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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The Power of the Four-Hour Work Day (even in retirement)

We live in a distracted world where depth of investigation is discouraged. Despite increases in scientific spending, the number of publications, or the amount of PhDs being awarded, major discoveries in science and engineering have declined significantly in recent decades. The new-music market is shrinking, and old hits are dominating. We are working more days and longer hours, but US productivity growth is way down. A society that produces meaningful output is a healthy society, but meaningful output is arguably on the decline in many fields.

I argue that distraction and “noise” are key inhibitors to a healthy and progressing society. In the nearly three years since I quit my job, I’ve been forced to examine my strong tendency toward distraction. What follows is a discussion of methods that I’ve found incredibly useful in retraining my brain for deep and focused work and why that matters so much today. Our peak potential resides in no more than four hours per day.

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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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Joy and Tyler Black on Career, Money Mindsets, and Parenting

Today’s guests on episode 51 are Joy and Tyler Black. Many of you may be familiar with Joy, who has rapidly built a successful online business as a coach for pregnant and postpartum rock climbers. If you follow Joy on Instagram, you know her as a fun-loving and engaging mother of three, with a reputation for solid technical and personal coaching. Tyler on the other hand, is not a climber at all. He’s a biologist with a contrasting, yet highly complementary personality. In that way, they make for fantastic interview subjects on the discussion of relationships, money, career, and parenting.

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Three Important Myths on Delaying a Career

A combination of economic and cultural influences are propelling the trend of delayed adulthood. Through low-commitment job grazing, one can pursue recreational pursuits into the years previously occupied by traditional adult responsibilities: marriage, careers, parenting, and even home ownership.

Some might say YOLO. Life isn’t as short as we think, but our ability to get ahead might be.

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It’s Not All Hard Luck with Shay Skinner

In her late teens and early twenties, Shay Skinner was disowned from her family. She struggled with crushing mental illness, which ultimately culminated in a suicide attempt that left her in financial ruin. From this dismal situation, Shay filed for bankruptcy and began a long and fruitful climb toward being whole again. How can we summon the courage to take such measures of personal accountability?

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Earning to Buy Time with Meghan and Jeff (A Way to FI)

Today’s guests on episode 44 are Meghan and Jeff, two Colorado climbers who are at very different positions on the spectrum of financial independence. Jeff achieved financial independence along with his wife, Rose, over four years ago. Meghan, along with her husband, were inspired to get serious about their personal finances after meeting and learning from Jeff and Rose. Jeff and Meghan now write about their experiences and learnings at awaytofi.com.

Today we discuss their different origin stories, long-term goals, and shed some light on the fraught balance between work, money, family, and the seemingly elusive control of our time.

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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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Ashley Green: How to Create Enjoyable Business Success at Age 27

Today on episode 42 I’m very pleased to host this enjoyable conversation with entrepreneur and climber Ashley Green of Climb On Equipment, a climbing specialty retailer in Squamish, BC.

Today we discuss how Ashley, at age 27 and with hardly a loonie to her name, came to own this business and turn it in to the thriving pillar of the community that it is today. We dive deep into the mechanics of funding this endeavor, maintaining a work/life balance of a serious climber and prospective mother, expanding and building a team, and the value of capitalizing on the serendipity that befalls us all. Finally, we touch on some of the specific town dynamics of Squamish in particular, a place like no other I’ve ever been.

This is the story of a young person getting two struggling businesses, taking risk, and building something amazing on the path toward financial independence.

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Peter Beal: Can You Afford to Be Sponsored?

Today on episode 39 I’m pleased to welcome long-time climber and Front Range local Peter Beal. Peter, at age 58, has been climbing for over 45 years, with notable achievements including multiple 5.14 first ascents and bagging V12 in his late forties!  But Peter is also known for his critical takes on the culture of outdoor life. Today we discuss some of the realities of meaningful work, family life, and the potential opportunity costs of a life of adventure.

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