Making Rentals Part of the American Dream

Jonas and Rosalind of Dwellsy

When you can’t find anyone else to fix a problem, sometimes you just have to do it yourself. Jonas Bordo, Co-founder and CEO of Dwellsy, realized the rental marketplace was broken, especially after the decline of Craigslist as a go-to rental site. In the real estate industry for more than 15 years, he previously worked at an investment management platform that managed about $40B in assets across North America. In his investment work, he ran a portfolio of 60K apartments for a REIT. In the process, Jonas saw many pain points for property managers and renters—unaddressed for fear of upsetting the status quo. In 2019 Jonas and his co-founder Rosalind Bordo launched Dwellsy, a comprehensive residential rentals marketplace based on the concept that organic search in a free ecosystem creates more value than the pay-to-play model embraced by rental listing services. Now Dwellsy has more than 12M listings and also supplies studies on rental trends in marketplaces nationwide.

We spoke with Jonas about how the rental marketplace has been disrupted on several fronts.

Why Dwellsy, why now?

I had the unique opportunity to see the way real estate rentals were failing both sides: renters and property managers. I also saw how hard it had become for renters to find a place. The apartment rental industry is brutal.. Craigslist was there for many years—not as a great tool, but an acceptable place with 80-90% of the inventory. Most of the renters knew it was a good first stop, in terms of looking for a place, and for most people [it] was the only place they needed to look. But around 2015 Craigslist started failing; there was fraud in the marketplace. And by 2018 it had pretty much disappeared as a major force in rentals. Nothing came to replace it. So it was a once-in-a-lifetime opportunity to really see this market failure up close and personal, and to build something completely different.

What strategies did you use to get your first customers?

We had to create a marketplace, and there is always a question: do you start with supply or do you start with demand? A big factor on our end was having relationships on the supply side. I had relationships that go back many years across the industry, and I was able to reach out to folks and get people to take a chance on us on the strength of those relationships. I can’t really say it was strategic so much as opportunistic, and we were able to use the assets that we had as an enterprise. Those initial relationships were incredibly valuable, and I feel very grateful.

What’s your best advice for new founders and fundraising?

You’ve got to find your people—find the true believers—and you never know who those folks might be. In fundraising, I took every meeting I could get, and I walked into every meeting expecting that they were going to want to invest in Dwellsy. If they didn’t, it was my responsibility to help them understand why they should be a part of this journey. I took lots of meetings and also got some great lessons along the way.

If you have the courage of your convictions and what you’re going after, then your business will get funded. If you can’t find any people interested, then that might be a critical message about whether your business is viable. But remember, the number of people you speak to needs to be pretty big. We spoke to hundreds of people in order to find the right investors to fund Dwellsy, and ended up working with some fabulous folks who’ve supported us along the way.

What’s been the most difficult part of building the business?

Product development has been the most surprising. We’re not developing groundbreaking technology; we’re not launching rockets to the moon or anything but the technical challenge has been really hard. As a non-technical founder, finding great folks to work with and creating a production approach and strategy that actually yields great product has been really challenging; I’m incredibly fortunate to have a great co-founder, Rosalind Bordo, who’s very focused on product and has done a great job making that happen. But not everybody has that.

Your industry was hugely impacted by COVID. What did the pandemic teach you about building a startup?

The pandemic caused things to go haywire and it has continued to be haywire. But we did realize that a window had opened where property managers were willing to try something new, when historically they have not been very open to new ideas. It’s tough business: there’s a lot of people selling them stuff and they’ve got to consider new ideas very carefully before implementing them, because they’re dealing with people’s homes.

What’s your dream for Dwellsy?

I think we need to recognize the American Dream has changed to some degree, and I think we also need to recognize that the pursuit of homeownership is not always a good idea. It’s not always the right thing for folks. Renting is a great option for most people, and homeownership shouldn’t always be the immediate goal. I think if we’re successful in doing what we’re doing at Dwellsy, renting will be recognized as just that – a great option for most people. And Dwellsy will become the ubiquitous platform that everybody uses when they think about renting—the first stop and, for most people, likely the only stop—when searching for their next rental home or apartment.

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Rusty Dornin
Rusty Dornin is the director of marketing and communications for Ulu Ventures. An award-winning radio and television journalist, she was a CNN correspondent for nearly 18 years covering domestic and world news ranging from war to natural disasters and tales of crime and politics.
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