Doug chats with Monica Levi, a former lawyer who retired early at the age of 40.  She shares her journey to FI, including her immigration to the US at 17, a battle with cancer, the transition from law to becoming a self-discipline coach, and her passion for travel.   Monica also delves into how she manages her time, expenses, and the challenges of having a working partner while being retired.

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

3:59 Immigrating to the US & financial upbringing

8:45 Starting to invest

15:33 Transitioning out of law

20:45 Other’s reaction to early retirement

24:56 Productivity & open space

30:58 Cancer diagnosis & recovery

35:21 Self-discipline coaching

39:22 Changing expenses & travel

48:59 Balancing a relationship & retirement

54:36 Soundcheck – Fitness goals

Doug continues his conversation with Josh Epley (9 to FI podcast) about life after early retirement.  Josh discusses how he spends his time, the challenges & surprises of early retirement, and the importance of having hobbies & goals.  He also shares his experiences with managing his workload, the benefits of being flexible, starting new activities like running, and the launch of his new podcast “9 to FI”. 

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

6:15 Balancing structure vs. free time

14:15 Pressure to make money in retirement

21:08 Designing a new schedule

26:17 Slow productivity & experimenting

31:59 Running

40:38 Launching a new podcast: 9 to FI

46:22 Engaging with pockets of the FI community

52:00 Scheduling & the art of saying no

59:43 Leaving open space

1:07:10 Soundcheck – FinCon

Doug chats with Josh Epley (9 to FI podcast) about his journey from $240K in debt to early retirement.  Josh discusses how he and his wife managed to turn their financial lives around including challenges they faced along the way and successful strategies they implemented such as real estate investing & rigorous budgeting.  Josh also shares insights into his recent post-retirement life from navigating personal challenges to the role of intentional living.

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

4:35 Overcoming financial struggles

11:41 Climbing out of debt & making changes

17:17 Dealing with professional identity

22:04 Catching the real estate bug

31:10 Real estate disaster stories

37:20 Future real estate plans

44:17 Thoughts on college 

52:05 A rich mindset & financial stages

59:24 Current expenses

1:04:32 9 to FI podcast

1:09:55 Soundcheck – HOAs

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

—

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