Own Boss Supply Denali Truck Giveaway – Win a GMC 3500 + $20K Cash

Get ready for the ultimate equipment upgrade! The Own Boss Supply Denali Truck Giveaway is giving one lucky winner the chance to take home a massive powerhouse prize package built for serious business owners, contractors, builders, and outdoor pros. This incredible grand prize includes a 2024 GMC 3500 Denali, one of the toughest heavy-duty trucks on the market — perfect for hauling, towing, and taking on any jobsite.

But that’s just the beginning…

The winner will also receive a Caterpillar 259 Skid Steer, a versatile, high-performance machine built for construction, landscaping, and heavy lifting. Paired with a Load Trail Gooseneck Trailer, you’ll have everything you need to transport equipment with ease and efficiency. And to top it all off, the prize pack includes a $20,000 cash award to invest in your business, cover operating costs, or fuel your next big move.

Whether you're building your business from the ground up or leveling up your current operation, this is your chance to win the ultimate workhorse package worth tens of thousands of dollars. Enter now for the opportunity to roll away with the truck, the gear, the trailer, and the cash that can truly change your business!

Enter to win 2024 GMC 3500, a Caterpillar 259 Skid Steer, a Load Trail gooseneck trailer and a $20,000 cash award

Limit: Each entrant can get up to 40000 entries during the promotion period. The minimum age limit to enter the giveaway is 18. It is void in Hawaii, Alaska and Michigan.

How to Enter in Own Boss Supply Denali Truck Giveaway:

An eligible individual may enter the Sweepstakes through one of the following four (4) methods:

Purchase on Website

• Visit ownbosssupplyco.com and complete a purchase during the Promotion Period.
• Receive one entry per $1 spent via approved credit card transaction. You must provide your full name, home address, telephone number, and email address.

Purchase at Sponsor Marketing Event

• Make a product purchase of at least $1.00 at the Sponsor’s booth during a Sponsor-hosted marketing event. Receive one entry per $1 spent

Subscription Enrollment

• Visit the Website and enroll in a subscription package. Receive the number of monthly Sweepstakes entries associated with the chosen subscription tier. Provide your full name, home address, telephone number, and email address.

Mail-In Entry (AMOE)

Handwrite the following on a 3” x 5” card: “OB40” Sweepstakes Entry, full name, address, city, state/province, ZIP/postal code, phone number, email address, and date of birth. Mail in a hand-addressed standard business envelope to:

CSS / “OB40” Sweepstakes
5607 Pittsford Palmyra Road
PO Box 828
Pittsford, NY 14534

Own Boss Supply Free Truck Giveaway Winner Selection:

One grand prize winner will be selected randomly on or about January 14, 2026 from all eligible entries.

Own Boss Supply OB40 Giveaway Prizes:

One Grand Prize Winner will receive:

• A 2024 GMC 3500 (used; approx. 12,000 miles) — ARV: $75,000
• A Caterpillar 259 Skid Steer — ARV: $37,000
• A Load Trail gooseneck trailer — ARV: $11,000
• A $20,000 cash award (awarded as a check)

Total ARV of the Grand Prize package: $143,000