-wife is still on the hook for a portion of his debts.
Yikes.
Jason shares tips on how to spot financial infidelity — and how to have healthy, productive conversations about money with your spouse or partner — in our interview.
Don’t miss this one. The stories are fire.
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Enjoy these three interviews — as well as all the Q&A episodes and economic updates that you’ll find on the podcast.
