Best Jesse Cramer Podcasts (2025)

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Are You Over-Optimizing? | Jesse Cramer | Ep 555 57:50

Play Pause

8d ago57:50

57:50

Effective financial planning resembles both a puzzle and a spider web, where each decision impacts interconnected aspects of one's financial life. Brad is joined by Jesse Cramer and explores the importance of resilience over perfection in financial planning, how minor choices can have significant implications, and the necessity of revisiting one's …

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Mailbag: Bond Funds, Roth Conversions, Advanced FI Strategies, Solo 401k and Backdoor Roth 1:01:04

14h ago1:01:04

1:01:04

Brad and Rachael Camp tackle listener-submitted questions focusing on bonds, retirement strategies, pensions, and optimizing Roth IRA conversions. Rachael Camp, a Certified Financial Planner, sheds light on various financial independence (FI) strategies—discussing the impact of interest rate volatility on bond investments, the importance of tax pla…

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How to Get the Courage to Travel More Adventurously | E174 Jon Otero 1:09:29

5d ago1:09:29

1:09:29

My first big trip abroad was in 2015. I had just graduated from college the week before and wanted to do something fun. So my girlfriend and I flew to Europe and visited Prague, Paris, and Barcelona. It was a blast, and it left a lasting impression. Since then, I’ve traveled to 10 more countries. Lately, I’ve been getting more comfortable with inte…

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When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111 1:00:06

8d ago1:00:06

1:00:06

Today’s episode is a special bonus episode, a companion to Jesse’s discussion on episode 555 of ChooseFI! Jesse examines the risks of over-optimization in personal finance, concentrating on tax-loss harvesting, asset allocation, Roth conversions, and dividend investing. He explains how each strategy can offer value when used thoughtfully, but warns…

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From Poverty to Semi-Retired | Kristen Knapp | Ep 554 58:59

15d ago58:59

58:59

Kristen Knapp shares her journey from a childhood marked by poverty to achieving financial independence and transitioning to part-time work as a television meteorologist. She introduces her new venture, FI Friends Travel, a travel initiative that connects financial independence enthusiasts through meaningful, shared travel experiences. Kristen emph…

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Money Moves That Sound Smart…But Aren’t (Part 2) | E173 17:34

19d ago17:34

17:34

Some money moves sound smart…until you actually try them. This is Part 2 of our special series where six personal finance experts share strategies that sound smart but rarely are. In this episode, you’ll hear from: Larry McMahon (Uncontrollable Me) on why doing everything yourself can be a costly mistake Sean Mullaney (FI Tax Guy) on when Tradition…

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Money Moves That Sound Smart…But Aren’t (Part 1) | E172 24:31

19d ago24:31

24:31

Some financial strategies sound really smart…until they aren’t. In part one of this special two-part series, we’re diving into real stories from personal finance pros who once made money moves that seemed like great ideas... but turned out to be anything but. You’ll hear honest reflections from: Diana Merriam (EconoMe) on the allure, and pitfalls, …

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Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110 44:09

20d ago44:09

44:09

Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust and character. Jesse breaks down Buffett’s approach to buying great businesses at fair prices, holding them long-term, and focusing on intrinsic value, margin of safety, and staying within one’s circle o…

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Deep Dive: Putting the Middle-Class Trap to Bed | Ep 553 1:06:57

22d ago1:06:57

1:06:57

Cody Garrett, (CFP), joins Brad to discuss the pervasive myth of the middle-class trap in the financial independence (FI) community. Through four case studies, they illustrate how individuals often feel trapped financially due to psychological barriers rather than actual limitations. The conversation provides insights into turning retirement accoun…

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Unraveling Your Relationship with Money | Shannah Game | Ep 552 52:02

29d ago52:02

52:02

Brad chats with certified financial planner Shannah Game, who shares insights from her book Unraveling Your Relationship with Money. They discuss the emotional and psychological aspects of finance, emphasizing the importance of understanding one's money stories, setting intentional spending boundaries, and achieving financial independence beyond ju…

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You’re Great at Saving. Are You Good at Giving? If not, start here. | E171 Spencer Reese 57:24

1M ago57:24

57:24

We’re great savers. Probably good earners, too. But what about givers? The FI community excels at building wealth, but often, we’re laser-focused on accumulating it for ourselves. Is that fair? Does that make us selfish? I’m not sure. On one hand, taking care of yourself should be step one - like the old adage goes: “Put on your own oxygen mask bef…

