As I committed to running the daunting 17.1-mile Imogene Pass Run, a rugged mountain course connecting Ouray, CO, to Telluride, CO, I never expected that it would become a masterclass in the fundamentals of being a savvy real estate investor. Yet, the striking parallels between conquering a 13,411-foot mountain pass and venturing into passive real estate turned out to be astonishingly similar.

Over the past six months of training for this epic run, I’ve uncovered priceless lessons in decision-making, thorough research, dedicated training, taking action, and, above all, adapting to unforeseen challenges. Let’s dive into these lessons and explore how summiting the pass mirrors mastering the world of real estate investment.

Five Lessons Learned

Commitment: Just as I committed to registering for the Imogene Pass Run—a process as competitive as the race itself—diving into real estate requires an equally resolute step. I’m not exactly an early riser, so waking up at 5:55 a.m. on registration day was a personal challenge. But if I wanted to secure my spot, I had to make it happen since registration closes in under 15 minutes. This mirrors the world of real estate, where there’s never a “perfect time” to start investing, and there are a wealth of unknowns to navigate. To turn your dreams into reality, you must summon the courage to take that first leap, doing what others won’t.

Research Your Path: Like my race preparation, merely studying the 17.1-mile course map with its 5,400+ feet of elevation gain in ten miles and a steep 4,500-foot, 7.1-mile descent wouldn’t suffice. I needed real-world knowledge of the course. I needed to find people who had not only run the course but completed it. Similarly, in real estate, online research is crucial groundwork, but the true gems of insight come from connecting with seasoned investors. Their experiences serve as a guiding light in navigating the complexities of the market.

Train For Your Event: With limited experience in an endurance event like this, I knew I had to break down my training into manageable chunks and then piece it all together on race day. For example, I’d tackle 5 miles of uphill running, then 2.5 miles of run/speed hiking, followed by 2.5 miles of a steep high peak grind in an exhausted state, and finally, 7.1 miles of downhill, with the first 1.5 miles being the riskiest due to terrain and exhaustion. Investing shares a similar pattern. You start with some knowledge and experience, but you must uncover what you don’t know, fill in the gaps, and connect the dots with every investment. Rarely do you have all the knowledge or data before you.

Just Do It: As the starting gun fired on race day in Ouray, and 1,637 of my fellow runners took off for the mountain pass, I realized that all the training had merely been preparation. Now, I had to run it! Similarly, meticulous planning and research can only take you so far in real estate. The real learning occurs when you vet the operator, market, and deal and actually invest. Tangible experience surpasses any amount of preparation.

Repeat and Optimize: After conquering the pass (all 13,114 feet of it!), I discovered the importance of continuous improvement. Though I completed the race within my anticipated five-hour mark, I knew that the real growth came from confronting unforeseen challenges on the terrain. I couldn’t help but think about optimizing my training runs to be better prepared, reworking my gear to trim precious weight, and shaving off critical minutes at aid stations next year. Like the world of real estate, adaptability is paramount. Market shifts, tenant dynamics, and unexpected expenses demand a willingness to refine and adapt your investment strategy and optimize your portfolio.

Wrapping Up

Summiting the Imogene Pass wasn’t just about conquering a physical challenge; it was an enlightening journey in mastering the art of adaptation (and yes, I am running again next year if you’d like to join me!). 

Surprisingly, these lessons translated seamlessly into the realm of real estate investment. This adventure taught me that there’s never a “perfect time” to start investing. There will always be a myriad of reasons to delay building and scaling your portfolio—work, travel, kids, illness, inflation, market volatility—you name it! But with determination, research, consistent and persistent action, and a readiness to adapt, success becomes not just possible but inevitable.

So, don’t wait for others—chart your own path and chase your dreams.