Snowboarding is JUST Like Real Estate Investing: Here’s How

Snowboarding is JUST Like Real Estate Investing: Here’s How

11 min read
Ali Boone

Ali Boone is a lifestyle entrepreneur, business consultant, and real estate investor, who has literally defined non-conformity when it comes to her career. Ali left her corporate 9-to-5 job as an Aerospace Engineer—despite the “dream job” status that came with it—to follow her passion for being her own boss and truly designing her lifestyle. She did this through real estate investing.

Using primarily creative financing to purchase five properties in her first 18 months of investing, Ali’s real estate portfolio started with pre-construction investments in Nicaragua and then moved toward turnkey rental properties in various markets throughout the U.S. With this success, she went on to create her company Hipster Investments, which focuses on turnkey rental properties and offers hands-on support for new investors and those going through the investing process.

Ali’s written roughly 190 articles for BiggerPockets and she’s been featured in FOX Business, The Motley Fool, and Personal Real Estate Investor magazine. She has over 300K views on her “Calculating Rental Property Numbers” video on YouTube, has sold over 200 copies of her Turnkey Rental Properties 101 eBook, and was awarded Top 100 Real Estate Investing Blogs & Websites. Her articles teach successful rental property fundamentals, investor psychology, and strategies to help get new investors started.

She still owns her first turnkey rental properties and she is also a co-owner and the landlord of a local property to her in Venice Beach.

In addition to running Hipster Investments and working as an active business consultant, she’s a pilot and teaches flying. She can often be found snowboarding, hiking, or volunteering in California prisons. Her ultimate goal is to one day challenge Tim Ferriss to a lifestyle design duel.

Ali has two master’s degrees: a master’s in Aerospace Engineering from Georgia Tech and a master’s in Spiritual Psychology from the University of Santa Monica. Her undergraduate degree is a bachelor’s in Aerospace from Middle Tennessee State University.

Hipster Investments on Facebook
Instagram & Twitter: @HipsterInvest or @aliboonedotcom

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Real estate investing is just like snowboarding. Wait, don’t stop reading if you don’t snowboard; you’ll still be able to follow along, I promise.

I love this time of year because my anticipations about getting back into snowboarding are getting stronger by the day (although obviously not strong enough because I haven’t driven out to the perfectly snowy slopes yet). As I was pondering my upcoming snowboarding season, I flashed back to last year, which was the first time I ever went backcountry snowboarding.

I remember when I did that how I almost immediately started thinking about how I could relate backcountry snowboarding to real estate investing (nerdy, I know). I even started to write my conclusions into a blog last year, but I was still so emotionally invested in the experience that the blog was about five pages long by the time I finished telling the story. You would have been snoring halfway through! So now I’m back, less emotionally tied to the story, and I can give you the quick and dirty about how I now relate snowboarding to real estate investing.

Hear me out…

Snowboarding Explained

This section is going to help you out if you fall into either the category of 1. never snowboarded at all, or 2. never backcountry snowboarded. I was in the latter category until last year. Even though I snowboard quite often, I had no idea the logistics of backcountry. Also, I am using snowboarding because that is what I do. I can’t speak exactly for backcountry skiing but I’m sure it is very similar to backcountry snowboarding, so feel free to interchange snowboarding for skiing if that is more applicable for you.

Okay, here we go. Typical snowboarding procedures:


This is just your basic snowboarding.


You go to a ski resort, you buy a lift ticket, you lock in one of your feet to your board, you scoot across the snow to the lift, you ride the lift to the top of the mountain, and you snowboard on down (with a huge frozen grin on your face). The only equipment needed is your board, which is attached to your feet with bindings, and that’s it. That’s the whole process, minus the technicalities of how one actually snowboards successfully.


$50-110 for lift tickets, depending on what slopes you are on.

Backcountry Snowboarding

Oh man, where do I even start? For the record, when the opportunity was presented to me to go backcountry snowboarding, there was not one mention of the reality of how this all works. All I heard was that there was an abandoned ski resort (in Estes Park, Colorado, for anyone interested) and people go boarding down it. Woohoo! I was in! Abandoned anything, and a ski resort no less? Sign me up.


First, you pack a backpack with all your necessary gear. Who knows what that even is? Then you attach your board to the outside of your backpack. What? Well, you have to carry it somehow, and your hands are too busy using ski poles, which, until that day I thought were essentially sissy-sticks. So your overly long board is now sticking out of your heavy backpack, and you put all of that on your back. Okay, got it. Then, you strap into snow shoes. Snow what? I didn’t even know these existed.

Related: Real Estate Investing is Just like Surfing

You are now harnessed into these long, wide, bright orange platforms that you walk through the snow with. They aren’t awkward at all {insert eyebrow-raised face here}. Then you are handed the sissy-sticks. You now have your sticks, your bright-orange huge footies, your board creeping out from behind your back hitting you in the head, and a look of concern on your face. But! No problem, you’re an athlete and hello, this is an abandoned ski resort! Doesn’t get better than this for cool points and Instagram.

