
In 2017 and 2018 I made some big moves in my life. I decided to depart from my Ph.D. candidacy and buy land as soon as possible. I don’t need to explain all of my motivations—they’re shared by many—but that was my goal.
By 2019, I found a place which I managed to pay off only two years later. At that point, I started to consider myself “retired” in some sense at around 30.
Back then in 2019, before even the lockdowns, prices were much less bad—it’s wrong to say they were good, but they weren’t the “New Normal” bad. I managed to buy a house for $80,000. Ultimately the most significant expense most people have, their housing, had been totally eliminated for me.
The money I need to live is relatively small and I don’t have to sacrifice much time or effort to make it now. I have a very free life, and I am glad I do because personal necessity in the last several years has absolutely required that.
A lot of people see what I did an envy it. They don’t have to envy it—because it’s not out their reach now either.
You might say that buying a house for less than $100,000, even in the countryside, is a tall order nowadays. It’s definitely more difficult, but I want to give some heuristics to others who are in a similar place I was.
Don’t ever let people tell you basic things like owning a house or land is impossible or even hard—even if you have nothing now.
Because most people speaking doom about this have never seriously tried.
They might look online and get discouraged, but that corresponds little to actually trying.
Good News: There is no market for most land.
First, I bought land where there was no “market.”
What I mean by that is I could manage to move to a place where there is absolutely no economic draw to it. There is neither industry nor significant skilled employment. Many of you in the digital age, especially with online work, can do the same much easier than I could.
The only people who live in rural places like this are people whose families have lived here for generations, and if anything, many but not all of their children choose to move elsewhere—to college or larger cities.
Of course you don’t have to find somewhere rural. You can also look to the many American cities where industries have evaporated, but still don’t have a crime issue.
If there is no economic draw to live somewhere, there is no firm calculus for people to actually price houses.
In most places like this, you might have five houses, nearly identical that could respectively go for $150k, $50k, $300k, $75k and ten dollars! You will see on Zillow that there will be houses here or in similar places for half a million dollars, but you can easily get a house for a fifth or even a tenth of that much.
Don’t use Zillow! Ignore the prices you know!
I will make this comment explicitly: Don’t look at Zillow or any other real estate site. If something is there, it’s probably for way too much. Certainly don’t go looking saying, “Hmm, lemme go see how much houses are here.” In general, to find a good deal you have to be in real life looking where others are not.
Also, for talking about places with no market, forget about the prices you know wherever you are! I saw a subdivision recently (not an even nice one) near where I grew up that said “Starting at $1.3 Million…” I pity people who think that that is what they have to have to live! Clean those evil numbers out of your head!
I bought a house for $80k. What did I do? Did I get lucky?
No.
…Or actually, maybe yes…
Because I waited for luck. I was consistent and waited for an opportunity.
I made a lot of trips to different places and met a lot of people until I was told of the offer I went with. I could have waited for an even better opportunity.
I’ll give you an example that might illustrate how you can get lucky.
I met an old woman in a small town near where I moved. She had a old house in a bit of disrepair, but could easily be fixed up, in an excellent location that made all the businesses of the town walkable. She also owned an old small store, mostly as a pastime. It was paid off (she had bought it for $30k decades ago), and she never made more than $5,000 a year.
Several years after I moved down, she unfortunately passed away.
A year or so later, I found out that both her house and her place of work had been sold by her children to two different buyers: The house had sold for less than $50,000 and the business had sold for $20,000! I was dumbstruck! In 2023, you could buy a house and business location for less than I signed for my house in early 2019.
This is one salient example of many I’ve run across. Sure, there are families that will hold their property on the market, put it on Zillow for years and hope for someone from New York will buy it for 250k or 350k, but ultimately, there is no clearinghouse price for properties in remote places off the internet. You should never, never, never be deterred by high prices. There are often people very desperate to sell as well.
What is the actual recipe for a good price for housing or land?
So how do you find a plot of land a little old lady or anyone else is willing to sell for cheap?
Consistency and the connections you make.
Consistency
People will sometimes be extremely judicious when choosing what bedsheets to buy, but will then go to one car lot once and pick make a decade’s long commitment to a car that is far more expensive than they want to pay for, just because they get tired out and want to go home.
When I knew I would need a new car soon (after 2020), I bookmarked a Craigslist search to my specifications and checked it once, maybe twice a day. I wanted a Toyota/Lexus or Honda/Acura (for durability), preferably with leather interiors (which hold up better used) and I certainly would not pay more than $5,000 for it. After months of seeing cars for 10k, 8k, 10k, 5k, 7k, 11k, etc., I eventually found a man selling a good condition Lexus ES 330 for only $1,900!
It was two hours away and took consistency of a month to catch, but when it saved me easily $7,000 versus the last identical one I saw in a shop, it was way worth my consistent twice daily checking of Craigslist.
It’s the same principle, even more so, when buying a house or land. With real estate, especially your consistency becomes about making connections.
Connections

If you want to live in a region or town, but haven’t found a good house, sometimes the best financial option is paying sometimes even hundreds or a couple thousand dollars to rent a place (or live free with a friend or relative) while you make connections at local businesses, churches and social areas which will unlock good places to buy that might be $100,000 or $200,000 cheaper than something else you might otherwise have bought.
You have to have a really high income for that to not be worth your time.