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Scrimping, Splurging, and Other Crazy Spending Stories - E109 50:04

1M ago50:04

50:04

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, Jeremy Schneider, Doc G, and Joe Saul-Sehy. Diania highlights the “iceberg principle” of stealth wealth—how true wealth is often what you don’t see, like deferred purchases and unspent money. Justin sha…

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Roundup: Buy vs. Rent, Mortgage Amortization, Minimalism and More | Ep 551 59:00

1M ago59:00

59:00

Lets dive into the emotional and practical considerations of paying off a mortgage early, explore the benefits and drawbacks, personal experiences, and broader financial implications of renting versus owning a home. Key Topics and Timestamps Introduction to Mortgage Conversations (00:00:00) Overview of the episode’s focus on mortgages, buying vs. r…

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Getting Personal with Personal Finance: Meghan & Ginger | Ep 550 46:51

1M ago46:51

46:51

Ginger interviews Meghan Combs, who shares her journey to financial independence after recently getting married. They discuss budgeting strategies, the significance of personal values in spending, and adapting financial goals amid life transitions. Meghan reflects on her net worth of $527,000 and the impact of automating savings, as well as her des…

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How to Live a FI Life Without the FI Bank Account | E170 Jess from Fioneers 57:26

2M ago57:26

57:26

Why are you chasing financial independence? It could be living a more adventurous life filled with travel or doing work you love, regardless of the pay. Whatever your dream looks like, it probably comes down to two things: freedom and flexibility. We want to be in the driver’s seat of our lives. And we know money is one of the biggest obstacles sta…

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Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108 1:22:17

2M ago1:22:17

1:22:17

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for high earners, healthcare in retirement, and investing during economic uncertainty. He explains that heirs to traditional IRAs must pay income tax on withdrawals, while taxable accounts benefit from a st…

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Deep Dive: Taxable Brokerage Accounts | Ep 549 52:04

2M ago52:04

52:04

Episode Summary: Taxable brokerage accounts are often overlooked but are essential for building wealth and achieving early retirement. Brad Barrett and Cody Garrett highlight their flexibility, tax advantages, and strategic value. Cody Garrett provides insights on how to effectively navigate these accounts, dismantling common misconceptions while s…

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The Women Who Disappeared...And Reappeared 63 Years Later | E169 4:16

2M ago4:16

4:16

What would you do if you had to start over, completely from scratch? In this episode, I share the wild true story of Audrey, a woman who vanished in 1962 and was just found alive, 63 years later. Her story sparked a thought experiment: if you had to reinvent yourself, new city, new career, new hobbies, what path would you choose? We’ll explore what…

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FI Service Corps | Ryan Brennan | Ep 548 50:57

2M ago50:57

50:57

In this episode of ChooseFI, Ryan Brennan, founder of the FI Service Corps, dives into his journey within the financial independence (FI) community and how he is merging it with the spirit of volunteering. The discussion explores Ryan's background as a recovering CPA, his transition into this new venture, and the pilot events that successfully comb…

1
Travel Hacks to Upgrade Your Next Vacation (Without Spending More) | E168 Chris Hutchins 47:27

2M ago47:27

47:27

I get why some people aren’t into traveling. Long flights crammed in a middle seat, overpriced hotels that smell like smoke, and being miles away from the city center - none of that screams “dream vacation.” Now, I’m past the days of budget airlines and sketchy motels but I’m also not flying first class with lay-down seats or staying in luxury hote…

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19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107 59:25

2M ago59:25

59:25

Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-retirees about misleading sales tactics that exploit fear - especially the fear of market losses. They emphasize the importance of working with fee-only, fiduciary advisors who are legally obligated to a…

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The Simple Path Revisited in 2025 With JL Collins | Ep 547 1:07:17

2M ago1:07:17

1:07:17

In this episode, JL Collins discusses the transformative principles of financial independence outlined in his renowned book, The Simple Path to Wealth. Collins emphasizes the simplicity of investing, the power of living below your means, and the crucial role of compounding returns in achieving financial freedom. The conversation also touches on the…

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Sleep Masterclass | Dr. Bobby Dubois | Ep 546 57:50

2M ago57:50

57:50

Dr. Bobby DuBois returns to discuss the essential role of sleep in achieving financial independence and enhancing overall health. He addresses the worrying trend of sleep deprivation among Americans and its significant consequences on heart health, weight management, and cognitive functionality. This episode is filled with evidence-based insights a…

