My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, so our conversation spans early-stage investing, business building, and entrepreneurship. I’ll not sure forget his analogy distinguishing between navigators and cartographers, nor the rest of the interesting ideas he shared after seeing and investing in so many great businesses. We also discuss how First Round has bucked the trend to build what I’d call a platform adjacent to the core investing business which does a lot for their entrepreneurs and is a model for other professional investing firms, both in venture and elsewhere. Please enjoy my conversation with Josh Kopelman.

This episode is brought to by Koyfin.

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Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:05) – (First question) – How pandemic has impacted their investing strategies

(3:54) – How this stressful environment impacts founders

(6:23) – His early career as a founder and how startup culture has changed

(10:15) – Most important lessons from his entrepreneurial career and building from just an idea

(11:50) – How to analyze a founder

(14:05) – Common disagreements when it comes to deciding on an investment

(15:33) – How many opportunities they evaluate in a meeting

(16:16) – The curvy road to their investment in Roadblox

(17:52) – Whether the concept for a platform is overused

(19:36) – Founders asking what google search they should build on

(20:46) – Solving existing or forecasted problems

(25:39) – How the startup scene is impacted by the huge legacy tech companies

(30:28) – What makes a great early stage investor

(32:19) – Do they focus on founders or themes

(33:19) – Where will valuations and returns come back to after the pandemic

(36:30) – How are business models evolving in technology entrepreneurship

(36:31) – Matt Clifford Podcast Episode

(39:40) – The Dorm Room Fund

(43:02) – Whether investment funds should have their own platform

(47:31) – Product mistakes in software building

(51:52) – What he’s most excited about for the future

(54:05) – The kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

Follow Patrick on Twitter at @patrick_oshag

Freedom is Non-Duality