Startup Advisor

Startup Advisor

When to Use

Use this skill when:

• The user is building a startup and needs guidance on lean methodology, MVP definition, or product-market fit measurement
• The user wants help with funding strategy, key metrics, or deciding whether to pivot
• The user needs stage-appropriate advice from ideation through scale for a venture-backed business
• The user wants to understand startup economics, fundraising rounds, or growth metrics

Do NOT use this skill when:

• The user is bootstrapping without plans to raise funding (use bootstrapper-playbook instead)
• The user wants to write a formal business plan (use business-planner instead)
• The user needs to build a specific pitch deck for investors (use pitch-deck-builder instead)

Process

1. Gather requirements. Ask the user clarifying questions about their specific context, goals, constraints, and experience level.

2. Analyze the situation. Review the information provided and identify key factors, challenges, and opportunities relevant to startup advisor.

3. Develop the framework. Create a structured approach tailored to the user's needs, incorporating best practices and domain-specific considerations.

4. Deliver actionable output. Present specific, implementable recommendations with clear rationale, timelines, and success criteria.

5. Address edge cases. Proactively identify potential issues, alternative approaches, and contingency plans.

Use this skill when:

• User needs guidance on startup advisor
• User asks about startup advisor best practices or techniques
• User wants a structured approach to startup advisor

Do NOT use this skill when:

• A more specialized skill exists for the specific subtopic
• The request is outside the scope of startup advisor

A comprehensive startup advisory skill that provides stage-appropriate guidance from ideation through scale. Built on Lean Startup methodology, product-market fit frameworks, and real-world startup operating practices. Covers strategy, metrics, fundraising, team building, and decision-making frameworks.

Questions to Ask the User First

1. What is your startup idea? (One sentence)
2. What stage are you at?
   • Ideation (just an idea)
   • Validation (testing assumptions)
   • MVP (building first version)
   • Early traction (first customers)
   • Growth (scaling what works)
   • Scale (optimizing and expanding)
3. Are you a solo founder or do you have co-founders?
4. What is your background/expertise?
5. Are you working on this full-time?
6. Do you have any traction? (Users, revenue, LOIs, waitlist)
7. How are you funded? (Self-funded, friends/family, angel, VC, revenue)
8. What is your biggest challenge right now?
9. What is your target customer?
10. What is your timeline / runway?

Startup Stage Framework

Stage 1: Ideation

Goal: Validate that a real problem exists worth solving.

IDEATION CHECKLIST:

PROBLEM VALIDATION:
- [ ] Can you describe the problem in one sentence?
- [ ] Have you experienced this problem yourself?
- [ ] Have you talked to 10+ people who have this problem?
- [ ] Can you quantify the cost of this problem? (time, money, frustration)
- [ ] Are people actively seeking solutions today?

SOLUTION BRAINSTORMING:
- [ ] List 5+ possible solutions
- [ ] Identify which solution is simplest to test
- [ ] Define what "better" means vs. existing alternatives
- [ ] Identify your unfair advantage for building this

FOUNDER-MARKET FIT:
- [ ] Why are YOU the right person to solve this?
- [ ] What unique insight do you have?
- [ ] What resources/connections do you bring?
- [ ] Are you passionate enough to work on this for 7-10 years?

QUICK TESTS:
- Create a landing page describing the solution
- Run a "fake door" test (CTA that measures interest)
- Post in relevant communities and measure response
- Talk to 20 potential customers (do NOT pitch -- just listen)

Stage 2: Validation

Goal: Prove that customers will pay for your solution.

VALIDATION EXPERIMENTS:

EXPERIMENT 1: Problem Interviews (Week 1-2)
  Target: 20 customer interviews
  Script: "Tell me about the last time you experienced {{problem}}..."
  Success metric: 80%+ confirm the problem is significant
  Result: [ ] Validated [ ] Invalidated

EXPERIMENT 2: Solution Interviews (Week 2-3)
  Target: 15 solution interviews with mockup/prototype
  Script: "Here is how we would solve {{problem}}. Would you use this?"
  Success metric: 60%+ express strong interest
  Result: [ ] Validated [ ] Invalidated

EXPERIMENT 3: Willingness to Pay (Week 3-4)
  Target: 10 pricing conversations
  Method: Van Westendorp or direct pricing question
  Script: "If this existed today, what would you expect to pay?"
  Success metric: Price supports viable business model
  Result: [ ] Validated [ ] Invalidated

EXPERIMENT 4: Pre-Sales (Week 4-6)
  Target: 5 pre-orders, LOIs, or deposits
  Method: Offer early access at discount for commitment
  Success metric: Real money or binding commitment changes hands
  Result: [ ] Validated [ ] Invalidated

Stage 3: MVP (Minimum Viable Product)

Goal: Build the smallest thing that delivers the core value.

