Most entrepreneurs dream about building a billion-dollar business—but the idea of giving things away for free feels counterintuitive. The truth is, some of today’s most successful companies like Zoom, Dropbox, and Canva were built on this exact model. If you’re still clinging to outdated go-to-market strategies, you’re leaving exponential growth on the table.
I sat down with JR Lay to unpack my new book, Freemium. With five SaaS exits behind me, I lay out a simple 3-step formula for freemium success: empathy, generosity, and metrics. We dig into how B2B entrepreneurs can use these principles to win in an AI-driven, self-service economy.
If you’re ready to create value first, monetize second, and future-proof your business, this conversation will help you level up.
What we got into
Why “free” works: How billion-dollar brands (Zoom, Dropbox, Canva) start with generosity—and why “free” accelerates adoption instead of devaluing your product.
The freemium formula: Empathy → Generosity → Metrics. Get into your customer’s head, solve a real problem with no strings attached, then use data to improve their journey.
Reciprocity in practice: Giving value first changes the relationship—from seller vs. buyer to partners solving a problem together.
Human in the loop (even with AI): Where people add outsized value in a product-led motion—and why some moments should stay human-to-human.
Factory thinking: Systematize the predictable so you can humanize the exceptional. Let automation handle repeatable GTM work; reserve humans for nuance and relationships.
Purpose & confidence: Why confidence (not competence) blocks most progress—and how small commitments build momentum.
AI in GTM today: What’s already automated (trials, upgrades, renewals) and where AI agents can guide choices, detect signals, and trigger the right human help.
Preparing for the next 36 months: Get hands-on with AI now; move from experiments to agentic, always-on workflows that remove predictable toil.
Betting with the horizons model: Invest in self-service and automated purchasing—your competitors already are.
Create value before you extract value: Make it easier to buy, center the customer, and let revenue be the second step.
Episode breakdown
00:00 Introduction and Guest Introduction
01:05 Personal Updates and Positive News
02:46 The Journey of Writing Freemium
03:42 The Rise of Self-Service in SaaS
07:19 Empathy, Generosity, and Metrics in Business
09:16 The Role of Reciprocity and Human Connection
15:24 Human Touch in the Age of AI
17:20 Human Touch in AI Integration
19:02 Systematizing the Predictable
21:56 Purpose and Confidence
24:36 AI in Go-to-Market Strategies
28:03 Preparing for AI’s Impact
33:41 Creating Value Before Extracting Value
35:07 Connecting and Growing Together