Épisodes

  • How to Build a Leadership Culture: Lessons from Bob Brennan, a Four-Time CEO

    How to Build a Leadership Culture: Lessons from Bob Brennan, a Four-Time CEO
    Oct 20 2026

    What if the most powerful tool a leader has isn’t a strategy, but a single question?


    In this episode of Built Not Born, host Sage Nye sits down with Bob Brennan, four-time CEO, executive coach, and board director, to unpack how great leaders use inquiry instead of instruction. Bob scaled Iron Mountain from $1.8 billion to $3.2 billion in revenue and led Veracode through its $614 million acquisition by CA Technologies. He explains why his psychology background shaped every company he ran, and why “What can I do to be more effective?” is the one question he insists every leader ask.


    Bob breaks down how to step into a company as CEO and cut through competing agendas, why withholding feedback is unkind rather than benevolent, and how getting defensiveness out of an organization changes everything. He shares the two red flags he never ignores in a hire, why most CEOs don’t give themselves time to think, and how to empower a team without micromanaging it.


    The conversation also covers managing investors as owners, why a high headline valuation can be a trap, and why the best founders make everyone else the hero. This episode is a practical playbook for founders and executives who want to lead through questions, build future leaders, and scale without losing the people who make it work.


    Chapters:

    00:00 Intro

    01:30 From Psychology Student to Four-Time CEO

    03:50 Selling Through Inquiry: People Don’t Argue With Their Own Conclusions

    05:05 Stepping In as CEO: Opening the Aperture, Closing the Priorities

    08:45 How to Develop Future CEOs

    11:00 The One Question Every Leader Should Ask

    12:15 Why Withholding Feedback Is Unkind

    14:20 Build Your Own Personal Board

    15:40 What CEOs Don’t See: The Time to Think

    18:05 Hiring for Seed vs. Scale and the Two Red Flags to Watch

    22:55 The Psychology of Leadership: Removing Defensiveness

    24:30 Managing Investors, Boards, and Term Sheets

    27:55 Empowering Teams Without Micromanaging

    29:10 Key Takeaways: Make Them the Hero


    Connect with the team:

    👉 Sage Nye on LinkedIn: https://www.linkedin.com/in/sage-nye/

    👉 Venture Guides Website: https://www.ventureguides.com/

    👉 Bob Brennan on LinkedIn: https://www.linkedin.com/in/bobbrennan236/


    You can also listen to our podcast here:

    👉 Apple - https://go.fame.so/built-not-born-podcast-apple

    👉 Spotify - https://go.fame.so/built-not-born-podcast-spotify

    👉 YouTube - https://go.fame.so/built-not-born-youtube
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    32 min
  • How AI Agents Are Breaking SaaS Economics with Ki-youn Jung & Abhishek Singh

    How AI Agents Are Breaking SaaS Economics with Ki-youn Jung & Abhishek Singh
    Sep 10 2026
    What happens when AI agents scale faster than their economics can support? In this episode of Built Not Born, host Sage Nye sits down with EON co-founders Ki-youn Jung, Co-founder and CEO, and Abhishek Singh, Co-founder and CTO, to explore the infrastructure challenges emerging as enterprises adopt AI agents at scale. They discuss how EON’s experience with escalating compute costs led them from a health-tech application toward building an inference layer designed to anticipate agent behavior, reduce redundant token usage, and lower latency. The conversation examines why token economics could undermine traditional SaaS models, how reusable and deterministic AI outputs can preserve trust through statistical verification, and why infrastructure may represent the bigger opportunity in AI. They also explore the challenges of running agents for weeks or months, including drift, oversight, and maintaining alignment. The episode offers a practical look at building infrastructure for the next era of computing.
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    30 min
  • How Founders Mistake Traction for Product-Market Fit and Scale Too Soon

    How Founders Mistake Traction for Product-Market Fit and Scale Too Soon
    Aug 6 2026
    What if the biggest bottleneck to scaling your startup isn't market demand; it's internal alignment? In this episode of Built Not Born, host Sage Nye sits down with Carter Cast, former CEO of Walmart.com and Professor of Entrepreneurship at Northwestern University, to unpack a hard truth: most startups don’t fail from lack of demand, they fail from lack of alignment. Carter explains why mission clarity must precede growth and how misalignment at the top quietly fractures teams as companies scale. He breaks down what real product-market fit looks like (hint: it’s not fueled by discounts), and why sustainable unit economics are the only green light to accelerate. The conversation also dives into leadership, what separates high-performing teams from dysfunctional ones, how to navigate the shift from generalists to specialists, and why motivation mismatch often masquerades as underperformance. Above all, Carter makes a compelling case that self-awareness isn’t a soft skill; it’s the ultimate competitive advantage that defines how far a founder can go.
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    32 min
  • Not All Capital Is Created Equal: Alejandro Diez Barroso on Choosing Investors Wisely

