20VC: Jason Calacanis on The 4 Questions Investors Must Ask Founders, Whether YC Have Scaled Their Process Successfully & Why Early Founder Liquidity Is Good Not Bad
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 14 August 2017
⏱️ 37 minutes
🧾️ Download transcript
Summary
Jason Calacanis is arguably one of the world's greatest angel investors, as he says he has "got lucky" 7 times and counting with a portfolio that includes the likes of Uber, Thumbtack, Evernote, Tumblr and more incredible companies. Jason has also previously been a scout for Sequoia Capital, where he made the original Uber investment. On the operational side, Jason was previously a Sequoia Founder with Weblogs, sold to AOL for a reported $25-40m. Today he is the Host of This Week In Startups and Founder of The Launch Festival, bringing entrepreneurs together with potential investors. You can buy his fantastic new book, Angel here!
In Today’s Episode You Will Learn:
1.) How did Jason make his move into the world of angel investing? Why was now the right time to write, Angel?
2.) What does Jason believe are the 4 questions investors must ask founders? What response to those questions excited Jason to hear? What responses make him nervous?
3.) Why does Jason believe that founders having the option for early liquidity is good? Why does he believe it does the opposite of what VCs think and actually makes them continue to work? What are the dangers of offering early liquidity to those founders?
4.) Why does Jason believe that companies are always bought and not sold? Does VC access to corporate development teams then become a futile exercise?
5.) How does Jason view the scaling of Y Combinator? How does Jason evaluate the valuations placed on YC companies? Why does Jason believe that progressive term sheets are ridiculous?
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
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Transcript
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| 0:00.0 | Welcome back to another week in the world of the 20 minute VC with your host Harry Stebbings at H. Debbings with two Bs on Snapchat. |
| 0:06.7 | It'd be fantastic to see you there. |
| 0:08.3 | However, to the show today, and today's episode is a slight fly on the wall show. |
| 0:12.1 | There was very much a schedule, but with this very special guest today, you have to be slightly willing to go off schedule. As I say on the back of his new book, Angel, he's arguably one of the world's |
| 0:20.9 | most successful angels and one of the biggest characters in the world of early stage start-ups. |
| 0:25.5 | So I'm thrilled to welcome back Jason Kalakanis to the show today. As he says, he's got |
| 0:29.6 | lucky seven times in counting with a portfolio that includes the likes of Uber, Thumbtack, |
| 0:34.7 | Evernote and Tumblr, just to name a few of the incredible companies in his |
| 0:38.0 | portfolio. Jason's also previously been a scout for Sequoia Capital, where he made the original |
| 0:42.7 | Uber investment. On the operational side, Jason was previously a Sequoia founder, with web blogs, |
| 0:47.7 | sold to AOL for a reported $25 to $40 million. Today, he's the host of this week in startups, |
| 0:53.3 | and founder of the launch festival, |
| 0:54.9 | bringing entrepreneurs together with potential investors. And if you haven't read his new book, |
| 0:58.8 | Angel, then that really is a must and you can find the link in the show notes on the 20 minute |
| 1:02.7 | VC.com. I absolutely loved it. But before we head into today's episode, Pendo helps companies |
| 1:08.0 | create products that customers love. He was founded when alumni from Raleigh, Google, Cisco and Red Hat combined their heads and their hearts to build something they wanted but never had as product managers, a complete platform for product teams. |
| 1:20.8 | With Pendo, you can understand product usage and rapidly make data-driven decisions. |
| 1:25.3 | Survey users in-app for NPS and feedback. |
| 1:28.4 | Deliver contextual help to improve UX and user onboarding. |
| 1:31.7 | Promote new features in product to drive adoption without requiring any engineering resources. |
| 1:36.7 | Pendo is the proven choice of innovative product leaders at Salesforce, optimizely, Citrix, and many more leading companies. |
| 1:43.2 | Learn more today at go.pendo.io slash harry. That's |
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