Milestone map
Milestone map
3 milestones
Define the subscription value proposition and pricing model
1–2 weeks
Define what subscribers pay for, why they keep paying, and how you price it. Subscription businesses fail most often not at launch but at month 3–6, when the initial novelty wears off and the recurring value has to justify the recurring charge. The most important question to answer before launch is: what specifically happens if a subscriber stops paying? If the answer is 'they lose access to content, features, or a service they were actively using', the value proposition is defensible. If the answer is 'they lose access to content they could have downloaded anyway', the value proposition is accumulation, not subscription. Pricing tiers, trial logic, and cancellation treatment are downstream of this core question.
Proof required
Write a subscription definition covering: (1) what a subscriber specifically gets — named, not described generically; (2) what specifically happens when they cancel — what they lose access to; (3) your pricing model (monthly/annual, tier structure if any, trial length if any); (4) one sentence on why you chose this pricing over the alternatives you considered.
What gets checked
- What subscribers get is specific — not 'access to premium content' but 'weekly deep-dive analysis + private community + live Q&A with named experts monthly'.
- What cancellation means is specific — the value loss on cancellation is the test of whether the subscription value proposition is real.
- Why this pricing is chosen over alternatives — pricing decisions are made in a competitive context; the reasoning reveals whether it was researched or guessed.
Common mistakes
- What subscribers get is described generically — 'premium access' is not a subscription value proposition.
- Cancellation consequence absent — 'they just lose access' without specifying what they lose access to is insufficient.
- Pricing rationale absent — 'we set it at $X' without a competitive or economic basis.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- The subscription value proposition should pass the cancellation test — ask 'what do subscribers lose the moment they cancel?' If the answer is unclear, the value proposition needs work.
- Pricing: ask whether competitors were researched and what their pricing is — a price set without competitive context is likely to be either too high or too low.
- Trial logic: if there's a free trial, ask how the trial-to-paid conversion rate will be measured — the absence of a conversion metric suggests trial is an afterthought.
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Launch and reach 25 paying subscribers with payment evidence
4–8 weeks from launch
Launch the subscription and reach 25 paying subscribers. 25 is a meaningful threshold — large enough to give a real signal about demand, small enough to be achievable in weeks rather than months for a new subscription business. The proof is payment evidence: a payment processor dashboard showing 25+ active subscribers, not 25+ signups or 25+ free-trial users. Month 1 churn should also be tracked — if 5 of the first 25 have already cancelled, that is important information.
Proof required
Share a screenshot of your payment processor dashboard showing 25+ active paying subscribers (Stripe, Paddle, or equivalent). State the current monthly revenue from these subscribers. State how many subscribers you have lost since launch (your month 1 churn number, even if zero).
What gets checked
- Payment processor dashboard shows 25+ active subscribers — signups or free trials are not sufficient.
- Monthly revenue from these subscribers is stated.
- Month 1 churn is stated honestly — zero churn in month 1 is unusual and should be noted; even one cancellation is worth mentioning.
Common mistakes
- 25 signups but fewer than 25 paying subscribers: free signups are not paying subscribers.
- 25 paying subscribers but no churn data: 'we haven't had any cancellations yet' is fine, but it needs to be stated, not omitted.
- Dashboard screenshot not provided: 'we have 25 subscribers' without evidence.
Resources
What a verifier looks for
- The screenshot must show active subscribers, not total signups or trials — ask what percentage of signups converted to paying.
- Month 1 churn: ask 'of the first 10 subscribers you acquired, how many are still paying?' — early cohort churn is a leading indicator of the retention problem.
- Monthly revenue should be consistent with 25 × (price per subscriber) — a significant discrepancy suggests different tier pricing, which is worth noting.
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Month 3 retention — cohort analysis and what it reveals
3 months from first subscriber
Measure month 3 retention for the first cohort of subscribers. Month 3 retention is the most important leading indicator of a subscription business's health: most casual subscribers cancel in months 1–2, and month 3 retention reveals whether the people who stayed are genuinely retained or simply have not got around to cancelling. A healthy subscription business retains 60–80% of subscribers to month 3 (the threshold varies by category); a struggling one sees continued attrition into month 3. The proof is a cohort analysis, not a current subscriber count.
Proof required
Share a cohort analysis for your first cohort of paying subscribers: how many subscribers joined in month 1, how many were still paying at the end of month 2, and how many at the end of month 3. State your interpretation: is this retention rate what you expected? What do cancelled subscribers have in common, if anything — did any tell you why they cancelled?
What gets checked
- Cohort analysis shows month 1 start, month 2 retention, and month 3 retention — three numbers, not just current subscriber count.
- Interpretation is honest — if month 3 retention is below 60%, that is the real finding, not a rounding problem.
- What cancelled subscribers have in common — even 'we don't know' is more useful than omitting the question.
Common mistakes
- Current subscriber count used instead of cohort retention: 'we now have 50 subscribers' does not tell you whether the first 25 are still paying.
- Retention described without the numbers: 'retention has been good' without the cohort percentages.
- Cancelled subscribers not investigated: 'we haven't asked them' — a single email to cancelled subscribers is worth a week of product work.
Resources
Foundationstart here
What a verifier looks for
- The cohort analysis must cover a real 3-month period — ask when the first subscriber was acquired and whether 3 months have elapsed.
- Retention rate below 60% at month 3 is a real finding — if the founder interprets this positively without acknowledging the churn rate, probe why.
- What cancelled subscribers said: ask whether the founder reached out to even one cancelled subscriber and what they heard.
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