What Snowboarding Can Teach Us About Real Estate Investing Strategy

by | BiggerPockets.com

It’s the right time of year for it, no? Well, for most parts of the country, it is definitely winter sports time—or at least winter sports temperature. Here in Los Angeles, not so much, as I was walking the beach in shorts and flip flops earlier. But my intent is not to rub in LA’s fantastic weather but rather to apply an analogy of winter season to real estate.

I’m going to compare basic snowboarding to backcountry snowboarding, and then I’m going to relate both of those to real estate investing. Why in the world would I do that, you ask? I’m doing it for two reasons: 1. I think it’s a great analogy for anyone wanting to get into real estate investing, so maybe it will help you with your journey, and 2. why not shake things up with a fun story and analogy rather than write something technical and stiff?

Don’t worry if you aren’t familiar with backcountry snowboarding. I’ll explain.

Put on your beanie and gloves and let’s do this! I’m going to start with the story of my first backcountry snowboarding experience.

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Backcountry Snowboarding

A couple years ago, I spent a few weeks in Colorado. My time there was quite amazing considering I think I saw more snow in those few weeks than I had in my whole life, having grown up in Georgia. While I was there, I made it known that I definitely wanted to go snowboarding. Some friends said, “Oh, you have to meet Cheryl! She goes snowboarding like four times a week before work.”

So I met Cheryl, and she told me what sounded like the absolute coolest thing I’d ever heard—she went to an abandoned ski resort right there in town to go snowboarding. All you have to say to me in a sentence is “abandoned” and “snowboarding,” and you’ve already won me over. I thought, “Snowboard an abandoned resort?! YES PLEASE.” I could think of nothing cooler. I did ask her though how one gets to the top of the mountain if there is no lift. She said we would walk up. I thought, “Awesome! Let’s do it.”

A little background, which is relevant for the analogy: I am very athletic, I’ve played multiple sports (rugby even), I go to the gym regularly, I love anything adventurous, and I am rarely pushed to my physical limits just because I can handle quite a bit, and I hike and snowboard as much as possible. With all that in mind, I thought this abandoned resort snowboard trip would be very doable.

For an entire week, I was excited for this adventure. I told everyone I would be boarding an abandoned resort and that it would most definitely be one of the coolest things I ever did.

Well, Cheryl picked me up, bringing what gear I didn’t have, and we made it to the base of the mountain. How cool! I was ecstatic. I loaded up on my layers of clothes, filled my backpack with water and a couple snacks, grabbed my board and walked to the snow. In the snow, Cheryl strapped my snowboard to my backpack after handing me a pair of snowshoes. Snowshoes, OK. I had never seen a pair of those in my life, but I was ready! Strap those puppies on. Last but not least, I was handed ski poles. I had never even held ski poles, and I secretly thought they were for sissies, but I was fine to humor them and go with it. Time to go!

To save space, I’m going to jump right to the conclusion of this story. I now deem backcountry snowboarding to be the most physically humbling experience of my life. While it all sounded fun in theory, theory flew out the window in less than about 15 minutes. Mind you, we were at 10,000 feet altitude. I live at sea level, and my lungs and cardiac system are acclimated as such. Then add to the high altitude a climb straight up about 1,000 feet. Then add to that climb 1-2 feet of fresh powder snow. Fresh powder snow is amazing, except when you are trying to hike uphill in it with snowshoes on. Snowshoes easily punch through the snow when it’s that fresh, which caused every step I took to be almost double what a normal step would take.

I’m not sure which to emphasize more—the time and muscle it took for every single step I had to take or how painful this was or how freakishly cold it was. I can’t tell you how many times I had to stop to catch my breath. The word “defibrillator” may have come out of my mouth a time or two. This wasn’t fun by any stretch. I had never felt such shooting pain in my Achilles tendons. But as I’m always up for a challenge and wanting to be in better shape, I kept on and persevered. I may have been half-wheezing, hunched over trying to save my ankle and calf muscles, and probably drooling (but too cold to know for sure), but I was making this happen. My entire body was numb from the cold . If you don’t believe me about being hunched over, check out this [actual]picture of me going up.

I finally got to where I could go no further. I had maxed out. I was nervous about whether or not my snowboarding skills were good enough to keep me out of the trees going down, but more so I was just excited that it was time to do the one thing I actually knew how to do—snowboard! The snowshoes came off, board went on, backpack was repacked, and it was time to go.

