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Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down

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. ----------------------------------------------- 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 ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Brian Halligan on X: / bhalligan Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #brianhalligan #figma #microsoft #meta #ai #cognition #ramp

Rory O’DriscollguestBrian HalliganguestHarry StebbingshostJason Lemkinguest
Aug 7, 20251h 28mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
August 7, 2025
Duration
1h 28m
Channel
The Twenty Minute VC
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

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. ----------------------------------------------- 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 ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Brian Halligan on X: / bhalligan Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #brianhalligan #figma #microsoft #meta #ai #cognition #ramp

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capitalist and board-level investor, focused on company building, IPO dynamics, and executive compensation.

  • Brian Halligan

    guest

    Co-founder and former CEO of HubSpot, with first-hand experience taking the company public.

  • Harry Stebbings

    host

    Founder and host of The Twenty Minute VC (20VC).

  • Jason Lemkin

    guest

    SaaS founder and investor known for operating/VC insights on growth, fundraising, and fund strategy.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Brian Halligan, Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down explores figma’s IPO pop, founder incentives, and AI-fueled market cycles explained Figma’s 250% first-day pop is framed less as “$3B left on the table” and more as a structural outcome of IPO bookbuilding, scarce float, and post-pricing demand that was not actually accessible at higher prices during the roadshow.

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