0:50 Jason intros Benchmark's Sarah Tavel 1:20 Aside from Slack, what other companies grew like consumer-facing but charge like enterprise? 3:19 How was Sarah recruited to Benchmark? How is Benchmark different from other major VC firms? 12:04 Limited upside of talking to the press in 2020 17:30 Growing up in NYC and going to Harvard 21:30 Jason on becoming a "Don't touch the thermostat" dad 23:58 How did the offer from Peter Fenton go down? What drew Sarah to Benchmark? 28:36 Sarah's thoughts on disrupting VC as a woman from the inside & from the outside 37:30 How going from operating to investing is trading stress for anxiety 40:51 Jason and Sarah discuss their most personal & significant investments: Calm & Pinterest 47:26 How Pinterest's business model was a mold of Facebook and Google 49:45 Jason tells regulators how to stop Google 58:14 Investing in Chainalysis & Crypto infrastructure 1:12:44 Are the best companies polarizing? 1:16:30 Investing in Hipcamp 1:29:43 Marc Andreessen asks Sarah a question

0:44 Jason shares some thoughts on hard work 1:52 Jason intros Anthemos Georgiades and they discuss how Zumper was launched at TechCrunch 4:02 How did Anthemos wind up as a founder after working in consulting 6:45 What is Zumper's origin story? How many iterations did they go through before coming up with an MVP? 15:34 How did Zumper monetize their marketplace? 18:30 Partnering with Facebook & diversifying revenue 27:12 Anthemos shares thoughts on growth vs. profitability, should Brandless exist? 31:03 Uber vs. Airbnb in terms of EBITDA, thoughts on current state of Airbnb with IPO pending 37:56 Differences between Airbnb and VRBO customers according to Jason 41:00 Airbnb's effect on the rental market 46:15 Thoughts on co-living spaces 48:35 Reactions to Zumper's monthly rent report 51:20 Co-living as a business from a VC perspective 53:02 Jason gives Anthemos some NYC hotel suggestions 54:01 Jason's Hertz car rental story 59:04 Increasing difficulty of building a major team in San Francisco 1:07:38 Jason calls Ben Horowitz & answers a question from a fan

0:36 Jason intros Monique & Wade 8:29 Tech Journalists vs. Founders/VCs 14:48 Is link-baiting press a systemic, societal issue? 19:21 Future of Founders/VCs controlling their own voice via podcasts, email newsletters, etc. 23:59 SpaceX sending passengers into space in late 2021, early 2022 28:02 Kickstarter employees vote to Unionize 41:28 Gray New World - how lucrative is the growing elderly demographic? 49:37 Twitter combatting fake/misleading news with potential new features 58:01 Blue Apron continues to plummet 1:04:13 Lambda School controversy 1:12:42 What is the path for Zapier? What is No-Code's impact on the startup industry?

0:50 Jason intros CRV's George Zachary 2:20 Passing on Google at MDV and coming to peace with the anti-portfolio 5:51 Differences between leadership & management, where Steve Jobs, Larry & Sergey fell on that scale 10:27 Why 1990's VC was sales & marketing-driven instead of product-driven as it is now 12:52 What shifted the philosophy to product-driven businesses? 18:00 Meeting Elon Musk in the 1990's and backing Zip2 21:59 What were Seed investors like in the '90s? Origins of Sand Hill Road 25:48 Elon pitching Zip2 to a conglomerate of venture firms & selling Zip2 for cash 28:07 How VCs can be conceptually right and wrong in the outcome, how X.com merged with Confinity and became PayPal 33:27 Why is it harder to 3x the massive venture funds? How is age a limiting factor in VC? 40:28 "It doesn't make a difference what you pass on. It only takes 1 company to make your career." Positive & negative feedback cycles in VC. 42:54 Battling through multiple portfolio companies dying at once 44:15 What was George's biggest investment hit, both economically & personal fulfillment? 52:37 George describes his recent health scares and how they shifted his investment focus 1:04:06 Reasons the life-expectancy in the US has gone sideways in recent years 1:07:39 Potential health-tech advancements in the near future 1:21:58 Thoughts on CRISPR & "designer babies" 1:30:27 Cell-based fish & meat 1:37:32 Potential coronavirus repercussions - what's real and what's not? 1:55:13 Jason calls for eliminating handshakes

0:56 Jason intros David Heinemeier Hansson (@DHH) and asks about the work-from-home paradigm shift 5:28 Measuring programming success via budgets instead of estimates, quantifying creativity 9:57 Are incentive systems inherently bad? 13:01 How terrible commutes turned the tides for remote work in Silicon Valley, why do executives subject themselves to horrible working conditions? 17:59 What is the optimal amount of work hours per week? 19:58 Benefits of higher minimum wage 23:28 How can America "get to Denmark"? Should we rein in capitalism? 27:19 How do educational stipends work in Denmark? Benefits of state-sponsored education & healthcare 32:27 Is American bureaucracy able to change quickly? 35:52 Are gig workers being exploited? Why or why not? 45:57 Flexibility vs. Security in the gig-economy 51:20 Has the American Dream become false in America? 1:00:26 Are ISA schools (like Lambda School) an innovation or a bandaid on the failing capitalist system? 1:06:30 What do successful numbers look like for ISAs? 1:12:28 Starting Basecamp & raising from Jeff Bezos in the early days 1:19:43 Roasting Jeff Bezos on Twitter, socialism, progressivism in America 1:28:13 Amazon disappointments & how can Bezos save face? 1:36:31 Wealth tax debate 1:43:23 Which major tech companies should be broken up? 1:52:04 Will GDPR-like policies work in America? 1:55:59 What is David doing with Hey.com? Should there be two-sided consent in email read-receipt tracking? 2:03:29 Could there ever be an open-source Twitter or messaging app? Was WhatsApp it before being bought by Facebook? 2:09:34 Thoughts on tech journalism vs. big-tech 2:12:22 Can big-tech regulation fix the competitive landscape?