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I started sliding along, very excited for what was about to be the coolest snowboarding I’d ever done. To sum up my trip down: I’ve never fallen so many times, I was constantly seeing my life flash before my eyes when a tree was heading my way, and I couldn’t do anything about it because my toes were so frozen in my boots that I had lost all directional control. As if the multiple falls weren’t exhausting enough, every time I fell, it was in probably three feet of fresh powder, so I had to constantly try to crawl out with no grip and with a board attached to my foot. Do you know how hard it is to climb out of three feet of fresh powder, especially with a snowboard attached to your feet? But I kept on! I admit half of my motivation was because I was determined to not fail at this, but the other half of my motivation was that I was truly starting to think I could have frostbite on my feet, and if I didn’t hurry and make it to the bottom that I may lose a few toes.

All in all, backcountry snowboarding humbled me out in ways I had never been humbled before. I didn’t even get to enjoy the actual snowboarding part of it because I was so bogged down with the advanced challenges of everything else associated with this trip.

Traditional Snowboarding

Traditional snowboarding typically happens at a ski resort that has lifts to take you to the top of the mountain, featuring several different levels of runs, ranging from kids/beginner to mega-advanced. We’ll call this type of snowboarding “resort-style” snowboarding.

While resort-style snowboarding has significantly fewer challenges than backcountry snowboarding, it isn’t a piece of cake. Snowboarding is generally a tough sport to pick up. It takes even naturally athletic people a little bit of time to get adjusted to having a very slippery board attached to their feet, learning how to effectively work those edges. It’s no amateur sport! You still have to do some work to make it happen, you have to have a good bit of education not only on snowboarding itself but trying to figure out what to wear for different temperatures and environments, you have to spend money on good gear in order to avoid a miserable ride, and you will still oftentimes have to fight off cold and fatigue. No matter how good you are, you will still fall. You’ll fall an insane amount of times when you first get started, and then even as you get better you can still expect to plop yourself down occasionally. And just when you stop triggering your own self to fall, you never know when that beginner boarder behind you will completely run you over.

Once you go through the misery of trying to learn the sport though, embedding it into your muscle memory, and getting a lot of practice, you can generally go to the resorts and really enjoy your time and have fun snowboarding down the mountain. You can move to different levels of difficulty, you can change your routes, and you can of course enjoy a hot totty at the bar after.

Now let’s bring all of this full circle.

The Two Types of Snowboarding

Let’s review the two types of snowboarding I brought forward in this article. Backcountry snowboarding and resort-style snowboarding.

Backcountry snowboarding involves two things: snowboarding, and a handful of other challenges in conjunction with the snowboarding. Resort-style snowboarding involves one thing: snowboarding. Snowboarding by itself is no easy task, even for the most athletic. It takes some getting used to, a lot of falls, and at least a smidge of guts. Simply put—if it were that easy, everybody would do it.

On the simpler side of snowboarding, resort-style snowboarding involves just the basic attire, strapping your board on, and letting a ski lift take you to the top of the mountain, at which point you can then enjoy your ride down. You don’t have to dodge trees if you don’t want to, you have plenty of room to turn and carve, you aren’t carrying a lot of gear on your back, and once you get to the bottom, you can hop right back on the lift and get carried back up. Essentially, the primary focus of the excursion is one thing: the snowboarding. Nothing else.

The downside to resort-style snowboarding is it will cost you more money, and you will have some restrictions on what you can do with your snowboarding. But in exchange for those downsides, you get to experience a much easier and simpler means of enjoying snowboarding.

If, however, you prefer to save money and/or have greater and more rewarding adventures, you can go backcountry snowboarding! The trade-off to the money savings and the freedom with backcountry snowboarding is you have to take on added challenges to get there. You will need more gear than with resort-style snowboarding, you will have to be physically capable for quite a few things more than just the normal exertion of snowboarding, and you will need an entirely different skill set in addition to the regular snowboarding skill set. I would also say that you need significantly warmer socks.

There are a lot of backcountry snowboarders who have done it so much that they are naturals, and it doesn’t feel like extra effort for them. You can definitely get to that point, but it won’t be without practice, falls, and a lot of cold toes. The learning curve for backcountry can be severe—you’re not only having to do everything it takes to learn to normally snowboard, but then you are at the same time having to learn snowshoeing, high altitude hiking, cold toe prevention, and how to climb out of severe powder with a board attached. The snowboarding level itself is generally more advanced.

