Episodes

  • 214. Chris Dixon of a16z
    Dec 22 2025

    Chris Dixon shares his journey from early programming experiences in the 1980s to becoming a prominent figure in venture capital and cryptocurrency. He discusses the founding of Site Advisor, the lessons learned from its acquisition by McAfee, and the challenges of starting Hunch. Dixon reflects on his experiences in angel investing, the creation of Founder Collective, and his role at Andreessen Horowitz, particularly in launching a crypto fund.


    Chapters:


    00:00 The Early Days of Programming

    02:46 Transitioning to Finance and Wall Street

    04:59 The Shift to Entrepreneurship

    09:03 Founding Site Advisor

    16:16 The Journey with Hunch

    20:50 Starting Founder Collective

    26:58 The Evolution of Angel Investing

    28:10 Joining Andreessen Horowitz

    30:37 Investing in Futuristic Ideas

    35:24 Key Investments: Oculus and Coinbase

    40:20 Establishing a Crypto Fund

    45:07 Current Landscape of Web 3 and Crypto

    49:41 Lessons from Mark Andreessen and Ben Horowitz

    51:22 New York vs. Silicon Valley: A Tech Hub Comparison

    Hosted on Acast. See acast.com/privacy for more information.

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    57 mins
  • 213. Datadog Founder Olivier Pomel
    Dec 15 2025
    Olivier Pomel is the cofounder/CEO of Datadog. We trace his path from French open-source tinkerer to NYC founder, the dev-vs-ops friction that sparked Datadog, finding product-market fit through integrations, and the choice to stay independent en route to a 2019 IPO and S&P 500. Olivier shares scaling war stories, culture and GTM lessons, and what observability means in an AI era. If you build software—or companies—this one’s packed with playbooks, from hiring to pricing to platform bets that work.

    Hosted on Acast. See acast.com/privacy for more information.

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    45 mins
  • 212. Susan Lyne Part 2
    Dec 8 2025
    Part 2 of the Amazing career of Susan Lyne. Working with Martha Stewart. Gilt Groupe. Becoming a VC.

    Hosted on Acast. See acast.com/privacy for more information.

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    45 mins
  • 211. Susan Lyne Part 1
    Dec 1 2025

    I’ve maybe never interviewed anyone in my entire time as a historian and podcaster who has had a career as broad and varied as Susan Lyne. Yes, I obviously wanted to talk to Susan about her role helping startup Gilt Group, and her current role as the managing partner of the VC firm BBG Ventures. But, holy how. Susan also launched and oversaw the golden era of Premiere Magazine. She was the CEO of Martha Stewart Living Omnimedia when Martha had to step away to, you know, go to prison. And she was the President of ABC Entertainment. She oversaw the development of shows like Grey’s Anatomy and Lost. So, like, yeah. We needed to do two episodes. So this is part one, with the great, Susan Lyne.


    Chapters:


    00:00 From Boston to Berkeley: A Transformative Journey

    08:00 The Rise of Alternative Media: Village Voice Era

    16:06 Hollywood Calling: The IPC Films Experience

    23:12 Launching Premier Magazine: Inside Hollywood

    36:14 Navigating the ABC Landscape: A New Era

    40:28 Developing Grey's Anatomy And Lost


    Takeaways


    • Susan's upbringing in Boston shaped her perspective on expectations and identity.
    • Her time at UC Berkeley was transformative, exposing her to diverse ideas.
    • Freelancing in journalism helped her develop a passion for storytelling.
    • Working at City Magazine under Francis Ford Coppola was a unique experience.
    • The Village Voice was a golden era for alternative media in New York.
    • Susan's transition to Hollywood was driven by her love for storytelling.
    • Premier Magazine aimed to provide in-depth insights into the film industry.
    • At ABC, she focused on creating shows that appealed to women.
    • Susan learned the importance of having a supportive partner in leadership.
    • Her experience at ABC taught her valuable lessons about resilience and change.

    Hosted on Acast. See acast.com/privacy for more information.

