Experience-focused Leaders & Investors

Your host Alex Shevelenko welcomes Dave Hersh, the visionary founder of Jive Software, an active investor, and the author of the upcoming book The Eros Advantage. In this episode, Dave shares his deep-dive into why human connection and psychological awareness are the ultimate competitive advantages in an era where AI is rapidly commoditizing traditional business "moats."

Dave discusses the evolution of his thinking from his journey leading Jive Software through its 2011 IPO to his work today coaching high-impact leaders. He explains why modern "hyper-growth" culture often creates a destructive monoculture, pushing startups to scale prematurely and hollow out the creative spirit of the organization. He introduces the concept of "Emotional Market Fit"—a blueprint for moving beyond functional pain points to understand the subconscious desires and identity shifts of the people a company serves. As the conversation explores the future of AI, Dave highlights why "ego-fueled" leadership is becoming a liability and why the most resilient brands will be those that prioritize "World Building" over mere transactional marketing.

The conversation also touches on the practicalities of leadership and the psychology of performance, including Dave’s advice on the "Inner Board Meeting." He shares a framework for diagnosing the "shadow parts" of a founder’s personality—such as the warrior, the child, or the hero—explaining how internal alignment can protect a company’s mission and even save a leader’s personal well-being. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is philosophically and technically equipped to stay "alive" in an era of unprecedented uncertainty.

To connect with Dave, find him on LinkedIn or follow his insights at davehersh.com. You can also subscribe to his newsletter to see his vision for human-first business moats in action. Don't just build a product—build a world where people want to belong!

Want to be a guest on the show? Contact us at relayto.com/contact.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Michael Marcon, the founder and CEO of Symphony Risk Solutions. In this episode, Michael shares his visionary take on why smart communication, human connection, and long-term relationships are the ultimate competitive advantages in a world increasingly dominated by trillion-dollar tech shifts and AI.

Michael discusses the evolution of his thinking from his early days as a multi-time founder to his team's decision to build Symphony Risk around industry-specific specialties that harmonize like a finely-tuned orchestra. He explains why modern corporate "best practices" of hiding behind massive legal disclaimers and industry jargon can often feel like a trap, hollowing out an organization's focus by prioritizing transactional metrics over earning genuine trust from real customers. He introduces the reality of presenting complex risk strategies—breaking through the noise of crowded markets by refusing to use confusing acronyms and prioritizing clarity above all else. As the conversation explores the future of corporate leadership and fast-paced client relationships, Michael highlights why his firm has become a core trusted advisory layer for high-stakes industries like private equity, and why the most resilient brands will be those that offer open, transparent solutions instead of burying their value behind endless caveats.

The conversation also touches on the practicalities of leadership and the psychology of client engagement, including Michael's advice on how to protect an organization from digital detachment by focusing presentations on a clear "headline" of expectations that buyers can easily digest. He shares insights from his four decades spent scaling firms, explaining how a simple, intentional focus on plain English and targeted analogies can blossom into an unbreakable foundation of client loyalty. He also breaks down his deliberate, highly personal playbooks for keeping a growing team and network deeply connected—from sending handwritten client notes to personally signing birthday cards for every employee. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is philosophically and humanly equipped to stay resilient in an era of unprecedented uncertainty.

To connect with Michael, find him on LinkedIn (Michael Marcon) or reach out directly to his team at [email protected]. You can also visit symphonyrisk.com to see his vision for authentic, high-value communication in action. Don't just build a product—build the skills to solve the world's problems!

Want to be a guest on the show? Contact us at [email protected].

To learn more about RELAYTO, visit: relayto.com.

our host Alex Shevelenko welcomes Nathan Christensen, entrepreneur, investor, and the co-founder and former CEO of Mineral. In this episode, Nathan shares his visionary take on why "trust" and "structural integrity" are the ultimate competitive advantages in a business world increasingly flooded with automated, AI-generated noise and short-term financial pressure.