Now, it’s time to start up the mountain. I have no idea why I didn’t think further into this when it was initially proposed to me, but here we went. You start walking. It’s kind of flat at first, no biggie (a little weird with your big orange shoes, but whatevs). Then you get to the part where the uphill starts. Remember, you are walking directly up to the top of a ski mountain, so it’s decently steep — steeper than you probably realize from your normal boarding or skiing because you go side-to-side going down the mountain (unless you’re a downhill skier with a death wish).

Now you are walking straight up. Straight…up. Well, something else happens as you climb the mountain that you probably hadn’t thought of. The higher up the mountain, the fresher the powder gets. What happens then? Well each time you put one of those big orange snow shoes down into the snow, it goes about an extra 3-5” in than if you were walking on packed snow. The problem? If your foot goes in an extra 3-5”, you have to pull it back out an extra 3-5”. Let me tell you about some snow shoes, 3-5”, and some Achilles tendons!

In my case, we walked a solid 1,000’ up the mountain. It’s not totally relevant, but I think worth noting is that I live at sea level, and this 1,000’ straight-up climb through fresh powder in snow shoes was happening around 10,000’ in altitude. I THOUGHT I WAS GOING TO DIE. Or my lungs were going to collapse, or… all I know is that is the first time I’ve ever used caps in a blog I’ve written. It was that severe.

Here’s proof this really happened:

Picture1 (1)


Back to the point: so, you walk straight up the mountain, in your snow shoes, with your snowboard hitting you in the head and your Achilles tendons ripping apart thread-by-thread, and then you are at the top (or in my case, your lungs can’t make it to the top, so you stop short).

Now, and only now, is it time to snowboard. Despite your hands being frozen to the point you can’t feel anything you touch, even though you were wearing gloves, you start unstrapping your snow shoes, breaking down your ski poles, and taking your board off your back. Then, in a last-ditch effort to use what is barely left of your hands, you strap into your board, shove the rest of your stuff into your backpack, and you’re ready to go.

Then, you begin snowboarding. But be aware, this is backcountry. These runs aren’t groomed. You have to dodge trees, weeds, streams (no idea how those weren’t frozen), big piles of dangerously deep powder, and watch out for tight turns (at which I’m not always skilled since I am not a double-black diamond level snowboarder yet). Meanwhile, your toes are completely frozen, so you really can’t control the snowboard.



Snowboarding & Real Estate Investing

Let’s look at the snowboarding. If you want to go snowboarding, there are two ways to do it:

  1. You can go the more expensive route, but have all of the work except the actual snowboarding professionally done for you, or
  2. You can go the cheaper (free) route, but you have to do all of the work yourself in order to be able to go snowboarding.

Both methods are amazingly fun and accomplishing, and neither method is wrong or bad — they are just different methods of snowboarding. There may be people out there who don’t have a preference for one over the other and enjoy both methods equally. There are other people out there who gawk at the thought of using a lift to climb the mountain and others (me) who gawk at the thought of doing all that work to the get to the top. No matter which preference someone has, they are all great!

But let’s do one more quick breakdown/understanding of these two methods:

Basic snowboarding, using the lifts to get to the top, is just about the snowboarding.

The only thing you do during that excursion is snowboard (other than scoot yourself to the lift). So the only thing you have to know how to do (other than know how to scoot yourself to the lift and get off of the lift) is know how to snowboard. For anyone who snowboards or has tried snowboarding, it’s not a quick thing to pick up. It takes most people more than one or a few solid days of falling all over the place to even be able to stand up on your board the whole way down the slope. It’s definitely not like riding a bicycle.

Even once you get the basics, and can stand up for longer than about three minutes, it takes an inordinate amount of time to continue building on the basics and getting the techniques into your muscle memory. Snowboarding isn’t easy, but at least with the lifts, you can focus solely just on improving your boarding skills.

Backcountry snowboarding, in reality (at least for beginners), isn’t as much about snowboarding.

In thinking of my backcountry snowboarding excursion, I would say maybe 15% of the whole thing was about the snowboarding. It was primarily about hiking up that stupid mountain. Time-wise, it probably took me over an hour to get to the top of the mountain and about 15 minutes to get down it (and it only took that long because I kept falling in deep powder and having to crawl myself out, so in reality the actual snowboarding maybe lasted 4 minutes).

When it was time to actually snowboard, I couldn’t even focus on the snowboarding because I was so overwhelmed with what had just happened on the trek up! Never mind that I couldn’t even feel my toes, so I had absolutely no directional control on my board for the trip down. So, in my opinion, backcountry snowboarding has very little to do with actual snowboarding — and everything to do with the work to get up the mountain.

