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The Motley Fool · May 6, 2026

Datasite's CEO on what deal data shows and where AI agents fit in M&A

The Motley Fool's Asit Sharma interviews Datasite CEO Rusty Wiley about what the company sees in its deal data and how AI agents fit into buy-side and sell-side work. Worth watching for his read of deal trends and his case for keeping AI inside permissioned data rooms. The platform claims are his own.

  • Rusty Wiley · CEO, Datasite
  • Asit Sharma · Senior analyst and lead advisor, The Motley Fool
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Key points
  • Wiley says deals usually start on Datasite about a year before they become public, and that first-quarter M&A starts on the platform were up 22% year over year, 42% in the Americas.
  • He puts the current deal success rate at about 34%, down two points, based on outcome data that clients provide.
  • Sell-side teams can use agents to find diligence hotspots, such as change of control provisions in HR contracts, before a sophisticated buyer finds them.
  • Wiley argues that uploading data room content to a file store for LLMs gives up the controls on confidentiality and compliance that permissioning and audit trails provide.
  • He expects sophisticated firms to work from their own Claude or ChatGPT environments through an MCP server, and most others to want AI inside the data room.
  • In private equity, he says, value now has to be created while you own a company rather than at the purchase.

A deal usually shows up in a data room about a year before anybody hears about it in public. That is Rusty Wiley's claim, and as CEO of Datasite he uses it to explain why the exhaust from a data room is worth something. By his count, M&A starts on the platform were up 22% year over year in the first quarter, with the Americas up 42%. Healthcare is sort of on fire, he says, industrials are doing quite well, and in software deals are taking longer with what's going on with AI (around 7:05).

“Now you can just have an agent go read all of them and come back and tell you, by the way, from that secure environment, here are 12 HR contracts that have a change of control provision that you need to analyze because the buyer is going to do the same thing on the other side if they're sophisticated, and they'll find these things along the way.”

Rusty Wiley, CEO, Datasite

Asit Sharma, senior analyst at The Motley Fool, does the interviewing, so this is a CEO describing his own company, and the platform figures are his. He says Datasite hosts about 55,000 deals a year and around 3.5 billion pages, with about 200,000 active users a month. He stresses that the first mission is to protect the data in the data room and that trend data is anonymised. Deal success rates, he says, are about 34% right now and down two points, based on outcomes that companies using the product provide.

“As opposed to just taking all of the content and uploading it into a file store and then allowing LLMs to effectively work against that, you don't have strong controls on protecting confidentiality or supporting compliance, particularly in regulated industries.”

Rusty Wiley, CEO, Datasite

For sellers, Wiley describes benchmarks across 48 sub-industries. Datasite could tell you how many similar deals are actively preparing, how long preparation typically takes before launch, and how long diligence lasts. A long preparation period, he says, usually indicates it takes more work to prepare the asset. A very short diligence period often means a bilateral market: one seller, one buyer, reaching agreement fairly early. He says this insight goes through the seller's banking partner, and that Datasite is not trying to disintermediate or sit in the middle.

“There was an old saying that you can make your money at the time you acquired the company, not the time you sold the company, right? Which is pretty common in private equity. I think that's changed, that you've got to create the value while you own the company.”

Rusty Wiley, CEO, Datasite

The diligence point most readers will recognise is preparation. Data rooms can hold 5 million pages, Wiley says, and today you find problems a document at a time. His example is change of control provisions in HR contracts: an agent can read all of them inside the secure environment and come back with the dozen that need analysis (around 17:18). The reason to do it as a seller, he says, is that a sophisticated buyer is going to do the same thing on the other side. Escalating commercial contracts are another of his examples.

“The risk for everyone right now, and it's very obvious, is what happens with the labs and the LLMs, and being able to the best of your ability anticipate how you make that an asset within your business and within your platform or within your software as opposed to it becoming a competitor to your platform.”

Rusty Wiley, CEO, Datasite

On the buy side, his example is mid-market private equity, which gets many teasers and CIMs. Wiley says clients on BlueFlame, the agentic AI company Datasite acquired, use it to read the inbound emails, summarise the CIM, check it against what the firm has been interested in before, draft an investment committee memo and build an LBO model. The bigger gain, in his account, comes when clients connect it to their internal systems: previous deals, messaging, calendars, email, and why they did or did not pursue companies in the past.

The security argument is the one to take into any vendor conversation. Wiley says everything on Datasite is permissioned down to the paragraph and audit ready, with the agentic tools layered on top. Taking all the content, uploading it into a file store and letting LLMs work against it leaves you without strong controls on confidentiality or compliance, particularly in regulated industries, he says. Datasite's route is an MCP server, which he calls a fancy name for collecting your APIs and putting them in one place. He says an announcement on working with Anthropic, OpenAI and Copilot through it was coming, and that it went from decision to operational in four weeks.

He sees two kinds of users. Hyper-sophisticated buyers and sellers will build their own environments in Claude or ChatGPT and reach the data room from there. An enormous number of people in the ecosystem, he says, just want to do a transaction. They want to be in the data room they are familiar with and ask a question about contracts or HR agreements from a side panel.

How Datasite got here is a short history of the category. Wiley joined Merrill, a 40-year-old financial printer, about 12 years ago, sold every other business in about two years and kept the data room. He says the team migrated the entire customer base to a new platform in 12 months. Under CapVest it bought Firmex in Canada and Ansarada in Australia, then Grata, an AI private company database with about 20 million profiles, Sourcescrub, and BlueFlame, a team of about 50 focused on M&A agentic workflows.

His view of the risk applies to every software vendor in this market: whether the labs and LLMs become an asset inside your platform or a competitor to it. The bigger risk, he says, is losing pace, and just bolting on some AI to defend the existing business. On private equity he makes a broader point. There was an old saying that you make your money when you buy the company, and he thinks that has changed: you have to create the value while you own it.

Why it matters

If you plan to run AI over a data room, ask whether permissions and audit trails follow the documents into the model, and whether your deal data feeds anonymised benchmarks. Wiley's change of control example is an easy first test for any sell-side team.

Summary and analysis by VirtualData-Room.com from the public video. Play it above; the original source is linked there.

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