On the podcast I talk with Tim about the importance of trust in web2app funnels, replacing free trials with money-back guarantees, and how they’ve found success with contractors after struggling with in-house marketing hires.

Top Takeaways:

🔁 Replace trials with trust to attract high-intent users

A 30-day money-back guarantee can outperform traditional free trials—especially in web funnels. Paying upfront sends a stronger signal to ad platforms, helping them optimize for the right users. And when refunds are rare, overall LTV improves. It’s a bet on product confidence and customer intent.

🧑‍🤝‍🧑 Learning apps work better when parents are part of the experience

Apps that require co-use between a parent and child show far better educational outcomes and retention. Research shows kids learn up to 19x more effectively with adult involvement. It’s a smaller market—but a deeper one—if you design for it.

🏗️ Rigid methods can stifle product innovation

Strict adherence to frameworks like Scrum can turn creative engineers into ticket-takers. Giving teams room to rethink and revise—even late in development—yields stronger products. Empower developers as collaborators, not executors.

🌐 Trusted domains outperform in web-to-app conversion

When onboarding flows are moved to the web, conversion often drops—unless users recognize and trust the brand. Memorable, credible domains help users feel confident making purchases off-platform. Trust is the friction reducer.

🧰 Specialized contractors deliver more with less overhead

Instead of building an in-house team of marketing generalists, using seasoned channel experts—paid media, lifecycle, SEO—can deliver faster results with less management. It’s a scalable model for lean teams aiming to punch above their weight.

About Tim Dikun:

🧑‍🏫COO of Teaching.com, a suite of educational apps for children that’s been helping kids learn to read and type for nearly 30 years.

📖 Tim is passionate about building world-class educational tools that leverage both the power of AI and the parent-child connection.

💡“There's a lot of tooling out there for mobile apps that we just can't use because Apple won't let us — because it's a kids’ app. And I get it, it makes sense. It just means we have to get a little creative and find ways to get the information that we're looking for.”

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David Barnard - @drbarnard
Jacob Eiting - @jeiting
RevenueCat - @RevenueCat
SubClub - @SubClubHQ

Episode Highlights:

[0:37] Storied history: How Teaching.com found product-market fit in the early days of subscription apps.

[4:41] (A)syncing up: Why Teaching.com disables Slack and Basecamp notifications in their team communications.

[8:12] Ch-ch-ch-changes: Teaching.com’s approach to product development encourages ideation and late-stage changes, rather than sticking to an arbitrary design.

[11:48] Intelligence (artificial and otherwise): Finding the right balance between AI and the human touch in an educational product.

[15:40] Testing the waters: Experimenting with higher prices, money-back guarantees, and annual plans to increase LTV.

[23:03] Context switching: Teaching.com’s experiments with web-to-app resulted in a 50% increase in trial starts and a 30% increase in paid conversions.

[28:35] Upselling: Increasing LTV with downloadable in-app purchases and physical products on Amazon.

[33:02] Land and expand: Increasing the size and LTV of your user base by serving additional customer needs.

[35:34] Kid-friendly: The unique challenges of developing subscription apps for children.

[38:36] Expert advice: Why Teaching.com contracts with marketing channel experts instead of building an in-house marketing team.

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