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 th...
Jul 15, 2025•57 min
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...
Jul 08, 2025•1 hr 2 min
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” and offers advice on investing, maintaining motivation, and the evolving nature of career paths. Jillian introdu...
Jul 01, 2025•1 hr 7 min
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...
Jun 24, 2025•1 hr 7 min
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 cop...
Jun 17, 2025•1 hr 6 min
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: h...
Jun 13, 2025•37 min
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...
Jun 10, 2025•1 hr 13 min
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=1008...
Jun 03, 2025•1 hr 5 min
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 pitfalls of social media and news consumption, the value of community connections, and the liberating perspective...
May 27, 2025•47 min
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, achieving flow state, and finding meaningful ways to spend one’s time while maintaining good mental and physical hea...
May 20, 2025•1 hr 13 min
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 experimentation. Win a ticket to CampFI Rocky Mountain – Week 1 Ticket (2025) Do you like the podcast and want t...
May 13, 2025•1 hr 12 min
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 investor. Win a ticket to CampFI Rocky Mountain – Week 1 Ticket (2025) Do you like the podcast and want to support ...
May 06, 2025•39 min
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 achieving Fat FI, helping family, and exploring content creation as a new career path. Jess and Corey also discuss ...
Apr 29, 2025•1 hr 3 min
JT and Doug talk about reading and books… Win a ticket to CampFI Rocky Mountain – Week 1 Ticket (2025) https://milehighfi.com/wincampfi Support the Show (and get exclusive content!) https://milehighfi.com/donate Check out the Mile High FI Store… https://milehighfi.com/store Outro music is a bastardization of Cry, Moan, & Wail by Marc Ford. Super cool blues chord progression… Join the Mile High FI Club – It’s our email list! https://milehighfi.club doug@milehighfi.com 00:00 Intro 13:07 Discus...
Apr 24, 2025•41 min
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, and frugality. Together they discuss lifestyle changes, managing finances as a couple, and the importance of clear ...
Apr 22, 2025•1 hr 2 min
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 away from work and towards more engaging subjects like travel and hobbies. Finally, they provide a glimpse int...
Apr 15, 2025•1 hr 7 min
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 how to handle Required Minimum Distributions (RMDs). Note: This is a rebroadcast of MHFI episode 190 Do you like t...
Apr 08, 2025•1 hr 18 min
Doug and Mark Trautman discuss a listener question regarding whether it’s better to pay off a low-interest mortgage (2.5%) or invest the money instead. They explore various strategies, including the psychological benefits of paying off a mortgage, the financial returns of investing, and a hybrid approach to manage risks. They also delve into the historical behavior of the stock market and emphasize the importance of aligning investments with personal goals. Follow the link for more details inclu...
Apr 01, 2025•50 min
Doug chats with Mark Trautman about non-frugal habits and some recent “fancy” spending that both of them have indulged in. They delve into the concept of easing away from frugality, the ‘fun bucket’ for guilt-free spending, and psychological tricks to spend more comfortably while also touching upon practical tips for managing money and making thoughtful spending decisions. Do you like the podcast and want to support the show? Follow the link to find out how: https://milehighfi.com/support/ Links...
Mar 25, 2025•1 hr 4 min
Doug and Kristen continue their conversation about travel hacking (picking up from MHFI 258), this time moving on to more advanced techniques & tips. They discuss credit card referral bonuses, maximizing redemptions, airline alliances, the intricacies of business credit cards, and the Chase 5/24 rule. Kristen also emphasizes the value of using tools & apps for tracking and optimizing points. You can check out all of Kristen’s notes here: https://milehighfi.com/travelhacking/ Kristen’s cr...
Mar 18, 2025•1 hr 5 min
Doug chats with Kristen Knapp about the world of travel hacking, beginning with the basic principles and strategies for earning and maximizing points & miles. Kristen shares her personal experience with travel hacking, highlights key rules and tips for getting started, offers practical advice on how to choose the right credit cards, the importance of being organized, and tips for utilizing various travel apps. You can check out all of Kristen’s notes here: https://milehighfi.com/travelhackin...