If you have never snowboarded, I can’t even imagine how it would be possible to learn to snowboard in a backcountry situation. Even if you could, your learning curve would be so much higher than at a resort that I don’t know how it couldn’t actually delay your success.

Because I’m a nerd, I drew this out for you.

See how the beginner level of backcountry snowboarding falls roughly between intermediate and advanced resort-style snowboarding? You can absolutely learn to snowboard backcountry, but it’s going to be significantly harder. You can eventually go further with backcountry boarding—skill-wise, adventure-wise, and in cost-savings—but generally it’s much more advanced.

If you are thinking of taking up snowboarding, you would want to look at both of these options and figure out where is best for you to start and what would be most conducive to your goals. Do you just want the ability to keep up with your friends on the slopes and aren’t trying to run the Ironman of snow and just want something enjoyable and fun to do on occasion? Then resort-style snowboarding might be more your jam. If you do want to become an Ironman of the snow, live in Colorado so you have easy access to backcountry terrain, and think lifts are for sissies, then backcountry may be your avenue of choice.

You want to be aware of what is out there and decide what is the best path for you. This decision will be based on your goals, skills, and interests. If you’re really slick, you would also consider what path would be most efficient to achieving your goals. Even if backcountry is your ultimate goal, you can certainly still start at the resorts with more-forgiving terrain to learn the basics before you take on all the additional challenges that come with backcountry. Learn the basics, get good at them, then slowly begin to add in the additional skill sets. Or dive right into the snowshoes, fresh powder, and the cold toes. Learning the hard way isn’t always horrible, but plan for it to be a rockier path to success.

Snowboarding and Real Estate Investing

Oh, right—this is a real estate investing article. I almost forgot. Don’t worry—I can sum this up very simply.

Real estate investing is a lot like snowboarding. There is literally every variation of difficulty, challenge, risk, cost, benefit, ease, and headache that you could ask for. There is the option to go the resort-style route or the backcountry route.

My investing career has always stuck with resort-style investing. I invest because I want investments, not because I want investing to become a job for me or to add challenge to my life or even to make my toes cold if they don’t have to be. However, even going just the resort-style investing route brought its challenges for quite a while. There’s a ton to learn with real estate investing! Even without the more advanced stuff, I still had to learn a significant amount of basics—numbers, market fundamentals, due diligence, property manager management, and investor psychology. That’s all just the minimal required info you need to know as an investor! It’s the equivalent of balance, edges, carving, and braking in snowboarding—on top of just being able to stand up on your board. Snowboarding is hard at its most basic level, as is real estate investing.

If I were to go the backcountry-equivalent route for investing, I would take on things like negotiating, rehabbing, landlording, and owning cheap properties with bad tenants. Having any of those things as part of your investing strategy isn’t wrong, as taking those on can lead to greater skills, more rewards, and a lot of cost-savings, but do you want to take on those things? Some people love them and are great at them, and I think they should definitely go this route. Still, I think there are some people who should absolutely background snowboard every day before work like Cheryl does. But if you are like me and live at sea level, have never put on snowshoes, and aren’t at the most advanced level of snowboarding, do you really want to put yourself in the backcountry position of investing? Maybe you do want to get to that point, but maybe it would be more efficient to your learning curve to start at the resort and learn all the skills of basic snowboarding and then move on to conquer the advanced skills of “backcountry” investing.

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I see so many people immediately strap on the snowshoes and go screaming up the 1,000-foot climb in fresh powder at 10,000 feet—just like I did the first time backcountry snowboarding. I couldn’t even function in the actual snowboarding part of the excursion because I was so bogged down with the advanced concepts of backcountry. I see so many people fail at real estate investing because they took on those advanced challenges before they had the proper level of basic snowboarding under their belts.

Keep in mind, these fluctuate with different levels of real estate investing as you go along. Shoot for the stars all you want, but don’t be naïve to the fact that very few people can just strap on the snowshoes and conquer all of the backcountry challenges and succeed all the way down the hill. My recommendation? Build your skill set in increments. Start with the bunny slope at the resort, build your snowboarding skills there, at some point, once you have a good handle on it at the resort, start introducing backcountry concepts and try that out—if you even want to! There is absolutely nothing wrong with staying at the resorts for snowboarding and never going backcountry. I’ve never gone backcountry with my investing, and I’m perfectly content with that.

Now, go book yourself a trip to a lovely ski resort and strap on your snowboard! And choose the appropriate run for your skill level.

