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We launched OutlierKit with a free plan back in April 2025.
Zero conversions. Zero revenue. Here's what we learned:
The Problem with Starting Freemium
When you don't know your value matrix, you can't draw the line between free and paid. We didn't know:
- Which features users actually needed vs wanted
- How much usage was "enough" for free users
- What would trigger someone to upgrade
Result: Lots of free signups. No paying customers.
The Switch That Changed Everything
We killed the free plan. Launched a 7-day free trial instead.
Our first five paying customers came within weeks. They tried it, saw value, subscribed.
The decision tree for free trials is simple:
- With credit card: Higher intent, higher friction, fewer signups, better conversion
- Without credit card: Lower friction, more signups, more feedback, lower conversion
We chose no credit card required. Early stage = prioritize feedback over revenue.
When to Use What
Free Trial (Where OutlierKit is now)
Use when:
- You're still validating the problem
- You don't know your value matrix
- You need early revenue and feedback
- You have limited social proof
Implementation:
- 7-14 day trial
- Limited time or credits
- No credit card required (initially)
- Full feature access
Freemium (Not yet ready)
Use when:
- Problem and solution are validated
- You have paying customers
- You understand exactly what to limit
- You need it as a marketing channel
Implementation:
- Clear feature limitations
- Usage-based restrictions
- Designed to create upgrade triggers
Reverse Trial (What Elephas uses)
Use when:
- Product is mature
- You want the best of both worlds
- You have strong activation metrics
Implementation:
- Start with full premium access
- After X days/uses, downgrade to free plan
- Users can upgrade to maintain premium features
The Playbook
- Start with paid-only or free trial
- Get your first 5-10 customers
- Document what features they use most
- Track where they hit limits
- Map your value matrix
- Core features everyone needs = potential free tier
- Power features pros want = paid tier
- Usage patterns = where to set limits
- Only then consider freemium
- Use it as marketing, not pricing
- Set clear upgrade triggers
- Monitor free-to-paid conversion religiously
The Bootstrap Reality Check
If you're bootstrapping, kill the idea of a free forever plan right now.
Free forever plans are a luxury for funded startups who can:
- Burn money for years building a brand
- Support thousands of non-paying users
- Wait for 1-2% conversion rates
- Subsidize free users with investor money
When you're bootstrapping, you need:
- Revenue from day one
- Feedback from people with skin in the game
- Customers who value your product enough to pay
- Profitability, not vanity metrics
Free users give you opinions. Paying customers give you truth.
A free user will request 10 features they'll never use. A paying customer will request one feature they desperately need. Guess which feedback actually matters?
Key Insight
Freemium isn't a pricing strategy. It's a marketing strategy.
And marketing strategies only work when you know what you're marketing, to whom, and why they should care.
Get paying customers first. Understand value second. Add free tiers third (maybe).
That's the order. And if you're bootstrapping? Maybe skip that third step entirely.
Also, listen to Jon on this -