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    50 mins
  • 210. Esther Dyson
    Nov 23 2025

    In the more than 200 episodes I’ve done for this podcast, never has the designation “legend” been more appropriate. Esther Dyson is a legend of modern technology, having been present for so many key moments from the early PC era through to the AI era. She’s advised, interviewed and mentored basically every major tech figure over the last several decades. Dyson shares her unique journey from growing up in a family of prominent scientists to becoming a leading figure in tech investing and journalism. She discusses her philosophy of embracing mistakes, the evolution of her career, and her insights into the tech landscape, including the dot-com bubble and the rise of AI. Dyson also reflects on her experiences in Eastern Europe, health tech initiatives, and her adventures in space, culminating in a captivating story about a cosmonaut suit.


    Chapters:


    00:00 Introduction and Connection

    03:42 Growing Up in a Unique Environment

    10:12 Transitioning to Tech and Investing

    18:03 Creating Impactful Conferences

    22:35 Navigating the Dot Com Bubble

    27:25 Reflections on Predictions and AI

    32:31 Governance and the Evolution of the Internet

    40:03 Investment Philosophy and Learning from Experience

    45:19 Eastern Europe: A Tech Narrative

    54:42 Investing in Space: A Personal Journey


    Takeaways


    Always make new mistakes to learn and grow.

    Understanding economics can change the world more than politics.

    Journalism trains you to ask the right questions.

    Investing is about learning, not just earning.

    Creating impactful conferences requires engaging formats.

    The dot-com bubble taught valuable lessons about business models.

    Investing in Eastern Europe was a rewarding experience.

    Health tech initiatives should aim to empower communities.

    AI's future is uncertain, but its impact is undeniable.

    Personal experiences shape investment decisions.

    Hosted on Acast. See acast.com/privacy for more information.

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    1 hr and 10 mins
  • 209. Henry Blodget, Founder Of Business Insider
    Nov 17 2025

    Henry Blodget shares his journey from a history major to a prominent figure in finance and journalism, discussing the rise of the internet, the dot-com bubble, and the lessons learned from that era. He reflects on his career, including his famous $400 price target Amazon prediction, the evolution of media with the launch of Business Insider, and the current landscape of AI and investing.


    Chapters


    00:00 Introduction and Early Life

    02:42 Career Beginnings in Journalism

    05:44 Transition to Finance and Technology

    08:19 Analyzing Internet Companies

    11:33 The Internet Boom and IPOs

    14:39 Lessons from the Dot-Com Bubble

    17:40 The Rise of Influencers in Finance

    20:34 The Amazon Call and Its Impact

    23:21 Wall Street's Perspective on Tech Companies

    26:45 The AOL Time Warner Lesson

    29:47 Merrill Lynch and Global Internet Research

    32:38 Post-Bubble Reflections and Reinvention

    35:31 The Birth of Business Insider

    38:39 The Evolution of Media and Journalism

    41:37 Building a Talented Newsroom

    44:28 Parallels Between AI and the Dot-Com Era

    47:46 Advice for Individual Investors

    50:33 New York City as a Startup Ecosystem

    53:44 Current Projects and Future Aspirations

    Hosted on Acast. See acast.com/privacy for more information.

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    1 hr and 6 mins
  • 207. John Borthwick Of Betaworks
    Nov 3 2025

    John Borthwick shares his journey from a tech-savvy youth to a prominent figure in the New York tech scene. He discusses his early experiences with computers, the transformative impact of the World Wide Web, and the vibrant tech culture of the 90s. Borthwick reflects on his role in creating Total New York, the lessons learned from the AOL acquisition, and the challenges faced during the dot-com bubble burst. He also highlights the rise of social media platforms like Photolog and the evolution of BetaWorks as a hub for innovation, particularly in the AI space. Throughout the discussion, Borthwick emphasizes the importance of creativity, constraints, and the ever-changing landscape of technology.


    Chapters:


    00:00 The Early Days of Tech and Personal Journey

    02:11 Education and Its Impact on Career

    05:15 Experiencing the World Wide Web

    08:09 The New York Tech Scene in the 90s

    11:08 Creative Projects and the Internet

    16:01 Total New York: A Local Information Hub

    21:40 Lessons in Distribution and Audience Engagement

    24:57 The Evolution of Internet Distribution

    27:58 AOL: The Internet's First Giant

    35:54 The Dot-Com Bubble and Its Aftermath

    37:46 Photolog: A Precursor to Social Media

    44:56 Navigating Abundance and Constraints in AI

    49:37 BetaWorks: A Hub for Founders and Innovation


    Hosted on Acast. See acast.com/privacy for more information.

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    57 mins