Startup Analysis

Startup Analysis

Produces a multi-perspective analysis of a startup, examining it through three lenses that each reveal different aspects of company health and potential:

1. VC Investor Lens — Is this a good investment? Market size, unit economics, growth trajectory, team quality, defensibility 2. Job Applicant Lens — Should I work here? Equity value, runway risk, culture signals, career growth, compensation fairness 3. CEO/Founder Lens — How healthy is this company? Product-market fit, burn efficiency, competitive moat, organizational health

Each perspective surfaces insights the others miss. A company can be a great investment but a terrible place to work (or vice versa). The goal is to give the user a 360-degree view so they can make informed decisions.

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Step 1: Gather Information

Before analyzing, collect as much public information as possible about the startup. Use web search, the company's website, Crunchbase data, press coverage, and any other available sources.

Key data to gather:

If certain data isn't publicly available (e.g., revenue for private companies), note the gap and infer what you can from indirect signals (hiring pace, customer logos, web traffic proxies, job postings).

When information is insufficient

Many startups — especially early-stage or niche ones — have limited public presence. If web search does not return enough information to produce a meaningful analysis (e.g., you can't determine what the company does, who founded it, or how it's funded), ask the user to provide the company's website URL before proceeding. The company website is often the single most information-dense source, and reading it directly (about page, pricing page, team page, blog) can fill most gaps.

You can also ask the user for:

• The company's website or landing page URL
• A Crunchbase, LinkedIn, or PitchBook link
• Any pitch deck, job listing, or press article they have
• Specific context they already know (e.g., "they just raised a Series A from Sequoia")

It is better to ask for a URL and produce an accurate analysis than to guess and produce a misleading one.

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Step 2: Determine Which Perspectives to Cover

By default, produce all three perspectives. If the user specifies a particular angle (e.g., "I'm considering joining them" or "should I invest"), emphasize that perspective but still include the others as context — they often reveal relevant information.

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Step 3: Analyze from Each Perspective

Read the relevant reference files for the detailed framework for each perspective. These contain the specific criteria, metrics, and red/green flags to evaluate.

VC Investor Analysis

Read references/vc-framework.md for the full evaluation framework.

Core areas to assess:

• Market opportunity — TAM/SAM/SOM, market timing, secular trends
• Product & traction — Product-market fit signals, growth metrics, retention
• Unit economics — CAC, LTV, margins, burn multiple, path to profitability
• Team — Founder-market fit, technical depth, hiring ability
• Defensibility — Moats (network effects, switching costs, data, brand, regulatory)
• Deal terms context — Stage-appropriate valuation, comparable exits

Produce a clear Investment Thesis (bull case) and Key Risks (bear case). End with a verdict: Strong Pass / Lean Pass / Lean Invest / Strong Invest, with reasoning.

Job Applicant Analysis

Read references/job-applicant-framework.md for the full evaluation framework.

Core areas to assess:

• Financial stability — Runway, burn rate, funding trajectory, revenue health
• Equity value — Option/equity package analysis, dilution risk, liquidation preferences, realistic exit scenarios
• Career growth — Role scope, learning opportunity, resume value, mentorship
• Culture & work-life — Glassdoor signals, employee tenure data, leadership style
• Product & market risk — Is PMF real? What happens if the startup fails?
• Red flags — High turnover, constant pivots, vague metrics, founders cashing out

Produce a clear Why Join (pros) and Watch Out For (risks). End with a verdict: Strong Pass / Lean Pass / Lean Join / Strong Join, with reasoning.

CEO/Founder Analysis

Read references/ceo-framework.md for the full evaluation framework.

Core areas to assess:

• Product-market fit — Retention curves, organic growth, Sean Ellis test proxy
• Growth efficiency — Burn multiple, CAC payback, magic number
• Competitive position — Moat strength, competitive dynamics, market share trajectory
• Organizational health — Hiring pipeline, attrition, team capability gaps
• Fundraising readiness — Metrics vs. benchmarks for next round, investor narrative
• Strategic risks — Platform dependency, customer concentration, regulatory exposure

Produce a clear Strengths to Double Down On and Urgent Areas to Address. End with a health grade: Critical / Struggling / Stable / Strong / Exceptional, with reasoning.