Nathan discusses the evolution of his startup journey, from early failure attempting to sell direct-to-consumer to scaling a partner-driven ecosystem that supported over one million small businesses. He explains why modern "best practices" often prioritize short-term hustle over the slow building of real relationships, hollowing out the long-term value of a brand. He introduces the concept of a "sacred bond" with partners and the powerful framework of "Fuel vs. Friction"—a blueprint for balancing a company's strategic character with the operational clarity required to resist the "mercenary" pressures of the modern market. As the conversation explores the future of AI, Nathan highlights why the speed of technology cannot replace the slow process of building human trust, and why the most resilient brands of the next century will be those that prioritize value creation over value extraction.

The conversation also touches on the practicalities of leadership and board-level buy-in, including Nathan’s advice on how a CEO must step back from being the "chief doer" to act as an empowering "orchestra conductor." He shares insights from his time building Mineral and advising private equity and venture-backed companies, explaining how true organizational culture can protect a company’s "spark" and allow it to scale past the personal limitations of its founders. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is legally and philosophically equipped to stay true to its mission in an era of unprecedented uncertainty.

To connect with Nathan, find him on LinkedIn or follow his insights at X. You can also visit his new AI-native startup, Huckleberry, to see his vision for closing the workplace coaching gap in action. Don't just build a product—build an organization that can survive the century!

Want to be a guest on the show? Contact us HERE.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Gleb Budman, the co-founder and CEO of publicly listed Backblaze (NASDAQ: BLZE). In this episode, Gleb shares his visionary take on why first-principles thinking and long-term organic growth are the ultimate competitive advantages in a world increasingly dominated by trillion-dollar tech hyperscalers.

Gleb discusses the evolution of his thinking from his early days as a multi-time exited founder to his team's decision to bootstrap Backblaze without initial venture capital funding. He explains why modern "best practices" of raising massive funding rounds early on can often feel like a trap, hollowing out a startup's focus by prioritizing investor pitches over earning a dollar from real customers. He introduces the reality of building an infrastructure company from a one-bedroom apartment—surviving on "rice and beans" while choosing to fund physical servers over founder salaries. As the conversation explores the future of cloud computing and AI workloads, Gleb highlights why Backblaze has become the core infrastructure layer for the "Neo-Cloud" gold rush, and why the most resilient brands will be those that offer open, flexible data storage without predatory egress fees.

The conversation also touches on the practicalities of leadership and the psychology of performance, including Gleb’s advice on how to protect an organization from the "cortisol fluctuations" of stock market volatility by focusing the team on metrics they can actually control. He shares insights from his decades spent scaling Backblaze, explaining how a single, open-source technical blog post 15 years ago blossomed into a sustainable marketing engine that now attracts millions of readers annually. He also breaks down their recent, deliberate decision to close their physical headquarters—acknowledging their remote-first reality while introducing highly intentional playbooks to keep a 400-person team deeply connected. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is philosophically and technically equipped to stay resilient in an era of unprecedented uncertainty.

To connect with Gleb, find him on LinkedIn (Gleb Budman) or follow his insights at @glebbudman on X. You can also visit backblaze.com/blog to see his vision for authentic, high-value communication in action. Don't just build a product—build the skills to solve the world's problems!

Want to be a guest on the show? Contact us at relayto.com/contact.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Barry Rhein, the founder of Barry Rhein & Associates and the legendary creator of the "Selling Through Curiosity" methodology. In this episode, Barry shares his visionary take on why genuine curiosity and human connection are the ultimate competitive advantages in a world increasingly flooded with automated, AI-generated noise and transactional sales pressure.

Barry discusses the evolution of his thinking from his early days as a 12-year-old "worm entrepreneur" to his current role as a faculty member at Stanford Business School. He explains why modern sales "best practices" often feel like a destructive monoculture, hollowing out the trust between companies and their customers. He introduces the "Triangle of Curiosity"—a blueprint for balancing information gathering and relationship building with the customized value required to solve a customer's highest business priorities. As the conversation explores the future of AI, Barry highlights why the speed of technology cannot replace the "muscle memory" of human learning, and why the most resilient brands will be those that prioritize authentic problem-solving over mere product demos.

