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

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.

In Today's Episode with Jeff Jordan We Discuss:

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?

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20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?

20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?

Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $50M ARR by the end of the year. Before Base44, Maor was the Co-Founder and CTO of Explorium. AGENDA: 00:05 – 00:10: How Vibe Coding is Going to Kill Salesforce and SaaS 00:13 – 00:15: Do Vibe Coding platforms have any defensibility? 00:22 – 00:24: I am not worried about Replit and Lovable, I am worried about Google… 00:28 – 00:29: Margins do not matter, the price of the models will go to zero 00:31 – 00:32: Speed to copy has never been lower; has the technical moat been eroded? 00:47 – 00:48: How does Base44 beat Cursor? 00:56 – 00:57: Do not pay attention to competition: focus on your business 00:57 – 00:58: How Base44 is helped, not hurt by not being in Silicon Valley? 00:58 – 00:59: What percent of code will be written by AI in 12 months? 01:01 – 01:02: OpenAI or Anthropic: Why Maor is Long Anthropic? 01:03 – 01:04: If I could have any board member in the world it would be Jack Dorsey

24 Nov 1h 11min

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20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund.  Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails 10:35 – The Rippling Deal That Changed Everything 12:40 – Living in Sam Altman's Shadow: The Confession 17:30 – $200M Fund Mistakes: Max's Brutal Lessons From Hydrazine 22:05 – The $2B Reddit Return… and the $2B Left on the Table 25:00 – Why Climate Tech Is a Total VC Mirage 28:40 – The New Seed War: Can Anyone Survive Sequoia & Andreessen? 46:55 – Max's Boldest Predictions

21 Nov 1h 19min

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20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will Never Go Public

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20 Nov 1h 22min

20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth?

20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth?

Dr. Andrew Ng is a globally recognized leader in AI. He is Founder of DeepLearning.AI, Executive Chairman of LandingAI, General Partner at AI Fund, Chairman and Co-Founder of Coursera. As a pioneer in machine learning Andrew has authored or co-authored over 200 research papers in machine learning, robotics and related fields. In 2023, he was named to the Time100 AI list of the most influential AI persons in the world. Agenda: 03:19 What are the Biggest Bottlenecks in AI Today?  08:51 How LLMs Can Be Used as a Geopolitical Weapon 15:48 Should AI Talent Really Be Paid Billions? 29:07 Why is the Application Layer the Most Exciting Layer? 36:22 Do Margins Matter in a World of AI? 38:02 Is Defensibility Dead in a World of AI? 45:29 Will AI Deliver Masa Son's Predictions of 5% GDP Growth? 49:39 Are We in an AI Bubble? 57:31 Will Human Labour Budgets Shift to AI Spend?

17 Nov 1h 2min

20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify

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Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era. AGENDA: 05:05 Biggest Lessons from Selling My Company to Shopify 09:55 Where Does Shopify Suck at Product: Lessons from that? 17:37 What makes Truly Great product Design: The Five Pillars 31:02 The Future of Design in an AI-Driven World 36:00 Do We Skip the Design Phase in AI: Figma's Evolving Role in Design 40:09 Remote Work vs. In-Person Collaboration: Where Remote Loses? 42:43 What Happens to the Vibe Coding Market 47:06 Product Management and Team Dynamics 59:48 Does AI Favour Incumbents or Startups

14 Nov 1h 11min

20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening

20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening

AGENDA: 04:22 Sequoia's Leadership Transition 09:46 Michael Burry's Big Short on Nvidia and Palantir 17:41 Gamma Raises $100M at a $2BN Valuation 32:34 Does Defensibility Exist Today When Copying is Easy 40:31 Should All Funds Be Way More Diversified 47:12 How to Run a Fundraising Process & What Not To Do 57:57 Datadog Surges 20% and Duolingo Crashes: What Happened

13 Nov 1h 15min

20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid

20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid

Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchmark, Ev was a Partner @ Kleiner Perkins and before Kleiner, Ev was an investor at Founders Fund and Bond.  AGENDA: 05:25 Biggest Investing Lessons from Peter Thiel, Mary Meeker and Mamoon Hamid 14:36 OpenAI Will Be a $TRN Company & OpenAI or Anthropic: Who Wins Coding? 22:27 Why We Should Not Focus on Margin But Gross Dollar Per Customer 30:25 Why AI Labs are the Biggest Threat to AI App Companies 44:26 Do Benchmark Fire Founders? If so… Truly the Best Partner? 54:38 People, Product, Market: Rank 1-3 and Why? 57:36 Why the Mega Funds Have Just Replaced Tiger 01:04:08 GC, Lightspeed and a16z Cannot Do 5x on Their Funds…  01:14:09 Single Biggest Threat to Benchmark

10 Nov 1h 25min

20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets

20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio. In Today's Discussion with Chad Peet's We Discuss: 1. You Need a CRO Pre-Product: Why does Chad believe that SaaS companies need a CRO pre-product? Should the founder not be the right person to create the sales playbook? What should the founder look for in their first CRO hire? Does any great CRO really want to go back to an early startup and do it again? 2. What Everyone Gets Wrong in Building Sales Teams: Why are most sales reps not performing? How long does it take for sales teams to ramp? How does this change with PLG and enterprise? What are the benchmarks of good vs great for average sales reps? How do founders and VCs most often hurt their sales teams and performance? 3. How to Build a Hiring Machine: What are the single biggest mistakes people make when hiring sales reps and teams? Are sales people money motivated? How to create comp plans that incentivise and align? Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first? Why is it harder than ever to recruit great sales leaders today? 4. Lessons from Scaling Sales at Snowflake: What are the single biggest lessons of what worked from scaling Snowflake's sales team? What did not work? What would he do differently with the team again? What did Snowflake teach Chad about success and culture and how they interplay together?

7 Nov 1h 9min

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