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Step 4: Synthesize Cross-Perspective Insights

After the three analyses, add a synthesis section that highlights:

1. Where perspectives agree — If all three lenses flag the same strength or weakness, it's probably real 2. Where perspectives diverge — A company can be VC-attractive (huge market) but employee-risky (high burn, low runway). Call these out. 3. The bottom line — One paragraph summary: what kind of company is this, what's its most likely trajectory, and what should the user do based on their stated (or implied) situation

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Step 5: Present the Report

Structure the output as a clean, scannable report:

# [Company Name] — Startup Analysis

## Summary
[2-3 sentence overview with key verdict]

## VC Investor Perspective
### Market Opportunity
### Product & Traction
### Unit Economics (if available)
### Team
### Defensibility
### Investment Verdict: [Strong Pass / Lean Pass / Lean Invest / Strong Invest]
[Reasoning]

## Job Applicant Perspective
### Financial Stability
### Equity Value Assessment
### Career Growth Potential
### Culture & Work-Life Signals
### Risk Factors
### Employment Verdict: [Strong Pass / Lean Pass / Lean Join / Strong Join]
[Reasoning]

## CEO/Founder Perspective
### Product-Market Fit Assessment
### Growth Efficiency
### Competitive Position
### Organizational Health
### Strategic Risks
### Health Grade: [Critical / Struggling / Stable / Strong / Exceptional]
[Reasoning]

## Cross-Perspective Synthesis
### Points of Agreement
### Points of Divergence
### Bottom Line

Adapt section depth to available data — if financials are completely opaque, say so and focus on what's observable. Don't fabricate metrics, but do make informed inferences and state your confidence level.

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Reference Files

• references/vc-framework.md — VC due diligence checklist with metrics, benchmarks, and red/green flags
• references/job-applicant-framework.md — Job seeker evaluation framework with equity analysis and culture assessment
• references/ceo-framework.md — CEO self-assessment framework with operational metrics and strategic analysis

Read these when you need the detailed criteria and benchmarks for each perspective.

startup-analysis

Multi-perspective startup analysis skill — evaluate any startup from VC investor, job applicant, and CEO/founder viewpoints.

What it does

Produces a comprehensive startup analysis by examining the company through three distinct lenses:

• VC Investor — Market opportunity, unit economics, team quality, defensibility, investment verdict
• Job Applicant — Financial stability, equity value, career growth, culture signals, employment verdict
• CEO/Founder — Product-market fit, growth efficiency, competitive position, organizational health, health grade

Each perspective surfaces different insights. A company can be a great investment but a terrible place to work (or vice versa). The skill cross-references findings to highlight where perspectives agree and diverge.

This skill uses web search to gather public information about the startup before analysis.

Triggers

• "analyze this startup", "evaluate [company]", "should I join [company]"
• "is [company] a good investment", "due diligence on [company]"
• "what do you think of [startup]", "research [company] for me"
• "startup assessment", "company analysis", "evaluate this company"
• Any mention of evaluating, analyzing, or assessing a startup from investment, career, or strategic perspectives

Platform

Works on Claude Code and other CLI-based agents (web search required). May work on Claude.ai with reduced data gathering capability.

Setup

# As a plugin (recommended — installs all skills)
npx plugins add himself65/finance-skills --plugin finance-startup-tools

# Or install just this skill
npx skills add himself65/finance-skills --skill startup-analysis

See the main README for more installation options.

Reference files

• references/vc-framework.md — VC due diligence checklist with metrics and benchmarks
• references/job-applicant-framework.md — Job seeker evaluation framework with equity analysis
• references/ceo-framework.md — CEO self-assessment with operational metrics

CEO / Founder Self-Assessment Framework

Detailed framework for a startup founder or CEO to assess their company's health, trajectory, and strategic position. This is the "view from inside" — honest self-assessment that surfaces what the founder might be too close to see.

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1. Product-Market Fit Assessment

Quantitative Signals

Qualitative Signals

• Are customers using the product without being asked/reminded?
• Are they pulling you into new use cases you didn't design for?
• Is word-of-mouth driving meaningful growth?
• Do customers complain more about missing features than about the core product?
• Would customers fight to keep the product if you tried to take it away?