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How to Start a Side Hustle in One Month | E167 Nick Loper 49:51

3M ago49:51

49:51

For most of us pursuing financial independence, the math is pretty straightforward: earn more, spend less, and invest the difference. But what if you could speed things up and discover a new passion along the way? That’s where side hustles come in. Not only can they give your FI plan a serious income boost, but they also let you explore projects th…

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Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106 28:14

3M ago28:14

28:14

Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning into retirement, especially those aged 50 to 75. With half of the participants recently retired and the other half preparing to retire within two years, the study offers a timely look at the "final glide …

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Tax Efficient Strategies for Early Retirement | Mailbag Episode | 545 | With Rachael Camp 53:56

3M ago53:56

53:56

In this mailbag episode, Brad and Rachael dive deep into strategies for efficiently withdrawing money from taxable brokerage and retirement accounts. With a focus on understanding the different tax treatments associated with these accounts, listeners gain crucial insights into managing tax liabilities for retirement. Key Takeaways Different Types o…

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The Tariffs You Should Really Be Paying Attention To | E166 6:07

3M ago6:07

6:07

Tariffs aren’t just for global trade - you can apply the concept to your personal life to protect your time, energy, and values. As we gain more financial freedom, how we spend and make money should evolve too. In this short and reflective episode, I explore the idea of personal tariffs and how I have applied this to things that may seem like a goo…

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Roundup With Ginger | Zero-Based Thinking: How to Rethink Your Life Choices 1:03:16

3M ago1:03:16

1:03:16

Join the conversation with the ChooseFI community on the brand NEW ChooseFI Members Site and participate in discussions about budgeting, travel rewards, and obviously all things financial independence! Register Your Free Account See the Group Discussion Ginger Mentioned in this Episode Hi, all! Ginger here. Brad and I discussed minimalism a bit, an…

Jesse Cramer Podcasts

1
Personal Finance for Long-Term Investors - The Best Interest

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1
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1
FI Minded: Achieve Financial Independence & Have Fun Doing It

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1
In Your Best Interest

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1
Are You Over-Optimizing? | Jesse Cramer | Ep 555 57:50

1
Mailbag: Bond Funds, Roth Conversions, Advanced FI Strategies, Solo 401k and Backdoor Roth 1:01:04

1
How to Get the Courage to Travel More Adventurously | E174 Jon Otero 1:09:29

1
When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111 1:00:06

1
From Poverty to Semi-Retired | Kristen Knapp | Ep 554 58:59

1
Money Moves That Sound Smart…But Aren’t (Part 2) | E173 17:34

1
Money Moves That Sound Smart…But Aren’t (Part 1) | E172 24:31

1
Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110 44:09

1
Deep Dive: Putting the Middle-Class Trap to Bed | Ep 553 1:06:57

1
Unraveling Your Relationship with Money | Shannah Game | Ep 552 52:02

1
You’re Great at Saving. Are You Good at Giving? If not, start here. | E171 Spencer Reese 57:24

1
Scrimping, Splurging, and Other Crazy Spending Stories - E109 50:04

1
Roundup: Buy vs. Rent, Mortgage Amortization, Minimalism and More | Ep 551 59:00

1
Getting Personal with Personal Finance: Meghan & Ginger | Ep 550 46:51

1
How to Live a FI Life Without the FI Bank Account | E170 Jess from Fioneers 57:26

1
Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108 1:22:17

1
Deep Dive: Taxable Brokerage Accounts | Ep 549 52:04

1
The Women Who Disappeared...And Reappeared 63 Years Later | E169 4:16

1
FI Service Corps | Ryan Brennan | Ep 548 50:57

1
Travel Hacks to Upgrade Your Next Vacation (Without Spending More) | E168 Chris Hutchins 47:27

1
19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107 59:25

1
The Simple Path Revisited in 2025 With JL Collins | Ep 547 1:07:17

1
Sleep Masterclass | Dr. Bobby Dubois | Ep 546 57:50

1
How to Start a Side Hustle in One Month | E167 Nick Loper 49:51

1
Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106 28:14

1
Tax Efficient Strategies for Early Retirement | Mailbag Episode | 545 | With Rachael Camp 53:56

1
The Tariffs You Should Really Be Paying Attention To | E166 6:07

1
Roundup With Ginger | Zero-Based Thinking: How to Rethink Your Life Choices 1:03:16