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497. Investing in Outsiders, Why Extreme Personalities Win, Weighing Timing versus Trends, and Rethinking Liquidity and Option Exercise Windows (Ethan Austin)

The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

Release Date: 12/01/2025

500. AI Native VC, Achieving 50%+ Graduation from Seed to Series A, Why Access Is the Key to Success, and Why Network Driven Firms Can No Longer Compete (Ben Orthlieb) show art 500. AI Native VC, Achieving 50%+ Graduation from Seed to Series A, Why Access Is the Key to Success, and Why Network Driven Firms Can No Longer Compete (Ben Orthlieb)

The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

Ben Orthlieb of Blue Moon joins Nick to discuss AI Native VC, Achieving 50%+ Graduation from Seed to Series A, Why Access Is the Key to Success, and Why Network Driven Firms Can No Longer Compete. In this episode we cover: Challenges of the Traditional Venture Model Blue Moon's AI-Assisted Human Judgment Evaluating Exceptional Founders Access vs. Picking in Venture Capital Blue Moon's Sourcing and Screening Process Non-Obvious Data Sources and Market Dynamics Winning Deals and Founder Relationships Future of Blue Moon and AI in Venture Capital Importance of Price and Pre-Commitments...

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On this special segment of The Full Ratchet, the following Investors are featured: Kyle York of York IE Vince Hsieh of Cypress Growth Capital Madhavan Ramanujam of 49 Palms Ventures We asked guests to share the best question they've ever been asked by an allocator. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to keep up to date with The Full...

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Investor Stories 452: Raising the Bar on Founders, What 100x Looks Like in Practice, and Why People Matter More Than Ever (Bussgang, Okike, Hudson) show art Investor Stories 452: Raising the Bar on Founders, What 100x Looks Like in Practice, and Why People Matter More Than Ever (Bussgang, Okike, Hudson)

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On this special segment of The Full Ratchet, the following Investors are featured: Jeff Bussgang of  Flybridge Capital Nnamdi Okike of 645 Ventures Charles Hudson of Precursor Ventures We asked guests to describe the biggest change to their investment philosophy over the course of their career The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to...

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Investor Stories 451: Why I Passed: Moving Too Slowly, Misreading Return Drivers, and Passing on Lyft (Banks, Tananbaum, Cohen) show art Investor Stories 451: Why I Passed: Moving Too Slowly, Misreading Return Drivers, and Passing on Lyft (Banks, Tananbaum, Cohen)

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On this special segment of The Full Ratchet, the following Investors are featured: Lara Banks of Makena Capital Management Jim Tananbaum of Foresite Capital David Cohen of Techstars Each investor highlights a situation where they decided not to invest, why they passed, and how it played out. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to keep up...

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499. A 17 Time Midas Lister on Greatness, the $6T AI Teammate Market, Why AI Sovereignty Is Critical, and Who Wins the Battle Between Incumbents and Startups (Navin Chaddha) show art 499. A 17 Time Midas Lister on Greatness, the $6T AI Teammate Market, Why AI Sovereignty Is Critical, and Who Wins the Battle Between Incumbents and Startups (Navin Chaddha)

The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

Navin Chaddha of Mayfield joins Nick to discuss A 17 Time Midas Lister on Greatness, the $6T AI Teammate Market, Why AI Sovereignty Is Critical, and Who Wins the Battle Between Incumbents and Startups. In this episode we cover: Challenges in Early Internet Video Lessons from Interacting with Tech Luminaries Investment Philosophy and Evaluation Process The Role of Psychology in Venture Capital The AI Collaboration Era Geopolitical Implications of AI Investment Strategy in a Competitive Market Guest Links: The host of The Full Ratchet is  of , a venture...

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Investor Stories 450. How to Succeed Early in VC: Slow Down, Commit to Relationships, and Become an Active Listener (Niehenke, York, Hilaly) show art Investor Stories 450. How to Succeed Early in VC: Slow Down, Commit to Relationships, and Become an Active Listener (Niehenke, York, Hilaly)

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On this special segment of The Full Ratchet, the following Investors are featured: Alexander Niehenke of Scale Venture Partners Kyle York of York IE Aaref Hilaly of Bain Capital Ventures We asked guests for the most important piece of advice that they'd share with folks early in their venture career. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want...

