Built Around the Founder
Windsor Drake was founded on a single conviction: the owner selling a company deserves representation as capable as the institutions sitting across the table. We built the firm to serve founder-led and family-owned businesses exclusively on the sell side.
Independence is not a marketing line for us; it is the structure of the firm. We take no lending relationships, run no research franchise for hire, and hold no proprietary capital that would compete with a client’s interests. When we advise an owner to accept, reject, or restructure an offer, that advice carries no agenda but theirs.
One Team, Two Markets
Our people work across offices in New York and Toronto, drawing on backgrounds in investment banking, private equity, and corporate development. It is a deliberately senior, cross-border team — deep enough to run a competitive process against sophisticated acquirers, lean enough that a principal is on every call. We hire deliberately for that model; open roles are listed on our careers page.
That reach matters. The right buyer for a founder’s company is often across a border or an ocean, and a process that reaches only the obvious domestic names leaves value on the table. We run North American and international outreach as a matter of course.
Research That Levels the Table
Founders sell once. The buyers across the table transact constantly, and they hold the information advantage — on valuation, on structure, on what a business like yours has actually changed hands for. That asymmetry is where owners lose value.
Windsor Drake closes it. We bring institutional-grade research and market intelligence to every engagement: sector maps, buyer behavior, valuation benchmarks, and deal-structure precedent — the kind of insight large corporates take for granted and most owners never see. We put that intelligence to work for the seller, so a founder walks into negotiation knowing at least as much as the party trying to buy the company.
Every Deal, Treated as Our Own
We take on a deliberately narrow set of engagements so senior bankers stay involved from first conversation to closing. We do not staff mandates with junior teams and step back. For the founder, the stakes are singular — the outcome of a career’s work. We treat every engagement accordingly.
