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20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success

Oct 26, 2020

Roelof Botha, a Partner at Sequoia Capital and former CFO of PayPal, shares insights from his remarkable journey in venture capital. He discusses key lessons learned from industry legends like Don Valentine, emphasizing the importance of founder assessment and strategic decision-making. Botha evaluates the current fundraising landscape while warning against overconfidence in investment success. He highlights the value of resilience, effective governance, and the power of vulnerability in team dynamics, all crucial for navigating the complex tech startup ecosystem.

40:42

Creator website

Episode guests

Roelof Botha

Highlights

AI Chapters

Episode notes

The balance of risk and resilience in investment partnerships

01:24

The Importance of Asking Questions and Finding Mentors

01:40

Intro

3min

From PayPal to Venture Capital: A Unique Journey

14min

Lessons in Resilience and Governance

13min

Navigating Crucible Moments in Tech: Key Decisions that Shape Success

2min

The Power of Vulnerability in Team Dynamics

2min

Purpose and Impact in Venture Capital

4min

Exciting New Investments and Innovative Communication Tools

4min

Roleof Botha is a Partner @ Sequoia Capital, one of the world’s leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Roelof, at Sequoia he has led rounds into the likes of YouTube, Instagram, Eventbrite, Square, MongoDB, 23andMe and Unity Technologies to name a few. Before joining the world of venture, Roelof was the CFO @ Paypal playing a key role in their hyper-growth from 2000-2003.

In Today’s Episode You Will Learn:

1.) How did Roelof go from actuary in South Africa to CFO @ Paypal? What were his biggest lessons from seeing Paypal burn $10M per month? How did Paypal lead to his joining Sequoia as a Partner?

2.) Market Evaluation: Does Roelof agree that the market is crazy today? How does today compare to prior vintages? How does Roelof assess the compression of fundraising timelines? With compressed timelines, how does he build relationships of trust with founders?

3.) Founder Evaluation: What were Roelof's lessons on founder assessment from Don Valentine? What matrix did Don teach Roelof to assess founders on? How does Roelof feel about the rise of competitive rounds? When should founders take them vs remain heads down on execution?

4.) Investment Mentality: How did Roelof prevent becoming too confident when early investments went well? How does Roelof prevent relying on past failures as a reason for turning down opportunities today? What can investors do to retain a very flexible mind? Why does Roelof believe you are only as good as your next investment?

5.) Sequoia's Edge: How does Roloef think about what it takes for Sequoia to retain it's edge at the top? How does Roloef measure the success of the Sequoia scout program? How did they structure it? How has the structure changed? What do they plan to do moving forward?

6.) Board Membership: How would Roloef evaluate his current style of board membership? How has that style changed over time? What elements did he find challenging? What advice would Roelof give to new board members adopting their first board seats?

Items Mentioned In Today’s Show:

Roelof’s Favourite Book: Man's Search For Meaning

Roelof’s Most Recent Investment: mmhmm

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