Today we’d like to introduce you to Jake Rockwell.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I grew up middle-class in Eastern Oregon, and from a really young age, I was completely driven by making money to buy the things I wanted. I was a natural hustler—shoveling snow, mowing lawns, and going door-to-door selling The Oregonian and greeting cards. By 14, I was doing manual labor for my dad’s carpet cleaning and fire restoration business. Around that time, I boldly told my mom that I was going to be a millionaire. I carried that hunger through high school in Bend, working as a dishwasher, a pizza parlor hand, and at the Sunriver golf course. I eventually landed some loans and grants to go to Southern Oregon University. I majorly focused on business administration and marketing with an economics minor, and even though I partied pretty hard in college, all I ever truly dreamed about was building my own business and working for myself.
Right out of college, I climbed the ranks quickly in the management training program at Enterprise Rent-A-Car, getting promoted to assistant manager within a year. It was a great salary, but I was still hungry for my own thing, constantly combing the classifieds. That’s when I saw an ad for a brewery for sale for $50k. It was a failing startup doing a pathetic $5,000 a month in gross sales—a massive red flag—but my manager at Enterprise and I decided to take a leap of faith. We scraped together $10,000 each from friends and family, put $8,000 down, and the seller carried the note. We walked away from $30k+ salaries to pay ourselves $800 a month, living on free beer and pretzels. We literally built the business by bowing to every person who walked through the door and shifting the hours to hit the evening sweet spot. We put our hearts and souls into it, started booking live music and food specials, and turned “The Osprey” into one of the hottest spots in Southern Oregon.
After we sold the brewery, I saw a friend go from rags to riches in e-commerce and decided to pivot. From 2004 to 2007, I launched a unique pet products website and an online billiards company called RockwellBilliards.com right out of my house. At one point, my three-car garage was completely overflowing with product—I’ve got a great story about buying pool table lights from Lowe’s that we’ll get into later. Within three years, it became one of the largest online billiards retailers in the country, doing hundreds of thousands a month in sales. In 2007, I sold both companies for $2.1 million. I had officially hit my childhood dream in my early 30s, and I celebrated by buying a Corvette.
But hitting that peak is where things started to unravel. I started flipping repo cars out of my driveway, and after the neighbors complained to the city, I rented a physical lot and opened ValleyBoys AutoSales. I poured my e-commerce millions into financing “Buy Here, Pay Here” car contracts, which initially generated tens of thousands a month in interest income. But with that kind of cash flowing, I lost my priorities. The partying lifestyle took over. We actually installed a Jägermeister machine in the back office of the car lot. My partner and I started blowing through nearly half a million dollars a year. To keep funding the lifestyle, we started selling off our profitable car contracts at a discount to other lenders. The financials completely collapsed, and I crashed hard.
The ultimate turning point happened on a morning in July 2013. I woke up after a brutal night of partying, looked into my wife’s eyes, and saw she was totally done with the shenanigans. Right then and there, I told her I was quitting drinking cold turkey, and I did. At the exact same time, I was drowning in debt and forced to file for bankruptcy. To find a way to refocus, I got my real estate license. I knew I had to give it absolutely everything because my reputation in the community was shot—I was known as the crazy, belligerent drunk who bought rounds for the whole bar.
I went into the office every single day to prospect. In my first year, through sheer grit, I sold 36 properties, but I was clocking 80 hours a week. I told my wife I didn’t care how much money it was, I wasn’t going to live like that. So, I started building a team. That decision evolved into what it is today: a massive mega-agent team of 50 agents and staff, closing nearly 500 transactions a year across Oregon and Arizona. Over the last 14 years since my crash, we’ve reinvested, acquired over 80 rental doors, and built a level of true financial freedom we never dreamed of.
When I share my story, the part people gravitate to the most isn’t the first two million—it’s the fact that I crashed, went bankrupt, got sober, and built something ten times bigger and smarter on the second run. Today, my joy comes from mentoring my team, traveling, playing golf, and enjoying my family.
Appreciate you sharing that. What should we know about Rockwell Group | eXp Realty, LLC?
The Rockwell Group is a premier, multi-state real estate powerhouse operating at the highest level across Oregon and Arizona. Built on a foundation of relentless work ethic, sharp market intelligence, and a true team-first culture, we have evolved from a solo endeavor into a massive mega-agent team. Today, our organization features a dedicated roster of 50 elite agents alongside a world-class administrative and management staff.
We don’t just facilitate transactions; we move markets. Closing nearly 500 transactions annually, the Rockwell Group combines high-volume production with an unwavering commitment to boutique-level consumer experiences. By shifting away from the traditional, exhausted “solo-agent” model, we leverage a specialized team approach—ensuring our clients receive unmatched marketing power, 24/7 operational support, and master-level negotiation from start to finish.
At its core, the Rockwell Group is an engine for growth. Our mission is two-fold: to deliver unparalleled wealth-building opportunities for our real estate clients, and to provide our agents with the systems, mentorship, and leadership they need to build careers they are deeply proud of. We don’t just sell properties—we build legacies.
What’s next?
We just launched a property management company and a home loan company and the last several months and look forward to growing those.
My son will be off to college in a couple years and who knows what life will look like for my wife and I, as we spend time in both Arizona and Oregon as well as travel the country.
Business wise, we will continue to help others find success within our company and pivot with the ever-changing industry of real estate.
Will continue to grow my portfolio of rental properties throughout Oregon, Arizona
Contact Info:
- Website: https://RockwellRealEstate.com
- Instagram: https://www.instagram.com/rockwell_real_estate/
- Facebook: https://www.facebook.com/RockwellGroupSouthernOregon/
- LinkedIn: https://www.linkedin.com/company/rockwell-real-estate/
- Twitter: https://twitter.com/4rockwell
- Youtube: https://www.youtube.com/@rockwellrealestate
- Yelp: https://m.yelp.com/biz/jake-rockwell-rockwell-group-exp-realty-medford