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Replay - The Biggest Misconceptions About AI Agents, Why Defensibility Doesn’t Matter at Seed, and Whether the AI Center of Gravity Is Shifting to China (Aaref Hilaly) show art Replay - The Biggest Misconceptions About AI Agents, Why Defensibility Doesn’t Matter at Seed, and Whether the AI Center of Gravity Is Shifting to China (Aaref Hilaly)

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In this special replay episode Aaref Hilaly of Bain Capital Ventures joins Nick to discuss The Biggest Misconceptions About AI Agents, Why Defensibility Doesn’t Matter at Seed, and Whether the AI Center of Gravity Is Shifting to China. In this episode we cover: AI Investment Strategy and Market Utility Impact of AI on Jobs and Early Instances of Reasoning Open vs. Closed Source Models and Data Control Scenario Planning and Unique Insights of Backed Companies Infrastructure and Application Investment Focus Future of Vertical Solutions and Infrastructure Investment Guest Links: ...

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Investor Stories 449: Exceptional Founders Up Close: Listening Over Posturing, Integrity Over Ease, and Deliberate Execution from Day One (Hsieh, Delk, Maples Jr.) show art Investor Stories 449: Exceptional Founders Up Close: Listening Over Posturing, Integrity Over Ease, and Deliberate Execution from Day One (Hsieh, Delk, Maples Jr.)

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On this special segment of The Full Ratchet, the following Investors are featured: Vince Hsieh of Cypress Growth Capital Ryan Delk of Primer Mike Maples Jr. of Floodgate We asked guests to discuss the most visionary founder that they've worked with and what makes them so special. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to keep up to date...

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Investor Stories 448: Hard Lessons in Investing: Mistiming Trends, Relying on Partnership Debate, and Avoiding Good Money After Bad (Hilaly, Dash, Rizik) show art Investor Stories 448: Hard Lessons in Investing: Mistiming Trends, Relying on Partnership Debate, and Avoiding Good Money After Bad (Hilaly, Dash, Rizik)

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On this special segment of The Full Ratchet, the following Investors are featured: Aaref Hilaly of Bain Capital Ventures Somesh Dash of IVP Chris Rizik of Renaissance Venture Capital We asked guests to tell the most important lesson they've learned in their career. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to keep up to date with The Full...

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Investor Stories 447: Choosing the Right VC: Understanding Value Add, Assessing Alignment, and Identifying the Best Board Partner (Jiang, Walsh, Saxena) show art Investor Stories 447: Choosing the Right VC: Understanding Value Add, Assessing Alignment, and Identifying the Best Board Partner (Jiang, Walsh, Saxena)

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On this special segment of The Full Ratchet, the following Investors are featured: Kevin Jiang of Mangusta Capital Shamin Walsh of BAM Ventures Shashank Saxena of Sierra Ventures We asked guests to share the best question they've ever been asked by an allocator. The host of The Full Ratchet is  of , a venture capital firm committed to investing in founders outside of the Bay Area. We’re proud to partner with Ramp, the modern finance automation platform.  and get $150—no strings attached.   Want to keep up to date with The Full...

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More Episodes

Ethan Austin of Outside VC joins Nick to discuss Investing in Outsiders, Why Extreme Personalities Win, Weighing Timing versus Trends, and Rethinking Liquidity and Option Exercise Windows. In this episode we cover:

  • Lessons from Founding Give Forward
  • Investment Philosophy and Timing
  • Founding Outside VC
  • Characteristics of Strong Investment Candidates
  • Supporting Founders and Building Knowledge
  • Trends in FinTech and Climate
  • Role of a VC and Early Liquidity

Guest Links:

The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area.

We’re proud to partner with Ramp, the modern finance automation platform. Book a demo and get $150—no strings attached.  

Want to keep up to date with The Full Ratchet? Follow us on social. You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter.