The Revenue Room™, by H2K Labs
Welcome to The Revenue Room™, brought to you by H2K Labs. Our podcast is designed for CEOs and their revenue-critical executive teams leading media, events, data/info, and marketplace businesses. We focus on boosting revenue, enhancing profitability, and elevating enterprise value. Each episode delves into cutting-edge data-driven strategies to accelerate revenue, manage risks, and establish scalable, predictable processes. We also discuss elevating revenue to the core of operational excellence, empowering you to consistently outperform your competitors.
The Revenue Room™, by H2K Labs
From Startup to Scale: Jerry Li’s Playbook for the Next Economy
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In this episode of Revenue Room™, Jerry Li shares his hard-won lessons on building, scaling, and thriving in the age of AI. From navigating the leap from startup scrappiness to sustainable scale, to reshaping work and leadership for the next economy, Jerry’s playbook is equal parts visionary and practical.
You’ll learn how to:
- Rethink growth strategies beyond short-term wins
- Lead teams through rapid innovation cycles
- Harness AI without losing the human edge
- Prepare your business for the economy that’s coming next
Whether you’re a founder, operator, or future-focused leader, Jerry’s insights will change how you think about growth, technology, and the future of work.
About Jerry Li
Jerry Li is the CEO and Co-Founder of Gradual, the all-in-one community platform built to turn engagement into insight and scale connection with purpose. Before starting Gradual, he led engineering teams at Amazon and Groupon, focusing on building systems at scale and mentoring emerging leaders. His passion for community took shape through building ELC—the Engineering Leadership Community—which has grown into the world’s largest and most recognized network for engineering leaders and executives. What began as small, in-person gatherings evolved into a global community. During the shift to virtual at the start of the pandemic, the internal tools created to support ELC became the foundation for Gradual. Today, Gradual powers communities for companies like OpenAI, Perplexity, Fiverr, Scale AI, and Siemens. Jerry remains focused on helping organizations build community-led ecosystems that drive growth, deepen relationships, and unlock collective intelligence.
About RevvedUP 2026
RevvedUP 2026 is where CEOs and revenue-critical C-Suite leaders reset their growth playbook for the AI-first economy. Taking place March 23–24, 2026 at The Vinoy Resort in St. Petersburg, FL, this two-day strategy lab helps leaders pressure-test how AI moves from cost center to growth driver and turn data and disruption into competitive advantage.
About Heather Holst-Knudsen
Heather Holst-Knudsen is the founder and CEO of H2K Labs and Revenue Room™ Connect. A seasoned executive and operator across media, marketplaces, events, and technology, she specializes in digital transformation, data-driven growth, and customer-centric value creation. Heather shares her insights on multisided business models through The Revenue Room™.
About Revenue Room™ CXO
Revenue Room™ CXO is a private executive community for CEOs and revenue-critical C-Suite leaders navigating growth in the data and AI economy. Through curated peer discussions and strategy sprints, members tackle real-world challenges in revenue transformation, customer intelligence, and business model innovation.
Learn more or apply for membership at info.h2klabs.com/apply-cxo.
00:00–02:00 | Introduction
Heather Holst-Knudsen introduces Jerry Li, CEO of Gradual and founder of the Engineering Leadership Community (ELC). Jerry’s career journey includes engineering leadership roles at Amazon and Groupon, before turning his passion for community into a business platform.
02:00–05:00 | The Pain of Leadership
Jerry explains how his early struggles as a manager—learning slowly and making painful mistakes—drove him to seek out shared knowledge. ELC was born from the need for engineering leaders to learn from each other instead of operating in silos.
05:00–08:00 | Why Meetups Weren’t Enough
Despite the abundance of meetups in Silicon Valley, Jerry found them too surface-level and serendipitous. True leadership growth required curated, ongoing peer-to-peer conversations supported by technology.
08:00–12:00 | Engineering + Community Building
Jerry’s dual background in engineering and leadership gave him a unique advantage to design Gradual. He built tools to create better user experiences for members while solving pain points for organizers.
12:00–16:00 | The Real Value of Community
Jerry highlights that the real value of communities lies beneath the surface—trust, curated groups, and intentional connections. He notes engineers often “like networking, but hate networking,” so structure and facilitation are crucial.
16:00–20:00 | Protecting the Mission
ELC succeeded because it stuck to its mission—strictly for engineering leaders. By excluding recruiters and marketers, members felt safe and invested, while outsiders respected (and even wanted into) the exclusivity.
20:00–25:00 | Events as Growth Engines
Events became ELC’s foundation, fueling trust and word-of-mouth growth. Jerry stresses that designing events with multiple value layers (insight, belonging, tools, connections) ensures members never leave disappointed.
25:00–30:00 | From ELC to Gradual
Gradual was born out of necessity—Jerry’s team coded tools for ELC in 2016 without realizing they were building a platform others would need. Years of iteration created a modular system now serving companies like OpenAI, Fiverr, and Siemens.
30:00–36:00 | The OpenAI Case Study
OpenAI’s first community on Gradual began with 200 elite researchers. Over time, it expanded into a global ecosystem, supporting champions, customers, and public education (e.g., OpenAI Academy). Jerry notes community success requires small, focused beginnings that grow gradually.
36:00–45:00 | Communities into Ecosystems
Jerry describes how communities evolve into ecosystems where members’ needs naturally introduce sponsors, vendors, and experts—if managed with intention. He outlines revenue models from paid events to sponsorships, while emphasizing that monetization follows genuine value creation.
45:00–47:00 | AI & the Future of Community
Jerry envisions AI-powered “agents” that act on behalf of community members, surfacing the right connections, events, and insights without requiring constant presence. AI makes personalized community engagement possible at scale.
47:00–50:00 | Rapid Fire & Closing
Jerry shares his favorite book (Extreme Ownership), and a personal story about learning to scuba dive in Bali before he could swim—a metaphor for trust in community. Heather closes with invitations to Revenue Room Connect and upcoming events.
