All Episodes

June 5, 2023 45 mins

Deep tech founders are either technically gifted or great at building a business. But it's seldom both, at least in the beginning.

 

So, what should venture investors pay attention to when we’re choosing founders in these disruptive technologies?

 

Greg Castle is Founder and Managing Director at Anorak Ventures, a firm that invests in early-stage deep tech startups.

 

An entrepreneur and corporate marketer turned VC, Greg has invested in 120 companies, including Oculus, Flexport and Mux.

 

On this episode of Boost VC, Greg joins us to explore how his view of venture investing has changed since he wrote his first check, explaining what he looks for in a founder and how he evaluates deep tech startups differently.

 

Greg shares his mixed feelings about the VR market right now and how he benefits from having a partner to engage in conviction-based decision-making.

 

Listen in for Greg’s advice on where to deploy capital in deep tech and learn how Anorak chooses founders who apply disruptive technologies to business problems in any industry.

 

Topics Covered

 

How Greg got into venture capital

  • Curious person who advocates for people he believes in
  • Got lucky in first few personal investments, e.g.: Oculus

 

The most important lessons Greg has learned as a VC

  • What high-functioning teams and companies look like
  • Not to take it personally when things don’t go as planned

 

What Greg pays attention to when he’s choosing founders

  • How they interact with cofounders, react to feedback
  • Punctuality at meetings, preparedness and responsiveness

 

The questions Greg asks himself before he invests in a startup

  • Do I believe in the founder?
  • Do I believe in the market?

 

How Greg evaluates deep tech companies differently

  • Move forward with presumption that anything’s possible
  • Consider if technically gifted person can build business

 

Greg’s mixed feelings about the VR market right now

  • Viable platform where developers make real money
  • Frustrated by lack of competition, Meta fumbling the ball

 

Greg’s thoughts on Apple entering the VR/AR market

  • ‘Nobody can make a product cool like Apple can’
  • Not well-positioned in immersive gaming (primary use case)

 

The Anorak investment thesis

  • Handful of technologies will have outsized impact on future
  • Find teams leveraging those technologies, industry agnostic

 

Greg’s advice on where to deploy capital in deep tech

  • Always comes down to people
  • Build out ecosystem of investors, founders

 

How Greg thinks about scale in venture investing

  • Find great people in areas that are not your strengths
  • Scale of funds = $15M to $25M per partner

 

How Greg benefits from taking on a partner

  • Need to explain yourself to thought partner
  • Can still move quickly when he needs to

 

Greg’s biggest accomplishments before age 20

  • Building group of friends in college
  • Still works with many of them

 

Greg’s definition of success

  • Confident and comfortable in your own skin
  • Content with what you have

 

Connect with Greg Castle

 

Anorak Ventures https://www.anorak.vc/

Anorak on Medium https://anorakvc.medium.com/

Anorak on Twitter https://twitter.com/AnorakVentures

Anorak on LinkedIn https://www.li


Advertise With Us

Popular Podcasts

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.