Pivot vs. Persevere

Consider pivoting when:

• 18+ months in with no clear retention or engagement improvement
• Multiple customer segments tried, none sticking
• The team is solving the problem better than anyone but nobody cares about the problem
• The market window has closed or shifted

Persevere when:

• Retention is strong but growth is slow (distribution problem, not product problem)
• A specific segment loves it even if the mass market doesn't
• Usage is increasing within existing accounts
• You're seeing increasing organic pull from a defined customer persona

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2. Growth Efficiency

Key Operating Metrics

Runway Management

Burn Efficiency Questions

• Could you get to profitability (or "default alive") by cutting to just the core team?
• What's the minimum viable burn rate to maintain the product and key relationships?
• Is the marginal dollar of spend generating more or less revenue than the last one?

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3. Competitive Position

Moat Assessment

For each potential moat, rate its current strength (0-5):

Competitive Dynamics

• Direct competitors: Who's building the same thing? What's their differentiation?
• Indirect competitors: What do customers use instead of your product today (including doing nothing)?
• Platform risk: Are you building on top of a platform that could compete with you or cut you off?
• Big tech risk: Could a FAANG company build this as a feature? Would they?
• Open source risk: Could an open-source alternative emerge that's "good enough"?

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4. Organizational Health

Team Metrics

Organizational Health Questions

• Do you have the team to execute the next 12-month plan?
• What are the 3 most critical hires you need to make?
• Is there a single-point-of-failure person (if they leave, you're in serious trouble)?
• Are decisions being made at the right level, or is everything bottlenecked at founders?
• Is the team aligned on what success looks like this quarter?

Culture Assessment

• Do people disagree openly in meetings, or is conflict avoided?
• Is information flowing freely, or are there silos?
• Do people voluntarily recommend working here to friends?
• Are people excited about the product and mission, or just collecting a paycheck?

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5. Fundraising Readiness

Benchmarks by Stage

Fundraising Readiness Checklist

• [ ] Metrics trending in the right direction (not just a good month)
• [ ] Clear narrative: problem → solution → traction → market → team → ask
• [ ] Data room prepared: financials, cap table, key metrics dashboard, customer references
• [ ] Target investor list with warm intros identified
• [ ] Board alignment on timing and terms expectations
• [ ] 6+ months of runway remaining when starting the process

Investor Narrative

• What's the big vision that makes this a $1B+ company?
• What's the specific milestone this funding will help you hit?
• Why is now the right time to raise?
• What's your unfair advantage that makes you the team to win this market?

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6. Strategic Risk Register

Risk Categories

Health Grade Framework

Job Applicant Startup Evaluation Framework

Detailed framework for evaluating whether to join a startup as an employee. The core question: is the risk/reward tradeoff worth it compared to a safer, better-paying job at an established company?

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1. Financial Stability Assessment

Runway & Funding

How to research

• Crunchbase / PitchBook — Funding history, investors, valuation
• LinkedIn headcount — Is the team growing, flat, or shrinking?
• Job postings — Lots of openings = growth; few = maintenance mode; mass closings = trouble
• News — Recent layoffs, pivots, leadership changes
• Glassdoor — Employee reviews, especially recent ones mentioning "runway" or "funding"

Questions to Ask in Interviews

• "What's your current runway?" (they should answer openly; evasion is a red flag)
• "When do you plan to raise next, and how's that process going?"
• "What's your revenue trajectory looking like?"
• "Has there been any restructuring or layoffs in the past year?"

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2. Equity & Compensation Analysis

Understanding Your Equity

Equity Valuation Reality Check

To estimate what your equity might actually be worth:

1. Start with the last 409A valuation (ask for it) 2. Estimate realistic exit scenarios — Most startups don't exit at unicorn valuations. Model: acquisition at 2-5x last round, IPO at 5-10x, and failure (0) 3. Apply the preference stack — Subtract total investor preferences before calculating common share value 4. Apply dilution — Assume 2-3 more rounds of 20% dilution each 5. Probability-weight — ~70-80% of VC-backed startups fail. Even "good" ones often exit below the preference stack

