Mile High FI Podcast

Doug Cunnington & Carl Jensen
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Jul 22, 2025 • 50min

Early Retirement Nightmare: Retiring Into a Bear Market | MHFI 277

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 on market timing, portfolio allocation, the importance of planning and adapting to financial uncertainties, and adjusting to life post-retirement. Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Need a fee only advisor?  Nectarine is a network of financial advisors where you just pay for investing & planning advice. Advisors don’t manage your money, sell products, or earn commissions. https://milehighfi.com/nectarine Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you! Guitar Accessories Hiking & Outdoor Essentials for Sleep Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington Links Connect with David Email: davidrmoser@gmail.com LinkedIn The New Yorker, “The Scold” (Mr. Money Mustache profile) JL Collins, “The Simple Path to Wealth” Kindle Hardcover Paperback Audiobook Morgan Housel MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 2:39 David’s financial journey 6:50 Future plans & investment decisions 13:06 This time is different 19:28 Keeping cash on-hand & withdrawing 27:53 Portfolio diversification 32:34 Contingency plans & advice for others 39:44 Life after retirement 45:16 Soundcheck – Credit card points
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Jul 18, 2025 • 1h

Mr. Money Mustache: Financial Strategies, Happiness, & Lifestyle Choices [bonus]

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.   Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you! Guitar Accessories Hiking & Outdoor Essentials for Sleep **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 00:00 Introduction and Welcome 00:54 Changing Perspectives: Pete’s New Outlook 02:37 Neighborhood Qualities and Preferences 05:04 Transition to One Car Lifestyle 09:33 Financial Strategies and Roth Conversions 24:28 Tracking Happiness and Meaning 30:18 Helping a Friend with a Basement Project 30:33 Jam Sessions at the Coworking Space 31:17 Balancing Productivity and Relaxation 32:21 Cooking and Socializing 33:07 Coaching Experiences and Financial Advice 37:31 Bootcamp and Email Series 42:06 Podcast Sponsorship and Recommendations 48:30 Live Streams and Community Engagement 49:23 Balancing Financial Goals with Living Intentionally 51:25 Parenting and Frugal Activities 55:08 Final Thoughts
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Jul 15, 2025 • 57min

Why are Timeshares Horrible? | MHFI 276

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 timeshares may fit into broader financial strategies. Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you! Guitar Accessories Hiking & Outdoor Essentials for Sleep Need custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington Links Connect with Chris Chris Rusin Music Chris Rusin YouTube Life Outside the Maze Chris Rusin on MHFI episode 020 Chris Rusin on MHFI episode 273 MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 2:43 A masterclass in sales 8:18 Analyzing the value of timeshares 15:14 Timeshare memories with Doug’s dad 21:10 The sales process 28:42 Maintenance fees & freebies 34:42 Getting rid of timeshares 41:31 Pros and cons 46:18 Opportunity cost of owning a timeshare 54:39 Soundcheck – Horseback riding
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Jul 8, 2025 • 1h 2min

Credit Card Points, Doug’s Cognitive Meltdown, Saying NO! [rebroadcast] | MHFI 275

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 rebroadcast of MHFI episode 178 Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you! Guitar Accessories Hiking & Outdoor Essentials for Sleep Need custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington Links Connect with Dusti: Instagram Facebook ChooseFI Travel Rewards Steven Keys (Trip of a Lifestyle) on The Doug Show Barry Schwartz, “The Paradox of Choice” Kindle Hardcover Paperback Audiobook Logan Ury, “How to Not Die Alone” Kindle Hardcover Paperback Audiobook Derek Sivers, “Hell Yeah or No” Kindle Hardcover Paperback Audiobook SideDish podcast MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 6:06 Puppy yoga, laziness, & napping 12:46 Credit card points 18:56 Hoarding points 24:21 Doug’s gym conundrum 29:32 Loss aversion & sunk cost 36:20 Maximizing vs. satisficing  42:19 Just say NO 47:40 Trade-offs & setting boundaries 55:42 Soundcheck – Go-karting
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12 snips
Jul 1, 2025 • 1h 7min

JL Collins & Jillian Johnsrud on FU Money & Mini-Retirements | MHFI 274

Join JL Collins, author of 'The Simple Path to Wealth', and Jillian Johnsrud, author of 'Retire Often', as they dive into the transformative concept of mini-retirements. JL shares his personal experiences of taking breaks from work, emphasizing financial freedom and the joy of not being ruled by money. Jillian introduces her framework for living a fulfilled life through mini-retirements, blending personal development with career breaks. Together, they redefine wealth by prioritizing experiences over material gains.
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Jun 24, 2025 • 1h 7min

