Jack Saville, Sam Rosati·September 22, 2025

Deciding to Exit After 2 Years of Ownership | Jack Saville and Sam Rosati Interview

Jack Saville, a West Point graduate and Army veteran who spent a decade at Capital One, bought Strategic Fence — a commercial, residential, and temporary fencing company in Breckenridge, Colorado — in January 2023 using an SBA loan plus a forgivable seller note structured at 20% of purchase price. He moved to Breckenridge while his family remained in Virginia, and operated the business for roughly two years before selling it to PSG (Perimeter Security Group), the large commercial fencing platform being built by co-guest Sam Rosati, on February 14, 2025. The business was financially solid and had a geographic moat, but Jack discovered that running a subscale lifestyle business in a small resort town — with its labor constraints, growth ceiling, and family separation — was not aligned with his deeper drive for large-scale impact. After PSG recapitalized with PE firm Bertram Capital, they acquired Strategic Fence and brought Jack on as Western Market President, giving him equity and a platform to pursue the entrepreneurial ambition that the single-business model couldn't satisfy. Sam Rosati, who runs SM Boot Camp for self-funded searchers and is Jack's partner in building PSG, appears throughout as mentor, co-investor, and business partner in the full-circle story.

Deal facts

sde ebitda: SDE in the 750k–1.5m range (not disclosed precisely; described as 'very cleanly within that range' of Jack's search criteria)
financing structure: SBA loan (primary debt) + seller note (20% of purchase price, structured as forgivable note with interest-only first two years, 5-year amortization thereafter, revenue-linked forgiveness provision) + equity from Jack/Ashley Saville and PSG/Chris (minority preferred, 80/20 common/pref split)
notes: Business closed January 2023. Strategic Fence subsequently acquired by PSG (Perimeter Security Group) on February 14, 2025. PSG had recapitalized with PE firm Bertram Capital (San Francisco) prior to acquiring Strategic. Sellers were a husband-and-wife team at retirement age. Sellers held a seller note and remained as landlord post-close. Jack used offshore deal-flow support team based in Pakistan during search.

Why this business

Jack was not specifically seeking a fencing business, but he had commercial construction experience from his post-military career and was comfortable with the project-based model. Strategic Fence ticked financial boxes (SDE in his target range, healthy margins, revenue diversity across commercial, residential, temporary/rental fencing), had high-integrity sellers, was in a resort market he wanted to live in (Breckenridge, CO), and offered a geographic moat given the difficulty for Denver contractors to service the mountain market. He was also betting on the Colorado resort market as a durable end market.

What's working

Geographic moat: limited direct competition in the Breckenridge resort market, with Denver contractors unwilling to drive up the mountain
Revenue diversity across commercial, residential, and temporary/rental fencing streams
Strong seller relationship: high-integrity husband-and-wife sellers who remained as landlord and held seller note, creating aligned incentives
PSG as equity partner provided optionality — Jack saw from the start that PSG could be a future acquirer or collaborator
Second year showed good revenue growth and a clearer path to sustainable cash flow
Ultimately sold to PSG and transitioned into Western Market President role, building wealth through PSG equity

What's hard

Within 12 months, three crew leaders left and two started competing directly with the business
Severe labor constraints in a resort town where workers prioritize lifestyle over work ambition
Inherent growth ceiling in a small, geographically constrained market — difficult to expand without significant capital and personal time
Living separately from family for the first six months (Jack in Breckenridge, family in Virginia), with visits only every three weeks
Son's school quality in Breckenridge was poor, ultimately forcing wife and son to relocate to Denver even after the family had finally reunited
Recognized that the business was a 'lifestyle business' that did not align with his desire for bigger impact and scale — came to see it as underutilizing his talents
Psychological difficulty of announcing the sale to his team after only two years as owner, feeling like he was abandoning them
Hiring a GM was expensive and required a recruiter; not an 'easy button'

Notable quotes

Jack, you have acquired a fantastic lifestyle business. Do you want to be a lifestyle business operator? And I think you're underutilizing your talents.

I got a lot of joy in leading the team and building the relationships and doing really hard things. I also recognized for me that like a huge part of my why is having a big impact like solving big problems and having a big impact operating a business of effectively 25 people right is like it is an impactful like you are impacting like you're writing the checks right they're paychecks every single week you're impacting the lives of 25 people um but I honestly wanted to do more and bigger and I missed having a peer group.

If this thing completely failed, right, and I lose my house and all the things that we all tell ourselves in those really, really bad days, without question, I would trade it all for the relationship that I now have with my son.

The experience Jack had is way more common than you would imagine. People think first of all, this is not a question for Jack or this is not an issue of do I want to be an entrepreneur or not? It's like what seat do I want to be in? What do I want my life to look like?