10 days of trailers - 10 days. 10 trailers. 10 winners. Ends December 21st.
Shop NowSee The Setup

Every day is a chance to take home a tandem axle trailer

22H 27M 10S LEFT

Shop NowSee OB40

Enter With The Latest Merch

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Platinum Quick Entry

(0)
$200
35,000 
100X+15000
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Gold Quick Entry

(2)
$125
17,500 
100X+5000
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Silver Quick Entry

(0)
$75
8,500 
100X+1000
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Loaded Dump Tee

(0)
$40
3,000 
75X
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10% off

OB40 Exclusive Bundle

(1)
$200
$180
13,500 
75X
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Garage Hat

(0)
$40
3,000 
75X
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OB40 Exclusive Setup Tee

(1)
$40
3,000 
75X
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OB40 Exclusive Setup Hoodie

(2)
$80
6,000 
75X
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Ruby Red Duramax Setup

1,200 LB-FT of pure rage — Radiant Red Metallic with attitude. The baddest GMC Denali on 26s, loaded and ready for anything. Tilt-deck, Cat skid steer, and $20K cash. You want to win? Step up and own it.

Build Details

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Always your highest multiplier

Quick Entry Gift Cards

get entries now & when you use your gift card
get entries now & when you use your gift card
get entries now & when you use your gift card
get entries now & when you use your gift card
$200 Gift Card
20,000 
100X
Buy now · $200
$100 Gift Card
10,000 
100X
Buy now · $100
$50 Gift Card
5,000 
100X
Buy now · $50
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Everything You Need To Be Your Own Boss

2025 Load Trail 26FT Gooseneck Deck Over Tilt

2025 Load Trail 26FT Gooseneck Deck Over Tilt

2021 Cat 259D3 Tracked Loader

2021 Cat 259D3 Tracked Loader

2024 GMC Denali 3500 Duramax

2024 GMC Denali 3500 Duramax

33,000 Customers

Who Love Own Boss

34263 reviews
CARSON C.
Fast an great apparel
Own Boss Secure Shipping
Kevin M.
Love it! My son jacked it from me to use. I have the larger one for my work bag as well
Everyday Tactical Backpack
James S.
I thought the 2xl would fit but it was too small so I gave it to my son and he lov e s them. I just wish they were 3xL instead
Warborn Hoodie
Greg R.
Pretty hand and compact!
Tactical Backseat Organizer
Kenneth D.
Cool
Double Your Entries
Chris S.
Works great in my truck
Tactical Backseat Organizer
Hunter k.
Very comfortable
American Made Hoodie
Gary N.
It was for my wife and she likes it. Fits her really well.
Hi Boss Crewneck
George S.
Love this lunch box, makes it so convenient to know where my food is, and the insulated bag is nice. Keeps things cold, when needed.
Lunch Box
Glenn D.
I think its pretty sweet u can double your entries for just a small fee more. I just wish after all these years buying something for every single giveaway there was a point system ...
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Double Your Entries
Joe H.
Seems good. Looks great on my backpack
Orange Camo Jet Tag
James .
She likes it a lot
Support Local Businesses Women's Tee
Thad B.
It’s a great company with great ideas
Double Your Entries
Matthew E.
Awesome
OBSC Gift Card $50
Jordan T.
My favorite hoodie so far
Disciple Hoodie
christopher k.
Absolutely love the products, the shirts are made of the best fabric and the goodies have the best fit
Double Your Entries
Rodney B.
Fit great right size love the comfort of them. Will be ordering more soon
Mystery Item | 1000 Bonus Entries
Damian G.
Works good
Multifunction Magnetic Work Light
Jonathan b.
Rocking my back pack errrday!
Gold Quick Entry
Neil A.
It fits perfectly. I know this is minor detail, but the hoodie size is perfect too. It stays right where it belongs and not to big to fall over your eyes. Thank you
Faith Over Fear Hoodie
chance W.
It’s a comfy sweatshirt
No Sh*t Hoodie
Leonard L.
My son enjoying the bracelet thanks!
"Never Forgotten" Tactical Bracelet
Leonard L.
Awesome hoodie Proverb28:1 a great selection from own boss. The righteous are bold as a lion.
Proverbs 28:1 Hoodie
Emmanuel P.
It was good
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Latest Own Boss News

August 11, 2025
Parker's picking up OB35!
WE FINALLY HAVE A WINNER!!!We know you’ve all been waiting for this one, so have we 😅…Parker Kinsley, from Arizona is taking home OB35 which was the High Country rig! This rig is going to look so sick out in the AZ country 🔥
May 29, 2025
Jordan took home OB33 to Harrison, GA
Jordan R. is officially our OB33 winner! 🏆 He drove home to Harrison, GA with his brand new 2023 Ford F-350 King Ranch with High Output Powerstroke Diesel, a John Deere 317G Skid Steer, a 25' Load Trail Gooseneck trailer, AND $20,000 in cash. He couldn't be more excited – and we couldn't be happier for him! Congratulations, Jordan! 👏🚚💰
April 15, 2025
Meet Orlando, Winner of OB32!
Orlando entered OB32 — but what we didn’t know until today… his own truck had just been stolen. The timing couldn’t have been crazier. He ended up driving off with a brand new setup that’ll help him keep grinding. This could be YOU.
April 8, 2025
OB33 Has Ended 🥃
Another MASSIVE giveaway in the books! Entries have closed for OB33 and are now being sent off for WINNER SELECTION! Keep your eyes on your phone and remember - we'll never DM you to tell you that you've won. GOOD LUCK!
January 13, 2025
After 2 years, he hit the jackpot!
We drove up to pick Ricky up and brought him back to the shop, where his life was about to change forever. Waiting for him was his incredible prize: a Ram Cummins, a T66 Bobcat skid steer, a low deck trailer, and $30,000 in cash.