Best Documentation Not Included Podcasts (2025)

1
Are We Hiding Something? Our Real FIRE Portfolio + Expenses 30:36

3d ago30:36

30:36

Are FIRE content creators being honest about their numbers? YouTuber Duane isn't so sure. In this episode, Eric and Jason share detailed insights about their own FIRE numbers, portfolios, withdrawal rates, and what it actually means to be "retired." They also explain why context matters more than a single number, and get honest about how content cr…

1
Our Biggest Fears About Early Retirement 50:45

17d ago50:45

50:45

What’s the scariest part of retiring early? For many, it's not just about money—it's the unknowns that come after leaving work behind. In this candid conversation, Eric and Jason unpack the biggest fears they and others faced on the path to FIRE, from financial worries and healthcare to identity shifts and societal judgment. Whether you're planning…

1
Life After FIRE: Your Toughest Questions, Answered 1:17:45

1M ago1:17:45

1:17:45

After five years of early retirement and 100 episodes of Two Sides of FI, what have we learned? A lot—and we're sharing it all. To mark this milestone, Eric and Jason sit down for an honest, wide-ranging AMA based on questions from our community. We cover everything from money and mindset shifts to healthcare, travel, and even music choices. Whethe…

1
2025 Market Chaos Blowing up our FIRE Plans? 38:53

1M ago38:53

38:53

With markets down at one point nearly 20% in 2025, is this the sequence risk moment we feared? In this episode, we reflect on recent market volatility, how it’s impacted our early retirement finances, and whether our original FIRE strategy can still hold up. We also catch up post-Liberation Day and share how our thinking has evolved after real-worl…

1
What Should We Do With Bonds and Cash in a Crazy Market? 35:37

2M ago35:37

35:37

How should you respond to market conditions to ensure financial stability? Like the famous Mike Tyson quote says, "Everyone has a plan until they get punched in the mouth". In this episode, Eric talks with Jason about an unexpected opportunity to update his early retirement portfolio. Topics discussed include bond and cash allocations, asset locati…

1
Investment Review

3M ago

—

April 2025: Equities are at maximum valuations, investors are at peak investedness, and now a regime change which markets have not yet digested. Jonathan Ruffer asks if this is one of the rare occasions when a market crisis not only foretells but contributes to the economic hardship to come.

1
It's Harder to Retire Than I Expected 32:13

3M ago32:13

32:13

Do some find it hard to retire because they don't know how to stop working? In today's episode, Eric talks with Jason about the challenges he's experienced after achieving FI, finding it hard to ramp down his business. Are we just wired to work hard or is there more to it? We discuss why Eric can't stop working, how it affects his spouse, and what …

1
How We're Using ProjectionLab in (Early) Retirement 50:18

4M ago50:18

50:18

Why has ProjectionLab quickly become one of the most popular early retirement planning tools? In this episode, learn why PL is an essential software package for both Eric and Jason. Topics covered include how to get started, best practices, and powerful new features. See the link below for how you can try ProjectionLab for free! Check out Projectio…

1
Modern-Day Seattle Lynching - Part 1 30:48

4M ago30:48

30:48

ABOUTEpisode 01 explores a letter written to Cielo Property Management in Seattle, Washington. This letter confronts the property manager's premeditated “Lynching Type” assault against a Black Male resident on December 27, 2022. This letter is the first of nine letters written to Cielo Property Management that will be explored in Season 01.RUN-OF-S…

1
Are You on Track? Our 2024 Financial Review 51:59

4M ago51:59

51:59

What are the critical financial elements to track and review each year pre- and post-FI? In this episode, Eric and Jason share their processes and learnings from their 2024 annual review. Topics covered include tracking net worth and withdrawal rate, portfolio management, taxes, and much more. Show notes: https://twosidesoffi.com/2024review…

1
How Do I Know When I'm Ready to Retire? 46:54

5M ago46:54

46:54

How do you know when it's the right time to retire? Most on the FIRE path focus on the financial elements because in essence, they're the easiest part of the equation. But many people struggle with the emotional elements of the decision. In this episode, Jason and Eric talk about their own experiences and what they've found most challenging. Show n…

1
Could 2025 challenge market optimism?

5M ago

—

January 2025: Fund Manager, Steve Russell discusses the investment risks we see in 2025 – overvalued US markets, Trumps return to office, rising bond yields.

