Mile High FI Podcast

JT interviews Doug at FinCon 2025 in Portland about his entrepreneurial journey after leaving the corporate world, detailing his move into self-employment, affiliate marketing, and content creation.  Doug discusses how he transitioned from management consulting to becoming a content creator, exploring his initial ventures, the creation of his keyword research method, and strategies for n...

Doug reconnects with Steve, a previous guest, for an update on the past few years of his financial journey, including a net worth increase from $1.7 million to $2.5 million.   Despite his financial success, Steve grapples with balancing work, family, and personal identity, contemplating a future shift towards more meaningful, public service-oriented work.  He also discusses the intricaci...

Doug catches up with Carl at FinCon 2025 in Portland to talk about health & fitness updates.  Carl shares his journey of losing weight, specifics of his workout regimen, dietary changes, and his brief use of microdosing Ozempic.  Both of them discuss exercise habits, how they handle travel and exercise while on the road, and the occasional disruptions caused by gym etiquette.  Doug w...

Doug chats with Elliot Gross (9 to FI podcast) about his path to Financial Independence.  He shares how he discovered FI at age 27 and details his journey from getting out of debt to strategically positioning himself to retire early in 18 months.  Elliot also discusses his detailed approach to managing finances, the milestones he hit along the way, future aspirations involving geo-arbitr...

Doug chats with Monica Levi, a former lawyer who retired early at the age of 40.  She shares her journey to FI, including her immigration to the US at 17, a battle with cancer, the transition from law to becoming a self-discipline coach, and her passion for travel.   Monica also delves into how she manages her time, expenses, and the challenges of having a working partner while being ret...

Doug continues his conversation with Josh Epley (9 to FI podcast) about life after early retirement.  Josh discusses how he spends his time, the challenges & surprises of early retirement, and the importance of having hobbies & goals.  He also shares his experiences with managing his workload, the benefits of being flexible, starting new activities like running, and the launch of...

Doug chats with Josh Epley (9 to FI podcast) about his journey from $240K in debt to early retirement.  Josh discusses how he and his wife managed to turn their financial lives around including challenges they faced along the way and successful strategies they implemented such as real estate investing & rigorous budgeting.  Josh also shares insights into his recent post-retirement li...

Doug chats with Brad Finley who is on the cusp of early retirement.  Brad discusses the decision to leave his W-2 job, steps he’s taking to prepare for the transition, the emotional journey that accompanies such a significant life change, and his plans to maintain a balanced & fulfilling lifestyle post-retirement.  Brad also shares his transformative experience at the Hoffman Process...

Doug chats with Jackie and Jacob, a couple who left their W2 jobs to pursue Financial Independence and extensive travel adventures.  They discuss traveling in South America, living a minimalist lifestyle, navigating challenges of geo-arbitrage, and how they manage finances while optimizing for travel & embracing flexibility.  They also share financial mistakes they’ve made along the ...

Doug chats with Jillian Johnsrud about all-things mini retirement including preparation, challenges, and key insights.  They explore how to test what retiring might look like through sabbaticals and mini retirements, touch on the importance of adapting to a new lifestyle, and address common issues that arise, such as maintaining productivity and managing professional identity post-retire...

Doug chats with a variety of guests at CampFI Rocky Mountain Week 1.5 including Pete Adeney (Mr. Money Mustache), Kristen Knapp (FI Friends Travel), and camp attendees Amanda, Tyler, & Roxanne.   Pete & Kristen delve into the distinction between being cheap and frugal, sharing personal anecdotes and philosophies.  The conversation shifts into other topics such as partner dynamics...

Mr. Money Mustache joins me to answer YOUR questions. It’s part 2 so if you missed part 1, check it out from July 18, 2025. If you dig the show, see ways to support mile high FI since we’re ad-free.

Questions… [time stamps below]

What have you changed your mind on?

Is Pete still Snowbirding to Arizona in the winters down to cul-de-sac? And was that an experiment or a permanent thing? Wha...

Doug and Carl chat with listener Steve to review his plans for early retirement.  Steve discloses his financial background, asset allocation, and current expenses, including a net worth of about 1.7 million dollars.  The group addresses retirement projections along with potential risks of retiring in a down market and the importance of having a contingency plan.  Beyond money, they talk...

Doug chats with his wife Elizabeth about her first year (and few months) of retirement while answering questions from the Facebook group.  They also discuss a post from Instagram called “The 6 Luxuries of Life”.

Questions answered:

• James C – How has the amount of time you spend managing your finances changed since retirement?

Doug chats with Karsten Jeske (aka Big ERN) about his journey to early retirement, living frugally yet enjoying luxuries like travel, and the balance between saving & spending effectively.  Karsten provides his thoughts on the book “Die With Zero”, analyzing its advice on spending & saving in retirement, and highlighting potential issues within its financial recommendations.  He ...

Doug chats with Frank Vasquez from the Risk Parity Radio Podcast about his extensive investing experience while offering insights into balancing life after achieving Financial Independence.  Frank discusses the importance of intentional spending, significance of meaningful relationships, psychology behind saving and spending, how to diversify investments to secure a sustainable future, a...

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 ...

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 ...

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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