The conversation also touches on the practicalities of leadership and the psychology of performance, including Barry’s advice on how to move beyond the "stigma" of sales by adopting an attitude of service. He shares insights from his decades spent training global giants like Salesforce, DocuSign, and SAP, explaining how practicing "open-ended" communication can protect a company’s mission and even save personal relationships. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is philosophically and technically equipped to stay curious in an era of unprecedented uncertainty.

To connect with Barry, find him on LinkedIn or follow his insights at barryrhein.com. You can also visit sellingthroughcuriosity.com to see his vision for high-integrity communication in action. Don't just build a product—build the skills to solve the world's problems!

Want to be a guest on the show? Contact us at relayto.com/contact.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Eric Ries, entrepreneur, author, and the pioneer of the Lean Startup movement. In this episode, Eric shares his visionary take on why "trust" and "structural integrity" are the ultimate competitive advantages in a world increasingly flooded with automated, AI-generated noise and short-term financial pressure.

Eric discusses the evolution of his thinking from the "Build-Measure-Learn" feedback loop to his new framework for "Incorruptible" organizations. He explains why modern "best practices" have become a destructive monoculture, hollowing out the missions of once-great companies. He introduces the concepts of Ethos and Integrity—a blueprint for balancing a company’s character with the legal strength required to resist the "mercenary" pressures of the modern market. As the conversation explores the future of AI, Eric highlights why the speed of technology cannot replace the slow process of human learning, and why the most resilient brands of the next century will be those that prioritize value creation over value extraction.

The conversation also touches on the practicalities of leadership and board-level buy-in, including Eric’s advice on how to talk to skeptical "amoral" investors about long-term goals. He shares insights from his time building the Long-Term Stock Exchange and working with global giants, explaining how "Industrial Foundations" and specific governance structures can protect a company’s "spark" for 50 to 100 years. This episode serves as a masterclass for any leader looking to move beyond "innovation theater" and build an organization that is legally and philosophically equipped to stay true to its mission in an era of unprecedented uncertainty.

To connect with Eric, find him on LinkedIn or follow his insights at Incorruptible.co. You can also visit ltse.com to see his vision for long-term capitalism in action. Don't just build a product—build an organization that can survive the century!

Want to be a guest on the show? Contact us HERE.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Adam Morgan, VP of Brand at Twilio and author of Sorry Spock, Emotions Drive Business. In this episode, Adam shares his visionary take on why the "human element" is the ultimate competitive advantage in a world increasingly flooded with automated, AI-generated noise.

Adam discusses the shift from purely "data-driven" demand generation to a brand-first strategy, explaining why B2B companies must move past technical "specs" to create deep emotional connections. He introduces his "Hierarchy of Messaging"—a neuroscience-backed framework for balancing the brain’s "fast" emotional systems with its "slow" logical ones. As the conversation explores the future of creativity, Adam highlights why "taste," "vision," and "bespoke experiences" are the only things AI cannot replicate, forming a "human moat" around successful modern brands.

The conversation also touches on the practicalities of leadership and buy-in, including Adam’s "manifesto" approach to winning over skeptical boards and C-suite executives. He shares the story behind Twilio’s "Builder" identity, explaining how a single, powerful archetype can unite a chaotic portfolio of products and inspire everyone from developers to CEOs. This episode serves as a masterclass for any leader looking to fight the "B2B snorefest" and build a brand that resonates in the hearts, not just the minds, of their audience.

To connect with Adam, find him on LinkedIn or follow his insights on Medium at The Creative Machine. You can also visit twilio.com to see the "Builder" story in action. Don't just execute—become the architect of your brand’s future!

Want to be a guest on the show? Contact us HERE.

To learn more about RELAYTO, visit: [relayto.com].

Your host Alex Shevelenko welcomes Greg Shove, the CEO of Section and a six-time CEO with a storied history of building companies that redefine how we work. In this episode, Greg shares his vision for the "Super Company," offering a candid masterclass on why AI transformation must start at the bottom of the organizational pyramid with the workforce, rather than being dictated from the top down by external consultants.

