Built Not Born: The Startup Go-To-Market Podcast

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/ 
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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. Here’s what you will learn:How to recognize when you're sitting on a bigger problem than your original business ideaWhy token costs are the hidden killer of AI agent ROIThe "inference layer that thinks ahead" frameworkHow to maintain verifiability and trust when reusing AI outputsWhy long-term thinking beats duct-tape solutions, especially in AI How to structure incentives and human oversight for week-long and month-long running agentsKi-youn Jung is a technology entrepreneur and strategist with deep expertise spanning semiconductors, AI, and complex technology systems. She began her career designing mobile application processors and semiconductor architectures before moving into strategic planning and AI-focused product development at LG Electronics. Her work included developing an on-device AI platform and business model implemented across a $20 billion business. With experience spanning mobile, EVs, and smart homes, Ki-youn combines engineering expertise with strategic foresight to identify emerging opportunities and build scalable technology solutions. Abhishek Singh is a scientist, engineer, and entrepreneur, and Co-founder and CTO of EON. He holds a PhD from MIT and specializes in decentralized AI, precision medicine, and large-scale intelligent systems. His research explores how networks of AI agents can coordinate, adapt, and scale to address complex real-world problems. At EON, he is developing an AI platform that combines health data, scientific research, and agentic intelligence to enable personalized health optimization. His work brings together advanced AI research, systems engineering, and human health. Episode Resources:Ki-youn Jung on LinkedInAbhishek Singh on LinkedIn EON WebsiteSage Nye on LinkedInVenture Guides WebsiteBuilt Not Born on Apple PodcastsBuilt Not Born on SpotifyBuilt Not Born: The Startup Go-To-Market Podcast is handcrafted by our friends over at: fame.so

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.Here’s what you will learn:How to establish alignment before scalingThe three non-negotiables of product-market fitWhy organic growth beats bought growthHow to validate unit economics before pressing the gasThe organizational structure shift that kills cultureWhy internal misalignment causes more damage than external competitionThe motivator framework that fixes struggling employeesThe metrics that actually matter while scalingCarter Cast is a Professor of Entrepreneurship at Northwestern University's Kellogg School of Management, a seasoned operator, advisor, and educator with extensive experience leading organizations at scale. As the former CEO of Walmart.com, he spearheaded the transformation of one of the world's largest e-commerce platforms during a pivotal moment in digital retail, ultimately helping Walmart build a $200+ billion internet business. With a background spanning senior leadership roles across consumer and technology companies, Carter brings real-world expertise in scaling, omnichannel strategy, and navigating organizational change. Episode Resources:Carter Cast on LinkedInKellogg School of Management Website5 Tips for Preparing to Scale Your Startup LinkThe Right and Wrong Stuff: How Brilliant Careers Are Made and Unmade LinkSage Nye on LinkedInVenture Guides WebsiteBuilt Not Born on Apple PodcastsBuilt Not Born on SpotifyBuilt Not Born: The Startup Go-To-Market Podcast is handcrafted by our friends over at: fame.so

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.Here’s what you will learn:The Four Pillars of Exceptional TeamsWhy "Not All Capital Is Created Equal"How to Leapfrog Infrastructure and Build Billion-Dollar ProblemsThe Operator's Advantage in Venture CapitalFocus Only on What You Can ControlLocalization Is Your Biggest Blind Spot When Entering New MarketsBuild Organizations That Work Without YouAlejandro Diez Barroso is the Managing Partner at Dila Capital, one of Latin America's leading early-stage venture capital firms. With a background as a serial founder who built and scaled multiple companies in Mexico during an era when venture capital was barely present in the region, Alejandro brings an operator's mindset to his investment strategy, emphasizing team quality, executional capability, and long-term value creation over short-term gains. His expertise spans early-stage venture investing, founder mentorship, and market entry strategy across Latin America, with a particular focus on identifying and supporting founders who demonstrate integrity, clarity, and resilience.Episode Resources:Alejandro Diez Barroso on LinkedInDila Capital WebsiteSage Nye on LinkedInVenture Guides WebsiteBuilt Not Born on Apple PodcastsBuilt Not Born on SpotifyBuilt Not Born: The Startup Go-To-Market Podcast is handcrafted by our friends over at: fame.so

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. Here’s what you will learn:How to define your ICP as the foundation for everythingThe whiteboarding exercise that aligns your entire company on messagingWhy a documented sales process scales faster than individual heroicsThe "unit of one" framework for hiring support roles, not just quota carriersHow to hire for the long term, not just growthWhy your CEO's 88th Floor "don't screw it up" moment should reshape how you leadThe difference between early-stage and scale-stage sales hiringHow to cut through AI noise and stay focused on timeless value creationTom Schodorf is a veteran sales and go-to-market executive best known for helping scale Splunk from startup to a $10B IPO. A former SVP of Field Operations at Splunk, he now serves as a board member, advisor, and coach to cybersecurity and AI infrastructure companies. With deep expertise across SaaS, cloud, and enterprise technology, Tom specializes in building scalable revenue organizations, aligning culture with execution, and driving long-term growth. His leadership philosophy combines disciplined processes, ethical decision-making, and customer-first thinking to create durable, high-performing teams. Episode Resources:Tom Schodorf on LinkedInThe Success Cadence, the definitive guide to building rapid growth sales culturesSage Nye on LinkedInVenture Guides WebsiteBuilt Not Born on Apple PodcastsBuilt Not Born on SpotifyBuilt Not Born: The Startup Go-To-Market Podcast is handcrafted by our friends over at: fame.so

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.Here’s what you will learn:How to evaluate founders using the "Know What You Don't Know" testThe critical difference between efficacy and efficiency in product-market fitWhy "painful problems" are your moat in B2B softwareThe cap table management principle that founders ignore at their perilHow to build a leadership team that scales without micromanagingThe "dysfunction guarantees failure" principle for board dynamicsWhy the "move fast and raise big" AI strategy works for only a fewHow to structure investor relationships that actually helpDave Fachetti is a Partner at Venture Guides, a seed-stage investment firm focused on helping early-stage founders navigate the path from idea to growth. With nearly three decades of experience at the intersection of venture capital, cybersecurity, and executive leadership, Dave brings a rare dual perspective as both operator and investor. His career spans managing directorships at GlobeSpan Capital Partners, where he backed companies acquired by Citrix and Pegasystems, to serve as Chief Strategy Officer at BitSight, a cyber risk intelligence leader with $200M+ in revenue. Dave's operating experience includes scaling Family Education Network to 4M+ monthly visitors before its $175M acquisition by Pearson.Episode Resources:Dave Fachetti on LinkedInSage Nye on LinkedInVenture Guides WebsiteBuilt Not Born on Apple PodcastsBuilt Not Born on SpotifyBuilt Not Born: The Startup Go-To-Market Podcast is handcrafted by our friends over at: fame.so