Three times in roughly 16 years, Matthew Fleeger has made a big move at a moment when the rest of his market was heading for the exits. The CEO of Dallas-based Gulf Coast Western kept funding prospects through the 2008 crisis, bought a Louisiana asset package during the 2015-2016 oil slump and, in 2024, purchased the office complex his company calls home while Dallas office values were sliding.
He’s been candid that the timing is deliberate. How he sets himself up to act on it says more about his approach to risk than any single deal.
Lean Years, Full Bench
The company was started in 1970 by Fleeger’s father, who began with small reserves in Louisiana and Texas. Gulf Coast Western reviews of that history credit decades of partnerships and acquisitions for its growth. Fleeger came back to run the family business after he sold his medical waste company to Stericycle.
Matthew Fleeger’s leadership lays out what happened when the 2008 financial crisis hit. Gulf Coast Western tightened operations and reduced overhead. Key personnel were kept on. Major prospect investments stayed funded, too.
Cost cuts in a recession are routine. Keeping the people who evaluate and close deals is the harder call, and it’s the one that decides whether a company can do anything once prices bottom out. Fleeger’s own version is blunt: the way out of a downturn is to “look for ways to cut overhead without losing talent.”
Buying When the Market Sells
The next test came with the 2015-2016 oil price slump. In January 2016, Gulf Coast Western said its subsidiary Orbit Gulf Coast Exploration had acquired substantially all of the assets of Lafayette, Louisiana-based Orbit Energy Partners. Working interests in 13 producing wells were included in the deal, along with 140 defined drilling locations and access to hundreds of square miles of 3D seismic data in southwestern Louisiana.
“Low oil prices make for a tremendous buying opportunity right now,” Fleeger told Mergermarket that month. The cost to drill wells had also dropped as demand for drilling services fell, he said.
Cheap assets and cheap services only help a buyer that has kept its team and its prospect pipeline intact. Gulf Coast Western had both, largely because of what it chose to protect in 2008. It also helped that the company knew the ground. Production had been taken over by Orbit Gulf Coast Exploration the previous October, so the purchase formalized a relationship that was already working.
An Office Complex, Same Playbook
The habit carries over to real estate. CoStar reported in September 2024 that Parkway Office Center, a two-building complex of about 230,000 square feet on the Dallas North Tollway, had been bought by Gulf Coast Western in partnership with Enverra Real Estate Partners. The company had leased space there for 12 years. The property’s $22 million loan was acquired at an undisclosed discount after a foreclosure.
Fleeger acknowledged that “a lot of people are running from commercial real estate.” He bought anyway. “My investment philosophy has always been contrarian,” he told CoStar, adding that he’s “not afraid of making what some may consider to be a risky investment.” He described the purchase as a way to diversify his holdings. An owner who also occupies a building is better placed to improve it, he argued. Between $8 million and $10 million was earmarked for renovations.
Where Partners See It
Look across those three moments and the risk is narrower than it first appears. Fleeger moves when sentiment is weak, but he moves on assets he already knows: a Louisiana position his team had been producing from, a building his company had occupied for over a decade. The preparation happens years before the purchase.
Partners tend to describe the same steadiness. Gulf Coast Western holds an A+ rating and accreditation from the Better Business Bureau, and Gulf Coast Western reviews posted there often mention clear communication and field visits.
The next downturn, in oil or office space or somewhere else, will probably find Matthew Fleeger doing what he’s done before: watching the exits fill up and looking at what’s been left behind.