Greg discusses the shift from being AI-proficient to becoming an "AI Maximalist," explaining why leaders must move past using technology for simple "parenting advice" and start using it as a high-stakes thought partner. He introduces the "Cut and Create" framework—a strategy for aggressively automating "busy work" to make room for high-value human creativity. As the conversation explores the future of the knowledge economy, Greg highlights why the "human element"—judgment, empathy, and storytelling—is becoming the most valuable premium in a world flooded with cheap, AI-generated noise.

The conversation also touches on the uncomfortable realities of modern leadership, including Greg’s "lead or retire" ultimatum for executives who are resistant to change. He shares fascinating insights into the "hidden 10%" of employees who are already using AI to finish their work weeks by Thursday night and explains why leaders must celebrate these early adopters rather than viewing their efficiency as "cheating." This episode serves as a powerful guide for any leader looking to navigate the existential anxieties of the AI era while building a more productive, mission-driven organization.

To connect with Greg, find him on LinkedIn or visit sectionai.com, where he shares his perspective on AI education, entrepreneurship, and the future of the global workforce. Embrace the opportunity to build a "Super Company" in this transformative era!

Want to be a guest on the show? Contact us here.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Brian Liu, the visionary founder and former CEO of LegalZoom, the company that redefined access to legal services and became the first publicly listed legal tech giant. In this episode, Brian shares his journey from a law school "misfit" to a pioneer of industry disruption, offering a rare look at how to scale a business in one of the world's most conservative professions.

Brian discusses the evolution of legal technology over the last two decades, from the early days of online document templates to the current era of AI-driven automation. He emphasizes that true disruption isn't just about software; it is about democratizing access and bridging the gap between complex academic theory and the practical needs of everyday Americans. As the conversation explores the rise of AI in the enterprise space, Brian highlights why the "human element"—authenticity, empathy, and storytelling—remains the ultimate competitive advantage that technology cannot replicate.

The conversation also touches on the intense challenges of navigating a highly regulated industry, including early legal battles and the nine-year journey from filing for an IPO to finally going public. Brian shares his philosophy on leadership, arguing that success is driven by group dynamics and trust rather than the ideas of a "lone genius." This episode serves as a powerful masterclass in resilience, showing how leaders can turn regulatory friction into a market-leading brand.

To connect with Brian, find him on LinkedIn, where he shares his perspective on entrepreneurship, board governance, and the future of the legal profession. Embrace the opportunity to build a mission-driven organization in this transformative era!

Want to be a guest on the show? Contact us HERE.

To learn more about RELAYTO, visit: relayto.com.

Your host Alex Shevelenko welcomes Amit Pande, an enterprise product leader with over two decades of experience at industry giants like Oracle, Yahoo, HP, and C3AI. In this episode, Amit shares his insights on the evolving landscape of go-to-market (GTM) strategies, particularly in the context of AI and enterprise applications. They delve into how GTM has transformed from a mere marketing and sales function into a foundational construct that drives innovation and revenue flow.

Amit discusses the significant changes he’s observed over the past decade, including the rise of GTM engineers and the integration of sales, marketing, and customer success into cohesive teams. He emphasizes the necessity of adapting to new technologies and the importance of understanding customer needs in a rapidly changing environment. As they explore the implications of AI on traditional systems of record and engagement, Amit highlights the need for organizations to evolve their approaches to data management and customer interaction.

The conversation also touches on the challenges faced by regulated industries and the importance of creating meaningful experiences for customers, even when human interaction is not present. Amit shares his vision for a future where AI enhances the sales process, enabling personalized engagements that resonate with buyers on a deeper level. This episode serves as a thought-provoking exploration of how leaders can navigate the complexities of modern GTM strategies while leveraging AI to drive meaningful change.

To connect with Amit, find him on LinkedIn and X, where he shares insights on content, storytelling, and the impact of AI on industries. Embrace the opportunity to redefine your identity in this transformative era!

To continue the conversation with Amit, visit his LinkedIn.

Want to be a guest on the show? Contact us HERE.

To learn more about RELAYTO, visit: relayto.com.