30-60-90 Day Startup Plan

30-60-90 Day Startup Plan

Your First 90 Days: Validate, Measure, Scale

Core Principle: Repeatability precedes scalability. VCs fund the repeatability signal.

Overview: The 3-Phase Framework

DAYS 1-30          DAYS 31-60         DAYS 61-90
─────────          ──────────         ──────────

• 20+              • 5 paying         • 5 MORE
  conversations      customers          customers

• Build v0.1       • Install SLOs     • Prove
                                        repeatability

• Legal            • Metrics          • Decide:
  foundation         dashboard          raise or fix

VALIDATE           MEASURE            SCALE

DAYS 1-30: VALIDATE

Goal: Prove people have the problem and will pay to solve it

Week 1: Foundation

Legal Setup (Do This First)

• [ ] Day 1: Incorporate (Delaware C-Corp)
• [ ] Day 1: Vesting agreement signed
• [ ] Day 1: IP assignment to company
• [ ] Day 2: Startup lawyer consultation ($500-$1K)
• [ ] Day 3: Bank account opened
• [ ] Day 5: Accounting system (QuickBooks, Xero)

Customer Discovery Prep

• [ ] List 50 people to talk to: Name, company, role, how to reach
• [ ] ICP hypothesis: Who has budget + urgency + authority?
• [ ] Problem hypothesis: What pain do they have?
• [ ] Interview script: Questions to ask (use Due Diligence template)

Week 2: Customer Conversations (Target: 10)

Monday Action: Send 20 outreach messages

Outreach Template:

Subject: Quick question about [their workflow]

Hi [Name],

I'm researching how [role] at [company type] handle [problem area].
I'm talking to a few people to understand the space better—not selling anything.

Would you have 20 minutes this week for a call?

Thanks,
[Your name]

After Each Call:

• [ ] Take notes (use Interview Notes Template)
• [ ] Send thank-you email
• [ ] Ask for 2-3 referrals
• [ ] Schedule follow-up if strong signal

Week 3: More Conversations + Pattern Recognition (Target: 10 more)

Look for patterns:

• What do 80% of people complain about?
• Which pain points are quantified ($, time)?
• Who has budget to solve it?
• What solutions have they tried?

Build v0.1 (Minimum Viable Product)

• [ ] Solve the ONE core problem
• [ ] Manual processes are fine (wizard behind the curtain)
• [ ] Make it work for 1 customer before scaling
• [ ] Ship something by end of Week 3

Example: Airbnb founders photographed apartments themselves before building the photo upload feature.

Week 4: Commitment Asks + Refine

Goal: Get 3 LOIs (Letters of Intent) or pilot agreements

What to say:

"Based on our conversation, it sounds like [problem] costs you
[quantified impact]. We're building [solution].

Would you be interested in a 30-day pilot for $[price]?
I can send you a simple agreement to review."

Don't build more until you have commitments.

DAYS 31-60: MEASURE

Goal: Get 5 paying customers and install metrics to track success

Week 5: First Paying Customers (Target: 2)

Convert LOIs to Pilots:

• [ ] Send pilot agreement (use lawyer template)
• [ ] Payment upfront (Stripe, wire, check)
• [ ] Set clear success criteria
• [ ] Weekly check-ins scheduled

Success Criteria Example:

Pilot Goals:
- Reduce deploy time from 2 hours → 30 minutes
- Zero production incidents during pilot
- 80% team adoption by end of pilot

Week 6: Install SLOs + Feedback Loops (Target: 2 more customers)

Service Level Objectives (Internal):

• [ ] Response time: Email replies within 4 hours
• [ ] Uptime: 99% availability
• [ ] Bug fixes: Critical bugs fixed within 24 hours
• [ ] Feature requests: Acknowledged within 1 week

Customer Feedback Loop:

• [ ] Weekly usage data review
• [ ] Bi-weekly customer calls
• [ ] Quarterly NPS survey
• [ ] Feature request tracking (Trello, Linear)

Week 7: Metrics Dashboard Setup (Target: 1 more customer)

Implement tracking:

• [ ] MRR calculation
• [ ] Customer count
• [ ] Churn tracking
• [ ] Usage metrics (product analytics)
• [ ] CAC estimation

Tools:

• Google Sheets: Start here (use Metrics Dashboard template)
• Product analytics: Amplitude, Mixpanel, PostHog
• Payments: Stripe (track MRR automatically)

Week 8: Refine + Prove Repeatability

You should now have:

• [ ] 5 paying customers
• [ ] Consistent onboarding process
• [ ] Metrics dashboard updated weekly
• [ ] Customer feedback loop running

Key Question: Can you repeatably acquire and retain customers?

