Marisa Franco built her career studying friendship and belonging. Her latest research pulled her somewhere unexpected: the connection between self-worth and net worth. In her data, people with high self-worth and high SAT scores earned close to double the income of people with low SAT scores. People with low self-worth showed no such pattern —...
Your S&P 500 index fund looks diversified — but Alec Litowitz says its concentration in AI stocks makes it one giant bet in disguise. Alec Litowitz joined a hedge fund with $100 million in assets and six employees. He had never made a trade in his life. That fund was Citadel, in its earliest days,...
Michael Hingson was on the 78th floor of the World Trade Center’s North Tower when a hijacked plane hit ninety feet above him.
He didn’t see any of it. Michael has been blind since birth.
A few hours earlier, his guide dog Roselle had panicked at an ordinary thunderstorm — pacing, [...]
“So to me, this is not a money management question.”
That’s what I told a listener partway into this episode — right after she told me she’s 42, makes $140,000 a year, and has $686,000 saved.
She wasn’t asking if she could afford a family gap year. Her numbers already answered [...]
Nine days after catastrophic floods, two men trapped 557 feet underground in a hydropower tunnel were found alive — one of the rescuers wasn’t even wearing shoes.
That’s the story we open with today, but it’s not the only headline. The August jobs report tripled expectations, and [...]
“Joe, I want to first talk about the elephant in the room.”
Before we get into any retirement math today, I need to talk about something personal: the disaster that just hit Nepal, my home country. My family is safe, but I’ve spent the last several days thinking, oddly enough, about why [...]
Think about how you spend an average day. Would the 10-year-old version of yourself be impressed? What about the 90-year-old version?
These two powerful questions frame our conversation with Sahil Bloom, founder and managing partner of an early-stage venture fund with investments in over 60 startups and author of The Curiosity Chronicle, a newsletter that reaches more than a million readers worldwide.
Sahil shares the story of his own wake-up call. While living in California and earning massive money as a venture inventor, he had a drink with an old friend who asked how often he saw his parents. When Sahil answered "about once a year," his friend asked how old they were. Learning they were in their mid-60s, his friend calculated: "So you're going to see your parents 15 more times before they die," assuming they'd live to about 80.
That gut-punch realization led to massive change. Within 45 days, Sahil had left his job, sold his house, and moved across the country to be closer to family.
This shift represents the core of Sahil's philosophy about the five types of wealth:
1. Time wealth: Control over your calendar and priorities
2. Social wealth: Deep, meaningful connections with others
3. Mental wealth: Curiosity, purpose, and personal growth
4. Physical wealth: Health and vitality
5. Financial wealth: Traditional money and assets
Most of us focus exclusively on financial wealth because it's easily measurable. But Sahil argues that true wealth encompasses all five domains, and we should intentionally invest in each one.
Sahil shares practical exercises for building each type of wealth:
- For time wealth, create an "energy calendar" by tracking which activities energize versus drain you
- For social wealth, map your relationships based on how healthy and frequent they are
- For purpose, ask yourself what your world (family, community, etc.) needs from you
- For physical wealth, focus on movement, nutrition, and recovery through simple practices
- For financial wealth, clearly define what "enough" looks like for you
These five domains aren't meant to be balanced perfectly every day. Instead, Sahil suggests thinking in seasons — some periods might emphasize financial growth while others prioritize family time.
Sahil also discusses powerful concepts like goals versus anti-goals (what you're unwilling to sacrifice to reach your goals) and "Memento Mori" — the ancient Roman practice of remembering one's mortality to inspire present action.
The conversation ends with a reminder that "your life has seasons" just like the weather — you don't expect to experience all four seasons in a single day, so don't expect perfect balance in every area of life simultaneously.
For more from Sahil Bloom, find him on major social platforms or visit fivetypesofwealth.com.
Joseph Moore is a crypto billionaire.
That’s technically true, and it means almost nothing. He printed over a billion tokens of his own currency, bought a sliver of the supply for a few hundred dollars, watched the exchange multiply that price by every token in existence, and became a “billionaire” on paper.
