The Story of How Two Advertising Creatives Became Landlords

Landlord Philosophy
Written By Krystle Lilliestierna

The idea of becoming landlords started during a brutal winter storm in Northern Michigan. What began as a casual pandemic conversation eventually grew into our philosophy around thoughtful rental housing and property investing. Krystle and I were renting an Airbnb in Traverse City in early February, just narrowly making it to town from our home in Detroit the day before eight inches of snow and frigid temperatures all but shut the city down. (Fun story: our vehicle actually got towed for being parked where it shouldn’t have been due to snow removal… but that’s a different story.)

Hunkered down in our rented loft overlooking the city’s quiet downtown, I had a random thought. Krystle had recently sold her house and moved in with me, and she was sitting on the proceeds from the sale. This was early in the pandemic, when the housing market absolutely popped off and buying a house almost felt like a social hobby — a fun way to kill time — with historically low interest rates fueling the fire.

I wondered: rather than put the money into a savings account, maybe we should try our hand at being landlords.

If that sounds like a weird leap, let me back up. I’ve loved houses, remodels, and the idea of “home” ever since I watched my first episode of This Old House. And as someone who’d rented apartments, condos, and houses for more than a decade, I had a pretty strong sense of what renters were actually looking for.

More importantly, I’d experienced a wide range of landlords during those years: hands-off, deeply engaged, incredibly considerate, totally absent, and everything in between. Through all of it, I always felt like I had the skills to create a space where other people could truly thrive, which was important to me.

Yes, I could see the financial benefit of investing the money into an asset that would hopefully generate income. But what I really saw — and what made Krystle almost immediately agree to put her money into this idea — was the chance to support communities we cared about. To provide the kind of places we ourselves had been looking for just a few years earlier. Places free of “Landlord Specials” and the negative associations that can come with renting: cumbersome processes, neglected properties, and spaces that never quite feel cared for.

And if I’m being totally honest, I think we also needed a distraction from the stagnant unknown that defined those early years of the pandemic.

So, however naive we may have been, we set off on a mission and joined the throngs of people buying houses. Eventually, we came across our first rental with the help of our amazing realtor, Nik Leible. We focused our search on areas we knew well: places we’d both lived or worked in, neighborhoods with a mix of younger professionals, young families, and pet owners. In other words, people a lot like us.

I wasn’t initially sold on the property. The kitchen was tight, and I thought the basement could have been nicer. But the bathroom had recently been remodeled, the wood floors were in great shape, and most importantly, since we wanted to cater to people with dogs, it had a fenced-in backyard.

Krystle recognized its potential almost immediately and said something that has since become our north star when evaluating properties. It’s the test by which every place either passes or fails.

She asked: Would you live here?

While we both saw areas where the house could improve, we both answered yes. 

That became our simple test for every property and is still how we judge every potential investment. If we wouldn’t live somewhere, either as it currently is or as we know we can get it with some elbow grease, then we don’t want anything to do with it.

Maybe it’s a product of working in advertising for so long, but we’re always thinking about the audience: the end user, the consumer. And I’m sure there are investors out there who would say that’s not the most profitable approach. After all, we aren’t the ones living there. So why spend extra, which we often do, making a place nicer, more homey, and more connected to the neighborhood?

For us, it all goes back to that original instinct: the desire to create spaces where people actually want to live. The belief that it’s possible to make a profit while also doing what’s best for the people who call those places home.

And we know we’re not alone in thinking this way. There are many wonderful landlords out there, and we’re happy to (hopefully) count ourselves among their ranks.

What we’ve learned since buying our first rental

  • If we wouldn’t live there, we won’t rent it.
    That question has become our filter for every property decision.

  • People deserve homes, not just housing units.
    Small design choices and thoughtful details can change how a place feels.

  • Clear expectations prevent most problems.
    Things like welcome guides, checklists, and written processes make everything smoother.

  • Profit and care don’t have to be opposites.
    Well-maintained homes and respectful relationships tend to produce better long-term outcomes.

If you have a similar instinct and are thinking about becoming a landlord, we’ve shared many of the systems and lessons we’ve learned here on the blog. And if you're looking for help getting organized — and maybe avoiding a few of the mistakes we made early on — take a look at our Thoughtful Landlord Toolkit.

Happy landlording,
Travis

Continue building your thoughtful landlord system

If you're thinking about becoming a landlord or improving how you manage your rentals, these resources can help.

Krystle Lilliestierna
Next

How to Organize Rental Property Receipts (Without Stress at Tax Time)