Matt O'Brien·April 3, 2025

FedEx & Fencing: A Pivot into Ownership | Matt O'Brien Interview

Matt O'Brien is a Louisville, Kentucky-based entrepreneur who built and exited a FedEx linehaul business (semi-truck contractor network) between 2018 and 2021, growing from a single lane in Knoxville to a nine-lane, 14-tractor operation centered in St. Louis, which he sold at the peak of the COVID e-commerce surge at 3.5x EV for approximately $3m in revenue. He then pivoted to acquiring Professional Fence, a commercial fencing company in LaGrange, KY (a Louisville suburb) in late 2022, buying it at a 2.4x SDE multiple on $550k-$700k in consistent annual EBITDA with $2.4m-$2.7m in revenue, using a 90% SBA 7(a) loan. The business specializes in B2B athletic field fencing (high schools, municipalities) and temporary fencing rentals, with a strong niche and recurring revenue element. Matt serves as CEO focused on strategy while the seller's son Chris, initially the biggest diligence risk, became the business's president and key operational driver. Revenue grew approximately 80% by end of 2024 to ~$4.95m with EBITDA nearly doubling, driven by repricing, operational systematization (SOPs, job pack organization, KPI tracking), and direct sales outreach. A third acquisition — a Kentucky trucking company purchased in March 2023 for ~$1m — failed within 13 months due to freight rate compression, rising insurance costs, and labor inflation, resulting in a loss of at least $500k; Matt attributes this partly to split attention and over-enthusiasm for building a holdco. He remains focused on growing Professional Fence toward $10m in revenue, which he believes could position it as a private equity platform acquisition target.

Deal facts

multiple: 2.4x SDE / 2.8x EBITDA (fencing acquisition); FedEx business sold at 3.5x EV
sde ebitda: SDE/EBITDA $550k-$700k (fencing, at acquisition); failed trucking acquisition bought for $1m
revenue: $2.4m-$2.7m (fencing at acquisition); ~$3m (FedEx business at sale); $3.95m (fencing 2023); $4.95m (fencing 2024)
financing structure: SBA 7(a) with 10% equity injection; working capital line of credit; no seller note on fencing deal. Additional $150k personal injection post-close for working capital.
notes: FedEx business (9 lanes, 14 tractors, St. Louis) sold Aug 2021. Fencing business (Professional Fence, LaGrange KY) acquired late 2022 after ~9 months of diligence/negotiation. Third acquisition: a trucking company in Kentucky, bought March 2023 for ~$1m, divested April 2024 at a loss of at least $500k.

Why this business

The fencing business was 20 minutes from his home in the same county, had a strong local reputation, was 100% commercial (B2B), had a recurring revenue rental component (temporary fencing), and had a specialized niche in athletic field fencing (baseball, softball, football). After running a business four hours away, proximity was extremely attractive. He also played college baseball, so there was a personal resonance with the athletic field work.

What's working

Elevating the seller's son (Chris) to President — originally seen as a key-person risk, he became the greatest asset post-acquisition and fully bought into new ownership
Pricing discipline: updated how they price projects and quotes, improving margins
Operational efficiency: implemented organized job packs, labeled materials, throughput systems, and SOPs that did not exist under prior ownership
KPI tracking introduced (e.g., AR target of 65 days or less) where none existed before
Revenue grew roughly 80% from acquisition to end of 2024 (~$2.5m to ~$4.95m) with EBITDA nearly doubling
Tertiary market thesis: located in LaGrange KY suburb of Louisville, drawing consistent, high-quality workforce from surrounding rural/exurban counties
Recurring temporary fencing rental revenue (state fair, festivals, construction sites) providing baseline forecasting
Niche specialization in athletic field fencing (backstops, football fields) creating a competitive moat

What's hard

Working capital was significantly underestimated at close — had to inject an additional $150k of personal funds 3-6 months post-close due to AR lag in commercial construction (receivables can run 90 days)
Key-employee risk: seller's son was the business — required a major leap of faith; mitigated with a 2-year employment agreement but was never fully de-risked at purchase
Employee attrition after acquisition was inevitable; some employees left due to loyalty to prior owner or disruption from change
Temporary fencing rental revenue turned out to be lower and less predictable than expected (some festivals are biennial, not annual); inventory is a constraint on growth of that segment
Third acquisition (Kentucky trucking company, 2023-2024) failed: rising insurance costs, freight rate compression (each load worth less), and increased labor costs converged to make the business unviable; lost at least $500k including working capital injections
Trying to run two businesses simultaneously (fencing + trucking) split attention and likely contributed to the trucking failure
In the failed trucking deal, had walked away from the same opportunity three times due to flags — persisted anyway out of enthusiasm for building a holdco, which in retrospect was a mistake
Equipment lifecycle mismatch with SBA loan terms is a structural risk in capital-intensive businesses (e.g., truck lifespan shorter than 10-year loan)

Notable quotes

if you make dynamic change you're going to have dynamic heartburn

what we thought was a concern truly ended up being like the greatest gift is for him to be very much on board with moving you know post acquisition

in a construction business whatever you calculate for what you think the working capital should be just double it to be safe

maybe like little mama and pop businesses and they're successful because they operate them in such a lean way that you can't replicate that