He hollered [...]
Luke Burgis built his first company by stocking vending machines.
He was 23. He and his business partner put pita chips and granola bars in machines that had only ever held Snickers, and called it “food distribution” because it sounded better than what it was.
Years later, after selling that company and [...]
“Joe, if you had to choose between retiring as soon as possible or paying off a mortgage, what would you go for?”
I ask Joe that right at the top of this episode, and his answer ends up being more prophetic than either of us realized.
Joe and I help [...]
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 [...]
Why did I just buy my first bond ever, after years of being 100% invested in stocks?
It comes down to a single number: 5.2%. That’s the highest 30-year Treasury yield we’ve seen since 2007, and it’s reshaping the calculus for every other investment out [...]
Hackers broke into a real estate closing company’s servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table.
Dr. Eric Cole was a former [...]
The stock market is near record highs. Unemployment is low. So why does it feel like young people have never been more pessimistic about money?
Beth Kobliner has been writing about personal finance for over 30 years, and she says today’s 20- and 30-somethings have [...]
“Joe, how much did you spend on your wedding?”
That’s how this episode kicks off, and it sets up the theme running through everything else.
Joe and I help a couple figure out if their plan to retire together in [...]
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 [...]
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 [...]
Would you trust someone with your money if the “interview” for the job was a fifty-page pitch deck and a decade-long commitment?
That’s essentially what happens every time someone becomes a limited partner in a venture capital fund.
I sat [...]
Why can’t you buy Vegemite in Philadelphia — and what does that have to do with building a wildly profitable online brand?
There are invisible forces shaping what you buy. Where you live. Who’s around you. What your local stores do — [...]
IQ scores have been sliding since 1970, and Lorraine Marchand thinks AI is quietly speeding that up.
She’s also in the middle of building an agentic AI board of directors for her own company — one she jokes could someday vote to fire her.
Lorraine teaches [...]
What does it actually mean to have “enough” — and how do you know when it’s time to stop optimizing and start living?
This week’s questions all circle the same tension: how do you keep building financial security without losing the years you’re supposedly securing it for?
[...]
Why did New York City just freeze rent for a million apartments — and who’s actually going to pay for it?
This month’s economic landscape is anything but simple: a job market that’s cooling faster than expected, a brand-new Fed chair rewriting the rulebook, and a policy [...]
What happens when a sudden $850,000 inheritance turns into eight different account balances, three rental properties, and one very big decision about your future?
When grief, real estate, and a six-figure windfall collide all at once, the fastest way to make an expensive mistake is to rush [...]
What if the biggest thing standing between you and your financial goals isn’t your income, your debt, or the housing market — but your own brain?
Dr. Julia Garcia is a psychologist, behavioral researcher, and author of The Five Habits of Hope — and she’s spent years studying why [...]
What happens when you look at a $862,000 portfolio and realize early retirement might actually be out of reach?
When a mountain of ticker symbols, account balances, and unexpected life updates come hitting you all at once, your money plan can quickly start to look like a complete mess.
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 [...]
What does it actually take to build a business that can routinely innovate without imploding?
Most of what we are taught about traditional, top-down leadership is completely wrong when it comes to driving innovation.
True innovation isn’t about having a single visionary leader who commands a room—it’s about creating [...]
It turns out that almost everything we’re taught about personal finance is completely backward if you try to use the same advice your entire life.
What works perfectly when you have $10,000 in the bank will completely stall you out once you hit $1 million.
Yet most money advice treats [...]
Ever feel like your money plan looks perfect on paper, but you’re still stressed out about it?
While spreadsheets give us the exact math, how we feel about our wealth is a whole different story.
Joe and I dive into the big gap between money logic and human psychology to help you [...]
The US economy showed surprisingly robust job growth in May, adding 172,000 new jobs and signaling a broadening recovery that extends far beyond essential services.
But underneath the strong labor market, headlines are flashing mixed signals: treasury yields are climbing on inflation worries, real estate markets are seeing regional corrections, and consumer sentiment is beginning [...]
Why is the finish line of financial independence so much scarier than the starting line?
