Zachary Bookman: Why Valuations and Fundraising are BS | E1235

ℹ️ EPISODE INFO

Released

December 6, 2024

Duration

1h 14m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

Zachary Bookman is Co-Founder and CEO of OpenGov, the GovTech cloud software leader that was acquired for a staggering $1.8BN earlier this year. Prior to acquisition, Zac raised over $180M from some of the best of the best including Marc Andreessen, Josh Kushner, Joe Lonsdale and Founder Collective to name a few. Zac is also a successful angel investor with investments in Flexport, Flock Safety and Addepar. ---------------------------------------------- In Today’s Show with Zac Bookman We Discuss: (00:00) Intro (00:59) Navigating Enterprise Sales & Pricing Strategies (05:19) The Importance of High Gross Retention in SaaS (08:27) Investor Relations and the Power Law in Venture Capital (12:27) WTF is Product Market Fit (16:37) What No One Knows About M&A (18:52) Fundraising Challenges & Lessons Learned (35:00) What Marc Andreessen Taught Me About Boards (39:21) The OpenGov Acquisition: Selling for $1.8BN (49:43) Why Venture Capital is a S*** Asset Class (53:58) Spicy Questions (57:36) Quick-Fire Round ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Zachary Bookman on Twitter: https://twitter.com/ZacBookman Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #zacbookman #opengov #ceo #venturecapital #founder #startup #leadership #marcandreessen #fundraising

🎤 SPEAKERS

• Zachary (Zac) Bookman

  guest

• Harry Stebbings

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Zachary (Zac) Bookman and Harry Stebbings, Zachary Bookman: Why Valuations and Fundraising are BS | E1235 explores zachary Bookman Exposes Venture Capital Myths, Vertical SaaS Truths, Timelines Zachary Bookman, founder and CEO of OpenGov, explains why venture valuations, fundraising headlines, and standard VC expectations are often disconnected from how enduring software businesses actually get built. He contrasts the slow, 15–20 year reality of company building with the power‑law, $10B‑outcome requirements of modern venture funds, arguing that most founders dramatically misunderstand investor incentives.

🔗 RELATED EPISODES

Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries

Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada

Inside Clay's Sales Playbook | Becca Lindquist

Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996

Tom Hulme & Stan Boland: Lessons from Jensen Huang & How to Fix the UK Tech Ecosystem