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.”

👋 LinkedIn

Follow us on X:

• 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.

On the podcast we talk with Chris about how to do freemium the right way, drafting a customer “Bill of Rights” to guide product decisions, and why blindly following A/B test results can lead to short-term gains but undermine your business long-term.

Top Takeaways:

🧮 Data has limits
Short-term data can lie. When every experiment looks like a win in isolation, it’s easy to miss the slow erosion of trust happening in the background. Real harm often builds quietly and cumulatively — too subtle for A/B tests to detect, and too long-term for analytics dashboards to surface.

🧊 Freemium is a strategy, not a stepping stone
Free users aren’t just a growth channel — they’re often the foundation of retention, virality, and brand. The key is not just giving something away, but building genuine value into the free tier while monetizing a clear, meaningful upgrade. Trying to monetize too early or too aggressively risks killing long-term compounding benefits.

🚪 Fake doors, real insights
Not every test needs statistical significance. Especially in the early stages of validation, it’s better to move fast, fake the backend, and just see what people click. When the goal is to gauge interest, not measure retention, scrappy beats precise.

🛑 Dark patterns don’t scale
Stacking minor friction points, misleading CTAs, or unclear pricing might bump conversions — but it quietly breaks trust. Even if the data looks fine, something more critical is breaking: your brand. When users stop recommending you, you’ll realize those small wins were expensive.

📐 Principles over process
When companies scale, the instinct is to build more process. But sometimes the best way to maintain speed and quality is through shared principles. A clear set of product values — what won’t be touched, how users are treated — provides clarity, autonomy, and momentum across teams.

About Chris Hulls:

👪 Founder and CEO of Life360, the family safety platform used by over 80 million active users worldwide.

🔒 Chris is passionate about building products that offer real daily utility while protecting user trust, focusing on long-term value instead of short-term growth hacks.

💡 “The core has to give real value to our customers, not kind of fake value. Like real, real value forever for free, period.”

👋 LinkedIn

Follow us on X:

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

Episode Highlights:

[1:33] A niche market: How the Life360 team found success by building an app in an under-served vertical.

[7:55] Free vs. paid: Striking the right balance of free versus paid features in a freemium app.

[11:37] A strong constitution: Why Chris and the Life360 team wrote a customer “Bill of Rights.”

[15:59] Data-driven: Why you may not always need to run tests on a large percentage of your users to get helpful results.

[22:17] Value ad(d): Creating helpful — not annoying — user experiences in ads and brand deals.

[29:12] Moving target: User privacy and the ethics of selling users’ raw versus de-identified versus aggregated data.

[38:31] The long haul: How to stay energized and excited working on the same product for multiple years.

[44:28] Unbreakable: Exercising caution with mission-critical features to maintain user trust.

[53:35] Future-proof: How Life360 is growing and expanding in 2025 and beyond.