Some early subscribers might remember me doing just this in 2018. I did a livestream with a very poor internet connection from a small town near Sewannee, Tennessee while renting a place and making connections out there. Although there was nothing that really jumped out at me during that trip (it was briefer) it certainly was not a bad memory or waste of too much time or money. I did this in other places until I found something that worked.
You are just not going to see good deals on the internet.—You have to see them in real life.
The internet is more of a clearinghouse market, because people from all over the world can see and scoop up places in the middle of nowhere. But everywhere in the country, probably even larger cities, there are some people who are just desperate to sell, or maybe lazy or sensitive and would almost feel guilty for selling for “too much.” There are a lot of people that are really what we could call noble sellers.
Your Noble Seller
I’ve met a lot of old people, either without children or with uninterested children who have business and houses they plan to sell and aren’t even looking for a profit, they just love their house or place of business and want to see it well taken care of and to see it have a good future. Befriending a person like that is not only an honor, but makes financial sense, and you’re not going to do it online.
More than that, there are a lot of simple people that just don’t care to broadcast their property for the world to see and would rather just sell in person. The best is always a property that someone is “thinking about selling.”—No real estate agent, no complicated finances, just a quick exchange of money or a rent-to-own contract for a little tract of land, tiny home or house.
A lot of normal people in the country will often have random unused small tracts of land aside from where they live that they inherited and can’t monetize. They just pay property tax every year and would love to dump them on someone who could live there and get a homestead exemption for themselves.
But I can’t afford a house or land!
I couldn’t either, but I managed. Let me give you some hints, some of which I used, but others which I think are good.
For me, my only source of income throughout my 20’s was my assistantships from graduate school. They were annualized at maybe $35k a year, but not working for summer, I made closer to $20k a year, about half of which was room and board and necessities. By the end, I might be putting away only $10k a year in savings.1 Compared to most sensible people today, I was not able to put away a significant amount of money, but after a number of years, I was in striking distance of something—I just had to find that something.
On Spending and Saving
Firstly, even if you are poor or directionless, if you can save money and abstain from frivolous spending, you will make it. Especially if you are a single man, you have absolutely no business buying anything that isn’t necessary to keep you alive and (at least slightly) presentable.
The Plunge: Lock it in now!
On the other side, what is funny to me is when I run across an urban professional easily making north of $50,000 a year, or often over $100,000, who wants to move to the countryside or elsewhere and they are dragging their feet about moving to a place where they can’t work for the same amount.
I am not a pessimist on anything, but if you think it’s bad in housing now remember this: it will always be worse later! More people, more Blackrocks, more immigrants, more AirBnBs—All the more reason to make moves soon and not the next decade.
The price of land and real estate is more likely to increase at a faster rate than your salary. Once you have enough saved up to make a move, I would do it, move and pivot to remote or entrepreneurial work, even if abandoning a much better salary.
The Podcast gets a house…

- A group of geese is a gaggle.
- A group of fish is a school.
- A group of young men is a podcast.
If you can’t manage to buy land or a house, your “podcast” needs to by one. For every disciplined and goal-oriented friend of yours you have, you can slice another part of the price off a house.
A lot of people talking about “how hard it is to live now” might forget that in 1900 or 1800 or 500 B.C., people were always living many more in a house than people today. Especially if you are starting out, and maybe can’t commit to a location permanently, you have no reason not to assemble a reliable group of friends and jointly buy a property for use now and perhaps as an investment later.
The easiest way to make a $200,000 4 bed, 2 bath house only $50,000 is to have three friends. The reliability of your friends or relatives with you will affect how much this investment will be a learning experience, but if you make your pick judiciously, you can be “set for life” significantly quicker.
Comments on the Psychology of Debt
I was lucky enough not to need a mortgage to get my house. I agreed to a rent-to-own arrangement which almost amounts to the same thing (with more and less of some risks), but it was quick and over successfully in several years.
One of the cleanest feelings of my life was when I paid off my house. But on the same day, I logged on to both my savings and checking accounts and both read a big “$0.00.” I had needed to empty both of them to buy the house. I had never been more happy to be cash poor.
I will say it is psychologically superior to not get a mortgage to buy a primary home, but don’t be allergic to it if you have to. But I do recommend the “irrational” behavior of paying it off as soon as possible, faster than your agreement, even if you have a fine interest rate.
The poison pill of debt is you signing up for a mortgage and forgetting that you’re in debt. You have a monthly payment schedule and just feel safe when you meet it, forgetting you might be $300,000 underwater.
You have huge debts, but you might still spend like you don’t have huge debts. If you’re saving to buy a house in cash, you will tighten your belt and perhaps even pride yourself in frugal living. But if you get a mortgage on a house, you don’t have the same motivating feeling, even though you are just as poor, perhaps more so because of accumulating interest.
If you want to get loans to pay for other properties, rentals, etc. I will certainly not knock that as a possibility, but there the interest rate and repayment schedule is part of a very dry economic calculus you have to do on your investment.
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I never really maxed YouTube for money out of a combination of personal principle and a desire to build my life on a social media cycle I firmly oppose. But I will say, I remember it did encourage me to be a little more risky. In 2019, when I was about to pull the trigger on moving and didn’t even have job prospects, I did encourage myself that at the size of my audience then, if I did a video every day a month, I might be about to squeeze get 1k in revenue which would let me pay off the house and live. When I actually moved, I found other employment and let the channel sit mostly unused. ↩︎