Five years, and two desperate moves with no master plan.
People ask me how long it took to go from sleeping in a van to owning a small multi-family. The technical answer is “less than five years, but not the way you’d think.”
The story that fits in an Instagram caption is I figured out the math, executed a plan, and crossed the finish line. That’s not actually what happened, and I suspect something that simple leaves out key details (like mom and dad gave me down-payment). What really happened is closer to I bumped into one good idea, made a big sacrifice, took a couple of baby steps, and stayed cheap for longer than was fun.
Here is the full story, one that maybe you might glean some useful insight from:
Move 1: into the van (no plan)
I’d believed the standard American Dream story I’d grown up with: work hard, save 10%, the rest takes care of itself. I tried it. I was 20-something, in a high-cost coastal city, working a dead-end job that paid an average wage. The math did not work. After rent, food, and a car payment, there was no 10% left to save. Some months it was 0% left to save, most months it was increased debt, which is even worse.
So I got a little desperate, and started making drastic changes in hopes that something would give me the angle I needed to break out of the poverty I was in. First one was moving into a van.
In order to afford the van, I sold my crappy car, which barely helped at all, and took out more debt. This was justified as the cost of the debt was lower than renting, which was an exorbitant cost. But a newer, empty, van without any amenities doesn’t quite make a person whole, and it wasn’t pretty. There were no string lights. There was no curated mountain backdrop. I took my time to build that van out as best I could, but by the time my lease was up and I moved in, the reality was I slept in a sleeping bag, settled into a parking-spot rotation I’d worked out by trial and error, and a routine that involved showering at the gym at night and using the bathroom at work in the morning to “get presentable.” I ate an unfortunate amount of Taco Bell and peanut butter sandwiches. It was not freeing. It was exhausting. It also didn’t seem to help me save. I had a small fridge, but not really any space/appliances for basics- cooking, going to the bathroom, etc. I’d given up more than I realized to save on rent, and it wasn’t sustainable.
I want to be clear about something: I while I wasn’t truly homeless, I also wasn’t doing van life as a lifestyle experiment. I was (and had been for years) housing-insecure, and I was using the cheapest housing I could find to keep myself solvent while I tried to figure out what came next. There’s a real distance between “minimalism is liberating” and “the math just doesn’t work this month.” I was always on the wrong side of it, and a lot of the rhetoric I was hearing — about budgeting, about hustle, about manifesting — was being delivered by people who’d never been on this side of that gap. The influencers and life coaches really only offered platitudes and formulas that simply weren’t helpful to me.
The van year ended, eventually, the way most bad situations end: I got tired enough of it to change something more drastic than the situation itself.
Move 2: out of my hometown (the unsexy answer)
I left the coast, my friends and family, the good weather. I moved to the Midwest. I had no job lined up, I knew no one, and I had barely anything to get me started (technically I had significantly more debt than I had assets at this time, so I actually had less than nothing to get started. That is modern American economics, for ya!).
This turned out to be probably the best of all the moves I made, but it was a major risk. My first piece of advice is somewhat obvious, but what it calls you to do if you want to change you financial situation is something that most people simply are not willing to consider. The balance between the Cost of Living and what you earn is not a constant. It’s a variable. And it’s the single biggest variable most aspiring homeowners refuse to touch.
In my old city at the time, a starter home cost roughly $700,000. In the Midwest, it cost roughly $200,000. Same square footage. Same number of bedrooms. The only thing that was different was the zip code, and the zip code was not paying my rent.
Alternatively, earnings in my city was relatively low. $30-40k/year over the last 3 years, and that was with a college degree. So the value proposition was $40k annual income against the cost of a home starting at $700k. The high cost of living wasn’t offset by an increased wage. So I picked a place that may pay $5-$10k less, but the cost of a home was $500k less.
Moving was hard. It took me away from friends, from a city I liked, from a job I was building. But the spreadsheet was unambiguous. If I stayed, I’d be a permanent renter. If I moved, I’d be a homeowner within a year. And that could be a spring-board to financial freedom. How could I stay put?
