We were lucky to catch up with Jake Huddelston recently and have shared our conversation below.
Jake, looking forward to hearing all of your stories today. Let’s start with the story of your mission. What should we know?
It’s hard to say that we are truly a mission driven company, because we aren’t out fighting global hunger or finding homes for lost puppies. However, I can tell you more about why I care deeply about what we do and why I do it.
Land investing, and more broadly real estate investing can feel like not only a lonely endeavor at times, but a selfish one. Our whole premise is based on finding an opportunity, and a lot of investors, my past self included, rely solely on people opportunities. These are finding people in tough situations where they need to quickly dispose of a property due to some unfortunate life circumstance. In exchange for a quick payout and way out of a normally illiquid asset (land), there is enough room left in the deal for an investor to throw some nice marketing behind the property, do a little clean up, and make a healthy profit.
There is nothing inherently wrong about the above business model, however, we have steered our business in recent years is more in what I call property opportunities. I’m looking for properties that have inherent issues like death on a deed, back taxes, landlocked property, or maybe they need driveways cut in and utilities brought to the site. I’m looking for how I can give the seller a fair deal that we both feel good about, and something I can then go and add more value to for the end buyer. That’s what I truly enjoy and why we do what we do.
We believe in helping both buyers and sellers of land. Buyers through becoming a partner with them in solving issues that seemed unworkable before we got involved. And sellers through providing high-quality land assets that they can fulfill their dreams of building, hunting, and creating memories with their family and friends for years to come. That’s what we truly enjoy doing.
Lastly, through being a real estate investor, I’m able to live a life with a very high level of autonomy which was always really important to me. I can work from home or from the mountains. I can work in the wee hours of the morning and even take off mid week to go golfing with a friend. It’s allowed me so much more time and flexibility in my day-to-day that I can’t imagine doing anything else. I feel extremely blessed that I get to work from anywhere, next to my wife, our family dog, and our soon to be baby boy. That’s the real reason behind why I do what I do. My mission, if you will.


As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I left my first job out of college to start an all-natural supplement company and take over the world! It was straight of the “follow your passion” movement and I thought I was headed for big things. We landed some big name retail locations and even opened our own gym.
It was a crash course in all things business: marketing, advertising, customer & vendor relations, inventory management, order workflow, social media, project management, finances, taxes… you name it. I loved it, but things didn’t work out like I hoped.
4 years later I was down to my last physical $3.17, plus about $30,000 in debt. I had to move back in with my parents and figure a way out of my failed businesses. At one time I was even buying groceries with only my spare change. It was a real hit to the ego more than anything else.
I had to leave that business and let it go. In order to get back on my own two feet, I had to do what no entrepreneur wants to… get a job.
Enter: Medical device sales.
It got me out of a hole financially, out of my parents house, gained more new skills than I can count, and even met my wife along the way. These were some of the longest and hardest days of my life, but I’m forever grateful for the opportunity and where it landed me.
Prior to this in 2017, I met a friend who introduced me to the world of land investing. I wasn’t quite ready at the time to go all in, but started investing small while working my job.
After 4 years of living a double life and growing my land business substantially, I was able to walk away from my sales job and live my dream as a full-time land investor.
Today I’m still living my dream. I get to buy and sell land across the nation, having worked in 13 different states, totaling over 2,100 acres, with ~ $4 million in equity created. I’ve been able to build a sizable portfolio of mortgages that we continue to build on. And most importantly, I get to work from anywhere, next to my wife, and I haven’t had to go back and get a job yet! Fingers crossed…


Can you open up about how you funded your business?
I initially started buying and selling land through purchasing properties that had been to the foreclosure auction for back taxes, yet had not sold at auction. The various counties in Arkansas now owned these properties and were willing to negotiate on the purchase price. Many of these were purchased for as little as $50.
I would then turn around and resell those properties on eBay or Facebook Marketplace for anywhere between $100-$1,000. Not massive returns, but every little bit counts.
This gave me the practice in buying and selling land, talking to buyers, and learning the anatomy of the transaction,. It also enabled me to build up a small buyer’s list and lended me credibility with future customers, because now I could say I had done a couple dozen deals.
Eventually, once I lined out a better business blueprint, I liquidated a rental property I had purchased when I was just out of college. This netted me around $30,000 which was the seed money I utilized to start up my actual land investing business, allowing me to send my first direct mail campaign targeted at motivated sellers and where I found my first few “larger” deals. I say “larger” because it’s all relative on where you are currently.


Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
I’ve purchased hundreds of properties, thousands of acres, without ever stepping foot on the land. Nearly everything I do is behind the computer and through the phone. That’s an amazing testament to where we are as a society. And that’s exactly what I thought I wanted, was to be able to work remotely, autonomously, and mainly solo.
However, looking back at not only my biggest and best deals, but also some of the most meaningful relationships in my life – they happened in real life.
Some of the best deals I’ve done are the ones I did not do, because I got out on the ground and saw the potential disaster through the eyes of a buyer. Maybe there was a few smelly oil pump jacks, or one end of the property held so much water that you couldn’t even reach that area, or there’s been a locked gate or even some boundary dispute. All these things I can’t see from behind my screen and I wouldn’t know about without getting on the ground and touching the land before purchasing. I don’t always do this and you can always send a trusted team member, but it’s also one of my favorite things to do when I can.
Additionally, when I look back at how I even got into land investing, it was through meeting someone at a local REI meet up. When I met my first business partner, it was at my local gym. I was recommended for a job through a friend I met at church. And even though I met my wife on a dating app, it wasn’t until we met in person for that first date that things really took off.
All this to say, we all have a tendency to want to analyze everything behind a screen, to email rather than call, to stay at home rather than go out and meet new people. And what I’ve realized, is that the best things really do happen when you’re out in the world, interacting with it.
Contact Info:
- Website: https://www.huddelston.com
- Instagram: @alljakenobrakes
- Facebook: https://www.facebook.com/jakehuddelston
- Linkedin: https://www.linkedin.com/in/jakehuddelston/
- Youtube: https://www.youtube.com/@alljakenobrakes
- Other: I do have a personal Instagram @jakehuddelston that is private. I’m about to start posting some of my daily life and business content to my newer Instagram, TikTok, and Youtube @alljakenobrakes. More coming soon!


Image Credits
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