Mile High FI Podcast

Mile High FI Podcast

Real talk about Financial Independence and life after corporate jobs. Doug Cunnington and Carl Jensen talk about FI, lifestyle, side hustles, health, and anything on their minds. Plus, they interview experts and non-experts interested in the FI lifestyle. It's raw, candid, pretty much like you get to sit in on a private conversation.

Episodes

July 29, 2025 61 mins

Doug and Carl answer mailbag questions in this Taylor Swift-infused episode from Leadville, CO. 

Questions answered:

  • Does it ever get any easier to ride the market swings mentally?
  • How would you reallocate your investments if there were no tax implications?
  • What did Doug’s (and Carl’s) parents do ...
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Doug chats with David about his recent transition into retirement amidst a fluctuating stock market environment.  David shares his decision to sell a significant portion of his portfolio near the market’s recent bottom, discussing the impact of market volatility on his investment decisions and the balance between seeking peace of mind and maximizing returns.  He also shares reflections ...

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Mr. Money Mustache, Pete Adeney, and Doug discuss the nuances of early retirement, staying financially agile, and how small lifestyle adjustments can make a big impact. The conversation also explores personal growth, meaningful living, and the joy of communal activities.

 

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Doug chats with both his dad and Chris Rusin about timeshares and each of their experiences with them.  They explore the aggressive sales tactics often used, financial pitfalls, hidden fees, the dubious resale market, harsh realities of escalating maintenance fees, and ultimately selling a timeshare.  They also highlight tactics for surviving timeshare presentations and explore how times...

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Doug and Dusti Young chat about a potpourri of topics on this random episode:

  • Credit card points – which cards Doug & Dusti each have, hoarding points
  • Cognitive biases – loss aversion, sunk cost, maximization (optimizing) vs. satisficing
  • Having a hard time saying NO

Note: This is a rebro...

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Doug chats with JL Collins and Jillian Johnsrud about the concept of mini-retirements and how they fit into the journey of Financial Independence.  JL shares experiences of taking multiple mini-retirements throughout his career, the benefits of these breaks, and the importance of not letting money become your master.  He also touches on the updated edition of “The Simple Path to Wealth” ...

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Doug chats with Chris Rusin, “The Indiana Jones of FI”, about his journey after reaching FI, the transition from a corporate career to personal passion projects, and the challenges associated with leaving a professional identity behind.  Chris shares his experiences in tackling a bucket list, the fear of failure, and his battle with cancer, which reshaped his perspective on life goals.  ...

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Doug chats with Rusty about the mental and emotional aspects of committing to leaving traditional work, focusing on mindset and building an identity outside of professional life.  They discuss the challenges of transitioning from being highly productive to a more relaxed lifestyle, the importance of taking all allotted vacation time, and asking for what you want from your employer.  Rust...

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Doug chats with Producer Chris about the identity crisis that often accompanies early retirement and the practicality of meal planning vs. food delivery services. They discuss how careers often shape one’s identity and the challenges some people face when stepping away from their professional life. They also explore the convenience and impact of food delivery, home cooking, and personal ...

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Doug chats with Joe Saul-Sehy from The Stacking Benjamins Show about habits of the happiest retirees, emphasizing the importance of community engagement, purpose-driven retirement, and the perils of isolation.  Joe shares insights from his own experiences and studies, highlighting the power of connection through group memberships, volunteering, and staying engaged in meaningful activitie...

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Doug chats with Rusty about the intricacies of the ‘Buy, Borrow, Die’ strategy.  They discuss the mechanics of how the strategy works, benefits, potential risks, and answer related questions from listeners Nate and Sophia.  They also answer Alex’s question from the mailbag about claiming unemployment benefits ethically and navigating asset allocation during market volatility.

Rusty’s “Ho...

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Doug and Carl continue the happiness series with part 3 which is focused on cultivating a happiness mindset.  They discuss various strategies to train the brain for maximum happiness, including the role of neural responses, the negative impact of constant busyness, the crucial importance of gratitude, and how voluntary struggles contribute to a fulfilled life.  They also touch upon the p...

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Doug and Carl continue the happiness series with part 2 which is focused on the concept of finding purpose in life.  They discuss the benefits of preparing for retirement by building a rich life outside of work, taking sabbaticals, and conducting small experiments to explore new hobbies and interests.  They also talk about the importance of community, the idea of redefining success, achi...

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Doug and Carl kick-off a multi-part series focused on happiness.  They discuss various elements of happiness including definitions, why it’s important, genetic & activity-based components of happiness, routines, the impact of jobs, mindset, and happiness by subtraction.  They also provide practical tips for fostering happiness, emphasizing that happiness requires continuous work and ...

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Doug chats with Brian Feroldi about Warren Buffett’s famous investing principles.  Brian discusses key Buffett investment criteria including understanding businesses, long-term prospects of a business, management integrity, financial metrics/health, and the importance of checklists.  He also shares his personal investment experiences and lessons learned as a seasoned individual stock inv...

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Doug chats with Jess and Corey from The Fioneers about their unique paths to Financial Independence, the Slow FI and Coast FI concepts, how their views on spending have evolved over the years, content creation, and balancing work with building a fulfilling life.  The group provides thoughts and advice in response to a listener email about reaching Financial Independence, potentially achi...

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JT and Doug talk about reading and books…

Win a ticket to CampFI Rocky Mountain – Week 1 Ticket (2025) https://milehighfi.com/wincampfi

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Outro music is a bastardization of Cry, Moan, & Wail by Marc Ford. Super cool blues chord progression…

Join t...

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Doug chats with David & Jill at the EconoMe Conference about their pursuit of Financial Independence.   David shares his background growing up with a scarcity mindset, the accidental path to FI, his recent mini-retirement, experience quitting alcohol, and a newfound passion for stand-up comedy.  Jill discusses her middle-class upbringing, balancing her full-time job and schooling, an...

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Doug chats with Producer Chris about a variety of topics including irrational money fears, why people commonly talk about their work in social settings, and what their day-to-day lives look like in early retirement. They explore common financial anxieties such as the fear of running out of money and how past experiences shape these fears. They share strategies for steering conversations ...

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Doug and Carl chat about some questions that listener Austin submitted regarding early retirement and withdrawal strategies.  They explore the nuances of early retirement, discussing happiness, daily life, and responsible financial drawdowns.   They also address withdrawal strategies, including rental properties, index funds, automated transfers, tax optimization, health insurance, and h...

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