Eyes on the big climb: Careful prep the name of the game for Trucker of the Month Greg Labosky

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Greg Labosky and his 2017 Freightliner Cascadia
June Trucker of the Month Greg Labosky's GDL Enterprise business is pulled behind the 450 horses under the hood of his no-frills 2017 Freightliner Cascadia, running van freight in short-term contracts in Amazon's system.
All photos courtesy of GDL Enterprise

Owner-operator Greg Labosky, with his authority today as GDL Enterprise and operating out of a home base in New Haven, Connecticut, has striven for stability with a business that operates power-only exclusively within the Amazon system pulling dry van freight.

Though he's had his CDL since the mid-1990s, his trucking business is a fairly recent-history development.

After a 20-year hauling hiatus, he went back to full-time trucking in 2018 as a company driver for Northeast regional liquor and tire distributors. He rented a truck shortly thereafter and worked contracted with a small carrier whose entire business was within Amazon. It's here the stage was set for a move toward getting authority, as he watched the small fleet owner fail and attempt to reorganize as a different company, then fail yet again with an abrupt company closure around the time of the onset of the COVID-19 pandemic. 

Labosky took a tack he recommends to any owner or prospective owner who crosses his path: lean on your own experience and willingness to learn, fundamentally, how to do as many things as you can yourself. "Have a good head on your shoulders," he said, "and be willing to look at your books and keep a good record of everything you’ve done in the past."

Take your cues from what you see, learning to "do the math yourself," he said, likewise as much as you can to maintain the truck and your personal credit with your own hands and knowhow. In a system like Amazon's, built to reward contracted carriers who are on-time, every time, and who experience the fewest service disruptions in-transit, those abilities will keep you in a position to command better freight with a high performance score. That's key to getting your early pick of spot and short-term contracted freight there. 

Labosky himself runs in the high 90s for a rating, enabling solid profitability the last couple of years, though repairs to his 2017 Freightliner Cascadia put a bit of a dent in 2023 income compared to 2022, when profits were slightly higher. All the same, he's living his best life behind the wheel of the business, according to his former pastor, current friend and personal counsel John Lafreniere in nearby Meriden, Connecticut. "You’re talking about a guy who really takes his work seriously and doesn’t fudge on anything," Lafreniere said. "He’s straight as an arrow on work ethic -- he's not afraid of hard work, but does have a working knowledge of a lot of things."

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Sometimes, and for some people, the pastor noted, that might come off as arrogance, but it's that working knowledge, and a willingness to develop and hone it, that's kept GDL Enterprise and its owner moving onward and upward through the market turbulence of the last four years. Owner-operator Greg Labosky is Overdrive's Trucker of the Month for June, putting him in the running for the 2024 Trucker of the Year award. 

overdrive trucker of the year 2024 logoOverdrive's 2024 Trucker of the Year program, sponsored by Commercial Vehicle Group and Bostrom Seating, recognizes clear business acumen and unique or time-honored recipes for success among owner-operators. Through October, we're naming Truckers of the Month to contend for the Trucker of the Year honor. Finalists will be named in December, and a winner crowned early next year. Nominations continue to be sought for exceptional owner-operators, whether leased or independent, throughout the year. Nominate your business or that of a fellow owner (up to three trucks) via this link for a chance to win a custom replica of your tractor and a Bostrom seat from Commercial Vehicle Group, among other perks.

Taking complete control, with a steady hand

John Lafreniere has known Greg Labosky going back about a decade, back before the time he made moves to go back to the full-time trucking he'd done for a few years at the start of his working life in the early-mid 1990s. After Labosky's return, that initial company driver job, and taking on the rental truck and working as a leased contractor, Lafreniere recalls the careful deliberation that underscored the truck-purchase decision.

"He took a lot of time to make that decision," Lafreniere said. 

The rental situation was "OK to start," said Labosky, yet it came with a significant expense that kept him from meeting savings targets to build beyond his rainy-day savings for a significant down payment. "Seven months to nine months of renting," and the nickel-and-diming he felt he was experiencing with the agreement, Labosky decided enough was enough and set a process in motion to find just what he needed. 

