EP 23: Erik Jenson: Real Estate Investing with Training Wheels

Today on episode 23 I’m happy to welcome climber, dentist, and real estate investor, Erik Jenson. In addition to paying down hundreds of thousands of dollars in student loan debt, Erik is now living rent- and mortgage-free through the process of house hacking. This form of real estate investing involves renting out rooms in the home where he lives, allowing him to build equity and repeat the process with additional properties. Referring to this process as “real estate investing with training wheels,” Erik is generating an outsized return compared to the single-family home so many of us consider “investments.”

Topics Discussed with Erik Jenson


• Erik’s 2021 goal to climb 80 boulders graded V8 or harder.
• The early career of a dentist and paying off $330,000 dollars in student loans in 4.5 years!
• Erik’s thoughts on real estate investing as a simple and faster alternative to stock market investing
• Guidelines on choosing properties and vetting roommates and tenants
• Real talk on maintenance, unexpected expenses, and the realities of being a landlord
• How losing his job helped Erik reframe his perspective around the idea of early retirement
• Erik’s new focus on stock market investing as a compliment to real estate investing
• Is real estate investing a reality in today’s high-price and competitive real estate market?

Erik Jenson on The Practitioner (V11), Leavenworth, Washington.
Erik Jenson on The Practitioner (V11), Leavenworth, Washington.
Erik Jenson on Lost and Found (V10), Lost Lake, Oregon. (Photo: Josh Champion)
Erik Jenson on Lost and Found (V10), Lost Lake, Oregon. (Photo: Josh Champion)
Erik Jenson on Valkyrie (5.13b), Columbia River Gorge, OR (Photo: Charlie Egan)
Erik Jenson on Valkyrie (5.13b), Columbia River Gorge, OR (Photo: Charlie Egan)

Get in Touch with Erik Jenson

Erik Jenson on Instagram

Six Important Reasons Not to Retire Early

Contentment: The Greenest Grass of Them All

The Fallacy of Happiness and Meaningful Work

Value Spending: How to Really Save Money

Market Timing: Why It (Still) Doesn’t Work

Should I Buy a Home? Part 1

Should I Buy a Home? Part 2: Opportunity Cost

Relocation: A Guide to Moving and Housing Affordability

This Just In: The Real Cost of Home Ownership

And We’re Back to Home Ownership! But Why Now?

Housing Affordability: This Isn’t Normal

A list of all posts is here.

Real Estate Investing Online Resources & Books

Bigger Pockets: Create and Build Wealth with Real Estate Investing

Coach Carson: Invest in Real Estate. Do What Matters

Afford Anything

Set for Life: Dominate Life, Money, and the American Dream (Scott Trench)

Other Investing Resources

The Little Book of Common Sense Investing (John Bogle)


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2 Replies to “EP 23: Erik Jenson: Real Estate Investing with Training Wheels”

  1. Great episode Chad! Funny enough I was considering being a dentist back in undergrad but the loans scared me away. Glad to see Erik made it work.

    Also, so cool to hear you were in Chattanooga! That’s where I was living when we first connected. Great place for climbing, people loved Sunset Rock and hanging out at the Crash Pad. A cool up and coming city, curious to see how you liked it.

What say you friend?