20VC: a16z's Jeff Jordan on The Ultimate Guide to Investing in Marketplaces, Two Core Features to Look for in All Marketplace Investments, Why Fragmented Supply is so Important & Lessons from Airbnb, Pinterest and Instacart on What Makes the Best Cohorts

Jeff Jordan is a General Partner @ a16z where he serves on the boards of Airbnb, Incredible Health, Instacart, Lookout, and Pinterest, just to name a few. Before a16z, Jeff was CEO OpenTable, where he led the company during a period of hyper-growth and oversaw its IPO. Prior to OpenTable, Jeff was Senior VP and General Manager of eBay North America where he oversaw eBay's early growth into one of the Internet's leading commerce brands. In this role, he drove the successful acquisitions of PayPal and Half.com and went on to become President of PayPal, where he was responsible for establishing the company as the global standard for online payments.  

1.) From Taking Opentable Public to Being a GP @ a16z:

• What led to Jeff making the jump from CEO @ Opentable to becoming a GP at a16z?
• How does Jeff believe his operating career impacted how he thinks and acts as an investor today, both positively and negatively?
• What is his 1 biggest learning from eBay and then Opentable that has really shaped his mindset today as an investor? How did those experiences impact what he looks for in companies?

2.) The Two Core Features To Look For in Marketplaces:

• Fragmentation of supply side: Why does Jeff look for fragmented supply sides? Does this not take longer and is more expensive? How fragmented is fragmented enough?
• What are the most common reasons founders fail to acquire a fragmented supply side?
• Intelligent Lead Generation: What does Jeff really want to see in the way that new marketplaces acquire their customers? How does this change with the rise of TikTok and short-form video?
• What are some other really core features or traits that excite Jeff when he sees them in an early marketplace? What are some massive red flags for Jeff when he sees them early?

3.) How to Acquire and Retain the Demand Side of a Marketplace:

• Messaging and Brand: What are the biggest lessons Jeff has on how to craft the messaging of a marketplace to make it resonate with the target consumer?
• What are Jeff's biggest lessons from working with Brian Chesky on how they craft their messaging at Airbnb? What works? What does not work?
• Perfect Customer Cohorts: What does Jeff most want to see when examining prospective marketplace investment cohorts? What do the best have?
• What is the sign of a truly retained user in a marketplace? What is a good date duration to measure retention against? What are the biggest mistakes founders make presenting their cohorts?
• Lessons from Instacart: What are Jeff's biggest lessons from being on the Instacart board on cohorts? What makes good cohorts? How cohorts can seem bad but be good?

4.) Growth vs Profitability, CACs and LTV:

• Uber, OfferUp, Instacart, Deliveroo, respectfully, the level of profits these businesses are able to drive is questionable, why does Jeff believe marketplaces are good investments still?
• Many marketplaces start with poor unit economics, how does Jeff think about having the mental plasticity to project out to a time when unit economics could be better?
• Does Jeff pay attention to CACs at all? When are they important? When are they not? How can they be misleading? What is the best way for founders to present their CACs?

5.) It's Time to VC: Jeff Jordan: The Board Member

• What are the single biggest misalignments between VCs and their founders?
• How would Jeff describe his style of board membership today? How has it changed with time?
• What is the best way to deliver hard feedback as a board member? What are the biggest mistakes board members make? What does Jeff advise young board members today?
• What are the single best and worst changes that have happened at a16z in the last 24 months?