Alyssa Ravasio is the Founder & CEO @ Hipcamp, the startup that allows you to book unique camping experiences on over 300,000 campsites, cabins, RV parks, public parks and more. To date, Alyssa has raised over $41M in funding from some of the best in the business including Benchmark, a16z, Brad Feld, Dave Morin, Sam Shank @ Hotel Tonight and more. Prior to founding Hipcamp, Alyssa enjoyed numerous diverse roles including being Director of Sales & Marketing @ Revel Systems to working on International Information and Communication Policy in the US State Department.

In Today’s Episode You Will Learn:

1.) How Alyssa made her way from the US State Department to founding the game-changer of camping experiences in the form of Hipcamp?

2.) How did Alyssa solve the classic chicken and egg problem for marketplaces in the early days with Hipcamp? How important does Alyssa believe it is for marketplaces to have truly differentiated supply? How does Alyssa think about what it takes to prevent leakage in marketplaces today? How can marketplace founders be strategic in building moats around their business? What works? What does not work when building marketplace defensibility?

3.) How does Alyssa manage the psychology of being CEO? What does Alyssa find to be the most challenging element of the role? What have been Alyssa's biggest lessons from her last 12 months in the role? How has she seen her style of leadership change and develop over time? How does Alyssa deal with the shit hit the fan moments?

4.) How did Alyssa find the fundraising process for Hipcamp? Why did Alyssa wait 5 years before raising the Series A? What changed in the business that made Alyssa realise then was the right time to raise big? How did the Series B with a16z and Andrew Chen catalyse so fast? Why did Alyssa select the investors she did? What investors did Alyssa not select or not select her that she would also loved to have worked with?

Items Mentioned In Today’s Show:

Alyssa’s Fave Book: The Overstory: Shortlisted for the Man Booker Prize 2018, Uncanny Valley: A Memoir

As always you can follow Harry, The Twenty Minute VC and Alyssa on Twitter here!

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