1
What No One Tells You About Purpose and Happiness in Retirement 36:39

5M ago36:39

36:39

Worried about finding purpose in retirement? Most people are, but in reality it's easy to address these fears head-on. In this episode, Eric + Jason are joined by Jordan "Doc G" Grumet, a hospice doctor, podcaster, blogger, and author. Topics discussed include how regret can be motivating, putting excuses behind us, the reality of purpose anxiety, …

1
BONUS: Retired Early and I Hated It - How NOT to FIRE, Part 2 (Post-FI/RE) 26:42

6M ago26:42

26:42

This is the second of two bonus episodes, pulled from the year one archives of Two Sides of FI. Imagine hitting your FI number, retiring early, and discovering you hate it? In this episode we discuss four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of depression and lack of purpose. Some are unable to f…

1
BONUS: How NOT to FIRE - Part 1 (Pre-FI/RE) 36:12

6M ago36:12

36:12

This is the first of two bonus episodes, pulled from the year one archives of Two Sides of FI. On the path to financial independence, there are ample opportunities for mistakes and missteps. In this episode, we review stories from people who shared their FIRE experiences online in the hopes of educating others. Here we review five of these tales: i…

1
Retiring (Early) in 5 Days. Am I Ready? 43:02

6M ago43:02

43:02

What's it really like to be 5 days away from early retirement? Join Laura, a 51-year-old scientist, as she discusses her final days running her research lab. From wrestling with the "Am I really ready?" question to unexpected tears at faculty meetings to cleaning out decades of research, she opens up about the reality of choosing early retirement a…

1
How Options Trading Led this Engineer to Financial Independence in His 30s 48:04

7M ago48:04

48:04

How can a hobby turn into a second career and lead to financial independence before 40? In this episode, Jason talks with David Sun, an electrical engineer who stumbled into options trading after hearing about it from a fellow grad student. Only ten years later he launched his first hedge fund. Now in his mid-30s, David shares the keys to his succe…

1
Early Retirement + Group Travel: What Works, What Doesn’t 59:17

7M ago59:17

59:17

Are group tours the ultimate hassle-free way to travel, or do they come with unexpected challenges? In this episode, Eric talks with Jason about his first experiences with group travel after a recent trip to Peru. They explore the pros, cons, and key lessons Jason learned—offering insights to help you plan your own adventure, whether you’re retired…

1
Does Retirement = Happiness? 46:46

8M ago46:46

46:46

How would you feel if you worked hard to retire early and later realized you hated being retired? Sadly, online forums make it clear that a number of people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement. In this episode, Eric and Jason discuss their feelings on this topic. Join us to hear Jason's thoughts in his fifth…

1
Empty Nest, New Challenges: What’s Next After Early Retirement? 42:03

9M ago42:03

42:03

In this episode Eric and Jason share their experiences as new empty nesters and reflect on the emotional and identity shifts that come with this major life change, especially after retiring early. They dive into how life changes when the kids are gone and work is no longer a primary focus. From adjusting to the quiet at home to rethinking purpose a…

1
Election 2024

9M ago

—

September 2024: As the US presidential race enters its final straight, Dr Tim Smith and Alexander Chartres join Rory McIvor to discuss how investors are weighing up the prospects of a new administration.

1
Financial Independence at 50 (Finally!) 43:06

10M ago43:06

43:06

After years of planning, Eric and Laura have finally reached their FI number at 50! They discovered the FIRE movement 5 years ago and set their sights on achieving financial independence by 2024. Now, with both of their boys off to college, a paid-off home, and a 80/15/5 split between equities, fixed income and cash, they’ve officially hit their fi…

1
He Earned a Million Dollars Trading This Option Strategy 51:56

10M ago51:56

51:56

How would you like to earn $80,000 a year trading options against your existing portfolio? That's exactly what our guest, Karsten "Big ERN" Jeske, has achieved. In today's episode, Jason talks with Karsten about his simple SPX options trading strategy. Be sure to see the show notes linked below for definitions, associated blog posts, and more. Show…

1
Our 80/20 Rules for Early Retirement: How We Did It 42:40

11M ago42:40

42:40

If you are not aggressive, you are not going to make money, and if you are not defensive, you are not going to keep money (Ray Dalio). In this episode, Eric and Jason talk about their personal "80/20 Rules" for retiring early. That is, the decisions they made along the journey that served as key pivot points towards ensuring their achievement of fi…

1
Checking In: Year One of Early Retirement 46:30

11M ago46:30

46:30

A year later, Jason and Eric check in with their friend Erik, who retired early at 49 while his wife continues to work. In this follow-up episode, we find out how things are going and what important lessons he learned during his first year of early retirement. Show notes and our earlier chat with Erik - https://twosidesoffi.com/erik…

1
Leaving the pack

11M ago

—

July 2024: Investors are herding into a narrow market and propelling stocks to new highs. Fund Manager Jasmine Yeo joins Rory McIvor to explain why this is a market well worth insuring against.

