Jake Rockwell

My Story

From "the guy buying rounds" to leading a team of about 50 agents, management and staff.

I don't tell this story because it's pretty. I tell it because someone out there is where I was.
Jake Rockwell, Founder & CEO of Rockwell Group
  1. Early years

    Eastern Oregon roots

    I grew up in a middle-class family in eastern Oregon. I shoveled snow, mowed lawns, and sold the Oregonian and greeting cards door to door. At 14 I was working in my dad's carpet cleaning and fire restoration business. I told my mom I was going to be a millionaire.

  2. High school

    Bend

    In high school in Bend I washed dishes, worked at a pizza parlor, and worked at the Sunriver golf course.

  3. College

    Southern Oregon University

    I earned a BA in business administration with a marketing focus and a minor in economics.

  4. After college

    Enterprise Rent-A-Car

    I went through Enterprise's management training and was promoted to assistant manager within a year.

  5. Then

    Osprey Brew Pub

    I left a $30k+ salary to buy a failing brewery listed at $50k, putting $8k down with the seller carrying the note. I paid myself $800 a month, and it was grossing $5k a month when we bought it. We switched to evening hours with live music and food specials and turned it into one of the hottest spots in Southern Oregon.

  6. 2004–2007

    E-commerce and Rockwell Billiards

    I started from my house with a three-car garage full of product and grew Rockwell Billiards into one of the largest online billiards retailers in the country, reaching hundreds of thousands a month in sales.

  7. After that

    $2.1 million and a childhood dream

    I sold rockwellbilliards.com together with a pet products company for $2.1 million total, fulfilling my childhood dream of becoming a millionaire in my early 30s.

  8. Next

    ValleyBoys AutoSales

    I started reselling repos from my driveway, then rented a lot. It became a buy-here-pay-here car lot bringing in tens of thousands a month in interest, and that success led to the crash.

  9. Before 2013

    Partying and bankruptcy

    I was the guy buying rounds, blowing about $500k a year. I sold contracts at a discount until it all unraveled. I lost the $2.1 million and went through bankruptcy.

    Jake Rockwell in his early entrepreneur years
  10. July 2013

    I quit drinking

    The turning point. I quit drinking in July 2013 and I've been sober ever since.

  11. 2013

    Got my real estate license, 36 sales my first year

    I worked about 80 hours a week and closed 36 sales in my first year. In a town that knew me for the wrong reasons, I showed up sober and prospected every day. That's what led to building the team.

  12. 2014

    John L Scott Rookie of the Year

  13. 2015

    Launched Rockwell Real Estate

    I launched my own independent brokerage, Rockwell Real Estate.

  14. 2018

    Joined eXp Realty

    I brought my team, The Rockwell Real Estate Group, to eXp. Today I'm Founder & CEO of Rockwell Group, headquartered in Medford with offices in Albany, Oregon and Scottsdale, Arizona.

  15. 2018–2026

    eXp ICON Agent

    Recognized as an eXp ICON Agent every year from 2018 through 2026.

    Jake Rockwell's name on screen at the 2018 eXp Realty ICON Agent Award ceremony
  16. Today

    Rockwell Group

    About 50 agents, management and staff, nearly 500 transactions a year across Oregon and Arizona, and 80+ rental doors.

  17. Recently

    Acquired Grants Pass Storage

    Self-storage in Grants Pass, Oregon.

  18. Now

    Writing the book

    Title TBD. The honest story of the comeback.

“Progress not Perfection”
— Jake Rockwell