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Free to Freemium: 5 lessons learned from

Today we have a fantastic guest blog from Ranjith Kumaran, on his adventure going from an ad-supported free service to a subscription-based freemium model. Ranjith is the Co-Founder & CTO of, a Silicon Valley company that allows businesses and individuals send, receive and track digital content securely and easily. Enjoy! -Andrew

Free to Freemium: 5 Lessons Learned
by Ranjith Kumaran

A tech reporter recently asked me if had made the switch from a free ad-based business model to a subscription-based freemium model “just in the nick of time”. After all, with death chasing every ad-revenue-fueled startup these days, surely we must have been scrambling over the last few months!

The truth is that we got our first paid subscriber at YouSendIt on the night of February 28th, 2006, over three years ago. The company recently passed the 100,000 paid subscriber mark but that first customer was where it all started: the transition from free to freemium. As startup pundits we expect business models to iterate but this particular switch was a thrill-a-minute ride.

So if you’re ready to take the plunge or are still on the fence between free vs. freemium then read on. I’ll highlight five key lessons learned over the last three years as we went from a 100% free model to freemium:

Lesson 1: It’s all about DNA
Lesson 2: Funnels come in all shapes and sizes
Lesson 3: Compound growth is a double-edged sword
Lesson 4: Don’t let pricing psyche you out
Lesson 5: “Boring” things can give you lots of conversion lift

It’s all about DNA
It doesn’t matter how smart your team is or how hard you work, everyone has to want to make the switch from free to freemium. The thesis of our first venture round of investment was to test both models to see how they scaled. But the reality was we already had a significant free business (advertising revenue helped my co-founders and I keep the lights on, sound familiar?) so the lion’s share of the first six months were spent building a team that could keep the viral, ad-impression-generating parts of the business growing. When the subscription service launched and showed great promise (we collected our first payment within 4 minutes of pushing the code live), the business model was changed but many of the team’s mindsets were not. Reconciling these differences was exhausting but we got there.

Do yourself a favor and pull the band-aid off quickly. If you re-channel all effort into improving conversion and building your brand your subscription business will get out of the blocks much faster. A change in DNA is the hardest thing a company can endure and some don’t; get through it early.

Funnels come in all shapes and sizes
Once you’ve made the switch a number of things will happen:

  • People who don’t believe in paying for web-based services will call you a sell-out. Unsurprisingly, these folks aren’t in your target market. If you provide a valuable service the majority of your users will stay with you (most for free and some percentage will subscribe right away).’s traffic took a 30% haircut in traffic during this process. If we didn’t have anything further down the funnel this would have been devastating.
  • Expect to see a drastic change in the mix of users you serve going forward. YouSendIt’s business is international (everyone sends files), including geographies that any startup will struggle to effectively monetize showing ads; in general the same geographies also yield weaker subscriber numbers. This pruning of who you serve and how much (by, say, asking for payment) is very, very, common and often more deliberate; it’s a cost-to-serve discussion every web business that thinks beyond customer acquisition will eventually have. Over time we found that the users who were willing to pay for our services attracted similar users to the site.
  • Plan to change the metrics by which you measure your business. Our dashboard went from plotting CPMs, impressions and make-goods to conversion rates, churn, and ARPU. Acquisition cost, cost-to-serve, and lifetime value start to rear their ugly heads. If you want to fully understand your freemium business, learn to love them.

Compound growth is a double-edged sword
Once the freemium engine has run for a while you’ll see that, unlike fluctuations in ad-impressions and CPMs, subscription revenue is very predictable; your shareholders will appreciate this. Step functions in revenue are seen when new products are launched (including up-selling to the current base and convincing more users to subscribe) and new channels into the top of the funnel are created (making our way onto the desktop was a big one). Compounded subscriber growth is very powerful: convert more users in January and you’ll have a chunk of the year’s revenue in the bag, provided you’ve got churn under control; fall behind and revenue shortfall amplifies just as quickly over time.

Don’t let pricing psyche you out
Balancing market penetration and the fear of leaving money on the table is no fun and more than one startup has failed to even launch a paid product because of the pricing hurdle. Here’s a quick and dirty way to put a stake in the ground:

  1. Make a list of your competitors or find adjacent markets / potential substitutes with similar users and use cases. You should already have this list.
  2. Plot the spectrum of all the price-points of their offerings.
  3. Plan to release at least two paid tiers: one at the bottom end of the spectrum that is driven by volume and one at the top that is clearly differentiated by value.

By doing this you can accomplish the following: fill in any market share vs. revenue maximization discussion rat-holes (now you can test both); give customers a way to compare between three offerings (free, a little more, and lot more; being able to compare is an important part of any purchase decision); feel good that you’ve done some diligence on pricing without prematurely shelling out a lot of cash on market research.

If the above exercise seems unscientific that’s because it is. Your pricing work has just begun: constantly observe the rates at which users move through the funnel at different price-points, use promotions to get buyers off the fence, and re-price as you get more price elasticity data. At YouSendIt we raised prices (yes, it can be done) successfully several times in the early days as we learned more and more about buying behavior.

“Boring” things can give you lots of conversion lift
Conversion lift doesn’t always come from groundbreaking changes in product, offers, or funnel analysis. These days I will look for ten 1% lifts in conversion before one 10% magic bullet; in reality there probably aren’t a lot of 10% lifts left after the first handful. Get into the groove of turning knobs a little at a time, learning, and iterating; you never did this further down the funnel when you were selling ads and you are likely out of practice. Other mundane things that you haven’t invested in start to get a lot of play: customer service SLAs, quality of service, and even the right terms of service are all areas which can drive conversion. Look for a 1% lift in conversion right now, it’s in there somewhere; then do it again a million times.

With any luck there are enough examples above to convince you that switching from free to a freemium business model can be done with a little perseverance and a lot of belief. I’ve experienced the rush of going from 0 loyal users, to thousands, hundreds of thousands, and millions a few times in my career. But there is a different kind of satisfaction you and your team will get when your business starts to amass paid subscribers: users who believe the things your company has worked so hard to create are good enough to pay for. This is the ultimate validation of your efforts.

These topics will be covered in more detail at a couple of panels (one on Understanding Freemium Business Models, another on Customer Acquisition in a Down Economy) I’m helping to organize in the coming weeks. If you’d like to participate as an attendee, panelist, or moderator or if you’re simply interested in hearing about more lessons learned (the hard way), please follow the Twitter feed I’ve set up.

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