How’d I get started with real estate?

In 2015 my friend convinced me to come visit his new ski condo in Colorado for a 10 day ski trip even though I’d never skied before. I loved both skiing and the Rocky Mountains immediately, by the end of the trip I made two predictions to the group: (1) Within two years I would move to Colorado and (2) Within two months I’d own my own ski condo in the same area. Both came true.

My friend introduced me to the realtor he had used on his ski condo and I walked a couple properties at different price points with her. I had no concept of “cashflow” in these days but prices were still depressed from the housing crash and I thought it would appreciate nicely over time. I also loved the idea, it was way more interesting to own a ski condo than a bunch of stock ETFs. I proceeded unsuccessfully offer on a couple properties, I didn’t get them but at least my realtor knew I was serious and not just a window shopper.

Finally the perfect property appeared!


This was a recently renovated condo, fully furnished, with a hot tub 15 seconds down the hall, priced in the bottom 10% of the market, in an excellent location in walking distance to every bar/restaurant/shop in town. Most importantly, I’d be able to have a place to stay in CO whenever I wanted to ski! The only catch was that I had to act fast, my realtor explained all of this to me in 10 minutes after waking me up at 6am and told me that if I didn’t have an offer in before 8am it would be listed on the MLS and I’d end up losing it in a bidding war.

Pictures weren’t available until the listing would go up, and I was told I shouldn’t wait that long. I had never owned property and I was 1,000 miles away – my realtor convinced me that this was low risk and that I should offer higher than the asking price. I was skeptical but after she explained that worst case I lose my earnest money I took the plunge. I offered above ask (with seller paid closing costs) within 30 minutes of that phone call and the sellers who were going through financial difficulty accepted on the spot.

I later learned that this was called a “pocket listing”

Fast forward two years and this ~$40k investment had already generated a higher return than any stock I’d ever bought. The property increased in value by $70k within two years and I was breaking even on my mortgage + all expenses including professional property management, HOAs, taxes, and insurance even while I used it a few weekends a year to go skiing myself. This meant that I was making ~$3k/yr just on mortgage paydown and I believed that rents and home values would only continue to increase in this area (both have been true). On top of all of this, I was actually able to report this as a loss on my taxes due to a wonderful thing called “depreciation”.

That was where I really got hooked. The idea that not only could I double the value of my investment while getting others to paydown the mortgage on a property in my favorite vacation place but I was paying negative taxes on this investment. I realized pretty quickly that this was a MUCH better investment than stocks when leverage and tax implications were taken into consideration.

I started to read everything I could about real estate. I learned what cashflow was, and why it mattered more than appreciation. I remember a friend’s dad saying about my ski condo that he used to own a 4-unit that had only studios and he wished he could buy more just like it – I thought the idea sounded crazy at the time. I thought “Well gee, I’d also love to own a full building of ski condos” but I wasn’t rich. Eventually I realized that while I couldn’t afford an apartment building in that area, I could in other areas of the country. As soon as that started to click, the rest of my real estate journey started to unfold.

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