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 and how it helped him work through personal issues and redefine his identity beyond his career.

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!

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

1:29 Brad’s journey to early retirement

7:30 Discovering the FIRE movement

12:54 Identity crisis & keeping busy

19:03 Stand-up comedy

22:46 The Hoffman Process

27:42 Planning for life after retirement

34:39 Finding structure & hobbies

41:33 Building social connections

46:35 Identity & journaling

52:40 Soundcheck – National parks

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 way while providing tips & advice for others who may want to follow a similar path in life.

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!

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

—

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

3:20 Discovering Financial Independence 

9:39 Embracing FI & making changes

15:36 Flexibility & dealing with uncertainty

23:26 Mindset adjustments

28:08 Backpacking adventures

34:43 Mistakes & lessons learned

38:11 Reverse robbed

46:39 Blogging & YouTube

53:33 Brewery visits & Mexican residency

58:01 Decumulation in early retirement

1:03:59 International travel tips & advice

1:08:41 Soundcheck – Longmont brewery crawl

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-retirement.  Jillian also offers practical tips from her new book ‘Retire Often’ and discusses the importance of being prepared for the emotional and practical adjustments that come with early retirement.

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!

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

—

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

1:11 Journey to early retirement & work-life balance

9:52 Testing retirement

14:15 Challenges of early retirement

20:24 Professional identity & personal value

29:29 Not as important as you think

33:57 The Messy Kitchen

38:51 Importance of rest & avoiding burnout

43:15 Retire Often

48:28 Soundcheck – Walking challenge

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 amongst FI couples, challenges & rewards of embracing frugality, and the power of community building & relationships.

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!

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

—

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

3:16 Cheap vs. frugal

11:07 Getting out of the cheap mindset

16:54 Amanda – First CampFI experience

24:10 Amanda – Partner dynamics & power of community

30:29 Tyler –  SoCo Mustachians

35:26 Tyler – FI meetups

41:48 Roxanne – Journey to Lean FI

49:50 Roxanne – Stand-up comedy

53:37 Soundcheck – Roxanne’s stand-up set

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? What’d you learn from the experience?

At age 50 plus, what are you focusing on for your health and fitness besides biking and eating healthy?

What things are you working on these days that light you up?

What’s your current stance and practice on charitable giving?

MMM charitable links:

Do you wish you lived a less frugally when you were younger?

What’s the biggest project that you’ve taken yourself and how did that go? And any advice for people that wanna do more repairs and improvement projects on their own?

Asked During the Conversation

Can you imagine working for someone else again? Or why not? (Doug to Pete)

Are there any other electric cars that are worth considering? (This was part of Neil’s longer question about buying a Tesla.)

—-

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!

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

—

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

00:00 Welcome to the Mile High Five Podcast

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 about the psychological and lifestyle adjustments that come with early retirement, including how to fill one’s time meaningfully, potential lifestyle changes, and the importance of staying engaged and balanced.

Note: This is a rebroadcast of MHFI episode 098

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!

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

—

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

3:54 Background & discovering FIRE

6:55 Steve’s financial situation

12:38 Separate finances

21:36 Considerations for withdrawing money

28:35 Exploring hobbies & passion projects

35:52 Community & networking

44:32 Soundcheck – Shaving

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:

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, including his beloved shade umbrella?  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

—

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

5:20 Question – Managing finances

9:20 Question – April’s downturn

14:44 Question – Lack of regular paychecks

18:44 Question – Quit sooner or done anything different?

23:00 Question – Unexpected benefits of retiring

31:19 Question – Doing one thing a day

35:27 Question – Managing time together

41:19 The 6 luxuries of life

45:31 Rushing vs. control over time

51:11 Soundcheck – Victor

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 also addresses the controversial topic of investing in small-cap value stocks and analyzes historical performance.  And of course, Doug & Karsten chat about a delicacy called asparagus.

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

10:34 Underspending & estate planning

16:35 Early retirement & time bucketing

22:30 Analysis of Die With Zero spending formula

30:52 Cherry-picking data 

37:46 (Increased) spending in retirement

46:02 Exploring small-cap value stocks

53:04 Diversification or Di-WORSE-fication?

1:02:22 Future plans

1:07:28 Soundcheck – Parallel foods

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, and giving back.  Doug & Frank also dive into a listener’s question about managing financial decisions during market volatility.

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

5:32 Asparagus vs. brussel sprouts

13:30 Evolution of the FI community

20:28 Wellbeing & contemplating death

27:06 Transitioning from saving to spending

33:33 Spending money to improve relationships

40:38 Experiences & building new friendships

46:59 Importance of giving

54:37 David’s financial journey

1:03:31 Diversification

1:11:05 Risk Parity Radio Podcast

1:17:19 Soundcheck – Bitcoin

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

Questions answered:

Note: This is a rebroadcast of MHFI episode 177

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

7:21 The Taylor Swift situation

13:39 Question – Riding the market swings

21:21 Question – Investment reallocation

27:26 Question – Parental influence

31:46 Question – Taking a gap year 

38:14 Thoughts on CampFI

43:39 Moving beyond FI

47:11 Question – Imposter syndrome

52:13 A perfect writing retreat

59:10 Soundcheck – Leadville