Darrow Kirkpatrick: Beyond Doubt on the Colorado Trail

Today on episode 55 I’m honored to welcome Darrow Kirkpatrick, former engineer, climber, investor, author, and the creator of the popular blog CanIRetireYet.com. Darrow began serious saving and investing in his mid-30s and retired at age 50 in 2011 from a career in software engineering.

In this wide-ranging interview, we explore why Darrow stepped away from personal finance writing after creating a popular blog, his adventures on the Colorado Trail and the inspiration for a memoir, and the journey and struggle to finding meaning and purpose at any stage in life.

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Lee Cujes: No Free Lunch on the Life We Really Want

Today on episode 53 I’m pleased to welcome back Lee Cujes, this time as a podcast guest. Some of you may recall the written interview with Lee back in late 2020. Lee is an elite Australian climber and route developer, with multiple 5.13+ and 5.14 first ascents to his name. But most importantly as it relates to this platform, Lee has managed to climb and develop routes continuously while carving a unique career niche and embracing a long-term investing strategy, an approach that provides the ultimate work and life balance.

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QA8: What If We Run Out of Water?

We’re back to the digital mailbag to answer your questions!

For this week:

  • Thoughts on the bear market
  • Getting invested with a Health Savings Account
  • Paying for education with retirement accounts
  • My philosophy on rest from climbing
  • How to develop financial mentorship in the climbing community
  • Travel and rescue insurance ideas
  • Determining a cost-effective approach to climbing destinations
  • Should I open an IRA if my employer doesn’t offer a 401(k) match?
  • How to not get wrecked moving from sport climbing or bouldering to trad climbing
  • The risks of owning property in an area that could be running out of water
  • Getting a home loan with inconsistent income history
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The Long Way to Squamish

I’ve journaled on-and-off for various periods of my life, but I was never a “regular contributor” until this past year. Switching from a form of writing meant for public consumption (this website) to something solely for me was at first awkward and revealing. Isn’t so much of what we do meant for someone else?

What follows is a selection of modified journal entries from the first phase of our recent trip to Squamish. These posts capture affectionate, curious, and questionable observations from the long road between Utah and British Columbia.

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Chris Weidner: Something More To The Story

Today on episode 43 I’m happy to have Chris Weidner, a long-time Colorado Front Range local, writer, husband, and father. This conversation is special to me for unexpected reasons. I hoped to interview Chris about his career as a writer, but what emerged was something far more interesting, and admittedly, brave on Chris’s part as it relates to career and finances. Chris is shockingly frank in many aspects of this conversation in ways I couldn’t have imagined. I really thank him for that, and I hope you will enjoy this truly fascinating discussion about his life, climbing, family, and career.

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Back (Pain) in the Saddle Again

I’ve been slack on writing, which is generally a reliable indicator of an overly stressed life. That busyness came to a screeching halt early last week. Five minutes before my partner—let’s call him Bob—arrived to pick me up for the new-school classic Spirit of Squamish (5.8, 8 pitches), everything changed. At the strike of 6am, just as the sun began to crest over the lush coastal mountains, I bent over to pick up a 1-pound water bottle and felt a lightning bolt of pain in my lower spine. I knew in that moment that I was hosed, but it felt too late to bail. Plus, I often find relief from (mild) back pain when climbing…or so I thought.

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Steven Dimmitt: The Simple Ways to Become Remarkable

Steven Dimmitt is the host of the popular Nugget Climbing Podcast, a show about performance climbing and the life-long journey of self-improvement. At the surface, it seems that Steven left his engineering job and moved into a van to pursue what might seem like a whimsical and youthful passion. Digging deeper, however, we see that the journey to critical and financial success is one of dedicated craftsmanship.

How can we all leverage the power and contentment of craftsmanship to build a satisfying and meaningful life?

I really enjoyed this one, and I hope you will too.

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EP 27: Homes and Vans with Tien and Brandon Rooney

Today on episode 27 we are taking a deeper dive on real estate investing with climbers Tien and Brandon Rooney of Five Twelve Real Estate. This couple shares a very intriguing history, spanning from college athletics to corporate world wake-up calls, the latter of which inspired them to uproot their lives and teach and travel throughout Asia.

Eventually, looking to rekindle the youthful days of travel and freedom, Tien and Brandon turned to real estate investment as a way to fast-track their path to financial independence. They even moved into a van full-time to further optimize their financial journey.

We carefully examine the many methods of real estate investment, including some key tips for first-time home buyers. Find out if this path is for you!

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EP 18: Kenzie King: Hiking the Pacific Crest Trail

Today on episode 18 I want to welcome Kenzie King. If you listened to last week’s interview with Michael Langer you will recognize Kenzie as Michael’s girlfriend. Kenzie and Michael walked away from lucrative engineering careers in Houston, Texas and moved into a van. Only months later, seemingly on a whim, they smashed the Pacific Crest Trail, hiking over 2,600 miles across California, Oregon, and Washington.

I promise that this is not a retelling of last week’s story. Kenzie has a very unique perspective on their journey. And regardless of your thoughts on the backpacking or thru-hiking, Kenzie shares a number of insightful opinions on the evolving dynamics of workplace culture, relationships in trying environments, and levels of financial or emotional security necessary to make bold and truly lasting changes in our lives. Hang on all the way to the end for some of the best moments of this conversation.

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