Which route are you choosing to go on your investing journey?

Comment below!

About Author

Ali Boone

Ali Boone is a lifestyle entrepreneur, business consultant, and real estate investor. Ali left her corporate job as an Aerospace Engineer to follow her passion for being her own boss and creating true lifestyle design. 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 towards 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. She’s written nearly 200 articles for BiggerPockets and has been featured in Fox Business, The Motley Fool, and Personal Real Estate Investor Magazine. She still owns her first turnkey rental properties and is a co-owner and the landlord of property local to her in Venice Beach.


  1. Kimberly H.

    As a skier myself, I am surprised to read an article about backcountry riding with no mention of avalanche detection, equipment, avoidance, etc. Backcounty means no resort to do avalanche control. All those people dying every year in avalanches in Colorado occur out-of-bounds aka backcountry. That, and the fact there is no ski patrol, unmarked cliffs, etc. are the biggest differences in risk between backcountry riding and resort riding.

  2. Ali Boone

    Good call, Kimberly! All huge risk factors, and all should be considered “advanced” issues with backcountry. Even more depth to the dangers of going at things on your own…all doable, but all added risk to going at things on your own and potentially without preparation!

  3. Ricardo G D'Alessandro on

    I loved this article and the metaphore, Ali !!!!

    Having gone backcountry snowboarding a couple of times myself… I can confidently say I much rather stick to my ski lifts, groomed trails and terrain parks. Maximize what I enjoy doing and minimize the work I do not enjoy doing and the risks I don’t enjoy taking on.

    Thanks for the read!

    • Ali Boone

      Hey Ricardo! Meeeee tooo. I figure I can get just enough adrenaline-excitement if I just pick up enough speed. No need to take on life-threatening advanced stuff, or destroy my Achilles tendons, for a little extra excitement. But I will say, I watched some experienced backcountry-ers fly up and down that mountain so fast it was like easy breezy for them! So clearly some people should definitely do it. I, however, am not one of them 🙂

      Good to hear from you!

  4. John Murray

    Like anything extreme preparation is critical. Changing conditions, windslab, wet snow and other dangerous condition can spell certain failure. Powder at 15F is perfect, hop aboard the bird and enjoy your ride up and down, RI is all about preparation, changing conditions and adapting to those will mean the difference between failure and success. My most epic moments were hopping out of the bird and 6K vertical, taking off at Pipeline on the 3rd reef and of course completing a project and making bank. Is not life the most exciting thing that a human can experience.

  5. Jay Rhodes

    Hi Ali,

    I love this article, because as I started looking into real estate investing just a few months ago, this was precisely the exact same metaphor that I used myself. I’m an avid snowboarder both on the resort and in the backcountry (most of my days were in the backcountry last year), and understanding the learning curve of snowboarding has helped me strategize my journey into real estate investing. Simply, I realized that some of the topics that I stumbled on as I started my search were in complex, multi-faceted strategies (finding deals well below market, fixing up rehabs, moving over to conventional loans after), and are great, but were much more complex than finding deals with experienced agents that have moderate, but good cash flow and are basically rent-ready. To me, it was the difference between shredding blue runs (where 90% of the people are) to shredding hike-to terrain (un-groomed, steep, but better snow and more challenging terrain) (5%), to backcountry (less than 1%). With this analogy I strategized to start with a “blue run, resort” property” and then following that seek out both additional blue, and then black run, or hike-to properties following. In a few years, I’d like to become the true backcountry level investor. I think the most important part aspect of this metaphor is recognizing that there is a learning curve to both, and understanding where you currently fall within that learning curve. And, recognizing where you most enjoy the experience, which may be on the sunny, resort days with long lunch breaks on the deck, or pursuing challenging peaks several hours away from the car, only accessible via human power.

    This article could not have resonated more with both of my current passions in life (one that is 20 years old, and the other 3 months old), so thank you for posting.

    • Ali Boone

      Hey Jay! Thanks for much for writing all of this, and I wish I could add it as like a summary or part 2 of my article 🙂 So glad it resonated with you… I admit I was a little hesitant to post it because it seemed like a bit of a stretch to put on an REI site and might irritate people (at the least the ones who only want technical how-to’s). I have no doubt you’ll become a backcountry investor in no time!!

      And don’t forget…even if someone decides to stay on the resort blues where most people want to be, there’s always the option of going on Tuesday versus the weekend for added enjoyment and less crowds 😉 (I may or may not have done that last week skiing. haha)

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