Compensation Benchmarking

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3. Career Growth Assessment

Signals of Good Growth Potential

When Startup Experience Is Most Valuable

• Early in career (first 5-7 years): maximum learning, acceptable risk
• When switching functions: startups let you wear many hats
• When building founder skills: closest thing to founding without the risk
• When the startup's domain aligns with your long-term career direction

When It's Less Valuable

• Deep specialization needed: big companies have more depth
• Financial obligations (mortgage, family): startup risk may not be appropriate
• Late career with established reputation: incremental resume value is lower

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4. Culture & Work-Life Signals

Positive Signals

• Founders are transparent about challenges, not just hype
• Employee tenure is reasonable (2+ years for early employees)
• Clear values that show up in decision-making, not just a poster
• Engineers/ICs have voice in product direction
• Reasonable on-call and work hours expectations

Red Flags

• Glassdoor reviews consistently mention burnout, toxicity, or chaos
• "We're a family" language combined with 60+ hour expectations
• High turnover in leadership positions
• Founders talk about "crushing it" but can't articulate product strategy
• No clear onboarding process or role definition
• "We work hard and play hard" as a substitute for compensation

Questions to Ask

• "What does a typical week look like for someone in this role?"
• "Tell me about someone who was recently promoted — what did they do?"
• "What's the biggest challenge the team is facing right now?"
• "How does the company handle disagreements between founders/leadership?"
• "What's the on-call rotation like?" (for engineering)

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5. Product & Market Risk

Assessing from the Outside

What Happens If It Fails?

Think about your personal downside:

• How long would it take to find a new job in your function/market?
• Have you burned cash on exercising options that are now worthless?
• Have you maintained your skills and network for a smooth transition?
• Is the experience itself valuable on your resume regardless of outcome?

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6. Verdict Framework

Scoring

Rate each area 1-5:

Verdict Scale

VC Investor Due Diligence Framework

Detailed evaluation criteria for assessing a startup as a potential venture investment. Organized by stage — earlier stages weight team and market heavier, later stages weight metrics and unit economics heavier.

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1. Market Opportunity

TAM / SAM / SOM

How to estimate: Use top-down (industry reports, public comp revenue) AND bottom-up (# of potential customers × average deal size). If these converge, the estimate is more credible.

Market Timing

• Why now? — What changed (technology, regulation, behavior, cost curve) that makes this possible today but not 5 years ago?
• Secular tailwinds — Is the market growing regardless of this company? (e.g., cloud migration, AI adoption, remote work)
• Headwinds — Regulatory risk, platform dependency, cyclical exposure

Green Flags

• Market growing >20% annually
• Clear "why now" with structural shifts
• Multiple adjacent markets to expand into
• Winner-take-most dynamics

Red Flags

• Market is shrinking or saturated
• "If only X% of a huge market" reasoning (lazy TAM)
• Heavy regulatory uncertainty with no clear path
• Market exists only because of a temporary condition

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2. Product & Traction

Product-Market Fit Signals

Growth Metrics by Stage

Engagement Depth

• How much of the product do users actually use?
• What's the "aha moment" and how quickly do users reach it?
• Is usage expanding within accounts (land-and-expand)?

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3. Unit Economics

Key Metrics

Burn & Runway

• Monthly burn rate — How fast are they spending?
• Runway — Months of cash left at current burn
• Burn trajectory — Is burn accelerating or decelerating?
• Good benchmark: 18-24 months runway post-raise; <12 months is danger zone

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4. Team Assessment

Founder Evaluation

Team Composition

• CTO / technical co-founder — Essential for technical products; red flag if all business people
• Full-stack founding team — Ideally covers product, engineering, and distribution
• Early hires — Quality of first 10-20 hires signals judgment and network
• Advisor/board quality — Who's helping them? Domain experts or just check-writers?

Red Flags

• Solo non-technical founder building a technical product
• Founder team that hasn't worked together before (for first-time founders)
• High executive turnover early on
• Founders with pattern of starting and quickly abandoning companies

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5. Defensibility & Moats

Competitive Dynamics

• Who are the direct competitors? Indirect competitors?
• What happens if a FAANG/big tech company enters this space?
• Is there a platform risk (building on top of someone else's platform)?

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6. Investment Verdict Framework

Scoring

Rate each area 1-5:

Verdict Scale