Keith is a Silicon Valley legend— an accomplished operator, founder, and investor. He started his career as an early executive at PayPal, LinkedIn and Square, before going on to co-found companies like OpenDoor (which IPO’d in 2020) and OpenStore.

He’s currently a General Partner at Founders Fund and Co-Founder/CEO of OpenStore. Along the way, he’s made incredible investments as an angel and VC in companies like DoorDash, Affirm, Stripe, YouTube, Palantir, Airbnb, Ramp, Faire, and many more.

In this conversation we ask questions that span three broad areas: how to grow through a downturn, how to develop good judgement, and how to build an iconic company.

This episode is packed with incredible insights and actionable advice from Keith. We hope you enjoy this conversation, and learn as much from it as we did.

In this episode we discuss:

1. Growing through a downturn 
   • Given the current market correction underway, what do you think happens next?
   • What advice do you have for founders starting companies in this market context?
   • You’ve said you believe the best companies are built in the public markets. What do you think needs to happen for more companies to go public within 4-6 years vs 10-15 years?
   • What do you think is the right time (or maturity level) for a company to go public?
2. Developing good judgement 
   • You have been extremely successfully at investing super early. What has been your approach to making investments when it’s just a team and a keynote deck?
   • You’ve talked about how you look for a “spark” when making early-stage investments. Could you describe a time you’ve seen that? What has it looked like?
   • Could you share some examples where things have not gone well and how you’ve approached those situations?
   • How have you honed your skill in evaluating people and opportunities, and what advice do you have for someone trying to improve their own judgement?
   • How much overlap do you think there is between the skills used to hire and the skills used to evaluate a founder? How do you approach assessing people in both those contexts?
3. Building an iconic company 
   • You’ve seen a lot of companies navigate the path to product-market fit. What approaches you’ve seen work particularly well? What has been your own approach to getting to PMF?
   • Post PMF, how do you think about the trade-off between growth and efficiency? Do you think the current market context changes the traditional blitz-scaling strategy?
   • When evaluating investment opportunities, to what extent are you thematically driven vs opportunistically driven?
   • You’ve talked about how people often don’t map their time to their priorities well. As a VC and an operator, how do you approach setting priorities and what does that look like on a week-to-week basis?
   • How have you approached coaching/helping founders and new managers/executives better prioritize their time towards the highest leverage activities?
4. Closeout questions 
   • What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?
   • What are your superpowers that you find yourself leaning on often?
   • Anything you’re reading right now that you’d recommend?

Links

• Follow Keith, Founders Fund and OpenStore on Twitter

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