Evan Stewart·June 9, 2025

Evolving a Legacy Business to $3.2m EBITDA | Evan Stewart Interview

Evan Stewart, a political operative and agency-side professional with 10-15 years of experience working with commercial print firms, bought Direct One — a 75-employee commercial print and direct mail services company in Winter Park, Florida — in April 2023 for $7.2m (4x EBITDA) via SBA financing secured in part against his personal home. At acquisition the business was doing $34m in total revenue (including significant postage pass-through) and $15m in pure services revenue with $1.8m EBITDA. Evan's thesis was that the contracting direct mail industry was evolving from commodity to value-added service through variable digital imaging and integrated omni-channel campaigns, and that his agency background uniquely positioned him to accelerate that shift. The transition was rocky: he underestimated the operational complexity of the business, the working capital demands of floating postage, the coming capex requirements for new inkjet presses, and the cultural resistance of a long-tenured workforce skeptical of new owners. He and his wife moved the family from Jacksonville to Orlando within months after the commuting arrangement nearly fractured their marriage. By end of 2024 — two years in — he had grown EBITDA to $3.2m and services revenue to $18.7m, helped by the 2024 election cycle, operational leverage, a new pledge-processing service line, and his wife joining the business. He is actively evaluating a $1.5m-$3m inkjet press investment and plans to continue acquiring.

Deal facts

purchase price: $7.2m
multiple: 4x SDE/EBITDA
sde ebitda: EBITDA $1.8m at acquisition
revenue: $34m total topline (includes postage pass-through); ~$15m services revenue
financing structure: SBA loan + personal lien on primary residence (used as collateral for a secondary loan)
notes: Business: Direct One, a commercial print and direct mail services firm in Winter Park, FL. 75 employees at acquisition, 60,000 sq ft across two facilities. Acquired April 2023. By end of 2024: $42m total revenue, $18.7m services revenue, $3.2m EBITDA.

Why this business

Evan had 10-15 years of agency-side experience working with commercial printers across the country on political and advocacy direct mail campaigns. A loan broker told him lenders would give more money if he bought something in an area where he had experience. He also realized he was drawn to tangible, manufacturing-type work — he couldn't see or feel the output of services work — and commercial printing satisfied that. He saw the industry contracting but believed the survivors who embraced variable digital imaging and integrated omni-channel marketing would thrive, and he felt uniquely positioned to bring that agency-side expertise into a print shop that already had the equipment but lacked the marketing vision.

What's working

Near-doubling of EBITDA in two years: from $1.8m at acquisition to $3.2m by end of 2024, with services revenue growing from $15m to $18.7m
Operational leverage in a fixed-cost-heavy business: once volume exceeds a certain monthly threshold, incremental revenue falls heavily to the bottom line
Election cycle tailwind in 2024 boosted direct mail volumes significantly
Strong existing customer base with long tenure — founding client still present after 30 years, low concentration risk with ~400 customers invoiced per year
Wife joined the business full-time after being laid off, adding marketing and operational capacity at a manageable part-time schedule
Building an actual org structure with junior management layers where none existed, creating career paths and accountability
New service line: 'Direct Collect,' an in-house pledge processing and check-handling operation for fundraising mail clients, expanding the service ecosystem
Forming partnerships with digital advertising agencies and texting companies (e.g., Rumble Up) to offer trigger mail and integrated omni-channel campaigns
Culture shift: employees moved from skepticism to engagement; one employee proactively brought a new product idea to Evan
Low employee turnover retained through first year; key people stayed; headcount grew from 75 to 84

What's hard

Postage float: for smaller customers, the company fronts postage costs (which can be 50% of a job's total) before being reimbursed, creating significant working capital strain
Capex-intensive: new inkjet/digital variable imaging presses cost $1.5m-$3m each, representing half the purchase price of the business for a single machine — a major upcoming investment decision
Industry is contracting and consolidating; private equity is accelerating that consolidation
Post-merger chaos: the prior owners had merged with a competitor in 2019, then immediately hit COVID and the 2021-2022 paper shortage, so there were no clean stable years to benchmark during diligence
Legacy ERP from 1992-1994 — owners couldn't even calculate average run rate, no modern operational data
Moved from Jacksonville to Orlando with family — two months of commuting nearly destroyed his marriage before they relocated; sold house with equity absorbed by the secondary loan
Culture of complacency and skepticism: long-tenured employees had seen PE-backed acquirers make promises then do layoffs; Evan had to earn trust before being heard
Impostor syndrome: realized quickly his agency-side knowledge of printing was surface-level; press operators with 43 years of experience were asking him for direction he didn't have
Seasonality risk: heavy fall business from political clients means the company must be strategic about client mix to avoid capacity constraints
Paid a 4x multiple in a tough, low-margin, capex-heavy industry — acknowledged it was likely a bit high for the category

Notable quotes

I thought I understood the industry having worked kind of tangently on the agency side, but you start to realize, man, there are a lot of things that your printer told you over the years that were totally untrue.

I remember I came home I told my wife it's like you know what I think I might be the dumbest person in that building when it comes to this industry.

Everyone has to earn the right to be heard.

We burned the boats. But that was the first like real like, oh wait, this is real. Like we're not in search mode anymore. Our whole lives are mortgaged now and like this has got to be a success.