The Big Idea

If you could find a therapist guaranteed to help you live a happier life, would you do it?

For anyone going through depression, anxiety, or addiction, finding a therapist can feel daunting and embarrassing. Who do you confide in? Where do you even start looking? This is the problem I set out to solve with Healify: a proven way to help you feel your best and the best support to get there.

Healify’s journey spanned four ambitious pivots. Over 25,000 sessions and 1 million moods later, we had achieved an average 260% improvement in people’s moods. But one obstacle proved to be our downfall, one that would ultimately reveal the secret to building a successful business.

Build to Fail Fast

Here's a mildly insane challenge: whatever you envision, prototype it in a single day.

At first, I had no idea how to pull this off—software takes time, and I’d certainly never built a search engine before. But with a little creativity, you can make anything happen. After a few moments of prayer on the top of a local mountain, "Shopify" popped into my mind. It made little sense until I realized that Shopify had the two things I needed - listings and search. All I needed to do was replace "products" with "therapists". Fast, free, and effective.

For content, I reached out to my friend Alex Clarke (who later became my co-founder) and my dad, a pioneer in CBT. We compiled a list of 20 local therapists. I added a “Free Consultation” button, wired to my cell phone, which would allow me to interview anyone who called in. And voila, Healify was live!

Insight

Our initial research showed genuine excitement, as many users were struggling to find quality therapy. But as we began to onboard providers, we discovered a shocking truth: fewer than 5% of therapists track anything at all! Without outcome data, we couldn’t build a ratings engine—making a pivot necessary.

Pivot #1: Tracking Therapy

Once we realized most therapists weren’t tracking client progress, we went straight to the source. Over 100 interviews with therapists helped us identify the key features they wanted in a tracking tool. Based on their feedback, we developed a streamlined tool therapists could integrate directly into their practice, measuring client moods, milestones, and session goals in real-time. This provided them with valuable insights and us with the data needed to fuel Healify’s search engine vision.

But as we began rolling it out, a different challenge emerged: while our initial test group saw value in the tool, many therapists hesitated to adopt digital tracking and even fewer were willing to pay for it. Outside of our testers, the broader market wasn’t ready to integrate tracking consistently into their practice.

Insight

Despite building a tool tailored to therapists' needs, adoption and monetization proved challenging. It became clear we’d need a fresh approach that could appeal directly to end users while continuing to gather data for our model.

Pivot #2: Consumer Engagement

With therapists slow to adopt our tracking tool, we pivoted to a new approach: what if consumers could track their own progress independently? Our strategy was twofold: empower consumers with data about their own moods, and create more demand for outcome-driven therapy. By enrolling consumers as advocates for our platform, perhaps we could encourage more therapists to adopt it too.

To test this idea, we entered the Y Combinator 2021 Winter Build Sprint. Over the course of a 30 day challenge, we developed a simple mobile app that allowed clients to log their moods, set goals, and observe trends over time. By the end of the sprint, we had a small but engaged base of 40 daily active users, all logging insights independently of their therapists. Y Combinator encouraged us to apply for funding, ultimately placing us in the top 10% of finalists—which, unfortunately, isn't quite the same as getting funded.

Insight

The consumer pivot opened up new possibilities: users found value in self-directed tracking, and their engagement gave us hope that consumer demand could influence therapists. However, scaling this user base—and sustaining it—would require creativity without a marketing budget.

Pivot #3: Freemium App

Could we reach a larger audience by offering our app as a free tool for therapists to share with clients? This pivot led us to a freemium model: therapists could introduce the app to clients, and users could access basic features for free, with premium options for a fee.

By giving therapists an easy-to-use tool for their clients, we hoped to drive adoption organically. Meanwhile, the freemium model allowed clients to experience Healify without an initial cost, letting

them “try before they buy.”

This approach grew our user base quickly as therapists became advocates, while premium upgrades revealed which features were most valuable to users.

Insight

The freemium model brought an influx of users, and engagement increased as therapists recommended the app. However, monetization remained challenging. While we had gained visibility, the challenge remained: could we convert free users into paying customers?

Pivot #4: Monetization?

With a strong user base but limited revenue from the freemium model, we pivoted one last time. Our goal was to directly monetize the app by offering premium features for highly engaged users. These included enhanced tools like personalized insights, advanced goal-setting, and in-depth analytics.

By focusing on our most active users, we hoped to create a sustainable revenue stream without disrupting the free experience. But despite positive feedback, conversions remained low. Many users valued the free features but were reluctant to invest in upgrades, and without a larger budget for marketing, we couldn’t boost premium adoption.

Insight

While premium features added value, converting free users to paying customers proved difficult. Healify had provided essential support to thousands, but without a stronger revenue model, we faced an insurmountable gap.

Moving On...

Healify was a profound learning experience in entrepreneurship, leadership, and resilience. Building a team of 12 on an equity-only basis taught me the importance of inspiring, focused goals to keep everyone motivated. I also learned the critical value of monetizing early to sustain our mission—passion alone can’t drive a business forward.

Moving ahead, I’m taking these lessons with me: motivate through shared vision, prioritize sustainable business models, and stay focused. Healify may have closed, but the team I got to work with and the thousands of customers we served will stay with me forever. And next time I start a consumer SaaS company, I'll be much better prepared to succeed.