Don Gourley·September 11, 2023

How to Buy a 45-Year-Old Business From Its Founder | Don Gourley Interview

Don Gourley is a former Army officer (10-plus years active duty, deployments to Iraq and Afghanistan, later Massachusetts Army National Guard) who earned an MBA from Babson and a mid-career master's from Harvard's Kennedy School before pivoting to search. He ran a geographically constrained, self-funded search focused on Eastern Massachusetts and New England, building an unusually large intern team (graduate students leading undergraduates) to exhaustively canvas the market. After a search disrupted by COVID-19 and a collapsed deal on a $6m China-supply-chain business, he found Boston Tree Preservation — a 40-plus-year-old organic plant healthcare company founded by serial entrepreneur Peter Wilde — listed on a search-fund website one town from his home. The deal nearly died because prior buyers could not clear the SBA lender's term sheet due to the seller's intermingled multi-company finances; Don solved this by having the seller front the quality-of-earnings report cost in exchange for reimbursement at closing, which also served as a strong trust signal. The business generates $2m-$5m in revenue with roughly 33% drop-through margins and a positive cash conversion cycle, operates with a deep bench of expert technicians, and competes in a highly specialized niche with almost no true standalone competitors. Don's primary near-term challenge and opportunity is completing the Salesforce integration to enable scalable growth without adding overhead, with longer-term ambitions including geographic expansion, potentially franchising, and creating a search/acquisition pathway for fellow military veterans.

Deal facts

revenue: $2m-$5m
financing structure: SBA loan (required QoE to obtain term sheet); seller fronted QoE cost, to be reimbursed by buyer at closing
notes: 40-plus year old business (Boston Tree Preservation). Pre-deal fell through on a $6m business (separate deal, supply chain in China) at start of pandemic. Seller (Peter Wilde) fronted the quality-of-earnings report cost to unblock the SBA term sheet; prior buyers could not get past SBA lender due to intermingled financials across seller's multiple companies. Business has ~33% margins and a positive cash conversion cycle with six-figure cash float for roughly half the year.

Why this business

It was one town over — proximity was a key filter as a geographically constrained self-funded searcher. Beyond location, Don was drawn to the niche nature of the business (organic plant healthcare, not landscaping or tree cutting), the strong margins (~33% drop-through), the people and existing employee knowledge base, and the fact it had a nascent e-commerce and digital marketing side that he could develop. He also valued that it was a business where he felt like 'a good guy when you come home at the end of the day' — organic, health-focused, no harmful chemicals. The operational complexity suited his military engineering background, while the digital and financial upside suited his MBA.

What's working

Highly specialized niche — organic/preventive plant healthcare — with very few true competitors doing it as a standalone offering; Boston Tree Preservation described as an anomaly or 'mutation' in the industry
Strong gross margins (~33% drop-through to bottom line), meaningfully above typical landscaping or tree-cutting businesses
Positive cash conversion cycle: customers pay upfront deposits, creating a six-figure cash float for roughly half the year
Deep, loyal residential customer base built over 40-plus years; customers have long relationships with individual technicians and value the high-touch service
Experienced, dedicated employee bench — technicians with deep trade knowledge and strong customer relationships, enabling the business to run without the founder's full engagement
Seller (Peter Wilde) had already invested in upgrading the vehicle fleet and implementing Salesforce and modern software, giving Don a strong operational foundation to build on
Business proved recession-resilient: customers may pause but return; pandemic actually drove a revenue bump as homeowners spent more on their properties
Recurring and repeat revenue from residential customers, contrasting with lower-repeat commercial work

What's hard

Salesforce integration was only 50-60% complete at acquisition; Don needed to reach ~90% integration before stepping on the marketing gas, making the first six months largely focused on software synchronization rather than growth
Financials were commingled across the seller's multiple companies, which blocked prior buyers from getting an SBA lender term sheet — required a quality-of-earnings report that the seller had to front
Business was middle-management light by design, which meant scaling required careful orchestration of the software to avoid adding excessive overhead
Don had no industry knowledge of arboriculture coming in and could not replace the founder's 40 years of expertise — had to rely entirely on the employee team for domain knowledge
Maintaining the high-touch customer relationship culture while introducing software-driven efficiency is a constant tension
Geographic constraint (self-funded, wanted to stay near Boston) meant fishing in a smaller pond and having to exhaustively canvas the market rather than search nationally

Notable quotes

I can't replace Peter Wilde he's got 40 years doing this I'm not going to try to replace him I'm going to try to be myself and come in and take what he's built and try to carry it forward

There are no such thing as bad units only bad officers and there are no such thing as bad companies only bad CEOs so when I looked around all the talent needed was right there I just had to lead the people to get the same job done in a slightly different way

We're kind of like a veterinarian for trees that makes nothing but house calls and doesn't have a veterinarian's office so that's pretty much exactly what the business is like

When he said yes I do that I knew we were going to get it done — it was a huge signal of seriousness and honesty from Peter which we were at the beginning stages of our relationship