Trial vs Freemium Decision Advisor for Bootstrapped Founders

Free v2.0.0 2 views

Your monetization model advisor for bootstrapped SaaS founders. Get context-aware recommendations on trial vs freemium based on your constraints—not generic scoring.

What You Get

Get strategic advice (not spreadsheets) on whether trial or freemium fits YOUR bootstrapped situation. Focuses on interpretation, founder constraints (runway, cash flow, support capacity), and actionable 90-day plans—not just metrics.

The Problem

Bootstrapped SaaS founders face a critical early decision: trial or freemium? Free calculators give generic scores, but ignore YOUR constraints—12-month runway, solo founder support burden, $2/user infrastructure costs. Choose wrong and you burn through runway supporting free users who never convert, or create signup friction that kills growth. You need context-aware advice that understands bootstrapped realities, not VC-funded playbooks.

The Solution

This skill acts as a strategic advisor for bootstrapped founders, analyzing your specific constraints (runway, team size, cash flow needs, cost-to-serve) and product characteristics to recommend trial vs freemium. Instead of generic scoring, you get interpretation: what your 10-month runway MEANS for the decision, what $2/user cost-to-serve MEANS for cash flow, what solo founder reality MEANS for support burden. Includes 3-5 bootstrapped case studies (not VC-funded), honest trade-off analysis, 6-month cash flow projections, and a concrete 90-day implementation plan. Differentiates from free calculators by focusing on actionable advice tailored to indie founder constraints.

How It Works

  1. 1 Understand founder constraints: runway, team size, revenue urgency, cash flow situation
  2. 2 Identify critical constraints and interpret what they mean for the decision (not just scoring)
  3. 3 Research 3-5 bootstrapped/indie case studies (prioritize non-VC examples) via WebSearch
  4. 4 Provide bottom-line recommendation with 2-3 key reasons tied to founder's situation
  5. 5 Share honest trade-offs: what founder is signing up for with each option
  6. 6 Generate 6-month cash flow projections showing burn/profitability scenarios
  7. 7 Deliver 90-day action plan with concrete implementation steps

What You'll Need

  • Product must be SaaS or software-based
  • Founder must share runway/cash flow situation (doesn't need exact numbers)
  • Must have rough cost-to-serve estimate (ballpark is fine)
  • Must have target pricing in mind
  • Should be pre-launch or early stage (not 5 years in with established model)

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Examples

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