Windsor Drake EngagementLast reviewed September 3, 2026
By Jeff Barrington, Founder and Managing Director
In brief
Approach Response is Windsor Drake’s engagement for founders who have received an unsolicited acquisition offer. Windsor Drake evaluates the offer against market evidence and establishes what the same business would clear in a competitive process. The first conversation is free and confidential, with no obligation to proceed. Windsor Drake works sell-side only and accepts fewer than 20 mandates per year, with the same senior advisor on each engagement from first call to close.
An unsolicited acquisition offer usually arrives by email, from a corporate development team at a company that buys businesses for a living. Approach Response is the Windsor Drake engagement built for founders in exactly that position. The sections below explain what the engagement is and what a founder should avoid doing before the first conversation.
Approach Response is Windsor Drake’s advisory engagement for founders who hold a live acquisition offer they did not solicit. Windsor Drake evaluates the offer against market evidence and establishes what the same business would clear in a competitive process. From that baseline, Windsor Drake either negotiates with the inbound buyer or opens the field to competing bidders, depending on what the founder wants.
Windsor Drake is a sell-side M&A advisory firm with offices in New York and Toronto, led by Managing Director Jeff Barrington. The firm represents founder-led technology companies in the lower middle market, with enterprise values of $5 million to $300 million. Windsor Drake accepts fewer than 20 mandates per year and works sell-side only, with no buy-side engagements. It does not raise capital, and when a transaction requires a registered broker-dealer, that work is handled by a registered broker-dealer partner.
A serial acquirer sends outbound offers because buying companies before they reach the open market is the cheapest way to buy them. Corporate development teams at consolidators run standing sourcing programs, and an email that praises the business and floats a conversation is the first step of a pipeline, not a compliment.
An offer made before any competing bidder exists is priced for the absence of competition. Whether the sender is a strategic operator or a private-equity-backed platform changes the playbook the founder is facing, and Windsor Drake breaks down that difference in strategic buyers vs financial buyers.
The Proprietary Discount is the gap between what a serial acquirer pays in an unbanked bilateral negotiation and what the same business clears in a competitive process. The discount exists because a single buyer negotiating against no one prices the deal against the founder’s uncertainty rather than against a market.
Windsor Drake measures that gap across lower-middle-market technology transactions and will publish the measurement quarterly as The Windsor Drake Proprietary Discount Index. No index readings are published yet, and Windsor Drake quotes no single discount percentage, because the gap moves with buyer concentration, sector, deal size, and structure. The direction is consistent: founders negotiating alone against one buyer accept less than founders whose businesses face competing bidders.
In the first 72 hours after an inbound offer, a founder should reply politely and commit to nothing. A confidential call with a sell-side advisor belongs in the same window, before any information changes hands.
| Reply cordially within two or three business days | Name a price or a valuation expectation |
| Ask what prompted the interest and how the acquisition would be funded | Sign an exclusivity agreement or a letter of intent |
| Save every email and log every call | Send financial statements before a signed NDA |
| Take a confidential call with a sell-side advisor | Say “I have no advisor” or admit the company has never run a process |
Each item in the second column surrenders negotiating ground permanently. A number stated by the founder becomes a ceiling in every later round. Exclusivity ends competition before competition exists. Financials shared without an NDA hand the buyer free diligence, and the phrase “I have no advisor” tells a corporate development team that The Proprietary Discount can be applied in full.
The first call is a confidential working session with a senior Windsor Drake advisor, and the founder leaves with a candid read on whether the offer is worth pursuing. The conversation covers the offer itself and the buyer’s acquisition history. A general sense of revenue and EBITDA is enough; no prepared materials are required.
Windsor Drake states the terms plainly: every conversation is confidential and without obligation, and nothing is shared without the founder’s consent. The call carries no commitment to run a process. Some first calls end with Windsor Drake advising the founder that the offer is not worth engaging, and that answer costs nothing.
No. Credible buyers expect representation, and an acquirer that has completed multiple deals has sat across from advisors on most of them. A buyer who threatens to walk away because the founder retained a sell-side advisor is revealing that the offer depended on the founder negotiating alone.
Windsor Drake runs controlled, confidential processes engineered to create competitive tension. Buyer outreach is senior-level and under NDA before any identifying information is shared, and company identity and financials go only to vetted parties. The full sequence, from preparation through diligence to close, is documented in the sell-side M&A process explained.
Approach Response does not require a full auction, and accepting the inbound offer at an improved price is a legitimate outcome. A founder can engage Windsor Drake to negotiate with the single inbound buyer from an informed position, with market evidence replacing guesswork on valuation and structure.
A founder who wants competition can widen the field. A full Windsor Drake process reaches the strategic operators and private equity platforms best placed to compete, and usually closes in about six months from engagement. The timeline moves with business type and with how quickly buyers complete diligence; a bilateral negotiation with one buyer compresses the outreach stages and closes faster.
Founders weighing the paths side by side can start with the offer received hub, which maps every scenario from a lowball first email to a signed letter of intent.
Contact Windsor Drake for a confidential conversation about the offer. Every inquiry is treated as strictly confidential, and nothing is shared without the founder’s consent. Windsor Drake operates from 375 Park Avenue in New York and 95 St Clair Avenue West in Toronto, and a senior advisor follows up directly.
Last reviewed July 28, 2026 by Jeff Barrington, Founder and Managing Director, Windsor Drake. Content on this page may be cited with attribution and a link to https://windsordrake.com/approach-response/
The Proprietary Discount
The Proprietary Discount is the gap between what a serial acquirer pays in an unbanked bilateral negotiation and what the same business clears in a competitive process. Windsor Drake publishes the measurement as The Windsor Drake Proprietary Discount Index.
FAQ
No. Every conversation is confidential and without obligation, and nothing is shared without the founder’s consent.
Windsor Drake’s core practice is sell-side representation. The firm also advises on capital, bank sponsorship and specialty finance, and does not represent an acquirer against a company it also represents. The founder’s sale outcome is the only outcome Windsor Drake is compensated on.
No. A number stated by the founder becomes a ceiling in every later negotiating round. Windsor Drake advises founders to withhold valuation expectations until market evidence establishes the range.
The Windsor Drake Proprietary Discount Index is a quarterly measurement of The Proprietary Discount, the gap between what serial acquirers pay in unbanked bilateral negotiations and what the same businesses clear in competitive processes. Windsor Drake will publish readings quarterly; no readings are published yet.
A Windsor Drake sale usually closes in about six months from engagement. A bilateral negotiation with a single inbound buyer moves faster because the outreach and marketing stages compress.
Windsor Drake represents founder-led technology companies in the lower middle market, with enterprise values of $5 million to $300 million, from its offices in New York and Toronto.
The senior Windsor Drake professional who wins the mandate runs the engagement from first call to close, with no handoff to junior staff. Windsor Drake is led by Managing Director Jeff Barrington and accepts fewer than 20 mandates per year.
No, that order destroys negotiating position. A signed letter of intent usually grants the buyer exclusivity, which ends competition and fixes the headline price before an advisor can test the market. Founders should take a confidential advisory call before signing anything.
Windsor Drake advises founder-led companies on sell-side M&A. A first conversation is confidential and starts with your numbers.
General information, not legal, tax or investment advice. Every transaction turns on its own facts and documents.
