Win a Ford F450, Skid Steer & $20,000 Cash!
Ready to build your dream business, or just take your projects to the next level? The Own Boss Supply 39 Giveaway is here to help you hit the ground running with one of the most powerful prize packages of the year. One lucky winner will drive away in a 2023 Ford F450, command any job site with a Caterpillar 259 Skid Steer, haul it all with a Load Trail Gooseneck Trailer, and pocket $20,000 in cash to make big moves.
This giveaway is about more than just prizes—it’s about independence, ambition, and the tools to shape your own success. Whether you’re starting a new venture, expanding your operations, or simply love rugged machines, this is your ticket to being your own boss in the boldest way possible.
Don’t wait—enter today and take the wheel toward your next great chapter.
Who Can Enter
Open to legal residents of the 48 contiguous United States and DC, ages 18 and older. Void in Alaska, Hawaii, and Michigan.
Giveaway Ends
November 23, 2025
How Often You Can Enter
Up to 40,000 total entries allowed per person through all entry methods.
Prize Details
Grand Prize (1 Winner):
2023 Ford F450 (used, approx. 2,500 miles) — ARV: $100,000
Caterpillar 259 Skid Steer — ARV: $35,000
Load Trail Gooseneck Trailer — ARV: $11,000
$20,000 Cash (awarded as a check)
Total ARV: $166,000
How to Enter
You can enter in four ways:
1. Online Purchase:
Visit ownbosssupplyco.com and make a purchase—earn one entry per $1 spent (excluding tax and shipping).
2. Event Purchase:
Buy merchandise at an Own Boss Supply event booth and register your purchase on-site to receive one entry per $1 spent.
3. Subscription Enrollment:
Subscribe to a plan at ownbosssupplyco.com to earn the listed number of entries based on your package.
4. Mail-In (No Purchase Necessary):
Handwrite your name, address, phone number, email, and date of birth on a 3"x5" card labeled “OB39 Sweepstakes Entry” and mail it to:
CSS / “OB39” Sweepstakes, 5607 Pittsford Palmyra Road, PO Box 828, Pittsford, NY 14534.
The grand prize winner will be selected by random drawing on or about December 3, 2025.
Rules and Regulations: Read the Official Rules & Regulations.