MVP DEFINITION WORKSHEET

CORE JOB TO BE DONE:
{{What is the #1 thing your product must do?}}

MVP FEATURE SET (be ruthless):
MUST HAVE (launch blockers):
  1. {{feature}} -- Why: {{it directly delivers core value}}
  2. {{feature}} -- Why: {{without it, product cannot function}}
  3. {{feature}} -- Why: {{required for payment/onboarding}}

SHOULD HAVE (Week 2-4 post-launch):
  1. {{feature}}
  2. {{feature}}

COULD HAVE (Month 2-3):
  1. {{feature}}
  2. {{feature}}

WILL NOT HAVE (explicitly excluded):
  1. {{feature}} -- Why: {{distraction from core value}}
  2. {{feature}} -- Why: {{premature optimization}}

MVP TYPE:
  [ ] Concierge MVP (manually deliver the value)
  [ ] Wizard of Oz (looks automated, human-powered behind scenes)
  [ ] Single-feature product (one thing done well)
  [ ] Landing page + manual process
  [ ] Piecemeal MVP (stitch together existing tools)

TIMELINE: {{weeks}} weeks
BUDGET: ${{budget}}
SUCCESS CRITERIA: {{measurable_outcome}}

Stage 4: Early Traction

Goal: Find repeatable customer acquisition and prove product-market fit.

PRODUCT-MARKET FIT ASSESSMENT

THE SEAN ELLIS TEST:
Ask existing users: "How would you feel if you could no longer use {{product}}?"
  Very disappointed: {{pct}}% (target: 40%+)
  Somewhat disappointed: {{pct}}%
  Not disappointed: {{pct}}%

RETENTION ANALYSIS:
  Day 1 retention: {{pct}}%
  Day 7 retention: {{pct}}%
  Day 30 retention: {{pct}}%
  Is retention flattening? {{yes/no}} (good = yes, curve flattens)

ORGANIC GROWTH SIGNALS:
  - [ ] Users referring other users without being asked
  - [ ] Inbound leads increasing
  - [ ] Usage frequency increasing over time
  - [ ] Users complaining when product is down
  - [ ] Users finding creative uses you did not anticipate

NET PROMOTER SCORE:
  NPS: {{score}} (-100 to +100, target: 50+)

VERDICT:
  [ ] Strong PMF -- Accelerate growth
  [ ] Emerging PMF -- Double down on what is working
  [ ] Weak PMF -- Iterate on product/positioning
  [ ] No PMF -- Consider pivot

Stage 5: Growth

Goal: Scale acquisition channels and optimize unit economics.

GROWTH FRAMEWORK

IDENTIFY YOUR GROWTH ENGINE:
  [ ] Viral: Users naturally invite others
      Key metric: Viral coefficient (target: >1.0)
  [ ] Sticky: High retention drives growth
      Key metric: Churn rate (target: <5% monthly)
  [ ] Paid: Profitable customer acquisition
      Key metric: LTV:CAC ratio (target: >3:1)

CHANNEL TESTING MATRIX:
| Channel           | Cost to Test | Timeline | Expected CAC | Status    |
|-------------------|-------------|----------|-------------|-----------|
| Content/SEO       | ${{}}       | 3-6 mo   | ${{}}       | {{}}      |
| Paid Search       | ${{}}       | 2-4 wk   | ${{}}       | {{}}      |
| Paid Social       | ${{}}       | 2-4 wk   | ${{}}       | {{}}      |
| Cold Outreach     | ${{}}       | 2-4 wk   | ${{}}       | {{}}      |
| Partnerships      | ${{}}       | 1-3 mo   | ${{}}       | {{}}      |
| Referral Program  | ${{}}       | 1-2 mo   | ${{}}       | {{}}      |
| Community/Events  | ${{}}       | 2-3 mo   | ${{}}       | {{}}      |
| PR/Media          | ${{}}       | 1-3 mo   | ${{}}       | {{}}      |

