20VC: The Rippling Memo: Bedrock's Geoff Lewis on The Conviction Building Process to Write a $200M Check and Co-Lead Rippling's Series D | Why No Competitor Can Out Execute Rippling | Uncapped SAFE's Why You Should Never Do Them and Why Geoff Broke The Ru

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. Additionally, he has led sizable early-stage venture capital investments in dozens of companies including Upstart (NASDAQ: UPST), Tilray (NASDAQ: TLRY), Leafly (NASDAQ: LFLY), Wish (NASDAQ: WISH), Workrise, and Rippling. Prior to founding Bedrock, Geoff served as a partner at Founders Fund for several years.

In Today's Episode with Geoff Lewis:

1.) Meeting Parker Conrad: A Generational Defining Entrepreneur:

• How did Geoff first come to meet Parker Conrad, over a decade prior to making the first Rippling investment?
• What was it about Parker that compelled Geoff so much in the early days?
• How did Geoff analyze the chip on Parker's shoulder from Zenefits? How does he believe it has driven him with Rippling?

2.) Searching for Narrative Violations in Rippling:

• Why does Geoff believe Parker himself is a "narrative violation"?
• What does Geoff believe is the foundational narrative violation in the way Parker is building Rippling?
• Rippling has a large portion of its team as former founders, how does Geoff believe this impacts the culture of Rippling?
• What does Geoff believe are the single biggest barriers to Rippling being the "App Store for Business"?
• On the upside case, if Rippling goes right, how big could this be?

3.) Rippling: The Financing:

• What has been Geoff's biggest lesson on price and price sensitivity that he has learned through Rippling?
• Why does Geoff never do uncapped notes? Why did Geoff break that rule with Rippling?
• What gave Geoff the conviction to write Bedrock's largest ever check in Rippling's Series D?
• What was the massive mistake that both Geoff and Bedrock made in not financing their Series C?

4.) Geoff Lewis: The Investor

• What single trait does Geoff believe all generational defining founders share? How does he test for it?
• Does Geoff believe he has a chip on his shoulder today? How has his relationship to the chip on his shoulder changed over time?
• To what extent does Geoff engage in outcome scenario planning when making investments?
• What upside scenario plan does Geoff need to be able to see for him to make an investment?
• Has Geoff ever lost money in an investment? What were his takeaways from this experience?