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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 16 October 2020
⏱️ 24 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | Welcome back to the 20 minute VC with me, Harry Stebbings, and today we have a guest I've wanted |
| 0:03.7 | to have on the show for a long time. I'd heard quietly under the radar about this company and what an |
| 0:08.2 | incredible CEO our guest today is. But only today do we make our episode happen. And so with that, |
| 0:12.9 | I'm very, very excited to welcome Spike Lipkin, founder and CEO at Newfront Insurance, the |
| 0:17.4 | modern insurance brokerage empowering risk management experts with advanced technology |
| 0:21.8 | to deliver innovative solutions to their clients. To date, Spike has raised over $100 million |
| 0:26.1 | with Newfront from some of the best in the business, including Founders Fund, Meritech, and of course |
| 0:30.8 | the newly founded 20 VC fund, disclaimer attached. And prior to founding Newfront, Spike was one of the |
| 0:36.1 | first employees at Open Door, where he helped grow the team from five people to an enterprise value of over $5 billion today. |
| 0:42.5 | Prior to Open Door, 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. |
| 0:51.0 | I do also have to say a huge thank you to Kevin Hart's and Max at Maritech for some |
| 0:54.5 | fantastic questions suggestions today. Really did make such a difference. But before we move into |
| 0:58.8 | the show today, I want to take a moment to mention HelloSign, a great example of a company that |
| 1:02.8 | found success in building a product focused on user experience. HelloSign is an effortless e-signature |
| 1:08.1 | solution used by millions to securely send and request legally valid |
| 1:12.2 | digital signatures and agreements. They raised a total of $16 million in funding and recently got |
| 1:17.2 | acquired by Dropbox for an impressive $230 million. Check out hellosign.com forward slash 20VC to join |
| 1:24.1 | the thousands of companies and founders who value fast, secure and simple e-signatures. |
| 1:29.6 | And if HelloSign helps you sign that term sheet, you need to get the term sheet in the first |
| 1:33.5 | place. And I want to give a mention to Draperer-a-Sprie, a publicly listed VC fund that invests in |
| 1:38.2 | high-growth European tech companies with global ambitions. Their portfolio includes |
| 1:42.5 | companies like Revolut, UiPath, Kazoo, Graphcore, |
... |
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