DAYS 61-90: SCALE

Goal: Prove repeatability, then decide to raise capital or keep bootstrapping

Week 9: Acquire 5 More Customers

Repeatability test:

• [ ] Use same process that got first 5 customers
• [ ] Track what works vs. doesn't
• [ ] Refine ICP based on who converts fastest
• [ ] Document sales process

What repeatability looks like:

• "I talk to 10 people, 3 become pilots, 2 convert to paid"
• "LinkedIn outreach has 20% response rate"
• "Engineers at 50-200 person companies convert best"

Week 10: Retention Checkpoint

Review first customers:

• [ ] Are they still using the product?
• [ ] Usage increasing or decreasing?
• [ ] Would they renew?
• [ ] Have they referred others?

Red flag: If first customers aren't engaged, fix product before adding more.

Green flag: Customers asking for more features = real engagement.

Week 11: Economic Model Validation

Calculate unit economics:

• [ ] CAC: What did it cost to acquire 10 customers?
• [ ] LTV: What's their projected lifetime value?
• [ ] LTV:CAC ratio: Is it ≥3:1?
• [ ] Payback period: How long to recover CAC?

Example:

Total spend (weeks 1-11): $5,000
Customers acquired: 10
CAC = $500

ARPA: $500/mo
Expected lifetime: 24 months (2% monthly churn)
LTV = $500 × 24 = $12,000

LTV:CAC = $12,000 / $500 = 24:1 ✅ (great!)

Week 12: Decision Point

You now have data to decide:

Option A: Raise Capital (If...)

• [ ] 10+ paying customers
• [ ] >90% retention
• [ ] LTV:CAC ≥3:1
• [ ] 15%+ MoM growth
• [ ] Clear path to $100M+ market

Next steps: Build pitch deck, start fundraising

Option B: Bootstrap (If...)

• [ ] Profitable or near-profitable
• [ ] Organic growth working
• [ ] Don't need to move fast
• [ ] Happy with slower growth

Next steps: Keep growing, stay lean

Option C: Pivot or Abandon (If...)

• [ ] <80% retention (people churning)
• [ ] CAC > LTV (unit economics broken)
• [ ] Can't find repeatable acquisition channel
• [ ] Market too small

Next steps: Pivot to adjacent problem or shut down gracefully

Weekly Habits to Install

Monday Morning (30 min)

• [ ] Review last week's metrics
• [ ] Set this week's goals
• [ ] Priority list (top 3 things only)

Wednesday (1 hour)

• [ ] Customer calls (2-3 per week minimum)
• [ ] Update metrics dashboard
• [ ] Review product analytics

Friday Afternoon (30 min)

• [ ] Week in review: What worked? What didn't?
• [ ] Document learnings
• [ ] Plan next week

What to Track: Weekly Scorecard

WEEK OF: __________

CUSTOMERS
├─ Total paying: ___
├─ New this week: ___
├─ Churned: ___
└─ Net new: ___

REVENUE
├─ MRR: $________
├─ MoM Growth: ____%
└─ ARPA: $________

PIPELINE
├─ Active conversations: ___
├─ LOIs sent: ___
├─ Pilots started: ___
└─ Conversion rate: ____%

PRODUCT
├─ Uptime: ____%
├─ Critical bugs: ___
├─ Feature requests: ___
└─ Weekly active users: ___

TOP 3 WINS
1.
2.
3.

TOP 3 CONCERNS
1.
2.
3.

NEXT WEEK PRIORITIES
[ ]
[ ]
[ ]

Common Mistakes to Avoid

Mistake #1: Building Too Much Before Validation

• Wrong: "I'll launch when it's perfect (month 6)"
• Right: "I'll get 3 customers with duct tape version (month 1)"

Mistake #2: Not Asking for Money Early

• Wrong: "I'll make it free until it's good enough"
• Right: "Will you pay $X for a pilot?" (Week 3)

Mistake #3: Ignoring Retention

• Wrong: Focus only on new customers
• Right: Keep first customers happy, they're your reference

Mistake #4: No Metrics

• Wrong: "I think it's going well"
• Right: "We have 90% retention and 15% MoM growth"

Mistake #5: Doing Everything Yourself

• Wrong: Build, sell, support, ops all alone
• Right: Find a cofounder or first hire by Week 8

Resources

Books

• The Lean Startup by Eric Ries: Validation methodology
• Traction by Gabriel Weinberg: 19 customer acquisition channels

Tools

• Notion: Doc everything
• Stripe: Payments and MRR tracking
• Calendly: Easy meeting scheduling
• Loom: Async video for customer communication

Download all 12 templates: sanscourier.ai/qconsf-2025

*From the QCon SF 2025 talk: "From Staff Platform Engineer to a16z Founder: What I Wish I'd Known" by Gonzalo (Glo) Maldonado*