VCupid Skills – AI Fundraising Toolkit for Founders

A set of Skills that turn your startup profile into a full VC fundraising workflow: pipeline research, fund matching, partner profiling, outreach drafting, meeting prep, post-meeting debrief, term sheet analysis, and strategy.

Run commands in this order for a complete fundraising campaign:

/vcraise

/vclist

/vcposer <fund name>              # Is this fund real and active? Drop if score < 40.

/vcmatch <fund name>              # Does their mandate fit your startup?
/vcperks <fund name>              # What do they offer beyond the check?

/vcdevil                          # 10 lethal questions — know what to defend
/vcangel                          # 10 strongest signals — know what to lead with

/vcpartner <fund> <partner name>
/vcintro vcmatch-<fund>.md        # send outreach
/vclp vcmatch-<fund>.md           # attach the one-pager

/vcprep vcmatch-<fund>.md

/vcdebrief vcmatch-<fund>.md        # signal read, follow-up email, next step

/vcterm termsheet-<fund>.md         # clause analysis, score, negotiation priority list

/vctrack

File naming convention:

File	Purpose
STARTUP_PROFILE.md
Your startup data — update as traction grows
vclist.md
Master fund pipeline
vcposer-<fund>.md
Poser check — fund vitality, thesis authenticity, lead capacity
vcmatch-<fund>.md
Deep analysis per fund
vcperks-<fund>.md
Perks breakdown — value beyond capital, scored by relevance
vcpartner-<fund>-<name>.md
Partner brief
vcintro-<fund>.md
Outreach drafts
vclp-<fund>.md
Fund-specific one-pager
vcprep-<fund>.md
Meeting prep
vcdebrief-<fund>.md
Post-meeting debrief — signals, follow-up email, next step
vcterm-<fund>.md
Term sheet analysis — clause scores, negotiation priority list
vctrack.md
Pipeline dashboard — status of all funds at a glance
vcraise.md
Fundraising strategy
vcdevil.md
Adversarial stress-test — 10 lethal questions
vcangel.md
Champion's brief — 10 strongest signals to lead with

These commands are available as the vcupid

Claude Code plugin. Install with a single command — works in Claude Code web or CLI:

curl -fsSL https://raw.githubusercontent.com/maxoliverbr/vcupid-plugin/main/install.sh | bash

The script clones the plugin to ~/.claude/plugins/vcupid/

, registers it in ~/.claude/plugins/installed_plugins.json

, and enables it in ~/.claude/settings.json

. It is idempotent — safe to re-run to update.

Restart Claude Code. All /vc*

commands will be available in any directory that contains a STARTUP_PROFILE.md

.

Local development install #

If you've cloned the repo locally, you can install from the clone directly:

cd ~/dev/vcupid-plugin && bash install.sh

This registers the local clone path so edits to skill files take effect immediately without re-running the installer.

Manual installation #

Register in ~/.claude/plugins/installed_plugins.json:

"vcupid@local": [{
  "scope": "user",
  "installPath": "/home/<you>/dev/vcupid",
  "version": "1.0.0",
  "installedAt": "<ISO timestamp>",
  "lastUpdated": "<ISO timestamp>"
}]

Enable in ~/.claude/settings.json:

"enabledPlugins": {
  "vcupid@local": true
}

Keep Every new traction milestone (signed LOI, new partnership, first revenue) changes what funds you can approach and what you can say. Update it and re-runSTARTUP_PROFILE.md

current./vcraise

monthly.Run A 40/100 fit score is a no-go — don't write the email./vcmatch

before spending time on outreach.Use Variant B ( A forwarded intro converts at 5–10x the rate of cold outreach./vcintro

) over cold email whenever a warm path exists.The vcprep is for rehearsal, not for the room. Print it, rehearse it, then leave it behind — the meeting is a conversation, not a recital.Run Memory fades fast and the follow-up email loses impact after 24 hours. Don't wait until the next morning./vcdebrief

the same day as the meeting.Share The term sheet analysis tells you what to fight for — your lawyer tells you how to fight for it without blowing the deal./vcterm

output with your attorney, not instead of one.Run If you're working 5+ funds in parallel, the pipeline table is the only way to see what's stale and what needs a nudge./vctrack

before every weekly review.Want to add or change a skill? SeeContributingbelow.