1
Four Years Later: What I Wish I Knew Before Retiring Early 43:10

12M ago43:10

43:10

Four years after retiring early at 47, Jason reflects on the key lessons he wishes he knew beforehand. He discusses his portfolio, spending habits, healthcare, mental health, relationships, and more. Show notes: https://twosidesoffi.com/fouryearsBy Jason and Eric

1
Retired Early? Here’s How to Pay Yourself 39:31

1y ago39:31

39:31

How do you plan to set up your retirement paycheck to avoid running out of money? In this episode, Jason talks with Eric about how he uses a free online tool to manage his finances in early retirement. Topics covered include his variable withdrawal strategy, managing cash, portfolio rebalancing, and much more. FREE SWR tool and show notes: https://…

1
When is Enough, Enough? Working After Financial Independence 45:03

1y ago45:03

45:03

Why would anyone continue to work for money once they've achieved financial independence? In this episode, Eric and Jason discuss this common practice, including why Jason and Lorri currently have part-time jobs post-FI. Topics covered include de-risking retirement, charitable giving, skill-building, and more. Show notes: https://twosidesoffi.com/e…

1
Unexpected Reactions to My Early Retirement 37:49

1y ago37:49

37:49

Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions an…

1
Ugly ducklings

1y ago

—

April 2024: Duncan MacInnes joins Rory McIvor to reflect on Q1 performance and discuss some of the portfolio’s key positions including gold and silver, derivative protections and the yen.

1
Retiring Early Made This Possible 43:52

1y ago43:52

43:52

What essential lessons did Jason learn from the most impactful travel he's done to date? In this episode, Eric and Jason catch up on a number of recent changes in their lives. Topics discussed include Eric and Laura's recent big announcement, Jason's Camino experience, the benefits and challenges of pre- and post-FI travel, and much more. Show note…

1
One Step Closer to FI/RE - Preparing to Give Notice 38:55

1+ y ago38:55

38:55

Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she's leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for release on the week that Laura submits her resignation letter (which she did on Thursday!) They discuss their hesitations, changes of he…

1
Retired Early to USVIs, Florida, and Spain: How They Did It 54:11

1+ y ago54:11

54:11

Have you considered living a life outside of your home country in retirement? Jeff went from broke at 38 to financially independent at 45 with six rental properties supporting them. He and his wife relocated to St Thomas, USVI for a few years, bought a rental property in Puerto Rico and now they’re preparing to relocate to Spain. So, if you’ve cons…

1
My Healthcare Costs in Early Retirement (Year 3) 34:33

1+ y ago34:33

34:33

What's the true cost of healthcare in early retirement and can it break your budget? In this episode, Jason shares his experiences with Eric after three years on an ACA health insurance plan. Topics discussed include selecting and evaluating plans, how to estimate your income, premium tax credits, and why 2023 was Jason's worst year for healthcare …

1
FI-nancial Checkup: New Year Routines + Goals for 2024 42:15

1+ y ago42:15

42:15

What financial lessons did we learn last year and what will we do differently in 2024? In today's episode, Eric and Jason discuss their end of year review processes. Topics include investing goals, their net worth reviews, lessons learned, and much more. Show notes: https://twosidesoffi.com/newyearBy Jason and Eric

1
Survival at 5?

1+ y ago

—

January 2024: Can the economy and markets survive interest rates at 5%? Not for long, suggests fund manager Matt Smith – either interest rates must come down or asset prices do.

1
Financially Independent, Recreationally Employed (FIRE) 43:04

1+ y ago43:04

43:04

Have you truly retired if you continue to do any work for money? In this episode, Eric and Jason talk about their own FIRE goals and how they've changed over time. Topics discussed include their respective journeys, why Jason has a part-time job after retiring, the internet retirement police, and much more. Show notes: https://twosidesoffi.com/bust…

1
Did We Budget Enough for Travel in Early Retirement? 38:27

1+ y ago38:27

38:27

What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more. Show notes: https://twosidesoffi.com/t…

1
Retired Early and Feeling Lost. What’s Next? 42:12

1+ y ago42:12

42:12

How does it feel when you haven't yet found your purpose after retiring early? In this episode, Jason talks with Eric about his three year journey exploring his post-FIRE purpose. In this episode, they discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. Show notes: https://twosidesoffi.co…

1
The Health Risks of Early Retirement 38:36

1+ y ago38:36

38:36

If you're not giving mental and physical health the same level of attention as your financial health, you're playing with fire. In this episode, Jason talks with Eric about what steps he's taking to prioritize his own wellness in early retirement, including a frank conversation about mental health. Here they discuss steps to promote wellness, the d…

1
One More Year: My Decision to Postpone Early Retirement 39:13

1+ y ago39:13

39:13

Can you imagine changing your mind about retiring early just as the finish line comes into view? What factors could cause someone to consider working one more year? In this episode, Eric talks with Jason about the idea to delay his retirement. Topics covered include why he's considering it, getting agreement with your spouse, how others reacted to …

1
From the Chairman

1+ y ago

—

October 2023: In this quarter’s episode of Ruffer Radio, Chairman Jonathan Ruffer shares his perspectives on the evolution of Ruffer’s all-weather investment approach since founding the firm in 1994.

1
Will This Get Us Kicked Out of the FIRE Movement? 45:00

1+ y ago45:00

45:00

Would you spend $1000 on dinner for a special occasion - or more? Eric and Jason recently enjoyed a milestone birthday celebration with their spouses + friends at a world famous restaurant. The total cost may shock you. In this episode, they talk about the experience, spending decisions pre- vs, post-financial independence, and whether it was actua…

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