While the early stages of accumulating wealth are full of possibility, approaching the moment where work becomes optional can trigger an unexpected wave of financial anxiety, causing many to stall out right at the edge of freedom.
Joe [...]
Did you know that the average modern office worker spends a staggering 93% of their life indoors?
While the hustle to achieve financial independence often pushes us to put our heads down, stare at monitors, and clock endless hours inside a climate-controlled box, we might be accidentally sacrificing our long-term cognitive and physical [...]
As we edge closer to financial independence, a funny thing happens to the finish line: it often starts to move.
But the goalposts don’t always shift because of lifestyle inflation or uncontrolled spending.
Sometimes, they move because our vision for our wealth expands—particularly when it comes to long-term charitable giving, family legacy, [...]
When a crisis hits the stock market, we tend to think that data, algorithms, and cold logic rule the day.
But behind every major investment portfolio is a human being subject to the exact same psychological traps, behavioral blind spots, and emotional relationships that affect everyday investors.
We sit down with Clare [...]
We are currently on the precipice of the largest transfer of wealth in human history.
Over the next two decades, an estimated $84 trillion to $100 trillion will pass from older generations to younger ones.
This shift will fundamentally change the economic landscape, but for the individuals involved, it often starts with [...]
She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s.
Haley Sacks—known online as Mrs. Dow Jones—joins us to talk about the five-step financial framework she calls IBIZA.
Despite every advantage, she spent her twenties anxious, financially dependent, and charging dinners to her parents’ [...]
The YFRP Webinar is happening today at 8pm ET! https://affordanything.com/rental2026
If you’ve ever wondered why some people thrive in real estate while others get burnt out, it usually comes down to one thing: understanding whether you’ve bought an investment or a job.
Joe and I tackle questions about the reality of scaling a rental [...]
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 [...]
At age 30, Tiffany Aliche hit a financial wall. She had lost her job, lost her home to foreclosure, and was facing $35,000 in credit card debt.
But just seven years later, she had completely transformed her life to become a self-made millionaire and one of the most trusted financial educators in the country.
[...]
What if you could earn short-term rental yields without the short-term rental headaches?
As major cities continue to regulate away 3-day stays, investors are shifting their focus to the “Goldilocks” of real estate: the midterm rental.
Jeff Hurst, the CEO of Furnished Finder and former President of VRBO, joins [...]
I sat down with Ron Lieber, the New York Times “Your Money” columnist, to tackle one of the most stressful financial decisions any family faces: the cost of college.
With headlines screaming about AI-driven job market disruptions and tuition hitting record highs, we’re digging into the math and the mindset shifts required to navigate [...]
Joe and I tackle questions about the complexities of early retirement at age 60 and the most efficient withdrawal strategies for lifelong security.
This episode explores both the technical and psychological aspects of “spending down”—from balancing Social Security timing with your investment accounts to deciding if you should spend every last penny before you’re [...]
Caregiving is a massive responsibility that often falls on family members, usually as an unpaid role.
For parents of children with autism, this doesn’t just mean managing the day-to-day, it means planning for a future that extends far beyond their own lives.
Keith Wargo, the CEO of Autism Speaks, joins me to bridge the [...]
Joe and I are catching up in person to dive into a new set of listener questions.
From navigating the complexities of the current real estate market to strategic tax planning for retirement, this episode explores both the technical and psychological aspects of building wealth.
Whether you’re wondering how to handle a sudden [...]
Joe and I traveled to the campus of Texas A&M University-Texarkana for a very special live recording.
We were joined by Jay Davis, the Executive Director of Financial and Entrepreneurship Engagement, to answer questions from an incredible audience of students.
Whether you’re just starting your career or looking to “reset” your habits, this [...]
What do student loans, early retirement, and Airbnb have in common?
They’re the three questions we’re tackling in today’s episode, and each one forces you to think about uncertainty, flexibility, and whether the “right” financial move on paper is actually the right move for your life.
Joe and I answer three listener questions. KJ [...]
Jon McNeill, the former President of Tesla and former COO of Lyft, discusses the intersection of innovation, leadership, and the future of technology.
