20VC: Why VC Subsidizes the Wrong Type of Business, Why Capital Gains Tax is Crazy, The Biggest Misalignments Between VCs, Founders and LPs, Why Business Model - Product Fit is as Important as Product-Market-Fit with Chris Paik @ Pace Capital

Chris Paik is a General Partner @ Pace Capital, an early-stage venture firm in NYC. Pace’s first fund was $150M and their second was $250M. Before co-founding Pace, Chris was a General Partner at Thrive Capital where he spent an incredible 8 years having joined the firm when they were on their first $10M Fund.

In Today’s Episode with Chris Paik We Discuss:

1. From Hipster to One of NYC’s Best VCs:

• How Chris made his way from not knowing about venture capital to being one of the most prominent in NYC?

• What are 1-2 of his biggest takeaways from his 8 years at Thrive? How did they impact how he thinks about building Pace today?

• What are Chris’ biggest lessons from working with Josh Kushner? What did Josh do to spot young talent in a way like no one else did?

2. The Core Pillars of Successful Venture Investing:

• “Invest in companies that can be described in a single sentence”. What does Chris mean by this? How does that impact the type of companies he looks to invest in?

• “Business Model Fit is as important as PMF”. What does Chris mean by this? How does he determine where a company has business model fit?

• How does Chris analyze his relationship to market sizing? How does Chris think about how willing he is to take a bet on market timing?

• Why does Chris believe that the more “virtuous” a company is, the less enterprise value it will have?

3. What is Wrong with Venture Capital: The Misalignments:

• What does Chris believe are the single biggest misalignments between VCs and Founders?

• What does Chris see as the biggest misalignments between VCs and LPs?

• Why does Chris believe we should scrap capital gains tax and all be taxed as an income tax?

• Why do acquisitions allow investors to be screwed over by the acquiring company?

4. The Future of Social and User Generated Content Platforms:

• How does Chris analyze consumer businesses according to “The Seven Deadly Sins”? Why does he call them, “The Seven Deadly Motivators”?

• What does Chris believe is the future for Substack? Why does it not have Business Model Fit?

• What are 1-2 of his biggest lessons from being on the Twitch board? How did that experience impact his mindset and approach to what good is in UGC and social?

• What does Chris believe is the number one thing to look for in a potential consumer social investment? What do so many miss?