AI Speeds M&A Data Rooms but Cannot Draft Legal Terms
Greg Holbrock and Kison Patel explain why buy-side AI works for querying data rooms but fails at legal drafting and negotiation.
How Winsupply Runs M&A With a Team of Four | Greg Holbrock
With Kison Patel, Greg Holbrock · Thursday, November 12, 2026
Greg Holbrock, VP of M&A at Winsupply, discusses how his core four-person team manages acquisitions across 680+ wholesale distributor locations while maintaining an 80%+ success rate. He breaks down Winsupply's unconventional deal mechanics, which include skipping rollover equity, factoring only one-third of goodwill into local share prices, and granting operational autonomy to local teams. Patel and Holbrock also explore negotiation psychology, due diligence discipline, and the integration of AI tools into modern M&A workflows.
Key takeaways
- Winsupply oversees acquisitions across 680+ wholesale distributor locations with a corporate M&A team of four people, sustaining an 80%+ deal success rate. Read more →
- Winsupply runs a lean four-person deal team managing acquisitions across more than 680 wholesale distributor locations with an 80%+ success rate. Read more →
- Greg Holbrock directs M&A across 680-plus wholesale locations for Winsupply with a lean four-person corporate team, sustaining an acquisition close-and-integration rate above 80 percent. Read more →
- Winsupply generates $9 billion in annual revenue across 680 distributor locations while running its corporate acquisition engine with four people: a deal lead, an operations lead, an analyst, and a project manager. Read more →
- Winsupply closes roughly 90% of its transactions entirely without earn-outs, avoiding post-close friction and complex accounting disputes. Read more →
- Winsupply runs a portfolio of more than 680 wholesale distributor locations with an M&A team of four people and an acquisition success rate above 80 percent. Read more →
6 articles from this episode
Winsupply Runs Due Diligence Like an Audit
Greg Holbrock explains how Winsupply uses forensic audit principles to screen acquisitions across 680 distributor locations.
Winsupply Caps Stalled Acquisitions at Two Lives
Greg Holbrock of Winsupply uses forensic listening on seller motives and enforces a strict two-life rule to kill bad acquisitions before deal fever sets in.
Winsupply Runs $9B in Volume With Four M&A Staff
Greg Holbrock explains how Winsupply manages deals across 680 locations with four corporate staff and centralized dealmaking authority.
Winsupply Skips Earn-Outs in 90 Percent of Acquisitions
Winsupply VP of M&A Greg Holbrock explains why clean cash deals and delayed ERP conversions beat standard roll-up playbooks.
Winsupply Sells Down Majority Stakes to Local Teams
Winsupply avoids rollover equity, discounts goodwill to one-third, and sells equity to local operators across 680 distributor locations.
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