20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance


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Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States.

In Today’s Episode You Will Learn:

1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront?

2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control?

3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do?

4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal?

5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How?

Items Mentioned In Today’s Show:

Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln

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