Jon shares behind-the-scenes stories of scaling two of the most disruptive companies in modern history and offers a masterclass on how to build “acceleration” into your own career and business [...]
In this Q&A episode, Joe and I answer three listener questions that wrestle with the gap between plans and reality.
Bringham is 23, recently awarded 100% VA disability ($4,300/month for life), and has mapped out a detailed 30-year plan: buy a house, have 2-3 kids, become a [...]
This month’s jobs report looks strong on the surface, with 178,000 jobs added and unemployment ticking down—but a closer look tells a more complicated story. When I compare it against other data like job openings and layoffs, it still points to a slower, low-hiring environment, raising the question: is this [...]
Where should you park money that you’ll need in three years? It’s a question that forces you to balance safety with returns, and resist the temptation to gamble on the stock market just because it’s been going up for 17 years.
In this Q&A episode, Joe and I answer three listener questions. Olivia is saving [...]
In this episode, I am joined by Jamie Hopkins, a leading retirement researcher and finance expert, to debunk the myth of the “magic number.” We explore why retirement planning is a dynamic process of constant adaptation rather than a static goal.
Jamie explains the psychological and mathematical flaws of focusing solely on a [...]
Should you take a $30,000 raise right before you retire? It’s the kind of question that forces you to ask what you’re really optimizing for—money, or something else entirely.
In this Q&A episode, Joe and I answer three questions: Melanie is four years from FI but a high-stress job with a big raise just opened [...]
Can your beliefs actually change your biology? What if the only thing standing between you and breakthrough results isn’t skill, resources, or luck—but the limiting beliefs you carry about what’s possible?
In this conversation, I talk with Nir Eyal, bestselling author of “Hooked,” “Indistractable,” and his latest book “Beyond Belief: The Science-Backed Way to Stop [...]
Should you reduce your retirement contributions to save for a house down payment faster?
It’s a question that forces you to choose between two competing financial goals—and the answer isn’t as simple as picking one over the other.
In this Q&A episode, Joe and I tackle three listener questions about financial trade-offs.
Hannah [...]
What does it take to find work you actually love—not just tolerate, not just survive, but genuinely love? And is it even possible if you’re in your 50s and still don’t know what that is?
In this conversation, I talk with Bill Gurley, general partner at Benchmark Capital and author of “Runnin’ Down a [...]
Should your emergency fund chase yields, or should you prioritize stability over returns? It’s a question we haven’t had to ask for years, but as interest rates drop, savers are facing a new reality.
In this Q&A episode, we tackle four listener questions that span the practical and the philosophical. We start with a listener [...]
The jobs report that dropped today sent shockwaves through the markets, the US lost 92,000 jobs in February, completely defying expectations of a 60,000 job gain. How do we make sense of data that seems to contradict itself?
In this First Friday episode, I break down the confusing signals coming from different employment reports (BLS [...]
Will AI take your job? In Part 2 of my conversation with Ben Zweig, we move beyond theory into the practical chaos of how work actually functions in today’s economy.
Ben and I dive deep into why there are 90 million unique job titles (yes, really), how LLMs are finally solving the job categorization problem [...]
Will AI take your job? It’s the question on everyone’s mind—but it might be the wrong question to ask.
In this interview, I talk with Dr. Ben Zweig, Chief Economist at Revelio Labs, about why we need to completely rethink how we understand work in the age of AI.
Ben explains that jobs aren’t [...]
Three listeners, three very different financial dilemmas, but all connected by the same underlying question: What do I do when life doesn’t follow the plan?
In this Q&A, we tackle three high-stakes money decisions. A post-divorce real estate leap overseas. A retiree with a suddenly swollen portfolio. And an investor questioning whether smarter returns cost [...]
What if the most important skill for thriving in an AI-driven economy isn’t intelligence or emotional awareness—but your ability to handle change itself?
In this interview, I talk with Liz Tran, executive coach and author of “AQ”, about a revolutionary framework for understanding how we navigate uncertainty.
Liz introduces the concept of AQ (Agility [...]