All commands read STARTUP_PROFILE.md

from your current working directory. Create this file before running any command.

Create a markdown file in your project root with the following structure. The more detail you provide, the more specific and accurate every command output will be. Vague inputs produce generic outputs.

## I. Company Overview
| Field | Detail |
|-------|--------|
| **Startup Name** | [Legal company name] |
| **One-Liner** | [One sentence: what you do and for whom] |
| **Core Problem** | [The specific problem you solve — include scale/urgency] |
| **Solution** | [What you built and how it works — be technical if relevant] |
| **Key Value Prop** | [The headline outcome you deliver: time saved, cost reduced, etc.] |
| **Category** | [e.g., Deep Tech / Infrastructure / Climate / SaaS] |
| **Location & Founded** | [City, State, Country. Month Year.] |
| **Website** | [URL] |

## II. Market & Business Model
| Field | Detail |
|-------|--------|
| **Target Customer** | [Specific buyer — not "enterprises", but "grid operators at electric cooperatives"] |
| **Market Opportunity** | [Beachhead TAM with source. Expansion path.] |
| **Business Model** | [How you charge: SaaS, value-based, usage, marketplace, etc.] |

## III. Traction & Milestones
| Field | Detail |
|-------|--------|
| **Product Stage** | [Idea / MVP / MVBP / Revenue / Growth] |
| **Product Launch** | [Target date or "Live as of [date]"] |
| **Traction** | [Be specific: design partners, LOIs, revenue, pilots, grants, gov partnerships] |
| **Referral** | [Any warm contacts who can open VC doors — Name, email, relationship] |

## IV. Team
| Role | Name | Key Highlights |
|------|------|---------------|
| **CEO** | [Name] | [3–5 most relevant credentials for investors] |
| **CTO** | [Name] | [3–5 most relevant credentials for investors] |
| [Other] | [Name] | [Credentials] |

## V. Fundraise
| Field | Detail |
|-------|--------|
| **Raise Amount** | [$XM] |
| **Instrument** | [SAFE / Priced Seed / TBD] |
| **Use of Funds** | [Top 3 line items] |
| **Milestone this raise funds** | [What you'll have accomplished when the money runs out] |

Tips for a strong profile:

• Use specific numbers everywhere: "$5M DOE proposal", "38,000-member LinkedIn group", "$30.2M transmission project" — not "large DOE proposal"
• Name your referrals with contact info — the outreach commands use them
• Describe the problem with the urgency a VC would feel, not just the solution you built
• List credentials that matter to investors, not your full resume

Start here. Synthesizes your profile and any existing vcmatch/vclist files into a full strategy.

/vcraise

Reads: STARTUP_PROFILE.md

• any vclist.md

and vcmatch-*.md

in the current directory

Saves: vcraise.md

Output sections:

• Current State — honest assessment of what you have and what's missing
• Raise Parameters — recommended amount, instrument, valuation cap, timeline
• Sequencing Strategy — who first, parallel vs. sequential, how to create urgency
• Milestone Map — which proof points unlock which tier of investors
• Month-by-Month Timeline — from today through close
• Risk Factors & Contingencies — what derails the raise and the fallback for each
• This Week — Next 3 Actions — concrete, specific, doable in 7 days

Research the VC landscape and produce a ranked list of 15–20 funds to target.

/vclist

Reads: STARTUP_PROFILE.md

Saves: vclist.md

Output: Three tiers of funds with rationale and suggested contact angle per fund:

Tier 1 — Pursue Now: Strong fit, correct stage, warm path existsTier 2 — Warm Up First: Good thesis fit, missing proof point or introTier 3 — Monitor: Stage mismatch or unclear path — revisit later

Run this before /vcmatch

to know which funds are worth the deep analysis.

