20VC: The Memo: Chris Sacca on Why We Are Breeding a Generation of Entitled Assholes, Harley Finkelstein on What Great Fatherhood Really Means, Deena Shakir on How Kids Make You a Better Investor and Anne Wojcicki on How Children Change Your Approach to R

20VC: The Memo: Chris Sacca on Why We Are Breeding a Generation of Entitled Assholes, Harley Finkelstein on What Great Fatherhood Really Means, Deena Shakir on How Kids Make You a Better Investor and Anne Wojcicki on How Children Change Your Approach to R

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more.
  • Why does Chris believe we have bred a generation of asshole kids?
  • What is the right way to negotiate with children? How has that impacted how he manages his team?

Anne Wojcicki is the Founder & CEO @ 23andMe, offering DNA testing with the most comprehensive ancestry breakdown, personalized health insights, and more.

  • How did having kids change Anne's approach to time allocation and risk?

Harley Finkelstein is the President of Shopify. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify's revenue to over $4.6BN in 2021 and the team to over 10,000 employees.

  • Does Harley believe he has always been a good father?
  • What changes has Harley made to be more present and there for his children?
  • Why does Harley advise couples therapy as early in a relationship as possible?

Deena Shakir is a Partner at Lux Capital, one of the leading firms investing in emerging science and technology ventures at the outermost edges of what is possible.

  • What specific negotiation tactics from parenting can be applied to business?
  • How can a parent show their children they listen, they understand and are there for them?
  • Why does Deena believe children make you more productive and more efficient?

Eric Liaw is a General Partner @ IVP, one of the leading later-stage venture capital and growth equity firms of the last decade with $8.7 billion of committed capital and a 40-year IRR of 43.1%.

  • What have been the biggest challenges for Eric of managing family and work?
  • What have been some of Eric's biggest lessons in terms of how he communicates about his work to his family?

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company's CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and
completed an IPO in 2015.

  • What can parents learn from nature programs?
  • What core elements of parenting are directly transferrable to management?

Episoder(1433)

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

AGENDA: 03:43 Anthropic Predicts $149B in ARR in 2029 09:27 Will FDEs Become More or Less Powerful 26:17 Harvey Raises $200M at an $11BN Valuation 42:45 Is Customer Support a Terrible or Terrific Inve...

12 Feb 1h 21min

20VC: Is SaaS Dead in a World of AI | Do Margins Matter Anymore | Is Triple, Triple, Double, Double Dead Today? | Who Wins the Dev Market: Cursor or Claude Code | Why We Are Not in an AI Bubble with Anish Acharya @ a16z

20VC: Is SaaS Dead in a World of AI | Do Margins Matter Anymore | Is Triple, Triple, Double, Double Dead Today? | Who Wins the Dev Market: Cursor or Claude Code | Why We Are Not in an AI Bubble with Anish Acharya @ a16z

Anish Acharya is a General Partner at Andreessen Horowitz (a16z), where he leads consumer and fintech investing at Series A. He serves on the boards of standout portfolio companies including Deel, Mos...

9 Feb 1h 24min

20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen

20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen

Ariel Cohen is the Co-Founder and CEO of Navan (formerly TripActions), an AI-powered travel and expense platform. Last month, Ariel took the company public, since being a public company, they have fac...

7 Feb 54min

20VC: SpaceX Completes Acquisition of xAI | The 2026 SaaS Massacre: Public Market Collapse | Microsoft's $360 Billion Market Cap Loss | NVIDIA's $100BN Investment Dispute with OpenAI | Waymo Raises $16 Billion at a $110 Billion Valuation

20VC: SpaceX Completes Acquisition of xAI | The 2026 SaaS Massacre: Public Market Collapse | Microsoft's $360 Billion Market Cap Loss | NVIDIA's $100BN Investment Dispute with OpenAI | Waymo Raises $16 Billion at a $110 Billion Valuation

AGENDA: 00:00 - SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger 08:44 - The Rehabilitation of the IPO and the End of "State Private Forever" 15:53 - The 2026 SaaS Massacre: Public Market ...

5 Feb 1h 34min

20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy

20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy

Oren Zeev is one of the most prominent solo capitalists in venture. He is one of the most no BS investors of our time. Oren manages over $1BN in AUM and is known for his "radical alignment" approach, ...

2 Feb 1h 8min

20Growth: How Wix Built a $100M Marketing Machine | Why LTV is BS and Why Time Return On Investment is the Most Important Metric | How to 10x Your Growth: What is the Next Great Channel with Omer Shai, CMO @ Wix

20Growth: How Wix Built a $100M Marketing Machine | Why LTV is BS and Why Time Return On Investment is the Most Important Metric | How to 10x Your Growth: What is the Next Great Channel with Omer Shai, CMO @ Wix

Omer Shai serves as the CMO at Wix. Shai leads a team of over 400 people and is responsible for the company's global online and offline marketing activity, which boasts an incredible growth of approxi...

31 Jan 1h 1min

20VC: Brex Acquired for $5.15BN | a16z Companies are 2/3 AI Revenues | Anthropic Inference Costs Skyrocket | OpenEvidence Raises at $12BN Valuation | The IPO Market: EquipmentShare, Wealthfront and Ethos Insurance

20VC: Brex Acquired for $5.15BN | a16z Companies are 2/3 AI Revenues | Anthropic Inference Costs Skyrocket | OpenEvidence Raises at $12BN Valuation | The IPO Market: EquipmentShare, Wealthfront and Ethos Insurance

AGENDA: 03:36 Brex Acquisition by Capital One for $5.15BN 10:54 Does Brex's Acquisition Help or Hurt Ramp? 16:28 TikTok Deal Completed: Who Won & Who Lost: Analysis 19:30 Anthropic Inference Costs Hig...

29 Jan 1h 15min

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

Max Junestrand is the Co-Founder and CEO @ Legora, the legal AI company that has scaled to 750 of the world's leading law firms as customers and over 300 employees in just 2 years. They have raised ov...

26 Jan 1h 3min

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