Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term “inbound marketing”, he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.
Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.
Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.
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In Today’s Episode We Discuss:
00:00 Intro
01:04 The Worst IPO Mis-Pricing Ever: What Really Happened at Figma
24:03 Why CEO Compensation is Broken
35:45 Is Canva Next? Why Founders Should “Run, Forrest, Run” to the NASDAQ
38:28 The Case for Going Public: VCs Are a Bigger Pain Than Public Markets
47:27 Can AI Even Work for SMBs? Why No One’s Cracked the Code (Yet)
54:40 Meta’s Monster Quarter: Growth, Cash Burn, and the Real AI Strategy
01:01:54 CEO of the Year? Why Jensen Huang Leaves Zuck & Satya in the Dust
01:06:59 Cognition’s $15B Deal & Mass Layoffs: The Most Savage M&A Move of 2025
01:12:32 Ramp’s $22B Raise: Genius Move or Suicide Round?
01:17:41 CRV Shrinks, Benchmark’s Bet, and the Future of Venture Strategy
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