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In this episode of How They Scaled It, I sit down with Rick Clark, VP of Strategic Partnerships at CloudNine and Co-Founder of The Masters Conference.

Rick has been on the frontlines of legal technology for over two decades. He has co-founded and developed several successful ventures including The Masters Conference, Wave Software, and ESI Analyst that have provided cutting-edge solutions and insights for complex data challenges.

From converting texts into court-ready evidence to crafting conferences that matter, Rick dives into the lessons and challenges of scaling in a niche, slow-to-change industry—and how strong partnerships made it all possible.

00:00:13 — How the pandemic changed digital evidence forever

00:00:36 — Meet Rick Clark: founder, innovator, connector

00:01:12 — Early days of discovery: from paper to digital

00:02:07 — Why 2006 was a turning point for eDiscovery

00:03:15 — Launching Wave Software at the perfect moment

00:04:16 — Starting The Masters Conference over coffee

00:05:55 — Differentiating in a sea of legal tech giants

00:07:16 — Creating ESG Analyst for chat and mobile data

00:09:11 — Pandemic-proof product-market fit

00:10:20 — From emails to WhatsApp: the new digital trail

00:12:42 — Scaling smart: how ESI Analyst stood out

00:14:28 — Cross-channel threading and human behavior

00:15:24 — Strategic differentiation in a crowded market

00:16:12 — When acquisition becomes the smartest path

00:19:51 — How The Masters Conference scaled to 15+ cities

00:21:34 — Why local relevance drives lasting impact

00:24:01 — AI adoption in legal: faster than ever before

00:26:45 — How lawyers are (finally) catching up

00:27:27 — Rick’s partnership strategy and why it works

00:30:04 — Build your network, protect your reputation

00:32:37 — Lessons Rick wishes he knew earlier

00:35:42 — What’s next: education, thought leadership, and mentorship