Damon Lembi brought me onto the Learn-It-All Podcast to talk about something that doesn’t get discussed enough in the growth conversation: retention. Getting users is one problem. Keeping them is a completely different one, and most companies conflate the two until it’s too late.
Listen to the full episode here: Episode page · Apple Podcasts · Spotify · YouTube
Damon and I pulled from a decade of building apps for over 100 million users, plus some moments I’m less proud of — an App Store ban, a major lawsuit, a co-founder’s burnout, and my own breaking point. All of it shaped how I think about building products that last.
A few things we dug into:
Technology is the wrong place to start
Most founders pour energy into building better features when the real gap is understanding the people they’re building for. Customer psychology and genuine empathy create a more durable competitive advantage than any product update. When my teams focused on truly understanding what users felt, growth followed. When we didn’t, we stalled.
Not all friction is bad
This one surprises people. The instinct is to remove every obstacle between a user and the product. But some friction builds trust, creates commitment, and makes people value what they’ve worked for. The skill is knowing which friction to remove and which to keep.
Resilience is a leadership competency, not a personality trait
Getting through an App Store ban, a Zynga lawsuit, and a near-burnout in the same year taught me that resilience isn’t something you either have or don’t. It’s something you build, deliberately, through how you process setbacks and how you protect the people around you while doing it.
Building empathy without going soft
Empathy has a reputation problem in business. Leaders worry it makes them seem weak. But the most effective growth decisions I’ve ever made came from deeply understanding what my users were actually going through. Empathy isn’t softness. It’s precision.
All of this and more is laid out in Outrageous Startup Growth.