Jack Raines liked his boss on Hinge.
It wasn’t reciprocal. A few months later, three beers deep at a bar, he told her he was quitting — then found a $250 plane ticket to Barcelona and left the country […]
Tag: financial freedom
#735: He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
Cody Berman was 19 when he learned about financial independence, and 25 when he reached it.
There’s no trust fund here, no lucky exit. Just a brutal train commute, over 30 side hustles, and a gap between what he earned and what he spent that […]
#734: Q&A: Her Brother Owns 3 Houses — Is That Why We Have a ‘Housing Shortage’?
Is there really a housing shortage — or do we just have a lot of wealthy people buying up all the good stuff?
That’s the question kicking off this episode.
Joe and I also help a woman simplify a $1.5 million portfolio she’s managing on her own for the first time.
And we help a […]
#725: What Most Families Get Wrong About Passing Down Wealth, with Andrea Baumann Lustig
When it comes to our money, the things we feel most certain about are often the exact blind spots that quietly derail our long-term plans.
We hold onto financial beliefs as if they’re religion or politics, rarely checking if they actually serve our long-term legacy goals.
Veteran […]
BONUS: The Economy Added 115,000 Jobs. Consumer Confidence Just Hit a 74-Year Low. Let’s Unpack This.
The U.S. economy added 115,000 new jobs in April, far exceeding general expectations.
But beneath that headline number lies a tale of two economies.
While sectors like healthcare, transportation, and retail are surging, the information technology sector is experiencing what can only be described as a “bloodbath.”
In this special bonus episode, we’re […]
#652: Why High Earners Stay Broke – with Rose Han
What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke?
That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path […]
#631: Q&A: Is ChatGPT’s Portfolio Better Than VTSAX?
Jason’s analysis of his retirement plan shows that the simple path beats the efficient frontier. Is he right or is he missing something?
Minerva is worried about the impacts of tax inefficiency to her wealth. Are her investments properly located?
Scott feels frozen because he doesn’t understand the nuances of the efficient frontier. Where can he get a simplified explainer so he can start taking action?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
Enjoy!
#629: Nick Maggiulli: The Wealth Ladder Has Six Rungs (and Most People Never Climb Past Four)
Here’s the thing about personal finance advice: what works when you have $10,000 won’t work when you have $1 million.
Yet most financial guidance treats everyone the same, whether you’re scraping together a $1,000 emergency fund or deciding whether to upgrade to business class.
Nick Maggiulli, author of “The Wealth Ladder,” joins us to break down how money strategies must evolve as your net worth grows. He’s mapped out 6 distinct wealth levels, each requiring different approaches to spending, saving and investing.
The levels start simple.
Level 1 covers anyone with less than $10,000 in net worth — that’s 20 percent of American households. Here, bad luck gets amplified. A flat tire that costs $200 could spiral into job loss and debt if you can’t afford the repair.
Level 2 spans $10,000 to $100,000 in net worth. Maggiulli calls this “grocery freedom” — you can splurge on the nicer eggs without checking your bank balance.
Level 3, from $100,000 to $1 million, brings “restaurant freedom.”
Level 4, the $1 million to $10 million range, unlocks “travel freedom.”
Getting beyond Level 4 — into the $10 million-plus territory — requires business ownership or extreme patience. Maggiulli calculates that even saving $100,000 annually after hitting $1 million takes 23 years to reach $10 million, assuming 5 percent annual returns.
The data shows income matters more than frugality, especially in the early levels. The median household income in Level 1 is $32,000, but in Level 4 it’s $197,000, and in Level 6 it reaches $4.3 million.
We discuss why homeownership dominates wealth in Levels 2 and 3, how investment assets become crucial in higher levels, and why many people in Level 4 choose “Coast FIRE” over the grinding path to Level 5.
#627: Q&A: When Being Good With Money … Isn’t Good Enough
Jlyn and her husband are 20 years from retirement, but they’ve got their eye on a second home they’ll live in when the time comes. Should they make the purchase now, or keep saving?
Reese was recently laid off, and she’s struggling to choose between two financially responsible paths. Should she continue her long-term disability insurance? Or is it wiser to save money?
Kip’s youngest has finally graduated from college, and he’s looking forward to an early retirement. But, with the eyewatering costs of long-term healthcare, is this still a viable path?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
#625: JL Collins Part 2: What Happens When You Don’t Need to Work Anymore?
What do you do when you’ve reached financial independence? JL Collins says it depends entirely on your spending rate, not just your net worth.
Collins joins us for part two of our conversation about what happens after you reach financial independence. He tackles the question of whether you should invest differently once you’ve “won the game.”
Someone with $5 million spending $100,000 per year sits in a completely different position than someone with the same amount spending $200,000 per year. The first person can afford to stay aggressive with stocks. The second person needs bonds to smooth the ride.
Collins walks through his withdrawal strategy using his daughter as an example. She stepped away from corporate life in her early thirties and now follows an 80-20 stock/bond allocation.
She pulls dividends from both funds into her checking account, covering about 2.5 percent of her target 4 percent withdrawal rate. Vanguard automatically sells shares to cover the remaining 1.5 percent.
We cover Collins’ thoughts on the 4 percent rule, which he calls extraordinarily conservative. He references Bill Bengen’s research showing that 5 percent withdrawals succeed 86 percent of the time.
Collins would take those odds to escape a soul-crushing job, especially since most financially independent people end up accidentally making money anyway.
We discuss the tension between frugal habits that build wealth – and learning to spend money once you have it. Collins flies first class, but he drives a basic car.
Collins explains why financially independent people often stay engaged with work — the problem was never work itself, but working without agency.