Laura Huang, author of 'Edge: Turning Adversity into Advantage,' shares insights on overcoming disadvantages based on race, ethnicity, and gender. She discusses structural bias against female entrepreneurs and how founders can turn adversity into an advantage. The podcast also explores the impact of being underestimated and the importance of reframing experiences. Overall, the podcast covers strategies for creating an edge in the face of disadvantages and biases.

0:50 Jason intros Coatue Management's Dan Rose 1:52 Dan takes Jason through getting his internship at Amazon in 1999 and meeting Jeff Bezos 6:55 What was Amazon's core business in 1999? What was it like incubating the Kindle in the mid-2000s? 10:04 How did Bezos grow as a leader and businessman during Dan's tenure at Amazon? 18:21 How does Bezos' ability to turn Amazon around in the eyes of public investors relate to Uber, Lyft and other large & unprofitable companies? How does Bezos inspire so much loyalty? 23:27 What was Amazon's company culture during Dan's tenure? How was AWS developed? 26:08 How did Dan wind up at Facebook as employee ~130? What did he see in a young Mark Zuckerberg? 32:13 Who created the original Facebook News Feed? 35:34 How did they get the ad-network to work at scale? 42:50 Where do Elon, Bezos & Zuckerberg rank in the Pantheon of Entrepreneurs? 44:06 How did the billion-dollar acquisition offer from Yahoo! fall apart? 46:42 Why launching open registration led to the billion-dollar investment by Microsoft 48:30 Insights on the Instagram deal 51:00 How Facebook bounced back from the stock dropping from $31 to $17 shortly after IPO & how Dan's experience at Amazon helped him rally the troops? 58:44 Zuckerberg's response to mistakes 1:03:01 How did Dan wind up at Coatue Management leading a $700M early-stage fund? 1:08:01 What is Coatue's strategy around data science? 1:11:20 Dan had over 100 Angel investments before joining Coatue 1:13:18 What is Coatue's new fund strategy? 1:16:09 How does Dan think of diligence in regards to early-stage companies? 1:20:25 What does Dan want to see in an ideal founder?

0:46 Jason intros Dr. Brian Moore 3:39 What does Orreco do and how do they help elite athletes? 4:46 Do they sample blood? 6:33 What teams do they work with? 7:50 What is a bio-marker? 9:05 Why has inflammation monitoring become so popular? 15:01 Brian demos the Orreco app 22:56 What are the top reasons for elite athletes to use Orreco? 28:06 How did Brian get into this business? 30:34 How does blood differ in elite athletes? Is it regional? 36:25 What does Orreco have the biggest impact on? 43:40 What kinds of performance optimization should or shouldn't be legal in pro sports 51:12 How have they monitored machine learning? 56:47 Importance of glucose monitoring 59:15 Correlation in NBA between minutes per game and years played? 1:01:29 Taking a personal loan out to fund Orreco in the early days 1:15:39 Marc Andreessen asks Jason a question

0:57 Jason intros Alex & Sachin 4:46 When and why did they start Cocoon? 6:40 Why did Facebook keep changing their developer tools platform? 9:22 What is the vision for Cocoon and who is it made for? 14:58 How did they get the cocoon.com domain name and why do strong domain names breed trust? 16:57 What are they doing with customer data and how will they monetize? 20:20 Cocoon demo and Alex takes us through some key features 29:45 How difficult was raising money going up against Facebook, iMessage, etc.? 33:04 Who is their ideal customer? 38:35 Building a company in San Francisco vs. outside of it 41:57 Jason tries to invest in Cocoon live on air 47:45 Growing Cocoon in the crowded app store 51:51 Why do Cocoon founders use Notion? 54:37 Jason calls Ben Horowitz

0:01 Jason intros Season 4 of Angel & Index Ventures' Sarah Cannon 3:22 How did working for the Obama administration lead Sarah into Venture Capital? 4:56 Picking a fight with Larry Summers as an intern 15:42 Choosing Harvard's MBA program over Stanford's 18:26 Getting into VC 20:27 Working at CapitalG 24:09 How was the foundation of Index built by Danny Rimer and what is Sarah's role? 31:42 What does Index focus on during a Series A and what is a partner meeting like at Index? 36:31 Thoughts on gig economy work and is there a better way to categorize freelancers and full-time workers in the gig economy? 44:54 Sarah's proposed solution for categorizing gig economy workers 46:36 Jason's thoughts on politicians evolving their views over time 50:15 Ideas to increase upward mobility in America 1:00:35 What was Sarah's first investment? How did it work out? 1:08:42 Founders getting distracted after raising large rounds of funding 1:11:05 Thoughts on emerging international startup markets like India & Australia 1:13:19 Is France an underrated startup market? 1:17:42 What is Sarah most passionate about investing in?