Pre-filter funds from your pipeline before committing to a full match analysis. Runs 8 evidence-based checks on whether a fund is actually active and writing checks — independent of whether their thesis fits your startup.

/vcposer <VC Fund Name>

Example: /vcposer "Slow Ventures"

or /vcposer a16z

Reads: STARTUP_PROFILE.md

(for stage/sector calibration)

Saves: vcposer-<fund>.md

Output — Poser Score (0–100) across 8 checks:

Fund Vitality— Last investment date. >18 months silent = zombie risk.** Fund Health**— Active fund with dry powder? Key partner departures?** Thesis Authenticity**— Does their portfolio actually match their stated sector thesis?** Lead vs. Follow**— Evidence of leading rounds, not just co-investing.** Stage Honesty**— Stated stage vs. actual entry stage of recent investments.** Check Size Reality**— Stated range vs. observable deal sizes.** Signal-to-Check Ratio**— Conference/content volume vs. actual new deals.** Founder Sentiment**— Public feedback patterns — ghosting, slow decisions, reneging.

Verdict tiers:

Legit (80–100): Active fund, real checks. Proceed to/vcmatch

.Probable (60–79): Yellow flags — prioritize if fit is strong, clarify open questions.Watch List (40–59): Material poser signals. De-prioritize unless a warm intro exists.Likely Poser (0–39): Don't waste cycles. Move to the next fund.

vcposer ≠ vcmatch.Poser Score answers "is this fund real and active?" Vcmatch answers "does their mandate fit our startup?" You need both. A fund can be fully legit but wrong for your stage — and a fund can claim a perfect thesis but be a zombie. Run/vcposer

first, then/vcmatch

only for funds that score 60+.

Deep research on a single fund against your startup profile. Spawns 4 parallel domain research sub-agents, synthesizes the results into a structured report, and scores the match across 8 dimensions summing to /100.

/vcmatch <VC Fund Name>

Example: /vcmatch a16z

or /vcmatch "Lowercarbon Capital"

Reads: STARTUP_PROFILE.md

Saves: vcmatch-<fund>.md

How it works: Four sub-agents run in parallel — Thesis & Mandate, Portfolio Intelligence, People & Network, and Deal & Process — each with domain-specific search queries. The main agent synthesizes all four returns and scores the fit.

Output sections:

• Firm Snapshot — founded, model, key GPs, standard deal, fund size, notable portfolio
• Investment Thesis & Current Focus — table with Theme / Signal / Verbatim Quote
• Portfolio Pattern Analysis — what the last 24 months of investments reveal about actual deployment priorities
• Key People — partner roster with background, sector focus, and access dynamics
• Fit Assessment — 8-dimension score table summing to /100
• Why It Works — positive signals with named portfolio analogs
• Key Risks & Objections — material mismatches with specific math
• Deal Process Intel — decision timeline, diligence style, known pass triggers
• Best Approach — intro strategy, lead-with bullets, avoid list
• Warm Intro Path — named intermediaries and specific actions, ranked by likelihood
• Diligence Questions to Prepare — 5–8 fund-specific questions
• Cold Email — subject + 4-sentence body with fund-specific hook
• LinkedIn Message — ≤150 chars
• Gaps / Things to Verify
• Sources
• Verdict — table including Recommended Action

Fit Score thresholds: 75–100 → Pursue · 50–74 → Warm Up First · 0–49 → No-Go

Run /vcmatch

before /vcpartner

, /vcintro

, /vclp

, or /vcprep

.

Understand what a fund delivers beyond the check before you sign. Researches the full value a fund delivers beyond the check — credits and services, but also brand signal, strategic expertise, media reach, policy access, and follow-on capital pathway — scored by relevance to your startup.

