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Peer Fund / Dealmaker·Accounting Roll-Ups

Tom Golisano

Founder & Managing Partner at Grand Oaks Capital

Victor, New York, USA

TG
Why they matter

Paychex founder turned active investor who already put capital directly into AI bookkeeping automation (Botkeeper) — a direct comparable and potential co-investor/reference in accounting roll-up diligence.

Background

Tom Golisano founded Paychex in 1971 and built it into one of the largest payroll and HR outsourcing companies in the U.S., stepping down as CEO in 2004 while remaining a major shareholder. In 2016 he launched Grand Oaks Capital, a Victor, NY-based family office/investment firm that provides seed and early-stage capital (typically $2M-$100M per deal) to entrepreneurs, with a strong tilt toward Western New York and fintech/accounting-adjacent software.

Notable deals

  • 2021
    Led Botkeeper's $42M Series C (AI-powered bookkeeping automation for accounting firms) and joined its board
  • 2023
    Grand Oaks Capital invested $17M in Heretto, a B2B SaaS content-operations platform
  • 2023
    Led $10M Series A in HelloTeam, an employee engagement and performance-management platform
  • 2025
    Converted a $100M Grand Oaks Capital loan into equity, becoming Eastman Kodak's largest shareholder (~15% stake)

Call-prep brief

Background

  • Founded Paychex in 1971; grew it into a Fortune 500 payroll/HR outsourcing leader before stepping back as CEO in 2004.
  • Launched Grand Oaks Capital in 2016 (Victor, NY) as his family-office investment vehicle — ~$500M+ deployed across ~14-20 businesses, mostly Western NY-linked.

Current focus

  • Seed/early-stage checks of $2M-$100M, equity stakes of 20-50%, active board involvement.
  • Recent bets cluster around accounting/bookkeeping automation (Botkeeper), workplace SaaS (HelloTeam), content ops (Heretto), plus a large legacy stake in Kodak.

What he cares about

  • Founder quality and "getting entrepreneurs closer to success" — he's explicit that his edge is capital plus operating experience from scaling Paychex.
  • Software that displaces manual back-office work (payroll/accounting parallels are a recurring theme in his public comments).

Recent moves / sensitivities

  • Sept 2025: converted a $100M loan into Kodak equity, becoming its largest shareholder after previously sitting on and leaving Kodak's board — signals patience with turnarounds but also scrutiny of his motives given the size of the position.
  • Now in his 80s; Grand Oaks is run day-to-day by CIO David Bovenzi and a small investment team, so outreach may route through staff rather than Golisano directly.

Questions to ask

  1. What did the Botkeeper diligence process reveal about accounting-firm adoption curves for AI bookkeeping tools?
  2. How does Grand Oaks think about roll-up economics vs. single-company bets in the accounting/bookkeeping software space?
  3. Would he or Grand Oaks have interest in co-investing or serving as an operating reference for a platform targeting accounting practices?

Outreach draft

Subject
Your Botkeeper investment and accounting roll-ups
Hi Tom, I'm building a diligence view on accounting/bookkeeping roll-up opportunities and your investment in Botkeeper stood out given your background scaling Paychex around the same pain point — manual, fragmented back-office work in accounting firms. Would you (or someone on the Grand Oaks investment team) be open to a 20-minute call to discuss what you saw in Botkeeper's model, how accounting firms are actually adopting AI bookkeeping tools, and where you think the next wave of value creation sits in this space? Happy to work around your schedule. Best, [Placeholder Name]

Linked companies

Sources