Fundraising

War-game a fundraising deck before the room

War-game the fundraising deck so the room does not discover the soft joints for you.

Raise decks fail on growth claims that outrun cohort math, competitive claims without a primary source, an ask without a credible plan B, and risk language that disappears when the appendix is open. Fluency is not readiness. Readiness is surviving hostile seats with sources you can show.

What to freeze

Lock the round size, use of funds, runway claim, lead scenario, and the two next-best paths if the round slips. Attach the model tabs, pipeline evidence, and customer proof you are willing to defend. If a slide implies certainty the backup does not support, mark it before the models do.

Separate vision language from operating claims. Vision can be ambitious. Operating claims need dates, definitions, and tabs. Mixed slides are where diligence starts poking holes.

Hostile seating chart

  • Investor seat: returns path, concentration, and what would make them pass.
  • Customer seat: whether the product story matches delivery reality.
  • Competitor seat: cheapest narrative that undercuts the wedge.
  • Counsel seat: what you cannot say yet and what disclosure the deck implies.
  • Operator seat: hiring, burn, and the first ninety days after close.

Write each seat with a goal and a failure mode, not a personality cartoon. Example: "Investor: attack the returns path if growth slows one segment. Customer: name the promise that would break trust in onboarding."

Private failure loop

Run the deck through Pingpong with those seats named in the prompt. Sequential review lets an early pass expand the story while later passes try to kill unsupported claims. Keep a change log of claims removed, sources added, and numbers redefined. If a model invents a customer logo or a metric, delete it.

Treat diligence Q&A as part of the same war game. The questions you hope nobody asks are the ones to put in the brief first. Ask the models to generate the ten hardest diligence questions from each seat, then answer them in writing with sources. Gaps that remain become either deck edits or a conscious decision to leave a known risk on the table.

Related: before you raise, before you close the round, stress-test your deck, bulletproof before you present, role-play strategy review, and A-minus to A-plus review. Process: how to run a Pingpong.