/vcperks <VC Fund Name>

Example: /vcperks a16z

or /vcperks "First Round Capital"

Reads: STARTUP_PROFILE.md

(for stage/sector calibration)

Saves: vcperks-<fund>.md

Part A — Financial Value (dollar estimates, [Confirmed]/[Reported] labels):

Cloud & Infrastructure— AWS/GCP/Azure credits, API platform discounts** Legal & Finance**— discounted counsel, accounting, cap table tools (Carta, Pulley)** Talent & Recruiting**— job boards, ATS discounts, executive recruiting relationships** Go-to-Market**— PR/comms support, CRM and sales tool discounts** Network & Introductions**— portfolio co. intros, LP relationships, co-investor paths** Operational Support**— office space, co-working, founder summits** Formal Programs**— structured accelerator tracks, office hours, mentorship

Part B — Non-Financial Value (impact ratings, qualitative assessment):

Brand & Signal Value— what the fund's name does for customer credibility, talent attraction, and future round momentum** Strategic Guidance & Pattern Recognition**— named GP expertise, comparable investments they've led, operating partners** Content & Media Amplification**— publishing access, newsletter reach, event speaking, social amplification** Policy & Regulatory Access**— government relations team, compliance guidance, agency relationships** Follow-on Capital Pathway**— pro rata appetite, reserve pool, bridge capacity, Series A syndication partners, fund lifecycle

Closes with a Gaps section (benchmarked against named peer funds) and a Questions to Ask the Fund Directly section from unresolved research.

For most seed-stage companies, the non-financial value — brand signal, strategic depth, follow-on pathway — is worth more over a 5-year relationship than the credits.

/vcperks

covers both.

Know who's in the room before you walk in. Research a specific GP's personal thesis, deals they've led, public writing, and how they map to your startup.

/vcpartner <fund> <partner name>

Example: /vcpartner a16z "Erin Price-Wright"

Reads: STARTUP_PROFILE.md

Saves: vcpartner-<fund>-<lastname>.md

Output sections:

• Background — career path and pre-VC experience
• Personal Thesis — what they personally care about, with direct quotes
• Deals They've Led — companies, stage, sector, why they backed them
• Public Writing & Key Quotes — specific essays and clips relevant to your startup
• Personal Touchpoints — conferences, topics they post about, shared background
• Fit Assessment — how this partner specifically maps to your team and problem
• Conversation Starters — 3 specific, sourced things to bring up in the meeting

Turn a vcmatch report into ready-to-send outreach. Three variants for every situation.

/vcintro <vcmatch-report.md>

Example: /vcintro vcmatch-a16z.md

Reads: STARTUP_PROFILE.md

• vcmatch report

Saves: vcintro-<fund>.md

Output — three variants:

Variant A — Cold Email: 4-sentence direct email to the target partner. Subject line references their thesis.Variant B — Warm Intro Request: A note to your referral contact (from your profile), ready to forward to the partner.Variant C — LinkedIn DM: 3 sentences. No deck link. Opens with the fund-specific hook.

Each variant uses the verbatim opening hook from the vcmatch report — never generic. The skill recommends which variant to use based on your available warm paths.

⚠️ If the vcmatch Recommended Action isNo-Go, this command will stop and tell you — don't send outreach to a no-go fund.

A one-page executive summary written entirely in the fund's language and framed around their thesis. Not a generic company description.

/vclp <vcmatch-report.md>

Example: /vclp vcmatch-a16z.md

Reads: STARTUP_PROFILE.md

• vcmatch report

Saves: vclp-<fund>.md

Output sections (≤500 words total):

• Headline — one-liner reframed in the fund's thesis language
• The Problem — uses the fund's own published framing
• The Solution — mapped to their portfolio language
• Traction — only the proof points that scored highest for this fund
• Market — sized in terms this fund cares about
• Team — only the credentials that matter to this fund
• The Ask — amount + milestone unlocked + timeline
• Why Now — fund-specific urgency tied to their thesis

⚠️ Each one-pager is fund-specific. Do not send to other funds without running/vcmatch <fund>

first.

Attach this to Variant A or B of /vcintro

.

