Acquiring Minds — Deciding to Exit After 2 Years of Ownership
Host: Will Smith
Guests: Jack Seville, Sam Rosati (Perimeter Solutions Group / PSG)
Air Date: September 22, 2025
Episode Overview
This episode dives into the acquisition story of Jack Seville, who bought a commercial fencing business, operated it for two years, and then decided to sell to PSG—a large fence business platform led, in part, by his mentor and original investor Sam Rosati. Through a rich three-way conversation, Jack, Sam, and Will discuss the motivations behind buying a business, the realities and challenges of SMB acquisition entrepreneurship, the unexpected twists in Jack’s journey, and how owning a subscale business interacted with Jack’s personal goals and family life.
Key themes include:
- Setting an example of ownership for your kids
- The unpredictability (and opportunity) of acquisition entrepreneurship
- The reality that business ownership can mean “buying a job”
- Evolving personal “why” and knowing when to pivot
- Turning an ownership journey into a leadership role in a rapidly growing platform
Key Discussion Points & Insights
1. Full Circle: From Search to Sellback (04:54)
- Jack bought Strategic Fence after going through Sam Rosati’s SM Boot Camp; years later, PSG (Sam’s platform) acquired Jack’s business.
- Both Jack and Sam shared introductions acknowledging their personal and professional connections, highlighting mutual mentorship, friendship, and complementary skill sets.
- Sam (on Jack): “He is a fantastic leader… a tremendous leader of people. Maybe that comes from your experience in the military.” [07:22]
2. Jack’s Background & Motivation to Buy (08:56)
- Jack’s journey began with a military background, then civil construction, a decade at Capital One (plus an MBA), and a desire for true ownership and control.
- A major motivator: being proud of his work and setting an example for his children.
- Jack: “As we all start to look at our legacy, right, I want for my kids to look at their father and say, he set the right example. Anything's possible. Just go do it.” [14:18]
- Ownership was both a personal challenge and a way to visibly pursue risk and ambition.
3. The Role of SMB Boot Camp (16:23)
- Sam describes SM Boot Camp as a tactical, in-person program for mostly older, career-changing searchers—focused on larger-than-average, self-funded deals.
- Jack credits boot camp with network-building and deal team formation.
- Jack: “Literally built my entire future deal team from that event.” [12:04]
- The importance of openness and honesty in mentorship and investment relationships.
4. Search Process & Willingness to Move (22:19)
- Jack ran an operator-focused, SBA-leveraged search, ultimately casting a wide geographic net (VA, FL, TX, CO).
- Unique for relocating his family—and engaged them in exploring Breckenridge, CO.
- Will: “That strikes me as unusual… the whole culture of the family is adventure.” [26:09]
- Used on-market deal flow (BizBuySell) and offshore assistants to generate and screen leads, emphasizing pragmatism over “proprietary” search purity.
5. Acquisition Parameters and Deal Structure (30:44)
- Targeted businesses with $750K–$1.5M SDE, solid margins, high-integrity sellers.
- Strategic Fence hit the sweet spot: right size, good financials, diverse revenue streams, seller partnership via a significant (20%) and forgivable seller note.
- Jack: “Of my total purchase price, 20% was through a seller note… first two years interest only… If we didn’t hit previous year’s revenue, that year’s principal payment would be declined by however much we missed.” [44:21]
- Sam: “A forgivable note is one of the few tools in the toolbox to bridge a valuation gap... I wouldn't start with one, but if you end up in a valuation gap, absolutely pull it out.” [47:19]
6. The Realities of SMB Ownership (53:55)
- Jack describes the emotional toll of being an owner—transitioning from operator to "getting punched in the mouth every single day."
- Jack: “I think until you're in it… you don't truly appreciate how hard it is and how challenging it could be.” [57:56]
- A tension: leading a 25-person team is meaningful but can feel limiting. Jack wanted bigger impact, missed a peer group, and realized he was called to solve larger problems.
- Jack: “I honestly wanted to do more and bigger, and I missed having a peer group. I missed having the impact on… really, really big problems instead of the small tactical problems.” [57:56]
- In small, remote markets like Breckenridge, even a successful business can cap out and feel constraining.
7. Pivoting into PSG Leadership (67:20)
- Big inflection: mentor Chris at PSG plants a seed—“You’ve acquired a fantastic lifestyle business. Do you want to be a lifestyle business operator? I think you're underutilizing your talents.”
- Jack: “Unless I pursued something differently, I was going to continue to own and operate a lifestyle business as long as I sat in that seat.” [63:12]
- Jack and PSG mutually recognized a great fit for a larger leadership role. PSG’s recapitalization with private equity (Bertram Capital) enabled Jack to sell his business to the platform and step into a “Western Market President” position, overseeing a major regional operation and driving further acquisitions.
- Sam: “We needed somebody that had fence experience… What that specifically means for Jack today is the Western Market president...responsible for the performance of our entire business essentially west of Texas.” [74:26]
8. Optionality and Partnership Dynamics (50:32)
- Jack was intentional about “optionality”—choosing PSG as sole investor to keep an exit/partnership path open.
- Also respected the importance of “value-added capital” over just money.
- Full transparency and honest board/partner structure helped Jack transition smoothly.
9. Exiting as an Exit, Not a Failure (83:42)
- It’s not always about building an empire alone—selling to a platform and integrating into a bigger organization is a valid, respectable entrepreneurial outcome.
- Sam: “It is okay if what you do is you buy a business where your goal is to sell it to a capital-backed group...and you become part of a broader organization, that can be a good outcome for entrepreneurs.” [84:00]
- Jack's “why” evolved through the journey, and periodic reflection led to a better fit both for his family and professional ambitions.
Notable Quotes & Moments
- Jack (on parenting and entrepreneurship), [14:18]:
"I want for my kids to look at their father and say, he set the right example. Anything's possible. Just go do it." - Sam (on mentoring and partnership), [07:22]:
"He is a fantastic leader... Maybe that comes from your experience in the military." - Jack (on limiting beliefs and impact), [59:49]:
“There was effectively a cap. So for me there was this recognition… something would fundamentally have to be different in order for me to get past that, you know, subscale small business.” - Sam (on entrepreneurship’s unpredictability), [66:06]:
“This is entrepreneurship. You have to weave it together with your life. And if you think the direct path is going to be the path that you take, that's not true. But if you never try, you'll never know.” - Jack (on evolving your ‘why’), [85:02]:
“It's also healthy and good to continue to question that why... and being willing to adjust when it makes sense for you and your family is important too.” - Sam (on the journey continuing), [83:42]:
“This story also is not yet done... Entrepreneurship is a winding road and that's okay.”
Important Episode Timestamps
- Jack’s Background & Why Ownership: [08:56–15:41]
- Family Decision to Relocate: [22:19–26:11]
- Deal Search & Offshore Outsourcing: [26:36–30:44]
- Deal Structure—Forgivable Seller Note: [44:21]
- Acquisition & PSG Investment: [47:25–53:36]
- Daily Operator Realities & Burnout: [53:55–63:48]
- Mentorship/Transitioning Into PSG: [67:20–77:04]
- Western Market President Role: [74:21–77:03]
- Philosophy On Exits & ‘Why’: [83:42–85:40]
Episode Takeaways
- Think deeply about your “why”—and keep questioning and evolving it.
- Don’t be afraid of using pragmatic, on-market, and outsourced solutions during search.
- Mentoring and peer networks matter—seek out smart, honest partners.
- Selling your SMB to a platform can be a win—not a failure.
- Entrepreneurial journeys are unpredictable—embrace the zig-zags.