Keith Rabois
Managing Director at Khosla Ventures
Description
Keith Rabois is a distinguished figure in the technology and venture capital sectors, best known for his pivotal roles at tech giants like PayPal and Square. As a seasoned investor, notably as a general partner at Founders Fund, Rabois has showcased a knack for spotting nascent startups poised for success. Renowned for his candidness and contrarian views, he consistently provides insights that diverge from mainstream tech discourse.
Suggested Questions
- Can I pitch you my startup?
- How should a startup reorganize for AI when the tech frontier shifts every 3–6 months?
- How do I balance top-down product vision with metrics without falling into A/B-test theater?
- What signals tell you a company's "office culture" will compound vs. decay?
- What are some of the leadership philosophies you have synthesized from your experiences with great leaders?
- What have you learned through osmosis from the extraordinary leaders you've worked for?
- How important is it for a leader to have intellectual heft and drive their own ideas?
- Can you explain why it is important for leaders to maintain credibility, especially in times of crisis or when asking for trust from the public?
- Can you give an example of a task that a leader might need to do that seems unrelated to managing a large organization?
- What is your strategy for managing stress, and is it something you've found impacts your success?
- What specific metrics or indicators should I consider when comparing the long-term potential of Brex and Ramp?
- How do you define consistency in life and work?
- What are some common traits of successful people you've observed from meeting with those in various fields?
- How do you prioritize being effective over being right?
- What unconventional traits have you found to be the most indicative of success in sales leadership roles?
- How do you handle fear and why do you think others are often fearful of things they shouldn't be?
- How does the office environment impact the productivity and culture of a company?
- What has led you to value being a contrarian so highly that you self-identify as an "Investor and contrarian"?
- Are there specific industries or sectors where undiscovered talent is more likely to be found?