    Not All Capital Is Created Equal: Alejandro Diez Barroso on Choosing Investors Wisely
    Jul 16 2026
    What if the biggest competitive advantage in emerging markets isn't capital, but the people who know how to operate without it? In this episode of Built Not Born, host Sage Nye sits down with Alejandro Diez Barroso, Managing Partner at Dila Capital, to unpack what it really takes to build enduring companies in emerging markets. Drawing on his journey as both operator and investor, Alejandro challenges the obsession with valuation, arguing that integrity, execution, and team quality are the true drivers of long-term success. He shares how founders can unlock massive opportunities by solving overlooked problems in underserved markets, and why localization, not capital, is often the biggest hurdle to scaling internationally. The conversation also explores how investors should think beyond check size, how disciplined capital deployment creates resilience, and why reputation compounds faster than money. Packed with practical insights, this episode is a playbook for founders and investors seeking to build durable, high-impact businesses in complex and fast-evolving markets.
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    36 min
  • How Splunk Scaled to a $10B IPO: Tom Schodorf’s GTM Playbook for Founders

    How Splunk Scaled to a $10B IPO: Tom Schodorf’s GTM Playbook for Founders
    Jun 30 2026
    What if the sales strategies that built a $10B IPO could transform your go-to-market engine? In this episode of Built Not Born, host Sage Nye sits down with Tom Schodorf, the sales leader who helped scale Splunk from startup to a $10B IPO, to unpack what actually builds a high-performing go-to-market engine. Tom explains why defining your ICP and aligning company-wide messaging matter far more than aggressive hiring, and how documenting a repeatable sales process creates sustainable growth. He also shares hard-earned lessons about hiring the right support structure around sales teams, avoiding short-term thinking, and building a culture rooted in discipline, coaching, and accountability. From the “unit of one” hiring framework to adapting sales strategies in the AI era, this conversation offers founders and revenue leaders a practical blueprint for scaling without losing focus, clarity, or long-term momentum in increasingly competitive markets today.
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    32 min
  • Why Most Startups Fail: Founders Don’t Know What They Don’t Know Yet

    Why Most Startups Fail: Founders Don’t Know What They Don’t Know Yet
    May 7 2026
    What if the real edge in building and investing in companies is knowing exactly where your knowledge stops? In this episode of Built Not Born, host Sage Nye sits down with Dave Fachetti, Partner at Venture Guides, to unpack the operator–investor mindset that drives durable outcomes. Drawing on decades of experience, Dave explains why great founders prioritize solving painful, urgent problems before optimizing execution, and how this “efficacy before efficiency” mindset underpins true product-market fit. He introduces his “know what you don’t know” test as a lens for evaluating founders, emphasizing self-awareness, curiosity, and coachability as critical traits. The conversation also explores cap table strategy as a long-term system, the importance of aligning all stakeholders, and why board dysfunction guarantees failure. Dave shares practical frameworks for hiring, leadership, and navigating AI opportunities, while highlighting the balance between conviction and listening. It’s a grounded playbook for founders and investors aiming to build resilient, high-performing companies.
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    35 min
  • The AI Hacker Era Is Here: Alissa Knight on Rewriting Cybersecurity

    The AI Hacker Era Is Here: Alissa Knight on Rewriting Cybersecurity
    Apr 2 2026
    What happens when a former teenage hacker builds AI that can find security vulnerabilities before attackers do? In this episode of Built Not Born, host Sage Nye speaks with cybersecurity expert, CAIO, Founder, and CEO of Assail, Alissa Knight, about the rapidly evolving intersection of AI and offensive security. Once arrested for hacking as a teenager, Alissa went on to build Ares, a powerful AI model that autonomously discovers vulnerabilities in APIs, mobile apps, and web applications. She explains why the age of adversarial AI means companies must shift from preventing attacks to continuously identifying weaknesses faster than attackers can exploit them. The conversation explores the rise of AI-driven security testing, the emerging “one-person unicorn” founder model, and how startups should think about hiring, fundraising, and defensibility in an AI-first world where directing intelligent systems may matter more than traditional expertise.
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    35 min
  • Why Your GPU Investments Are Running at 40% Efficiency, and How AI Fixes It

    Why Your GPU Investments Are Running at 40% Efficiency, and How AI Fixes It
    Mar 18 2026
    What if your multi-million-dollar GPU investment was quietly delivering less than half its potential? In this episode of Built Not Born, the conversation focuses on why AI infrastructure performance often lags far behind spend, and how continuous profiling is emerging as a real competitive edge. Join host Sage Nye as she sits down with Israel Ogbole, CEO and cofounder of zymtrace, to explore why most GPU clusters run at just 20–40% utilisation, how traditional observability tools miss the real bottlenecks, and why profile-guided optimisation can unlock massive efficiency gains without demanding deep CUDA expertise. Israel shares hard-won lessons from building a must-have infrastructure product: validating real willingness to pay, avoiding “nice-to-have” traps, and navigating early founder dynamics. The discussion also dives into the growing talent gap in low-level systems engineering, and how rich profiling data can become context for LLM-driven optimisation workflows. It’s a practical, insight-dense conversation for founders, operators, and AI leaders focused on extracting real returns from AI infrastructure, not just scaling hardware.
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    35 min