How do you decide what features should be free and what should be paid?
Let me start from the creator’s perspective:
I personally don’t have a product (apart from hiring people for creative work or offering personal consultations).
But as a creator, I constantly share content, insights, and information, value that helps me build trust (for free). Based on that perceived expertise, people eventually decide to work with me (a paid service).
So some things I share for free to eventually move toward a paid collaboration.
Personally, it’s sometimes hard to judge when I might be giving away too much for free.
And I assume it’s similarly tricky for builders.
You want users to try the product, but then comes the question of paid features, or a trial limited by time or usage.
How do you decide which parts of your product or service remain free, and which become paid?
When I share content publicly, I usually provide generalised advice. But when it comes to a specific case or a tailored strategy that requires a personal approach, that’s where it becomes paid.
Replies
Going thru this calculus as we speak; I'm planning a product launch with heavy S3 storage. First launch will be LTD in 4 tiers to gauge interest and build a user base. I need to be very careful about hemming in all data egress leaks and making sure tier limits are reasonable, balancing average costs and making sure I've left myself a workable runway of 3 years or so. Then it comes down to add-ons and how to price them so users hit reasonable limits and feel compelled to upgrade to monthly add-ons. Storage and transfer is of course the main cost driver, but I've decided that certain things like seat limits on teams can drive upgrades, even though they're technically arbitrary limits. Honestly, bigger teams use storage faster and hit upgrade targets sooner, but a 5 seat limit on tier 1 might drive more users to invest in higher tiers earlier. Figuring out this exact math is the biggest reason I haven't launched yet.
This is a very hard question answer, but it generally boils down to your product and goals. We are currently offering a paid lifetime deal for our product. As we are early stage we want committed users to direct development of the product rather than volume, we are also self funded at this time so paid allows us to cover support costs and generate revenue to extend our runway.
I think as a creator, your strategy seems good, sharing your knowledge for free certainly works to help build credibility and attract customers, including case studies of results you delivered for your paid clients would perhaps lend to more paid conversions.
First of all, there is nothing free. When you give something for free, you are actually incurring an advertising cost. My view is, a user should be able to discover enough of the features to help them decide whether to use the app or not.
As a builder, I'm okay keeping things free as long as it does not increase the cost notably.
We decided to use limit certain features to our site that offered extensive value to the customer. Easiest way to decide is asking customers what they found most valuable and what features they would pay for.
Been rotating between Lenny's Podcast and 20VC lately. Anyone have recommendations for more product-focused ones?
For my app (TokenBar, a macOS menu bar utility that tracks AI token usage), I went with a simple one-time purchase. $5 for Basic, $10 for Pro. No free tier, no subscription.
My reasoning: the app solves a clear, specific problem (you are paying for 5+ AI tools and have no idea what you are actually spending). If someone has that problem, $5 is an easy yes. If they do not have that problem, a free tier would not convert them anyway.
I think the "freemium" model works when your product has network effects or when users need time to discover value. But for a simple utility tool, I would rather charge a fair price upfront and skip the whole conversion funnel. Fewer support tickets from free users, no pressure to gate useful features behind a paywall, and the people who buy it actually want it.
The hardest part was resisting the urge to add a subscription. Recurring revenue sounds nice on paper, but for a utility app that runs locally on your Mac, a subscription feels wrong to me as a user, so I did not want to do that to others.
My take (I'm launching soon too):
I'm doing exactly what you're considering, all features free during the free trial. No gating.
Because I want a real test. If I hide features behind a paywall, users never see the full value. They churn thinking "it's missing something" when that something was the killer feature all along.
So my plan: 30 days, everything unlocked. Then pay or lose access. Some people will use it, finish their project, and never pay. Honest feedback. If they don't pay after experiencing everything, either my product isn't valuable enough, or my price is wrong. That's real data I need.
Has anyone tried full-featured time-limited trials? Did it convert better or worse than feature-gated freemium? Am I doing right or not?
I'd rather have 10 paying customers who love the product than 100 free users who never saw what it can really do.
For me the answer came down to one simple rule: if the feature creates immediate value, it should be in the paid tier. If it builds trust and lets people understand the product, keep it free.
I built a Mac menu bar app called TokenBar that tracks AI spending across 20+ providers. The free/paid split was tough but I landed on: Basic tier ($5 one-time) gives you real-time spending tracking for up to 5 providers. Pro tier ($10 one-time) unlocks all 20+ providers, budget alerts, and detailed breakdowns.
The key insight was making the free-to-paid boundary feel like a natural upgrade rather than a paywall. People who only use ChatGPT and Claude don't need 20 provider integrations. But once they see the value of tracking even 2 providers, upgrading to Pro when they add more tools is a no-brainer.
Also - one-time pricing instead of subscriptions. In a world where every tool wants $20/month, charging $5 once creates instant goodwill and removes the "is this worth it every month" anxiety. My conversion rate is way higher than I expected because of this.
I see free as onboarding, not limitation.
If people get real results for free, conversion becomes natural—not forced.
Great question — this was one of the hardest decisions I faced building DealNotify, a price drop and restock alert tool for Amazon, Walmart, Best Buy and more.
My rule was simple: the free tier has to deliver real value, not just a taste of it. If someone can't genuinely use the product for free, they'll never trust it enough to pay.
So here's where I drew the line:
Free gets:
Real price drop and restock alerts (the core value)
Up to 3 products tracked
Checks every 6 hours
30-day trial
Pro ($4.99/mo) gets:
Unlimited products
Checks every 2 hours
The key insight: I didn't gate the feature, I gated the frequency and scale. A free user still gets the "wow" moment when they receive their first alert email. That experience is what converts them — not a paywall.
The things I kept firmly free: no ads, no selling data, no watermarks on emails. Those would have killed trust immediately.