Mar 11, 2025•1 hr 14 min
This is a Bonus episode with producer Chris! We talk about: the correlation between happiness and income key inflection points in their lives their spending habits on toys and experiences Doug also shares insights on Elizabeth’s retirement and its impact on their lives. Happiness Study Links: High income improves evaluation of life but not emotional well-being – 2010 Study by Kahneman and Deaton Income and emotional well-being: A conflict resolved – 2022 Study by Killingsworth and Kahneman and M...
Mar 08, 2025•47 min
Doug chats with JT about practical, actionable strategies for introverts attending conferences like EconoMe, Camp FI, and others. They cover topics such as social anxiety, taking breaks, participating in structured activities, and effectively interacting with content creators. They also share tips on the types of questions to ask to keep conversations flowing, how to gracefully exit interactions, maintaining self-care during events, and the importance of not overextending oneself. This episode i...
Mar 04, 2025•1 hr 17 min
Doug chats with friends Chris & JT from a partially-disclosed location in Breckenridge about a potpourri of topics. The trio discusses happiness, dives into the controversial & confusing topic of tipping (with input from listener Kris), and provides their thoughts on high net-worth individuals (based on a correction pointed out by listener Bill). The group also analyzes Amber’s ambition of reaching FI by age 40-45 (full details below). Be sure to check out Chris’s music… His first single...
Feb 25, 2025•57 min
Doug and guest host Kristen Knapp chat with Colorado native Suzy about her financial independence journey and world travel with her family, including extended periods of time living abroad. Suzy shares her journey toward Coast FI, early money mistakes, taking sabbaticals, and the importance of community. She elaborates on her family’s experience with worldschooling, the benefits of living in Spain (both cultural & financial), the intricacies of living abroad, and how her family managed healt...
Feb 18, 2025•1 hr 6 min
Elizabeth retired 10 months ago. We talk about her system to make sure she’s doing things… I’m doing bonus episodes now! Introvert Instagram Clip we mention Join the Mile High FI Club – It’s our email list! MHFI Facebook group Help Doug publish more shows by supporting at Buy Me A Coffee . Brought To You By: The Doug Show, aka Affiliate Marketing & Side Hustles Email the show: doug@milehighfi.com —- Timestamps 00:00 Welcome to the Mile High 5 Podcast 00:26 Retirement Reflections: 10 Months I...
Feb 13, 2025•37 min
Doug chats with Lyn Mettler, travel rewards expert and founder of Families Fly Free/Families Travel Free. Lyn shares insights on how to maximize travel rewards, including practical tips on using programs like the Southwest Companion Pass and flexible travel cards. She also discusses upcoming changes in the airline industry, the importance of using points wisely, tips for booking flexible travel, accessing airport lounges, and potential trends in travel accommodations. Doug and Lyn also answer a ...
Feb 11, 2025•1 hr 1 min
Doug chats with Adam Coelho, host of the Mindful FIRE podcast, about the limitations of FU money and how a big vision can change your life. Adam shares his journey of transitioning from Google to fully embracing entrepreneurship, the importance of having a clear vision, and how mindfulness & meditation have played a pivotal role in his life. He talks about the role of FI in creating options and building a life from a place of sufficiency rather than lack and the power of neuroplasticity &...
Feb 04, 2025•1 hr 4 min
Doug chats with Colorado resident Rusty about life after achieving financial independence. Rusty shares his journey from growing up debt-averse to his career as a lawyer and then retiring at a young age. He shares challenges with securing mortgages without traditional income, tackling healthcare, and the importance of learning new skills & staying active. Rusty also describes a unique withdrawal strategy called “Buy, Borrow, Then Die”. This episode is brought to you by GhostBed . Doug has th...
Jan 28, 2025•1 hr 8 min
Doug chats with Colorado resident Neil about his inspiring journey of perseverance, self-improvement, and financial growth. Neil shares his approach to budgeting, strategies for overcoming financial challenges, side hustles, rental properties, and the emotional aspects of financial stability. He also explains the 50/20/30 budgeting framework and provides advice for those just starting their FI journey. This episode is brought to you by GhostBed . Doug has the GhostBed Luxe Mattress and loves it!...
Jan 21, 2025•1 hr 1 min
