Christopher Gent

Background

• Co-Founder & Co-Head of M&A at Green Sail Capital Partners (Boston, founded 2023), a boutique sell-side advisory shop exclusively serving RIA and broker-dealer owners.
• Spent 20+ years in banking pre-Green Sail; built and ran LPL Financial's top-producing large-transaction M&A advisory team, setting records on deal value and revenue multiples.
• Earlier career: Tully & Holland (consumer-focused boutique IB), State Street Bank (Wells Fargo/Wachovia Securities merger), MFS Investment Management.

Current focus

• Running sell-side engagements for independent RIAs and broker-dealers navigating a hot but, in his view, precarious consolidation market.
• Publicly vocal (InvestmentNews, Aug 2026) that current 7x-18x EBITDA multiples and heavy use of rollover equity in consolidator deals are fragile — "one bad year" could collapse acquirer models.

What he cares about

• Deal structure and downside protection for sellers, particularly scrutiny of equity holdbacks/rollover stakes that sellers may be overvaluing relative to cash.
• Credibility and discipline in an industry he sees as prone to hype-driven pricing.

Sensitivities

• He is openly skeptical of the RIA roll-up/consolidator model — approach any aggregator pitch from a position that assumes he will pressure-test valuation and structure, not accept a growth narrative at face value.
• As a sell-side advisor, he may see a PE-backed acquirer as a counterparty to negotiate against, not simply a partner.

Questions to ask

1. Which specific deal terms (earnout structure, equity %, non-competes) do you see sellers most regretting 12-24 months later?
2. Where do you think the 7x-18x multiple range is headed over the next 18 months, and what would trigger a correction?
3. What separates a buyer sellers actively seek out from one they're wary of, in your current deal flow?