20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov

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 Andreesen, 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:

04:27 Navigating Enterprise Sales and Pricing Strategies

07:49 The Importance of High Gross Retention in SaaS

11:03 Investor Relations and the Power Law in Venture Capital

14:32 WTF is Product Market Fit

18:14 What No One Knows About M&A

20:05 Fundraising Challenges and Lessons Learned

32:51 What Marc Andreesen Taught Me About Boards

34:18 Why Founders and Investors are Misaligned

35:29 The OpenGov Acquisition: Selling for $1.8BN

37:22 What Does It Feel Like to Sell for $1.8BN

43:58 Why Venture Capital is a S*** Asset Class

45:13 Investment Mistakes and Lessons

01:02:05 The Importance of In-Person Collaboration