Doug chats with Rebecca Herbst about her post-FI life including challenges of finding community & the right place to live, experimenting with increased spending, the mental shift from a scarcity to an abundance mindset, and the complexities of personal identity after leaving a career.  Rebecca also discusses her work with Yield and Spread, a nonprofit promoting generosity in the personal finance community including a call to action and The FI-lanthropy Pledge.

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

0:00 Introduction

3:10 Search for a post-FI home

11:23 Experimenting with increased spending

21:04 The role of financial advisors

29:21 Rebecca’s path to FI & bold career moves

37:43 Longmont vs. Salt Lake City showdown

46:12 Finding chemistry & community in Utah

52:52 Housing & lifestyle choices

1:00:59 Transitioning from career to early retirement

1:09:30 Laziness, productivity, & digital minimalism

Doug chats with Kristen Knapp (FI Friends Travel) about the challenges of unwinding deep-seated frugal habits and learning to spend at the “right level” after achieving FI.  Inspired by a recent blog post from the Mad Fientist, Doug & Kristen explore the nuances of maintaining a balance between saving & spending and discuss why many people struggle to actually spend money once they hit their financial goals.  They also emphasize the importance of spending on what brings joy and the necessary shift in mindset that’s required to enjoy financial freedom without guilt.

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

2:19 Frugality

9:02 Spending after FI

16:43 Reframing expenses

24:41 FI Friends Travel

31:44 Award travel using points

37:05 The Fun Fund

44:18 Balancing present & future spending

51:25 Shared experiences

55:39 Soundcheck – Winter weather

Doug chats with Nik Johnson (Everyday Money Heroes) about his journey to Financial Independence and retiring early.  He discusses an early passion for personal finance, how he discovered FI during the pandemic, the value of being part of a community, and the importance of a supportive spouse.  Nik describes his post-retirement life emphasizing a commitment to community service & financial literacy.  And excitingly he also describes what it’s like to be featured on national television (CBS Sunday Morning).

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

0:57 CBS Sunday Morning experience

7:48 Discovering FI & building community

15:15 Career & financial journey

23:52 CENT & achieving FI

29:58 Quitting work & emotional impact

38:53 Changes in expenses & spending in retirement

45:26 Everyday Money Heroes

52:33 Soundcheck – CampFI

Doug chats with Rusty about an intense neighborhood dispute involving prairie dog conservation, highlighting how ethical frameworks and philosophical approaches can guide community decisions.  Doug shares his experience working through this issue while emphasizing the importance of patience, humor, and effective communication in resolving disputes.  Rusty provides additional philosophical and ethical considerations while touching upon related communication strategies & improved community engagement.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Interested in a pair of Xero shoes so that you can be just like Doug & Rusty?  Check them out here: https://milehighfi.com/shoe

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

1:53 Philosophy & ethics background

7:27 The prairie dog situation

14:27 Exploring people’s intentions

23:17 Levelheadedness

29:17 3 main schools of ethics

36:20 Contractualism

41:45 The Trolley Problem

46:12 Aristotle’s 12 virtues

54:18 Stoicism & communication

58:28 Philosophy & ethics resources

1:04:19 Prairie dog outcome

1:09:01 Soundcheck – Shoes

Please support the show if you like it! I play a couple of highlights from Mad Fientist and Mr. Money Mustache after my pitch.

Mile High FI stats and a correction:

Spotify is 28% of the audience, so that’s grown in 2025 and higher than I said in this episode.

If you extrapolate the Spotify year end review data to the total downloads, here is what you get…

Mile High FI is a:

I don’t have ads anymore so I want to cover production costs. Most of the costs are related to software and tools and hosting. Many other podcasts have sucky ads every 15 minutes. I don’t want to do that.

Producer Chris volunteers to edit and produce the show. We’re not trying to get rich doing the show, but it takes a lot of time, effort, and planning.

You can donate via Buy Me a Coffee. You get extra content and know that you’re making the show possible

You can also check out the affiliate offers here, which are products that I recommend. Mile High FI usually gets a small percentage, say 1% to 15%, depending on the arrangement. It helps, but direct donations are the best.

Doug chats with Justin David Carl (Fit Rich Life) about his journey from being deep in debt to achieving FI.  Justin shares his experience leaving a high-earning sales job and the burnout he faced, followed by how he started the Fit Rich Life podcast & coaching and dealt with the psychological challenges of early retirement.  He also shares some of the specific thoughts & actions that eventually made him comfortable with his own semi-retirement 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

0:00 Introduction

1:50 The Golden Goose job

8:16 Identity crisis & self-worth

14:25 Burnout & recovery

22:02 Overachiever personality

30:28 Building a purposeful life

38:40 The power of competition

43:54 Embracing semi-retirement

49:00 Overcoming retirement fear

54:25 Navigating post-FI life

1:03:13 Soundcheck – Caffeine

Doug chats with Pete Adeney, Mr. Money Mustache, about how to ensure a good life by tracking daily habits while comparing Cal Newport’s “The Good Life Algorithm” to Pete’s own Badassity-tracking system.  They discuss the concept of shifting identities after retirement, emphasize the importance of finding purpose beyond traditional work roles, and the value of nurturing friendships.  Pete also answers a few listener questions from the Mile High FI Facebook group.

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

2:38 Badassity Tracker

8:29 The Good Life Algorithm

13:38 Social overload

18:24 Eating, sleeping, & colonoscopies

26:36 Identity (crisis) after quitting

33:36 Curiosity & lifelong learning

38:23 Tips for finding identity after retirement

42:42 Productivity & purpose

50:53 Question: Margin accounts

55:31 Question: Culdesac

59:45 Question: Gravel bikes & bikepacking

1:03:22 Soundcheck – Electric vehicles

Doug chats with Chris Luger (Heavy Metal Money) about his path to retiring early at age 50.  Chris shares his journey to financial literacy, changes he made since discovering FI, the impact of his  career in tech, and experience investing in real estate.  He also discusses the importance of finding purpose, how he’s balanced passions & activities after retirement, his struggles with identity, and philanthropic efforts through his nonprofit organization.

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

4:33 Learning about finances

11:38 Job fulfillment & optionality

16:50 Identity & career growth

21:36 Discussing early retirement with others

26:29 Transitioning to retirement

32:41 Structure & preparing for retirement

40:22 Purpose & productivity

48:53 Teaching financial literacy

57:14 The Luger Foundation

1:05:04 Soundcheck – Guitar gear

Doug chats with Pete Adeney, Mr. Money Mustache, about exciting changes at the MMM Headquarters in Longmont, Colorado.  Originally envisioned as a coworking space, the HQ is being rebranded to better reflect its true nature as a vibrant social club.  Pete covers the origin story of the HQ, the decision to shift direction, opportunities for increased member involvement in organizing events, and plans for future growth.

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

1:01 The FI Collective

8:08 The value of community

12:32 Influence of CampFI

16:59 The HQ origin story

21:24 Organizing community events

24:51 Transitioning to a social club

31:31 Soundcheck – Playing music

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 navigating changes in the online landscape.

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

2:07 Curiosity about Doug’s mysterious background

7:58 Affiliate marketing journey

14:43 Challenges & changes in the industry

20:48 Done chasing trends

26:37 Future podcast ideas & direction