Greg Shapiro, Zach Cooper-Vastola·June 4, 2026

The Origin Story of a Compounder ($80m and Counting) | Greg Shapiro & Zach Cooper-Vastola Interview

Greg Shapiro and Zach Cooper-Vastola, along with third partner John Holesapple, founded Hickory — a residential HVAC roll-up platform built around proprietary tech-enabled sourcing, long-term ownership, and an explicit anti-PE culture. Starting from software and finance backgrounds (not private equity), they developed data-driven outreach tools before the market became crowded, then pivoted to owning and operating the businesses themselves rather than selling the software. Their first acquisition in 2018 was Stanley Ruth, a 100-plus-year-old Manhattan HVAC company serving high-net-worth co-op residents, purchased for $4.5 million (approximately $1.2 million EBITDA) using non-SBA bank debt, a seller note from the two founding brothers, and roughly $1 million of angel equity raised deal-by-deal. The early years were shaped by severe owner dependency they underestimated, the difficulty of true digitization (extracting institutional knowledge before any tech can be layered in), and near-total shutdown during COVID in 2020. Growth accelerated in 2022 with a Westchester acquisition that doubled revenue overnight, and the platform now projects $125 million in revenue across 14 acquisitions and roughly 500 employees. A key strategic pivot was narrowing targets to operators who want to roll equity and stay on long-term, and in 2025 they raised outside capital for the first time from Pacific Lake Partners' 30-year hold fund — aligned with their compounding, indefinite-hold thesis. By 2026 they are also opportunistically acquiring distressed businesses that failed under PE ownership, leveraging their operational depth as competitive advantage.

Deal facts

purchase price: $4.5m (Stanley Ruth, first acquisition)
sde ebitda: EBITDA ~$1.2m (Stanley Ruth)
revenue: $4.5m (Stanley Ruth at acquisition); ~$125m projected by end of 2026 across platform
financing structure: Traditional (non-SBA) bank debt + seller note (two brothers) + equity (~$1m raised from angel-style investors for first deal)
notes: 14 acquisitions total by mid-2026; ~$80m+ revenue at time of episode; ~300 employees growing to ~500; 13 locations; raised external long-term hold capital in 2025 from Pacific Lake Partners (30-year hold fund); Will Thorndike is an LP and early backer; deal-by-deal equity raises for approximately first 8 acquisitions; later acquisitions use partial equity roll from selling operators

Why this business

We thought we could bring just 10% of the technology and data-forward approaches that exist in other realms to the idea of finding great small businesses, and we could do way better than what the baseline would look like. We were attracted to Stanley Ruth specifically because it had a primarily recurring and repeating customer base — high-net-worth individuals in Manhattan with long-tenured contracts, some customers with families using them for 40 years — and about $1.2 million in EBITDA on $4.5 million in revenue from a 100-plus-year-old company.

What's working

Proprietary tech-enabled deal sourcing that predated the crowded outreach market, allowing off-market access to quality targets
Recurring revenue base of high-net-worth Manhattan HVAC customers with multi-decade loyalty
Partnership model: buying partial stakes from operators who stay on and roll equity, aligning incentives and avoiding the need to recruit outside management
Long-term hold orientation (no fund timeline pressure), backed by Pacific Lake Partners' 30-year hold fund, which differentiates Hickory from PE consolidators
Positioning as 'anti-PE' — employee-friendly culture, wage-based compensation vs. full commission, no pressure to maximize single-visit ticket — allowing them to attract talent fleeing PE-acquired competitors
Acquiring distressed or failed PE-backed HVAC businesses at low cost as a new growth channel, leveraging operational capability
In-house technology team built from experienced software engineers, including former colleagues of Greg's, enabling scalable operational systems
Elevating internal leaders and delegating decision-making so founders can work on rather than in the business

What's hard

Owner dependency: the non-primary brother at Stanley Ruth was running the business 12-14 hours a day and handwriting proposals — the depth of dependency was not apparent during diligence
Digitization is far harder than anticipated: before tech can be applied, institutional knowledge must be extracted from the owner's head and converted into replicable processes
COVID hit during their New York City-only period, shutting operations for nearly 13 weeks in 2020, just after their bolt-on acquisition closed in February 2020
Insurance costs in New York City are approximately 10x those of their businesses outside New York State
Living on small salaries for years — none of the three founders was among the highest-paid employees at the company for a long time
Hiring senior external leaders proved difficult; it was not until 2024 that truly capable senior hires joined and stayed
Work-life balance sacrifices over the early years: missed weddings, family events, early bedtimes, no vacations
Competing with PE on multiples as HVAC became a hot consolidation target in 2022-2023, inflating prices and creating employee poaching dynamics

Notable quotes

If we could bring just 10% of the technology and the data-forward approaches that exist in these other realms to the idea of finding great small businesses, we could do way better than what that baseline would look like.

There's a huge amount of value that comes from owning a business and running it well. We thought that we could approach that world, but because we would have a better process for finding and acquiring businesses, we could build something really big without having to raise a large fund or be backed by a large fund.

Digitizing a business is really about changing the things that people do every day. And so that was hard.

We kind of want to be the apex predators of our space, and we think that we can do that by really building the culture from the ground up and making sure that we really are the best residential HVAC company out there so that both customers and employees would see that and have a really clear choice.