GROWTH PRIORITIES (ICE Framework):
  Impact (1-10) x Confidence (1-10) x Ease (1-10) = ICE Score

| Experiment               | Impact | Confidence | Ease | Score |
|--------------------------|--------|------------|------|-------|
| {{experiment_1}}         | {{}}   | {{}}       | {{}} | {{}}  |
| {{experiment_2}}         | {{}}   | {{}}       | {{}} | {{}}  |
| {{experiment_3}}         | {{}}   | {{}}       | {{}} | {{}}  |

Stage 6: Scale

Goal: Build organizational capacity and expand markets.

SCALING READINESS CHECKLIST:

PRODUCT:
- [ ] Core product is stable and reliable
- [ ] Infrastructure can handle 10x current load
- [ ] Customer onboarding is self-serve or semi-automated
- [ ] Support is scalable (help docs, chatbot, tiered support)

TEAM:
- [ ] Key leadership roles are filled
- [ ] Hiring pipeline is established
- [ ] Culture and values are documented
- [ ] Management structure exists for 3x current headcount

OPERATIONS:
- [ ] Key processes are documented
- [ ] Financial controls and reporting are in place
- [ ] Legal and compliance requirements are met
- [ ] Vendor/partner relationships are formalized

GROWTH:
- [ ] At least 2 acquisition channels are working
- [ ] Unit economics are positive and improving
- [ ] Expansion revenue (upsell/cross-sell) strategy exists
- [ ] International/geographic expansion plan (if applicable)

Key Startup Metrics

Metric Definitions and Benchmarks

CORE METRICS DASHBOARD

ACQUISITION:
  Customer Acquisition Cost (CAC):
    Formula: Total sales & marketing spend / New customers acquired
    Benchmark: Varies by industry, but LTV:CAC should be >3:1
    Your CAC: ${{cac}}

  Monthly Recurring Revenue (MRR):
    Formula: Sum of all monthly subscription revenue
    Growth rate: {{mrr_growth}}% MoM (healthy: 10-20% early stage)
    Your MRR: ${{mrr}}

  Annual Recurring Revenue (ARR):
    Formula: MRR x 12
    Your ARR: ${{arr}}

RETENTION:
  Churn Rate (Monthly):
    Formula: Customers lost in month / Customers at start of month
    Benchmark: <5% monthly for SMB, <1% for enterprise
    Your churn: {{churn}}%

  Net Revenue Retention (NRR):
    Formula: (Starting MRR + Expansion - Contraction - Churn) / Starting MRR
    Benchmark: >100% (best-in-class: >120%)
    Your NRR: {{nrr}}%

ECONOMICS:
  Lifetime Value (LTV):
    Formula: ARPU / Monthly churn rate
    Your LTV: ${{ltv}}

  LTV:CAC Ratio:
    Formula: LTV / CAC
    Benchmark: 3:1 minimum, 5:1+ for healthy businesses
    Your ratio: {{ratio}}:1

  Payback Period:
    Formula: CAC / Monthly gross profit per customer
    Benchmark: <12 months
    Your payback: {{months}} months

ENGAGEMENT:
  Daily Active Users (DAU): {{dau}}
  Monthly Active Users (MAU): {{mau}}
  DAU/MAU Ratio: {{ratio}}% (benchmark: 20%+ is good, 50%+ is excellent)

BURN:
  Monthly Burn Rate: ${{burn}}
  Runway: {{months}} months (cash / monthly burn)
  Months to default (if declining runway): {{months}}

Pivot vs. Persevere Decision Framework

PIVOT ASSESSMENT

Answer each question honestly:

TRACTION SIGNALS:
1. Are users/customers actively using the product? {{yes/no}}
2. Is there organic growth (word-of-mouth)? {{yes/no}}
3. Are users willing to pay the target price? {{yes/no}}
4. Is usage increasing over time? {{yes/no}}
5. Do users get upset when the product is unavailable? {{yes/no}}

Score: {{count}}/5 -- If < 2, strongly consider a pivot.

