E1152: Keith Rabois on leaving Silicon Valley for Miami, Roaring Twenties 2.0, IPO spree & more

Early Investing

Keith Rabois shares his philosophy on investing in startups at their earliest stages, often before a product even exists. He emphasizes the importance of believing in both the founders and their ideas, as demonstrated by his early support for companies like Airbnb and Palantir. Rabois explains that investing early allows him to make a meaningful impact on a company's trajectory, especially when others may not see the potential.

I prefer to invest as early as possible in seed rounds before there's even a product, certainly before there's metrics.

--- Keith Rabois

He finds psychological rewards in backing companies that others overlook, helping them validate their ideas and gain broader acceptance 1 2 3.

   

Coping with Losses

Rabois discusses the inevitability of losses in venture capital and how he copes with them. He believes that if you're not experiencing failures, you're not taking enough risks, as the nature of startups involves ambitious goals that often don't pan out. Rabois compares this to sports, where not every talented player becomes an NBA All-Star, yet the journey itself holds value.

If you're not failing a certain amount, you're probably not taking enough risk.

--- Keith Rabois

He finds more frustration in successes that don't reach their full potential, as they could have been much larger with different decisions 4 5.

   

Future Meetings

The future of venture capital meetings is shifting towards a hybrid model, combining virtual and in-person interactions. Rabois notes that while Zoom calls offer efficiency, they lack the personal connection and dynamic interaction of face-to-face meetings. He hopes for a return to real-world meetings, especially for later-stage investments, where metrics and financials are more critical.

I prefer to do more real world meetings for the reasons we discussed, but I actually think founders are starting to enjoy the Zoom call.

--- Keith Rabois

Additionally, he sees opportunities for investing beyond Silicon Valley, as remote work and different time zones open up new possibilities 6 7 8.