Michael Fletcher

Background

• Co-founded Sica | Fletcher in 2014 with Al Sica, formerly a senior partner at Hales & Company; the two were previously direct competitors before joining forces.
• Firm is the S&P Global #1-ranked insurance M&A advisor by deal count every year since 2017, with $19B+ in closed agency/brokerage transactions.
• Based in New York, NY.

Current Focus

• Running a high-volume sell-side advisory practice for insurance agencies and brokerages (dozens of closings per year, including a steady cadence of ALKEME, High Street, World Insurance Associates, and Hilb Group buyouts in 2025-2026).
• Advised the investor consortium behind Acrisure's $2.9B management-led buyout — a landmark deal structure putting majority ownership back with agency partners and management.

What He Cares About

• Deal complexity and cost of capital's effect on valuations — has publicly flagged high rates as a headwind to transaction volume.
• Positioning Sica | Fletcher as the trusted advisor for maximizing exit value for mid-market agency owners.

Sensitivities

• Deeply embedded with strategic acquirers (Brown & Brown, Acrisure, High Street, ALKEME) — treat him as a market-maker, not a neutral source; assume any conversation may circulate among his buyer relationships.
• Firm's business model depends on deal volume staying high, so read his market commentary with that incentive in mind.

Questions to Ask

1. Which acquirers are currently most aggressive on multiples for lower-middle-market brokerages, and has that shifted with rate moves in 2026?
2. How is the Acrisure-style management-buyout structure being replicated elsewhere, and would he flag any similar targets?
3. What's he seeing on seller expectations vs. buyer discipline right now — is the gap widening or closing?