Navigating Controversy in Business Leadership

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. 

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.

In Today’s Episode We Discuss:

04:23 What is Wrong with Billionaires on Twitter: Are They Depressed?

08:49 Why Does product Market Fit Mean Less Than Ever

11:50 Why is Venture Capital More Risky Than Ever and No One is Discussing It

16:17 Will Private Equity Save a Generation of SaaS Companies and VCs

23:53 a16z’s $20BN Fund: Seriously?

31:29 Why Josh Kushner and Thrive Capital are Masters of the World

38:21 Why is Seed Investing for Suckers

45:49 Why Are $50 Million Seed Funds Useless

46:21 Founders Fund Raises $4.6BN: Analysis

52:00 How WIll LPs Change Their Approach to Venture in the Next Five Years

59:53 When Will IPOs Comeback?

01:09:15 Why Does it Not Make Sense for the Best Companies to IPO

01:09:51 Lost Ethics and Morals in Founder Secondaries and Term Sheets

01:22:58 Quickfire: OpenAI, Cursor, Deel vs Rippling