Full prep for a pitch meeting: timed agenda, verbatim talking points per segment, preemptive answers to every diligence question from the vcmatch report, red flag rebuttals, and the exact ask.

/vcprep <vcmatch-report.md>

Example: /vcprep vcmatch-a16z.md

Reads: STARTUP_PROFILE.md

• vcmatch report

Saves: vcprep-<fund>.md

Output:

• 15-minute timed agenda (8 segments)
• Segment scripts: what to say, what to show, what NOT to say — for each segment
• Preemptive answers to every diligence question from the vcmatch report (with "if they push" follow-ups)
• Red flag rebuttals — one-liner responses for each vcmatch red flag
• The Ask — exact amount, 90-day plan, leave-behind action
• Meeting discipline — 3 rules for controlling the room

Before you pitch anyone, get destroyed first. A cocky, arrogant VC partner who's seen a thousand pitches like yours tears your startup apart with the 10 hardest questions he can find in your profile.

/vcdevil

Reads: STARTUP_PROFILE.md

Saves: vcdevil.md

Output: 10 lethal questions derived from your actual profile — not generic diligence, but the specific traps your startup walks into. Each question includes:

• A setup line in character (bored, contemptuous, or mocking)
• The question itself, phrased to sting Why this kills you— the exact vulnerability it exposes** What a real answer looks like**— the framework for a rebuttal that shuts him up

Run this before any outreach. The questions you can't answer in 30 seconds are the gaps to close first.

The other side of /vcdevil

. A seasoned VC partner who champions deals in the partner meeting surfaces the 10 strongest signals in your profile — not cheerleading, but pattern recognition. The things that make skeptics go quiet and interested.

/vcangel

Reads: STARTUP_PROFILE.md

Saves: vcangel.md

Output: 10 insights derived from your actual profile — the specific assets most investors would overlook or underweight. Each insight includes:

• A setup line in character (warm, perceptive, strategically excited)
• The insight itself, phrased as the angel would say it in the partner meeting Why this wins the room— the specific strength it names, with evidence from your profile** How to amplify this**— a coaching prompt for making the point land harder

Run this alongside /vcdevil

. Together they give you full-spectrum pitch prep: know what to defend, know what to lead with.

Turn your raw meeting memory into a structured debrief. Produces a signal read, an open diligence queue, a send-ready follow-up email, and a clear recommended next step.

/vcdebrief <vcmatch-report.md>

Example: /vcdebrief vcmatch-a16z.md

Reads: STARTUP_PROFILE.md

• vcmatch report (+ asks you for meeting notes)

Saves: vcdebrief-<fund>.md

Output sections:

• Meeting Summary — attendees, duration, format
• Signal Read — green (interest), yellow (hesitation), red (pushback) signals from the meeting
• Diligence Prediction vs. Reality — which vcmatch questions came up, which didn't, what surprised you
• Open Diligence Queue — every item raised in the meeting with a draft answer and deadline
• Pitch Landing Assessment — what from the vcmatch angle resonated vs. missed
• Follow-Up Email — send-ready, subject line and body, references something specific from the meeting
• Recommended Next Step — one of: Request Second Meeting / Send Deck / Send Data Room / Give Space / Drop Fund
• Updated Fit Signal — revised read on interest level vs. the vcmatch prediction

Run this within 24 hours of every meeting. The follow-up email degrades sharply after that.

Benchmark every clause in a VC term sheet against current market norms, flag founder-unfriendly terms, and produce a ranked negotiation priority list with suggested pushback language.

