20VC: Investing Lessons from Fred Wilson and Why Small Funds Outperform Large Funds | Why the Secret to Winning in Venture is Splitting Deals |Learnings From the Biggest Hits and Biggest Losses | Why Anyone That Always Does Their Pro-Rata is Wrong with Mo Koyfman @ Shine Capital

Mo Koyfman is the Founder and General Partner @ Shine Capital, who announced earlier this year Shine II, a $200M early-stage fund, and Shine Opportunities I, a $100M vehicle. Prior to founding Shine, Mo was the Managing Member @ Moko Brands where he made angel investments in Coinbase, Polychain, Harry’s to name a few. Before Moko, Mo spent over 7 years as a General Partner @ Spark Capital where he made investments in Plaid, Warby Parker, Skillshare and Hivemapper, to name a few. Finally prior to Spark, Mo spent over 5 years at IAC where he oversaw group of companies that included Connected Ventures, parent of Vimeo, CollegeHumor & BustedTees.

In Today’s Episode with Mo Koyfman:

1.) From Entrepreneurial Parents to IAC, Spark Capital and Founding Shine:

• How did Mo make his way into the world of venture having worked with Dara Khros, Barry Diller and Jeremy Liew?

• What were some of the biggest takeaways from his time with Barry Diller and IAC?

• How did Mo’s time at Spark impact his investing mindset? What did he learn that he took with him to founding Shine?

2.) Investment Firm vs Investment Partnership:

• What are the biggest differences between investment firms and investment partnerships?

• What are the biggest risks founders are taking when they take money from investment firms?

• Mo has very strong beliefs, how does he manage and inspire debates within his firm without shutting down or intimidating younger, less experienced team members?

• What does Mo mean when he says, “firms are great but partners matter”.

3.) How To Win in Venture:

• Why does Mo always believe that small funds outperform large funds?

• What have been some of Mo’s biggest lessons from Fred Wilson on fund strategy and sizing?

• How much of an emphasis does Mo place on the importance of ownership?

• Why does Mo believe the way to win in venture is to be collaborative?

• Why does Mo believe in the macro conditions we are entering, the landscape is about to become a lot more collaborative?

• Why does Mo believe any firm that says they will always do their pro rata is lying?

4.) The Lessons: Success and Failure:

• What are some of Mo’s biggest lessons from his biggest wins, like Plaid at seed?

• That said, why does Mo believe it is so dangerous to try and learn lessons from the wins?

• What failures have been most impactful to Mo? What did he take away from them?

• Why does Mo believe that making great burgers is like building great companies?

Items Mentioned in Today’s Episode:

Mo’s Favourite Book: Portnoy’s Complaint by Philip Roth