His approach was a veritable textbook example of how to narrow a wide field of used-truck possibilities to make the best financial decision possible, though the used-truck market during that early-pandemic period was already tight and prices were inflated. 

"I had a good idea of the specs I was looking for," Labosky said -- 450 hp, manual transmission, a sleeper with a length beyond the veritable coffin he recalled from his 1990s years trucking (a 48-incher in an old cabover).

His process closely resembled one outlined in Overdrive's Partners in Business manual in the equipment-purchase-focused Chapter 10. He set a budget he would keep to, agreeing with longtime fiancee Jenny Meng about the amount the pair would spend, coming in part from savings Meng had built over years running her own small business. He identified eight potential trucks on the used market, then looked for reasons to disqualify each one. 

"I was looking then at overall quality of the engine, the mileage, the way it performed," Labosky said, "the shift pattern and overall tightness of each vehicle." An International LT he drove felt loose in the transmission, like "it wasn't well-maintained."

Soon enough, he'd narrowed the field to a final three, driving all and honing in on a no-frills 2017 Freightliner Cascadia. 

Labosky's 2017 CascadiaThe Cascadia (pictured) pushes 450 horse with a 10-speed manual, 3.64 rears and the ability to "pull decent weight and with a little more top end than I would care for," he said. "But it does the job that I need it to do." Bumper-to-back of cab is 125 inches, with the 60-inch factory sleeper that continues to be "adequate for right now" for the work he's doing, which keeps him on the road for much of the week, generally speaking.

You can fly by the seat of your pants, so to speak, with spot loads in the Amazon Relay system if you want to. But Labosky's more deliberate about planning, he said. "I take the contracts three-five weeks in advance," he said, giving him a rough idea of "what my start date is," likewise the end date, and "how many loads per a given week" and at what general rate for the given block of time. Rates vary up and down block to block, depending on a variety of factors, he's seen. There's a fuel surcharge based on a national rate built in, plus toll reimbursement that's based on the Amazon mapping system and recommended routes. 

"If you know how to use the old-school map" so many of us grew up with, Labosky said, sometimes it works out to your advantage to avoid tolled routes, plentiful in his hauling region around Connecticut, and "pocket the toll reimbursements." Other times, though, to meet the time windows given for pickup and delivery, "sometimes it's not to your advantage."

[Related: Effective insurance, exacting analysis deliver Trucker of the Month's success]  

Uptime key to maintaining high service ratings, early access to freight

Jenny Meng's local business has benefited from her long relationship with Greg Labosky, the pair engaged now for years. They're not officially husband and wife as yet, though they make most financial decisions together, including the one that moved Labosky into outright truck ownership, both said. 

Owner-operator Greg Labosky and Jenny MengOwner-operator Greg Labosky and Jenny Meng"He has helped me with my business," Meng said, with a general mechanical prowess extending from time as an auto mechanic in high school through to the present day, replacing air-conditioning units and repairing some of the equipment that comes with running a spa. 

"He is very tight with his budget, and doesn’t spend money on unnecessary items," she said.

The instinct to learn, to take better control of all aspects of the business, has seen him "doing more of the work on the truck himself to save money on repairs that other people would charge a lot for," Meng added.

That's helped a high rating for access to better-paying freight in the Amazon system, as Labosky himself sees it. The drive for dependability factored into the truck-purchase evaluation, too. The 2017 Cascadia had more than half a million miles on it when he purchased it. Documentation showed it'd been a single-owner unit, "but may have been a team."

The driver's seat had seen plenty of action, though. "It may have been a slip-seat truck," he said. He replaced the seat about a year into his ownership. Otherwise, repairs since that time -- the rig's now well on its way to a million miles at about 820,000 -- have been minimal. He did his evaluation work on the front end, choosing the rig after noting a fair amount of somewhat recent work had been done to "a lot of the components on the upper portion of the engine. Gaskets were fairly new," for instance.

He knows a true rebuild will be a matter of time. Labosky changes oil at 3 months or 25,000 miles, whichever comes first, having an oil sample analyzed each time. "So far, samples show the engine is holding up in terms of internal wear and tear," he said, though he may see extra soot if he's idled more than usual. 

