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Trucker of the Year: Page 4
Overdrive Radio
Owner-operator Leslie Bitterman claws back from near-death to success
Bitterman was nominated for the 2024 Trucker of the Year award by her daughter, Ashley, who’s long been inspired by the toughness and strong old-school, no-frills handle on business that the owner puts into action.
February 12, 2024
Trucker of the Year
Bitterman Trucking bounces back to build on long, strong trucking legacy
One-truck owner-operator Leslie Bitterman won a near-fatal bout with COVID, fighting back to the truck to keep her business going. Her perseverance, and more, shines through with her nomination as Overdrive's January Trucker of the Month.
January 31, 2024
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March 24, 2025
Trucker of the Year
They said he'd fail: Overdrive's Trucker of the Year Jay Hosty
Owner-op Jay Hosty has been proving naysayers wrong since the early days of his career, when he paid off a brand-new truck pulling containers in the Southeast. Read -- and hear -- why Hosty came out on top in Overdrive's Trucker of the Year competition.
January 12, 2024
Overdrive Radio
Truckers' New Year's Resolutions: Get closer to the freight source, and back to basics on costs
Worried about the percentage "a broker might keep?" Owner-ops should ask how much is needlessly lost daily. Three Trucker of the Year finalists and an Overdrive contributor here offer ways to reassess -- and fully engage your primary freight partners.
January 8, 2024
Trucker of the Year
Overdrive's Trucker of the Year finalists revealed
With the announcement of three finalists for our 2023 award, Overdrive also officially opens the nomination period for the 2024 Trucker of the Year award. Pulling tanks, RGNs and hoppers, dry vans and more: Find which owners came out at the top here.
December 18, 2023
Overdrive Radio
'Never give up' in drive to trucking success
Part 2 of our "exit interview" series with Trucker of the Year contenders for 2023 included a strong current of advice for new and/or aspiring owner-operators, as five contenders detailed cost-control and other tactics keeping them in the black.
December 11, 2023
Overdrive Radio
Overdrive's 2023 Truckers of the Year: The 'exit interviews' toward the finale, Part 1
This Overdrive Radio roundtable, the first two of sets of talks featuring Trucker of the Year semi-finalists, focused on the year just passed -- the challenges faced, and just how the businesses chose to overcome.
December 4, 2023
Overdrive Radio
Behind the owner-operator: An exemplary business and life partner
October Trucker of the Month John Schiltz owes a lot of his early success just to "hustle," as he puts it, yet he credits his wife and business partner, fellow owner-op Sarah Schiltz, with big parts of recent-history excellence.
November 6, 2023
Trucker of the Year
Hustle, never-quit attitude pay off for owner-operator John Schiltz
John Schiltz is Overdrive's Trucker of the Month for October, putting him in contention for 2023 Trucker of the Year. His perseverance as an owner-operator since 2010, with a keen eye toward maintenance, is one among many reasons for his success.
October 30, 2023
Overdrive Radio
Super-sweet spot hauling chocolate for Roger and Rita Wilson's two-truck operation
In this week's Overdrive Radio, hear the clarion voices of a spectacular pair of owner-operators: Roger and Rita Wilson and their Chicago-area-based, two-truck Rita’s Absolute Trucking, pulling direct for an appreciative shipper in Blommer chocolate.
October 9, 2023
Trucker of the Year
It's 'Absolute Trucking' for two-rig team Rita and Roger Wilson: Truckers of the Month
At its height, the Wilsons' Rita's Absolute Trucking hit 15 trucks running consolidated LTL out of a warehouse the pair operated. Post-Great Recession, however, the pair found a sweet spot with a go-to customer and two trucks. "Life's a lot easier" since.
September 26, 2023
Overdrive Radio
Beating the odds in a 1989 Marmon, from Chicago construction dump to OTR
August Trucker of the Month Steven Massat on Overdrive Radio: After decades of dump work with various Chicago construction outfits as an owner-operator, what used to be his wintertime home leased to T Max is now a year-round affair.
September 11, 2023
Trucker of the Year
Owner-op overcomes physical challenge for successful career
Despite being diagnosed with psoriatic arthritis and being eligible for 100% disability more than three decades ago, owner-operator Steve Massat's love of the business has kept him going since buying his first truck in 1988.
August 29, 2023
Overdrive Radio
She makes car-haul look easy: Trucker of the Month Crystal Rives
After hauling in the Texas oilfields as well as side dump, end dump, and liquid-bulk tanker and more, she's growing a base of car-haul customers under her own shingle. All this while guided by lessons learned from her grandfather.
August 7, 2023
Trucker of the Year
Owner-operator Crystal Rives makes hay of car-haul work in Texas
'She's got her business in line' -- that's the single biggest thing that makes owner-operator Rives an inspiration to fellow car haulers, in the words of one. Seven years into business with authority, she's serving Texas-based customers intrastate.
July 28, 2023
Overdrive Radio
Writing the book on trucking as an independent: Owner-operator Debbie Desiderato
Overdrive's June Trucker of the Month is not afraid to tell it like it is -- nor to give back in the form of advice for those coming up, always willing to share the tools and processes she's built for her success.
July 3, 2023
Trucker of the Year
Master management, mechanical prowess pay off for 20-year independent
Her 27 years in trucking and two decades as an independent have played out in numerous niches, leading her to where she is today, hauling for a direct shipper customer pulling a van, and hauling logs as a side gig.
June 27, 2023
Overdrive Radio
Trucking with authority, take two: Another run at independence for owner-operator Matthew Karr
"Strike when the market's cold" -- you could consider it a maxim for the outlook on small business for Overdrive May Trucker of the Month Matthew Karr, coming off an excellent profit year hauling fuel leased. Run through his history on Overdrive Radio.
June 12, 2023
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