Plan a bridge or down-round conversation with my existing investors
A plan and talking points for raising an insider bridge or a lower-valuation round, with options, terms to expect, and how to keep trust.
The prompt
Help me prepare to ask my existing investors for a bridge round, or to discuss a round at a lower valuation.
Cash and runway today: [CASH, monthly burn, months of runway]
Why we need it: [e.g. "fundraise taking longer", "missed milestones", "market reset valuations"]
What the money would achieve: [MILESTONES and timeline it buys]
Last round terms: [valuation, preferences, investors and their ownership]
Investor relationships: [who is supportive, who has reserves, who is frustrated]
Plan B options: [cost cuts, venture debt, strategic sale, wind-down]
Build:
1. Options compared in a table: insider bridge (convertible note or SAFE), priced down round, venture debt, cutting to profitability, or a sale. For each: cash raised, dilution, control impact, signaling risk, and time to close.
2. Typical terms to expect for a bridge (discount, cap, interest, maturity) and in a down round (anti-dilution adjustments, pay-to-play), explained in plain English. Don't state market norms as fact; mark [CHECK WITH COUNSEL].
3. A milestone plan: what the bridge buys and how we'll prove progress, because investors fund milestones, not runway.
4. Sequencing: which investor to speak to first, and how to get a lead insider before going to the group.
5. Talking points for the first conversation: candid on what went wrong, clear on the plan, specific on the ask.
6. Effects on employees (options underwater, morale) and how to address them.
General information only: have a startup lawyer review terms, and check fiduciary and consent requirements with the board.
Highlighted [brackets] are blanks to replace with your own details.
Fill in the blanks and use this promptMore Finance & Accounting prompts
What to fill in
- CASH, monthly burn, months of runway
- MILESTONES and timeline it buys
- valuation, preferences, investors and their ownership
- who is supportive, who has reserves, who is frustrated
- cost cuts, venture debt, strategic sale, wind-down
- CHECK WITH COUNSEL
How this prompt is built
This prompt follows the RTF structure (Role, Task, Format). RTF tells the model who to be, what to do and what shape the answer should take. It is the quickest structure that still gives noticeably better results than a bare request.
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