Keeping on top of a sound maintenance schedule, he feels, drives his high rating in the Amazon system given he avoids having to "cancel loads due to mechanical issues."

At once, "keeping an eye on their equipment" is key, too, he added. Ninety percent of his loads are drop/hook, all with Amazon-owned trailers. He's careful to make certain "their trailers are up to spec" and to "stand your ground when it needs to be repaired."

It's happened several times now that he's avoided potential service failures by identifying trailer maintenance issues. Generally, "they've just taken me off the load and given me another," he said.

He runs at a 6.5-7.5 mpg average, and he's curious about what he's heard of mileages one or even two mpg higher in similarly-spec'd rigs with automated manual transmissions optimized for the engine they're paired with. He's open to the prospect in future, yet for now is happy with what he's got, with plenty power and manual versatility to anticipate changes in terrain to minimize the adverse safety consequences of, for instance, losing speed uphill in more-dense Northeast traffic. 

Cascadia parked, view from the back of the tractorGreg Labosky at once does "take time to relax and knows how to decompress," said his friend John Lafrienere. "When he’s on the clock and he’s doing the work," though, "he’s super-focused."

Looking ahead, prepping for the best outcomes

Jenny Meng sees her fiance's biggest strength as a business owner in prepping for that hill ahead, ultimately. "Key to him being successful," she said, is keeping a close eye on expenses he can control, and catching maintenance items "old and worn out before they get to be a problem" requiring a big repair job. 

Every owner-operator deals with the unforeseen, Greg Labosky included. He kicked up debris rolling along the Cross-Bronx Expressway in a construction zone that cracked the Cascadia's crankcase breather and resulted in a loss of oil pressure, for instance, among the bigger repairs -- rewiring the starter, replacement of hoses to the DEF heater -- he's been forced into by circumstance. It required replacing the oil pan, the crankcase breather housing and the oil pump, ultimately.

Generally, though, he strives and largely succeeds in keeping "unexpected occurrences" to a minimum, and he's got the profits to show for it, banking $20K more in income now as an owner versus his time hauling as a driver after he returned to the road. 

Enter your business in Overdrive's Trucker of the Year competition for a chance to win a seat from program sponsor Bostrom Seating, among other perks and prizes.Enter your business in Overdrive's Trucker of the Year competition for a chance to win a seat from program sponsor Bostrom Seating, among other perks and prizes.Preparation for the future extends to putting aside money from retirement in an individual 401(k) rolled over from prior employment, carrying health insurance with Blue Cross Blue Shield, and regular emergency-fund set-asides for those unforeseen maintenance expenses. It's the last in particular that he offers any new or prospective owner as critical for success in small business. His goal there is "10 cents of every dollar" of revenue, he said, though occasionally he misses that mark when rates are slack as they have been in recent times. 

"Longer-term," he's looking out with expansion in mind within the Amazon system as potential, he said. "I would like to buy a brand-new truck to see what the emissions systems go to, though I do want to run this unit without a payment" before that time comes. He's a year and a little more out from completing the note entirely. "It's just a matter of getting to the point where I'm comfortable" enough to balance the debt load that would come with a new truck with new revenue opportunities.

Odds are, he knows, he'll get a better deal today than what he got with his pandemic purchase, when prices were high and, being a first-time truck buyer, interest was high, too.  

Pastor John Lafreniere sees an attitude of give and ye shall receive in Labosky, whose current church, Fairfield Baptist in Fairfield, Connecticut, Lafreniere led in the relatively recent past and saw plenty of contributions from the owner-operator in volunteer work done there. "He’s just been a really good guy," the pastor said. "If I was in a pinch and I needed someone who I could count on, Greg’s one of my first phone calls. He’s just demonstrated his character to me over and over again."

Enter your own or another deserving owner's business (up to 3 trucks) in Overdrive's 2024 Trucker of the Year competition via this link

[Related: Fuel-mileage gains, business prowess power Trucker of the Month, Alpha Drivers owner Alec Costerus]

Hear interviews with this year's Truckers of the Month via the playlist below.