Friends, Romans, Fintech Aficionados - We are back with the first Fintech Founder interview of 2023. And we’re going to be talking about the one thing that Millennials far and wide all love, but will never have. No, I am not talking about unlimited access to avocado toast (always thought that was a stupid media narrative), I’m talking about homeownership.

Obviously I’m being tongue-in-cheek here, but let’s look at some of the data. The median home price in the US has soared 145% since 2002, in that same period median household income has only risen 67%. At age 30, the average Millenial is 13% and 18% less likely to own a home, than their Gen X and Baby Boomer peers were at the same age, respectively.

I share all of that to generally frame up for discussion: In modern American life, is homeownership an attainable goal for the average American? Has the American dream been fundamentally altered? Are technology companies capable of reframing our relationship with owning a home?

My take on all of the above is no, yes, and yes. And as a result, I wanted to spend some time with Ali Nichols, the CEO & Co-Founder of Getaway, a real estate startup looking to provide consumers with access to commercial-grade real estate investments in the vacation rental space. Part of their mission is to help people navigate the changing landscape of home ownership in this country by providing them access to financial assets that have the ability to both appreciate in value, and generate cash flow, while simultaneously building up a distributed network of properties where Getaway members can stay. It’s like staying at an Airbnb, but throw in the fact that any time anyone in the world stays at that Airbnb - you get paid. Ali and I had such a fun, wide-ranging, but most importantly honest conversation about homeownership, building a startup, and navigating the ups and downs of building a career in tech & VC. Ali is an absolute badass, and I’m really excited to share this conversation with all of you, so without any further ado - let’s dive right in.

My first question for you, Ali, is, let's talk about that founding moment for Getaway. What led you to want to start a company? And was there any sort of crucible moment?

Yeah, it's a great question. I've known my whole life that I wanted to start my own company and I had this idea, this notion of becoming my own boss at some point. That was instilled in me, at a young age as the true merit of success. I didn't know until I started in the tech industry that I would be a startup founder, but that's been ingrained in me since I was a little kid. So that's always been the goal. When it came to Getaway one of my passions, even since I was a kid, has been residential real estate, and in my previous role I was running the real estate team at another prop tech startup called Bungalow and had the opportunity to really scale out some really awesome programs, including launching a large fund and I realized, "Wow, I'm getting to use all this expertise in my professional life. How could I translate that into my own investing and start to build my own personal portfolio of properties?" And, actually, I was joking around with my now co-founder, Amr, one day: "Should we start a small fund together? We've built all this technology and tooling and product to be able to identify awesome rental properties. Let's go out and do this for ourselves personally."