To rehearse against a skeptical investor before a fundraising meeting, put the deck, the financial model, the retention and pipeline exports, and a short profile of the investor most likely to say no into one request. Then instruct Pingpong to argue as that investor: open with the reason they would pass, press every metric the exports do not support, and say what would have to be true for them to keep going. Do it before the partner meeting, while metric definitions can still change.
This page is for founders and chief executives raising a priced round, or asking existing investors to lead an inside round. For a director deciding a board vote, see role-play the skeptical director. For the written letter to your current cap table, see war-game an investor update before you send it. Executive starting points live under Pingpong for executives.
What a skeptical investor tests
An investor who is leaning toward a pass usually has one main reason and looks for evidence to confirm it. The common reasons are a market smaller than the deck claims, retention that looks better than it is because of a price increase or one large account, customer acquisition cost that leaves out the salespeople, and a use of funds that spends on growth before the growth engine is proven. These problems usually come from how the team defined each metric months ago.
Many funds decide at a partner meeting where your champion presents to partners who have never met you. The investor you need to rehearse against is often one of those partners, so the profile you give Pingpong should describe that person: the companies in your category they passed on, the metric they always ask about, and what they said the last time a similar deal came up.
A worked example
This example is illustrative and does not describe a customer. A 38-person company sells scheduling and payroll software to independent restaurant groups. It has $3.1 million in annual recurring revenue, up 2.4 times in a year, and is raising a $14 million Series A. A partner at the likely lead fund will present it at Monday's partner meeting.
The request names one reader: a partner at that fund who has passed on two restaurant software companies, citing small-business churn both times, and who asks every founder for fully loaded payback.
A useful pass opens with churn. The deck shows net revenue retention of 118 percent, but a price increase in the second quarter accounts for most of it, and logo churn in the export runs about 2 percent a month. The 9-month payback on slide 8 counts only paid marketing and leaves out the four account executives hired in the third quarter. The market slide counts every restaurant in the country, while the customers in the export are groups with 3 to 20 locations. The use of funds puts 60 percent into sales hiring before the current reps have a full year of results.
The chief executive makes changes before Monday. Retention is shown with and without the price increase. Payback is restated fully loaded at 14 months, with the quarterly trend beside it. The market slide is rebuilt from the count of restaurant groups in the target range multiplied by current contract value. Sales hiring is split into two stages, with the second tied to rep productivity. The chief executive also writes a one-page note the champion can forward, answering the churn question directly.
When the investor is already on your board
In an inside round, the skeptic may be a current investor deciding whether to take its full share, and other funds will ask that investor why. Run the role-play as that director, using what they said at recent board meetings, and ask what they would tell an outside fund that called for a reference.
A request you can copy
Below are my fundraising deck, financial model, retention and pipeline exports, and a profile of the investor most likely to pass. Role-play as that investor for the whole reply. Open with the main reason you would pass. Then list every metric or claim you would challenge, quote the slide or cell, and say what the attached data actually shows. Tell me what would have to be true for you to take this to your partners, and which question your partners would ask that I have not answered. Stay in the investor's seat. Don't rewrite the deck for me.
Paste the cohort export, the hiring plan, and notes from earlier calls with that fund.
How Pingpong runs the role-play
The web review app sends your request through several models in order. Each later model receives the original request and every earlier answer, with instructions to assess the work so far. Check every flagged figure against the export before you change a slide. For the steps inside the app, see running your first review.
What a model can't role-play
A model does not know what a fund's partners said about your category last month, how much reserve capital the fund has left, or whether another company in its portfolio competes with yours. Securities and disclosure questions belong with your counsel.
When the round needs board approval, see war-game a decision before the board meeting. More guides live under work decisions before you commit.