/vcterm <termsheet-file.md>

Example: /vcterm termsheet-a16z.md

Reads: STARTUP_PROFILE.md

• term sheet file

Saves: vcterm-<fund>.md

Output sections:

• Term Sheet at a Glance — instrument, amount, cap, discount, key dates
• Founder-Friendliness Score — /100 with breakdown (–15 per red flag, –5 per yellow flag)
• Clause Analysis Table — each term vs. market norm with 🟢🟡🔴 verdict
• Red Flag Deep Dives — real-world impact for each 🔴 clause
• Negotiation Priority List — ranked by founder harm, with suggested pushback language and likelihood of success
• Questions to Ask Before Signing — 5–8 diligence questions for the fund or your attorney

Verdict tiers:

85–100 — Founder-Friendly: Standard or better. Sign with standard review.** 65–84 — Acceptable**: Negotiate the reds.** 45–64 — Investor-Favorable**: Push back on all reds, escalate yellows.** 0–44 — Aggressive**: Get a second legal opinion before proceeding.

⚠️ This skill is informational only — it does not constitute legal advice. Share the output with your attorney before responding to the fund.

Scan all vcupid output files in the current directory and generate a single status table showing every fund's stage, scores, and next recommended action.

/vctrack

No argument needed. Reads from the current working directory.

Saves: vctrack.md

Output:

• Summary counts (total, active, no-go, stale)
• Pipeline table: Fund | Poser Score | Fit Score | Recommended Action | Stage Reached | Next Step
• Urgent Actions list — funds with missing follow-through flagged with the specific command to run

Run this any time to get a bird's-eye view of where your pipeline stands. Especially useful before investor update calls or weekly reviews.

Contributions are welcome — bug fixes, clearer skill instructions, new commands, and documentation improvements.

We seek help testing the skills in other tools (Opencode, Codex, Cursor...) and llms.

• Fork and clone the repo:

git clone https://github.com/<your-username>/vcupid-plugin.git
cd vcupid-plugin

• Install from your local clone (registers this path with Claude Code):

bash install.sh

Restart Claude Code. Skill changes inskills/

are picked up from the registered install path; you do not need to re-run the installer after every edit.

To validate skill structure (optional, requires skills-ref):

skills-ref validate skills/vcmatch/

install.sh

runs the same validation automatically when skills-ref

is on your PATH

.

Path	Purpose
skills/<name>/SKILL.md
Skill definition — frontmatter, invocation, execution steps, output rules
skills/<name>/references/
Optional templates (e.g. output-format.md ) linked from the skill
assets/
Shared assets (logo, STARTUP_PROFILE_TEMPLATE.md )
.claude-plugin/plugin.json
Plugin metadata for Claude Code
install.sh
Registers the plugin in ~/.claude/plugins/ and enables it in settings

Claude Code discovers skills from every skills/*/SKILL.md

file. There is no separate manifest to update when you add a folder.

• Open skills/<name>/SKILL.md

. - Keep the YAML frontmatter consistent with sibling skills ( name

,description

,license

,compatibility

,allowed-tools

,metadata

). - If the skill references an output template, update skills/<name>/references/output-format.md

in the same change when the on-disk report format changes. - Smoke-test in Claude Code: create a STARTUP_PROFILE.md

in a test directory, run the/vc*

command, and confirm the saved markdown matches the skill’s rules.

• Create skills/<command-name>/SKILL.md

(command name should match the folder, e.g.skills/vcmatch/

→/vcmatch

). - Follow the structure used by existing skills:

• Frontmatter with a one-line description

that includes usage (Usage: /vcfoo ...

) Invocation— syntax and examples** Execution Steps**— ordered steps the agent must follow** Output Format**/** Output Rules**— what to write and where to save (vcfoo-<fund>.md

, etc.)

• Frontmatter with a one-line
• Add optional references/output-format.md

if the report has a fixed section layout. - Document the command in this README under Commandsand, if it fits the fundraising flow, inFull Fundraising Workflow. - Run skills-ref validate skills/<command-name>/

if available.

• Branch from main

with a focused change (one skill or one doc area per PR when possible). - Describe what you changed and how you tested it (which /vc*

command you ran, and whether output looked correct). - Open a PR against main

on GitHub. Issues and ideas are also welcome viaGitHub Issues.

By contributing, you agree that your contributions are licensed under the same terms as the project (LICENSE).

source & further reading

github.com — original article