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.

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!

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

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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: [email protected]

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

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!

**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: [email protected]

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!

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

—

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: [email protected]

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

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

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!

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

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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: [email protected]

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

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 introduces her upcoming book “Retire Often”, which provides a framework for integrating mini-retirements into one’s life and how these breaks can contribute to long-term wealth building and life satisfaction.

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!

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

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

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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: [email protected]

0:00 Introduction

1:55 Retire Often

11:16 FU Money & Seasons of Life

19:23 JL’s 1st mini-retirement

28:21 Negotiating career breaks & their benefits

38:04 The importance of attitude

43:46 Updating The Simple Path to Wealth

48:46 Thoughts on Bitcoin & gambling

55:08 Building wealth over the long-term

1:02:13 Soundcheck – Upcoming trips

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

—

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: [email protected]

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

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

—

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: [email protected]

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

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

—

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: [email protected]

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

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

—

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: [email protected]

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

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

—

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: [email protected]

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