20VC: Why It Is BS That You Never Regret Paying A High Price To Get Into A Good Company, Why There Are Only 2 Price Points That Work in SaaS and Why eSports Will Be Bigger Than Traditional Sports in 5 Years Time with Jason Pressman, Managing Director @ Shasta Ventures

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Jason Pressman is a Managing Director @ Shasta Ventures who have made investments in the likes of Nest, Dollar Shave Club, Smule, Class Dojo and more. With 10 portfolio company investments under his belt, Jason invests in both enterprise and consumer, currently serving on the boards of Crittercism, subscription billing unicorn Zuora, as well as Nextdoor and mobile music platform Smule. Prior to joining Shasta, Jason was Vice President, Strategy and Operations at venture-backed Walmart.com, where he took the online retailer from zero to large scale revenue in five years.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of venture from Walmart? What were the big takeaways from seeing Walmart enter their hyper-growth phase?

2.) Why does Jason believe it is bullshit to say, “you never regret paying a high price for getting into a good company”? How does Jason evaluate entry point? What makes one entry point attractive and another not?

3.) What does Jason see as the catalysts for the opening of public markets to tech companies? How long does he think this will continue? Is he concerned by the likes of Yext, IPOing with less than aggressive growth rates?

4.) Why does Jason believe there are only 2 price points that work in SaaS? What are they? How does this affect the structure and operations of your SaaS startup? What are the circumstances in which these price points do not apply?

5.) Why does Jason believe that eSports will be bigger than the NBA in 5 years? What are the catalysts driving this change? What needs to be formulated within eSports for this to happen?

Items Mentioned In Today’s Show:

Jason’s Fave Book: First, Break All The Rules

Jason’s Most Recent Investment: Plays.tv

As always you can follow HarryThe 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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