PIVOT OPTIONS:
  Zoom-in pivot: One feature becomes the whole product
  Zoom-out pivot: Whole product becomes one feature of larger product
  Customer segment pivot: Same product, different customer
  Customer need pivot: Same customer, different problem
  Platform pivot: Change from app to platform (or vice versa)
  Business model pivot: Change how you monetize
  Channel pivot: Change how you reach customers
  Technology pivot: Same solution, different technology
  Value capture pivot: Change your pricing/revenue model

DECISION MATRIX:
| Factor                      | Persevere | Pivot |
|-----------------------------|-----------|-------|
| Customer feedback           | {{}}      | {{}}  |
| Metrics trend               | {{}}      | {{}}  |
| Team energy/conviction      | {{}}      | {{}}  |
| Market timing               | {{}}      | {{}}  |
| Competitive landscape       | {{}}      | {{}}  |
| Runway remaining            | {{}}      | {{}}  |

DECISION: [ ] Persevere  [ ] Pivot to: {{pivot_type}}
RATIONALE: {{why}}

Funding Options by Stage

FUNDING ROADMAP

PRE-SEED ($25K - $500K):
  Sources:
  - Personal savings / Friends & family
  - Accelerators (Y Combinator, Techstars, etc.)
  - Angel investors
  - SAFE notes or convertible notes
  - Government grants (SBIR/STTR in US)
  What investors expect: Team + idea + initial validation

SEED ($500K - $3M):
  Sources:
  - Angel groups and syndicates
  - Seed-stage VC funds
  - Revenue-based financing (if revenue exists)
  - Crowdfunding (Republic, Wefunder)
  What investors expect: MVP + early traction + clear market

SERIES A ($3M - $15M):
  Sources:
  - Institutional VC funds
  - Corporate venture capital
  What investors expect: Product-market fit + $1M+ ARR + growth rate

SERIES B+ ($15M+):
  Sources:
  - Growth-stage VC
  - Private equity
  - Strategic investors
  What investors expect: Proven unit economics + scalable growth engine

ALTERNATIVE FUNDING:
  - Bootstrapping: Fund from revenue
  - Revenue-based financing: Percentage of revenue until repaid
  - Venture debt: Debt alongside equity raise
  - Grants: Non-dilutive government/foundation funding
  - Strategic partnerships: Advance payments or joint ventures

Common Startup Pitfalls

Top 20 Reasons Startups Fail (and How to Avoid Them)

Founder Operating System

Weekly Startup Cadence

WEEKLY OPERATING RHYTHM

MONDAY:
  - Review key metrics dashboard (30 min)
  - Set 3 weekly priorities with team (30 min)
  - Customer outreach / check-ins (1 hr)

TUESDAY-THURSDAY:
  - Heads-down execution on priorities
  - Daily standup (15 min max)
  - Customer interviews or sales calls (scheduled)

FRIDAY:
  - Week in review: What worked? What did not? (30 min)
  - Update investors / advisors (if applicable)
  - Plan next week
  - Reflect: Are we closer to product-market fit?

MONTHLY:
  - Full metrics review and trend analysis
  - Board update or advisor call
  - Financial review (burn rate, runway)
  - One strategic deep-dive (pricing, positioning, roadmap)

QUARTERLY:
  - OKR review and reset
  - Competitive landscape review
  - Team retrospective
  - Fundraising status assessment

Output Checklist

• Advice is appropriate for the user's current stage
• Recommendations are specific and actionable (not generic)
• Metrics and benchmarks are cited for context
• Next steps are clearly defined with timelines
• Risks and potential pitfalls are flagged
• Founder is encouraged but given honest feedback
• Templates provided are ready to use immediately

Output Format

Deliver the response as a structured document with clear headings and actionable content. Use tables for comparisons, numbered lists for sequential steps, and bullet points for options. Include specific examples where applicable.

[Startup Advisor deliverable]
1. Context and objectives
2. Analysis or framework
3. Specific recommendations with rationale
4. Action items with timeline

Example

Input: "Help me with startup advisor for a mid-size project."

Output: A complete startup advisor framework tailored to the specific context, with actionable steps, relevant considerations, and measurable outcomes.

Edge Cases

• Incomplete information: Ask clarifying questions before proceeding rather than making assumptions
• Conflicting requirements: Identify trade-offs explicitly and present options with pros and cons
• Scale mismatch: Adapt recommendations to match the user's context (individual vs. team vs. organization)
• Domain crossover: When the request overlaps with other skill domains, address what falls within scope and reference specialized skills for the rest