20VC: Keith Rabois on Why Buy Low, Sell High Does Not Work in Venture, Keith's Biggest Lessons from Prior Crashes, Why Today's Public Markets are not an Over-Reaction, Why Valuation is a Trap & Why Wokeness is a Function of Entitlement

20VC: Keith Rabois on Why Buy Low, Sell High Does Not Work in Venture, Keith's Biggest Lessons from Prior Crashes, Why Today's Public Markets are not an Over-Reaction, Why Valuation is a Trap & Why Wokeness is a Function of Entitlement

Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. As for Keith, he has led the first institutional investments in DoorDash, Affirm and co-founded Opendoor. He has also led investments in Faire, Ramp, Trade Republic, and Stripe. As an operator, Keith has an unparalleled track record as a Senior Exec at Paypal, he then went on to influential roles at Linkedin and being COO at Square. Finally, as an angel, Keith made early investments into Airbnb, Lyft, Palantir, Wish and more.

In Today's Episode with Keith Rabois:

1.) Buy Low, Sell High: What BS!

  • Why does Keith believe that "buy low, sell high" does not work in venture?
  • Why would it lead you to very dangerous investment decisions at the early stage?
  • How does the size of your fund impact the appropriateness of "buy low, sell high"?

2.) The Current Landscape:

  • Does Keith believe the current state of public markets is an over-reaction or a new normal?
  • How does Keith respond to the suggestion that Founders Fund has paused new investments given the uncertainty in the market?
  • How does Keith think about investing through cycles and temporal diversification?
  • How does Keith advise young investors today questioning whether they are actually any good at this?
  • What does Keith believe are his biggest fears and insecurities today?

3.) Outcome Scenario Planning and Competitor Analysis:

  • Does Keith believe outcome scenario planning is important?
  • Why does Keith believe you can always tell your biggest hits early? What have been the core signs for him?
  • What have been some of Keith's biggest lessons from Mike Moritz and Vinod Khosla when it comes to upside maximization? What are the right questions to ask?
  • Why does Keith believe you do need to look through public market comps when investing in startups?

4.) Time Allocation and Losing Faith in Founders:

  • How does Keith approach time allocation across the portfolio? Spend time with the winners or help the struggling companies? What have been his biggest lessons here?
  • What does Keith do when he has lost faith in the founder? How does he communicate it to them?
  • What does Kieth believe VCs do wrong when they no longer believe in the founder or company?

5.) Do VCs Add Value?

  • What does Keith believe is the acid test for whether he is doing his job as a VC properly?
  • Why does Keith believe there are only 5 board members that add true value to their companies at scale?
  • Who is the best board member Keith has ever worked with? Why?
  • Why does Keith believe that age is not your friend as an investor? How does he combat this?

6.) The Downfall of SF and Wokeness:

  • Will we see a reduction of wokeness in companies with the public markets correcting and power shifting from employees to employers?
  • Is Keith concerned by the lack of coherence in the US today when it comes to politics?
  • What are the core reasons for the downfall of SF to Keith?
  • Why does he believe it is a net negative to build a company in SF today?

Items Mentioned in Today's Episode:

Keith's Most Recent Investment: Found

Episoder(1388)

20 VC 004: David Hornik on the Magic of Stanford and Startups

20 VC 004: David Hornik on the Magic of Stanford and Startups

Welcome to Session 4 of The Twenty Minute VC, on today's incredible show, I am hugely excited to present David Hornik. David started his career as legal attorney to some of the hottest startups in Silicon Valley before making his foray into the Venture Capital Industry with August Capital in 2000. If that wasn't enough, David created the 1st Venture Capital blog, VentureBlog and is also the presenter of VentureCast. In today's episode you will learn: Why David made the transition from the legal world into the VC industry? What is so special about Stanford that enables a continuous flow of revlolutionary companies? Whether legal skills are attributable to the funding industry? What David looks for when investing in a company? Does it always have to be a big market opportunity for VCs to invest? What the best piece of business advice David has ever received? What book David would recommend to a Startup Founder? We then progress into a quick fire round where we hear David's views on Peter Thiel's 20 Under 20 and the 1st $Trillion business.

18 Jan 201522min

20 VC 003: Bob Ghoorah on Startups, The Pitch and Uber

20 VC 003: Bob Ghoorah on Startups, The Pitch and Uber

On today's episode I am thrilled to welcome Bob Ghoorah, Managing Director at Columubus Nova Technology Partners. Bob has experienced both sides of the table having been an early employee at three technology companies in Silicon Valley; LoudCloud (Nasdaq: LDCL), Opsware (Nasdaq: OPSW) and Ning, a privately-held software platform (sold to Glam Media in 2011). In this episode we find out: The benefits of having a legal knowledge in the Startup community. What characteristics make the best entrepreneurs? Who does Bob think of, when the word 'success' is mentioned and why? Where Bob sees the future of Uber? What aspects of a Startup are essential in order to obtain VC funding? Is it important for Startups to be located in Silicon Valley? What books Bob woulg give to an aspring entrepreneur and startup founder? What advice Bob would give to anyone looking to get into the Venture Capital Industry? Finally, we head to the quick fire round. Here, we get Bob's immediate reactions to the latests tech topics including tech bubble, company valuations and the first trillion dollar company. For all the resources mentioned in todays show head over to The Twenty Minute VC.

13 Jan 201522min

20 VC 002: How to become a VC with Kris Jones

20 VC 002: How to become a VC with Kris Jones

In this session of The Twenty Minute VC, I'm so excited to have the opportunity to interview Kris Jones. Kris has enjoyed an amazing career in the technology industry, founding PepperJam, an internet marketing agency in 1999 and later selling it to Ebay in April of 2010. More recently, Kris has made his transition into the Venture Capital Industry through the founding of an early stage technology investment fund, KBJ Capital, which includes portfolio companies Highlighter.com, French Girls App, ReferLocal.com, LSEO.com and many more incredible companies. In this session you'll learn: Why Kris decided to make the transition from the Startup ecosystem to the world of Venture Capital. How did it feel for Kris, selling his company to Ebay? What was the most important lesson Kris learnt in the journey from having the idea for PepperJam to being acquired by Ebay? What is the key characteristic a Founder must have? What can an individual do to get employed in the Venture Capital industry. Kris is also a prolific writer here are some of his articles, you can check out! Forbes: 15 Steps to Set Your Company Up for a Successful M&A Mashable: 9 Ways Social Media Marketing Will Change in 2014 Citibank: How to Impress a Potential Investor

13 Jan 201522min

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

Welcome to the 1st episode of The Twenty Minute VC, on today's show we have Guy Kawasaki, Guy is the Founding Partner of Garage Technology Ventures, a seed & early stage venture capital fund investing in extraordinary entrepreneurs with unique technologies. Previously, he was Chief Evangelist of Apple Inc and an advisor to the Motorala Business Unit of Google. Guy is also the author of many best selling books including the recent best seller, The Art of Social Media: Power Tips for Power Users. In this episode we delve into: Why Guy made the transition into the VC industry? What is the most important aspect for a startup to have? What drives Guy insane about startup founders today? What books Guy gives to aspiring entrepreneurs? What software & apps Guy cannot live without? We then finish on a quick fire round where we discover Guy's thoughts on the future of Amazon, Tesla and whether we really are in the midst of a tech bubble. All of the products mentioned in todays show can be found at www.thetwentyminutevc.com If you love the show, please do leave a review on the iTunes store and don't forget to subscribe!

13 Jan 201519min

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