Beyond the 4% Rule: Indiana Jones of FI (Update) - Chris Rusin | MHFI 273

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.  He also dives into his latest venture — recording a music album! Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Use code MILEHIGHFI at GhostBed checkout for an additional 10% Off Already Low Prices! June 25, 2025 Livestream: https://youtube.com/live/LX9a2Caw-Gs Come hang out with Doug at CampFI Week 1.5, Mon July 7, 2025 – Thurs July 10, 2025: https://campfi.org/event/campfi-rm-250707/ Links Connect with Chris Chris Rusin Music Chris Rusin YouTube Life Outside the Maze Chris Rusin on MHFI episode 020 Bucketlist.com Ernest Becker, “The Denial of Death” Kindle Hardcover Paperback Audiobook Duff McKagan, “It’s So Easy” Kindle Hardcover Paperback Audiobook MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 2:28 Bucket lists & facing fears 8:02 Reflections on mortality & life’s priorities 16:13 Musical endeavors 22:15 Personal growth 28:17 The creative process & finding identity 36:56 Transitioning to new roles & challenges 45:21 Teaching & unplugging 52:43 Joy of collaboration 57:43 Soundcheck – Music 1:03:44 Chris Rusin, Cinders
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Jun 17, 2025 • 1h 6min

Mentally Prepare to Retire - Rusty | MHFI 272

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.  Rusty also touches on mental health therapies such as body-based trauma therapy and somatic therapy as tools for coping with the stress and trauma associated with demanding careers. Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Use code MILEHIGHFI at GhostBed checkout for an additional 10% Off Already Low Prices! June 2025 Livestreams: https://youtube.com/live/d2lTp4FMe4A?feature=share Come hang out with Doug at CampFI Week 1.5, Mon July 7, 2025 – Thurs July 10, 2025: https://campfi.org/event/campfi-rm-250707/ Links Rusty on MHFI episode 252 Bessel van der Kolk, “The Body Keeps the Score” Kindle Hardcover Paperback Audiobook Feel Better, Live More podcast Gabor Mate “When the Body Says No” Hardcover Paperback Audiobook Russell Kennedy “Anxiety Rx” Kindle Hardcover Paperback Audiobook MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 1:55 Identity & career transition 6:21 Mindset shift 11:35 Building an identity separate from work 16:59 Productivity 24:00 Importance of taking vacation 30:18 Traveling & cultural perspectives on work 38:06 Recurring dreams & nightmares 43:33 Body-based trauma therapy 49:40 Negotiating with employers 56:43 Soundcheck – One car household
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Jun 13, 2025 • 37min

Delivering Identity - BONUS | MHFI 271.5

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 shopping preferences. Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ June 2025 Livestreams: https://youtube.com/live/d2lTp4FMe4A?feature=share Come hang out with Doug at CampFI Week 1.5, Mon July 7, 2025 – Thurs July 10, 2025: https://campfi.org/event/campfi-rm-250707/ Links MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 2:53 Chris’s lost identity 9:15 Doug’s career reflections 18:26 Grocery & food delivery 22:57 Grocery shopping preferences 29:56 Soundcheck – Never again
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Jun 10, 2025 • 1h 13min

What the Happiest Retirees Know - Joe Saul-Sehy | MHFI 271

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 activities post-retirement. Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Use code MILEHIGHFI at GhostBed checkout for an additional 10% Off Already Low Prices! June 2025 Livestreams: https://youtube.com/live/d2lTp4FMe4A?feature=share Come hang out with Doug at CampFI Week 1.5, Mon July 7, 2025 – Thurs July 10, 2025: https://campfi.org/event/campfi-rm-250707/ Links The Stacking Benjamins Show Joe Saul-Sehy, “Stacked” Kindle Hardcover Audiobook Afford Anything, “The Truth About Making the Efficient Frontier Work in Real Life” Christine Benz, “How to Retire” Kindle Paperback Audiobook Retiremeet Anna Corwin “Embracing Age” Kindle Hardcover Paperback Audiobook MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 5:17 Livestreaming! 14:10 Habits of the happiest retirees 22:16 Exploring opportunities in retirement 30:04 The power of connection 38:27 Community involvement 44:54 Finding common ground 49:21 A purpose bigger than yourself 56:27 Starting in the wrong place 1:03:12 Soundcheck – National parks
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Jun 3, 2025 • 1h 5min

Buy Borrow Die for FI and Mailbag Questions - Rusty | MHFI 270

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 “Homework”: https://docs.google.com/spreadsheets/d/1qflSynVvMlxcBw1kkKBfG3HFQNJV05b8/edit?usp=sharing&ouid=100827824204716910905&rtpof=true&sd=true Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/ Use code MILEHIGHFI at GhostBed checkout for an additional 10% Off Already Low Prices! June 2025 Livestreams: https://youtube.com/live/d2lTp4FMe4A?feature=share Come hang out with Doug at CampFI Week 1.5, Mon July 7, 2025 – Thurs July 10, 2025: https://campfi.org/event/campfi-rm-250707/ Links Rusty on MHFI episode 252 NBER Working Paper Series, “Buffett’s Alpha” Mad Fientist, “How to Access Retirement Funds Early” MHFI Facebook group Doug’s site Check out Producer Chris’s new blog: Epic Financial Journey — Join the Mile High FI Club – It’s the email list! Get MHFi Merch – It helps support the show. Get t-shirts & more **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com 0:00 Introduction 3:15 Basics steps of Buy, Borrow, Die 9:01 Mechanics & benefits of the strategy 13:51 Risks & downsides 23:18 Mathematical projections & comparisons 28:33 ACA & tax considerations 36:53 Question: Claiming unemployment 44:02 Entitlement to unemployment benefits 48:46 Question: Reallocating due to market volatility 55:55 Market predictions 1:00:14 Soundcheck – Vacation packing

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