And the math here worked. Within a year of moving to the midwest, I closed on a tiny single-family house — less than 700 square feet, the kind of place that looks like a starter cottage from the 1940s, because that’s exactly what it is. It wasn’t impressive. But it was mine, and I was building equity.
That house was always a stepping stone, but it was also a massive leap. 2,000 miles from home, from a sleeping in a van to my own house. I don’t want to downplay that. Three years later, I sold the starter-home, and bought my duplex.
The morning the duplex showed up in the spreadsheet
Even after I got into my first home, I would often take a little time in the morning and look at Zillow listings for fun, and run some of the numbers on homes I was interested in. I do this the way other people scroll Instagram — same pleasure/pain circuit, different inputs. It wasn’t great feedback. It seemed like it would be a very long time before I was out of my “starter” home. As in, I’d be in that home until the end, or near it. That was not the idea I had when I moved across the country.
So one Sunday morning, sitting on my Facebook marketplace couch by the window, with some coffee, I expanded my criteria and looked at condos, MFH, land, etc. A local duplex listing caught my eye. I made a few adjustments to my spreadsheet and plugged it in, with the idea that I’d have two units. I’d live in one. The other unit’s existing rent would cover a significant chunk of the mortgage.
The number that came back didn’t look like a fantasy. It looked like my actual housing cost would be lower than the rent on one of the slum apartments I’d lived in in my early 20s.
I read it twice. I built a more careful model. I started looking into FHA loans for owner-occupied MFH financing, and came across the term house hack — which I’d never heard before, despite a year of looking at real estate. I learned that the financing programs that existed for someone in my position were significantly more generous than the financing programs that existed for an investor buying the same property as a pure rental, because it would be my primary residence. Less cash down, favorable local property tax rules.
Thats when I started looking at duplexes seriously.
About six months later, I closed on my current duplex.
What changed in my thinking at each pivot
Financial Freedom was worth major sacrifices. When you’re broke, the flow of money feels like weather. It rains, it doesn’t, you don’t control it. And that isn’t ideal for most people, but our priorities are elsewhere- hobbies, friends, family, etc., and these can keep you in the same situation financially if you never take a moment to evaluate. Being chained to rent and poverty, for me, became non-negotiable- it wasn’t something I could continue to endure.
Housing stopped being a fixed expense I had to accept. I’d treated rent like a utility bill — something I paid because I had to, in whatever amount the market demanded. Before I moved into the van, I was thinking about how I could “beat” that market. Eventually I came to see the market as wrong for me entirely, and that to moving to the correct market may be the best option. How much is cutting your housing cost by $500k worth when you make less than $50k (compared to “saving 10%” of almost nothing)? Especially when it requires no income increase? Looking at my income and expenses, I came to see housing costs as my biggest obstacle but also the variable I could move the most.
The standard playbook stopped being the only playbook. “Buy a house in your 20s and pay it off” doesn’t work for people who can’t afford a starter home in their city. “Save into a 401(k)” doesn’t work for people who can’t save. The standard playbook assumes a starting line that not everyone shares. The math doesn’t care about the starting line — it cares about what you do with the inputs you actually have. Once I accepted that the playbook was optional, the moves got easier to make.
What I’d tell the van-year version of me
If I could get a 30-second window with the version of me eating Taco Bell in a parking lot at 11pm:
I’d tell him that the math wasn’t lying and nothing was going to come out of left field and change my situation. I’d tell him that he’d have to take control of his life if he wanted change. I’d tell him that the city he loves is also the city that is making his math impossible, and that the move he doesn’t want to make is the one that buys him everything else. I’d tell him to stop being embarrassed about being broke, because being broke is not a character flaw — it’s an arithmetic outcome, and arithmetic outcomes can be changed.
I’d tell him financial freedom was possible and that it is coming, but it’s not going to look the way he thinks. It’s not going to be a single triumphant moment. It’s going to be a couple of major sacrifices, a couple of shrewd decisions and a Sunday morning spreadsheet adjustment with the quiet realization that suddenly the numbers work for a path out.
That’s how it actually happened.
Want to see what the math looks like on a real duplex? Open the calculator. Want the full breakdown of my own deal, with actual numbers? That post is [coming next / linked here].