20VC: How To Assess Founder Psychology, Why Talking About Financial Returns In The First Meeting Is Always Wrong & How To Allocate Time Amongst A VC Portfolio with Kara Nortman, Partner @ Upfront Ventures

20VC: How To Assess Founder Psychology, Why Talking About Financial Returns In The First Meeting Is Always Wrong & How To Allocate Time Amongst A VC Portfolio with Kara Nortman, Partner @ Upfront Ventures

Kara Nortman is a Partner @ Upfront Ventures, one of LA's leading venture funds. Kara is also co-founder of Seedling where she currently serves as Chairman. Prior to starting Seedling, Kara spent close to seven years at IAC where she acted as the Senior Vice President and General Manager of Urbanspoon and Citysearch. Prior to Urbanspoon/Citysearch, Kara co-headed the M&A group at IAC where she lead some of their most successful acquisitions, notably Urbanspoon, Dictionary.com and Aston Hotels. While at IAC, Kara also served as a board member to Hatch Labs, IAC's mobile technology incubator, where she recruited and advised Tinder. Kara also spent time at Morgan Stanley, Microsoft, and Battery Ventures.

In Today's Episode You Will Learn:

1.) How Kara made her way into the wonderful world of VC?

2.) Question from Greg Betinelli and Jenny Lefcourt: What is the most surprising thing about moving from an operator to a VC? What does Kara prefer more about being a VC?

3.) Having been an entrepreneur with a board, what does a good board member look like to Kara? How does Kara allocate her time amongst her portfolio?

4.) How does Kara assess founder psychology? How does Kara look to get to know the founder both post and pre-investment? What are some signs and tells for Kara of the truly successful operators?

5.) How does Kara view diversity in the VC landscape? What are prime examples of where it is going wrong? What can be done to change this? What are Kara's hopes and concerns for the future?

Items Mentioned In Today's Show:

Kara's Fave Blog: Both Sides of The Table

Kara's Fave Book: Grit by Angela Duckworth

Kara's Most Recent Investment: Stem

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

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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20VC: Carvana CEO on Buiding a $50B Company, Losing 99% and Coming Back | Ernest Garcia: Inside the Mind of the Most Misunderstood CEO in America

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20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech

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20VC: Microsoft CTO on Where Value Accrues in an AI World | Why Scaling Laws are BS | An Evaluation of Deepseek and How We Underestimate the Chinese | The Future of Software Development and The Future of Agents with Kevin Scott

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