Barker Squire·February 27, 2025

How to Build a Holdco Foundation Patiently | Barker Squire Interview

Barker Squire is a Marine Corps infantry veteran and Darden MBA who conducted a self-funded search from 2017 to 2019 and acquired Crane Works — a government-contracting business that inspects, maintains, repairs, and fabricates overhead and mobile cranes for U.S. military installations — in January 2019 for approximately 4x EBITDA. Unable to use SBA financing because the founder rolled 25% equity and stayed on as a field engineer, Barker assembled an unconventional capital stack of two regional conventional loans (~45%), a seller note (~20%), the founder's equity roll (~25%), and his own savings (~10%). The first six weeks were rocky — a division imploded and roughly $500k in enterprise value evaporated from pre-existing employee tensions — but by month six the Core Business stabilized and Barker implemented EOS/Traction, growing revenue and EBITDA roughly 3x and headcount from 11 to 26 over six years with no formal sales function. In mid-2024 he promoted an internal successor as CEO, and at the time of recording was searching for bolt-on acquisitions to expand Crane Works geographically while simultaneously laying groundwork for a broader personal holding company, with a stated vision of long-term ownership across multiple businesses rather than build-and-exit cycles.

Deal facts

multiple: ~4x EBITDA
sde ebitda: lower half of $500k–$1m range (per search criteria)
revenue: approximately 3x current vs. 2019 baseline; ~$2.5m–$5m at acquisition (implied by margins/headcount)
financing structure: ~45% conventional senior debt (two regional lenders) + ~20% seller note + ~25% equity roll by founder + ~10% buyer equity; SBA 7(a) ineligible due to founder equity roll
notes: Stock sale (required for government contract novation). Founder Jeff rolled 25% equity and stayed on as employee/field engineer. No SBA loan used. Closed January 2019. Buyer had 'a few hundred thousand' on personal balance sheet.

Why this business

Barker wanted to continue leading people and organizations after leaving the Marine Corps. He chose search/ETA to be a majority owner of a small business rather than climbing a corporate ladder. Crane Works specifically fit because it checked traditional search criteria (profitable, contracted recurring revenues, 3–5 year contracts), was headquartered near where he grew up in Virginia, served military bases he had trained and served aboard, and fell in his target industry of industrial servicing. He also felt culturally connected to the workforce.

What's working

Long-term government contracts (3–5 year terms) provide stable, recurring revenue that 'pays the bills and keeps the lights on'
High barrier to entry in government contracting — competing with Crane Works would take years and millions of dollars
Revenue mix of recurring maintenance contracts plus higher-margin non-recurring repair/overhaul/new crane projects
Founder Jeff stayed on as field engineer and equity holder, providing technical continuity and becoming a champion for the brand
EOS/Traction framework implemented at six-month mark, enabling disciplined execution and 3x revenue and EBITDA growth over six years
Word-of-mouth growth with no formal sales function, driven by quality and reputation
Promoted internal successor (Marshall) to CEO after five-plus years, freeing Barker to pursue inorganic growth and holdco expansion
Military background gave Barker credibility with government customers and comfort with the regulatory environment

What's hard

A division of Crane Works imploded within the first six weeks of ownership — approximately $500k in enterprise value disappeared due to employee departures stemming from pre-existing interpersonal tensions that could not be fully diligenced
Sales were below prior-year levels for the first six months before recovering
Conventional bank financing (no SBA) was extremely difficult to arrange — Barker contacted roughly 25 lenders and received offers varying by 300%; only two regional lenders stepped up
Federal acquisition regulations are 'insanely long' and compliance is burdensome for small businesses, growing more difficult every year
Reinvested 100% of free cash flow back into the business for six years, at times reducing his own salary to zero, before reaching financial optionality
Managing the chain-of-command transition when the founder remained as an employee required careful upfront alignment with both the founder and the workforce

Notable quotes

I wanted to have a certain amount of autonomy and control and to learn that with the traditional search granted it's typically a larger business but Searchers end up with 20, 25% equity something like that at the end of the day and I was really looking for a situation where I could be the majority owner even if it meant it was a smaller company.

Every single one of the top five deals was a broker deal and so at that point I decided to solely focus on the business broker investment banker kind of channel.

I believe that leading a small business whether it's your CEO or key manager or owner is probably the best way to positively impact other people — there's no other position I can think of where you have such direct influence over what someone's paid, their benefits and, I'd say more importantly, the hopefully the purpose that they feel when they come to work every day.

I really view the financial side of this process as a tool to help us accomplish and achieve our goals and for me what's most important is building outstanding teams that deliver great value to our customers.