David Fialkow - Paint Outside the Lines

**Patrick O'Shaughnessy** (0:00)
This episode of Invest Like the Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. Founded by a former buy side analyst who encountered friction sourcing, building and updating models, Canalyst is now used by over 400 institutions, including the largest money managers globally and by a number of guests on the show. With detailed company specific models and data on virtually every public company, Canalyst clients are able to ramp up faster, update models instantly, and incorporate the highest quality fundamental data into any workflow. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalist.com/patrick. That's canalyst.com/patrick. If you're curious to hear more about Canalyst, stay tuned at the end of the episode where I talk to Canalyst customer Brandon Weir from BWCP to discuss Canalyst in more detail. This episode of Invest Like the Best is sponsored by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced solution on the market.
Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55 degrees or as hot as 110 degrees. It also splits your bed in half so your partner can choose a totally different temperature.
I was so impressed after using Eight Sleep that I became an investor. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use the code PATRICK.
Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts and you can access all our podcasts including edited transcripts, show notes and other resources to keep learning at joincolossus.com.

**SPEAKER_3** (2:00)
Patrick O'Shaughnessy is the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

**Patrick O'Shaughnessy** (2:24)
My guest today is David Fialkow, co-founder of General Catalyst. If you're looking for a dose of fun, charismatic energy from a very unique investor, then this is the conversation for you.
David has a diverse background, not only as an investor, but also as a philanthropist and filmmaker. He won an Academy Award for his role as the producer of the 2018 documentary Icarus. During our conversation, David and I dive into what makes a great founder, the importance of storytelling, and the value of effectively convening people within your network. After listening to all his great stories, I think you'll see why David has so much fun and success helping founders. Please enjoy My Great Conversation with David Fialkow.
My sense is this conversation is gonna be all over the place. I don't think the entry point matters all that much, but I have to pick one since I recently watched the documentary and was so interested by it in how you came to start the process that ended up with Icarus. I start here because I'm sort of fascinated by the human will to win and the ends justifying the means or vice versa and what you've learned about people and competition as a result of building Icarus.

**David Fialkow** (3:32)
Well, first of all, thank you. It's great to be here with you, Patrick. Icarus is very much in the same combination of venture capital, which is the art of luck, the pivot, backing great people and doing things along the way that make sense based on three main things. Number one, always, always, always deferring to your founder or filmmaker and trusting their instincts on things. Number two, never giving up. Failure is only defined by giving up. When we say that there's no more gas in the tank or fuel or legs on a bicycle or something, the third thing is surrounding yourself with people that are going to be super positive, treat founders, filmmakers with empathy and understand how difficult it is to do it. My background was I was a filmmaker.
My wife's a filmmaker.
I couldn't make a living coming out of college with a degree in filmmaking. So me and my best friend, Joel Cutler, started a travel company and that travel company became one of the largest travel companies in the US. Then we built in a very simple premise that Joel came up with, that everybody likes travel, travels fun, travels great enjoyment. Why not wait till the last minute and book it? Who really cares whether you go to Aruba or St. Martin or Antigua, or whether you go to London or Paris? So if it's half price or a third price, why not just go where you can afford to go? And we caught the wave of everything at the same time, more leisure time for people, people wanting to travel.