Of course, once you get better at backcountry, you won’t experience the trauma I did, and you will get up the mountain much faster; your toes won’t be frozen, you will be able to snowboard successfully (with directional control) down the mountain, and you will enjoy it much more than I did. But it takes a while to get to that point, so you do have to be ready to learn it and get accustomed to it.

Once you get more advanced with backcountry, you can also do a lot of things to make it easier for you. You can use a splitboard instead of a snowboard, which means your board actually serves as your snow shoes, and then you just clamp them together when you are ready to go down the hill and it’s back to a normal snowboard (less to carry, easier to walk through snow, and you don’t have to deal with bindings). Your lungs will also acclimate to the altitude, and your Achilles tendons will have gotten really sturdy. But to get to the point of backcountry snowboarding becoming easy, it takes a while and involves a lot of pain and falling. And don’t forget — this is all on top of learning the fundamentals of just straight snowboarding, which in and of itself is a tough feat.

Oh wait, the header of this section said snowboarding and real estate investing! Have you figured out yet how I might relate these two snowboarding options to buying real estate investments? I’m going to use the exact same format I just talked about snowboarding with and talk about real estate investing.

If you want to invest in real estate (let’s think rental properties to keep it simple), there are two ways to do it:

  1. You can go the more expensive route, but have all of the work except the actual owning of the property professionally done for you, or
  2. You can go the cheaper (free) route, but you have to do all of the work yourself in order to own the property.

Both methods are very rewarding, very financially smart, and neither method is wrong or bad — they are just different methods of buying properties. There may be people out there who don’t have a preference for one over the other and enjoy both methods equally. There are other people out there who gawk at the thought of not doing all the work themselves on their properties and others (me) who gawk at the thought of doing all that work to buy a property. No matter which preference someone has, they are all great!

But let’s do one more quick breakdown/understanding of these two methods:

Buying a rent-ready and performing property, and not forcing yourself to do all the hard work to get the property, is just about investing.

The only thing you have to know how to do is how to properly buy and own an investment property. It’s not a quick thing to pick up. It takes most people quite a bit of time to learn these fundamentals and put them into play. It’s definitely not like riding a bicycle.

Even once you get the basics and have started in on buying properties, it takes an inordinate amount of time to continue building on the basics, fail (a.k.a. fall) at least a couple times and have to pick yourself back up, and really hone in on how to do it right.

Buying do-it-yourself properties (finding motivated sellers, rehabbing, landlording…) isn’t as much about investing.

Investing is the driving premise behind the whole thing (as snowboarding is to backcountry snowboarding), but it the focus becomes primarily about all of the work it takes to make a rental property ready and performing. Finding motivated sellers — how long does that take to learn and to succeed? Rehabbing a property — how on earth do you learn that? And then landlording?

Related: Real Estate Investing Like a Game of Blackjack

Those are all great thing to know how to do, but they all take a crazy amount of time to learn and to do correctly. While you are focused on those things, you aren’t even focused on the fundamentals of investing and what makes for a good investment property. Hopefully, you have already learned the fundamentals prior to taking on this kind of work! Otherwise, you now have to learn the fundamentals, rehabbing, landlording — all of those things at once.

And trust me, that will make you feel like you are at 10,000’ altitude! Not one of those tasks is easy to learn, and now you’ve just taken on a handful of them at once.

Performing Properties vs. DIY Properties

Of course, as with backcountry snowboarding, you can get extremely good at do-it-yourself real estate investing. There are ways to make the processes smoother — you can get very fast with it and become very profitable. But if you haven’t started along that path yet, just realize what you are getting into. Don’t be like me and not realize how painful the process is for inexperienced people until you are halfway up the mountain. Halfway up the mountain, in terms of investing, could mean a lot of money at risk.

In terms of how to go about buying fully performing properties versus do-it-yourself properties, I can tell you all day long that I only buy turnkey properties (meaning, everything is already professionally done and in place for you), but that isn’t the only way to find performing properties. You can build individual teams to find these properties and go various routes with that concept in mind. So the latter may seem a little more do-it-yourself, but what I am really referring to by using the do-it-yourself term is taking everything on yourself, rather than using team members to help you.

Of course, you may still use a contractor for a rehab, but essentially you are managing all of the moving parts of the purchase of a non-performing property and having to get it to performing status. While going that route may seem cheaper, you are also taking on a lot more risk, you may very well experience unexpected costs which will suddenly make it not a cheaper option, and the time required to do everything can be extensive, which can be exhausting and costly (things like not having tenants in place and paying rent, holding costs on construction loans, utilities, etc.).

So there are of course variations of both of these methods, ranging from zero work (turnkeys) to extreme amounts of work (full rehabs), but thinking of the extreme sides helps demonstrate the point and hopefully puts reality more into perspective.

Clearly, I’m a lazy snowboarder and investor (but I still do both very well!). How about you? Which methods of each do you prefer?

Let’s talk winter sports and investing in the comments below!