Ask AI on a Deal

Where to find it

Ask AI lives on the deal page, the view you open from your pipeline.

• Desktop: at the top of the AI Intelligence panel on the right, click the box that reads Ask about this deal.
• Panel collapsed: click the speech bubble icon in the narrow strip on the right edge (the tooltip reads "Ask AI about this deal"). It opens Ask AI without expanding the panel.
• Mobile: open the Intel tab. The same box is at the top, and the conversation opens full screen.
• Keyboard: press / on the deal page when you are not typing in a field.

Type your question and press Enter to send. Shift+Enter adds a new line. Questions can be up to 1,000 characters. While an answer is being written you can click Stop.

What it reads

Ask AI answers from one deal at a time: the deal you have open. The line under the header ("Using: ...") shows the main sources it has for this deal. Hover over any item to see what it covers. Depending on the deal, that can include:

• The listing: asking price, financials, location and summary
• Your CIM: the analysis, the EBITDA audit lines and the text of the CIM pages
• Your private notes and logged activity (the newest 25)
• Broker emails matched to this deal (the newest 10)
• Mark's email thread for this deal
• Your calculator inputs and saved scenarios
• Tasks for this deal
• Your latest Pricing Report for the listing
• Market comps: how the asking multiple compares with similar listings

For general questions, such as what lenders usually look for, it can also use up to 2 Searcher OS playbook guides, cited as "Playbook: ...". Those are general guidance, never facts about this deal.

It never reads your other deals, other users' data, or the web. If the deal has no CIM yet, you will see "No CIM yet. Answers use the listing and your notes." with a link to upload one. If your CIM is still processing, answers use the other sources and include the CIM once it is done.

Citations and figures to double-check

Answers carry small numbered chips after the sentences they support. Click a chip to see the source and the exact text quoted from it. A citation to a CIM page includes a button that opens the CIM analysis. A calc chip marks a number Ask AI worked out, such as a margin, multiple or DSCR, and shows the formula and the inputs. Searcher OS rechecks those calculations. If a result is off, the calc chip shows the corrected value and says it was recalculated by Searcher OS. The answer text itself is not rewritten, so check the chip.

Every dollar amount, percentage and multiple has to sit in a sentence backed by a checked citation or a calc chip. A figure that is not is highlighted with a dotted underline, and the answer ends with "Some figures above could not be matched to a source." Treat highlighted figures as unverified and check them yourself before relying on them.

When the answer is not in the data

Ask AI will not guess this deal's numbers. If the deal's data does not answer your question, it says so plainly. Those answers come with an Add as a broker question button that opens an email to the broker so you can ask directly. If the deal has no CIM, you also get an Upload CIM button. When an answer suggests a next step, its button opens the matching form (log a note, email the broker, or upload a CIM). Where the answer suggested some text, the button copies it first so you can paste it in. Nothing is saved or sent until you do it yourself.

Suggested questions

A new conversation shows up to 4 suggested questions. They differ from deal to deal because each one is offered only when this deal's data can actually answer it. For example, a question about the lease appears only when a source mentions a lease, a question about the asking multiple needs market comps or a Pricing Report, a DSCR question needs a saved calculator scenario or calculator inputs, and add-back questions need a finished CIM. The suggestions also follow the deal's stage and the risks in its CIM, and they refresh when the deal gets new data, such as a new CIM, email or note.

Market comps as a source

Ask AI can tell you how the asking multiple compares with similar listings, using the same comparison as the market comps on your deal cards. On a paid plan or during the trial it can quote the median, the range and the number of similar listings. On the Free and The Hunter plans it gets the verdict only (for example, priced above most similar listings), so it will not give you those numbers. When a deal cannot be compared, for example because its figures are estimated, Ask AI tells you why. Comps are asking prices of listings, not sold prices.

Monthly question limits

• Monthly limits reset on the 1st of each month (UTC). The trial's 50 questions cover the whole trial.
• When you are close to your limit, the box shows how many questions you have left.
• A question that fails with an error does not count. An answer you stop after it has started does count.
• Questions on the example deal are free and never count.
• To keep things fair, there is also a limit of 6 questions a minute and 150 a day. If you hit it, wait and try again.

Once you reach your limit, the box is disabled and a notice shows the date your questions reset. Free and The Hunter accounts can upgrade from Settings → Billing.

Read-only accounts

If a payment fails, you keep full access, including Ask AI, for 7 days. After that the account is read-only until billing is updated: you can still open Ask AI and read past conversations, but you cannot ask new questions or clear a conversation. See Billing & Account.

Clearing a conversation

Each deal has one running conversation, and follow-up questions use its recent turns. To start fresh, click the ... menu at the top of Ask AI and choose Clear conversation. Cleared messages disappear from the app and are no longer used for follow-ups. Clearing does not give back questions you already used this month.

How long your questions are kept

Your Ask AI conversations are visible to you in the app for 90 days, and you can remove them sooner by clearing the conversation. Separately, we keep a copy of your questions and the answers for up to 12 months in restricted internal logs, used only to investigate problems and improve answer quality. Only authorized staff can access these logs. They are deleted when your account is deleted. See our Privacy Policy.

Rating answers

Under each answer you can give a thumbs up or thumbs down, and copy the answer. A thumbs down lets you pick what was wrong (Wrong number, Missing info, Not what I asked, Other) and add a short note.

Tips for good questions

• Ask about one thing at a time: "How much of the adjusted EBITDA is add-backs?"
• Name the source when it matters: "What did the broker say about the lease in their emails?"
• Upload the CIM first. Most detailed questions need it.
• Save a calculator scenario before asking what price it supports.
• Follow up in the same conversation instead of repeating context.

Limitations

• Ask AI only reads and answers. It never changes your deal, moves a stage, or sends email.
• It covers one deal at a time. It cannot compare deals or search the feed.
• It does not use the web or any data outside Searcher OS.
• It can still be wrong. Use the citations to check anything you plan to act on, especially highlighted figures.

Need Help?

Questions about Ask AI? Contact support.