The Product Leader's Edge

KJ Green | Solo Star

The New York–based flagship publication and broadcast of Solo Star, exploring enterprise cloud architecture, applied AI, platform governance, and product leadership for a global audience. Hosted by KJ Green, each episode delivers practical frameworks, technical blueprints, and conversations for leaders building what lasts. solostarbykjg.substack.com

  1. 5 Oct

    Ep 16: Executive Edge: Before You Scale AI — With Hemang Upadhyay

    The Executive Edge begins with a conversation about what organizations need before AI can create meaningful value. KJ Green sits down with Hemang Upadhyay, a product leader and AI strategist with more than 16 years of experience across engineering, digital commerce, enterprise platforms, and AI-powered products. Hemang traces his journey from engineering into product leadership and explains how his questions evolved from “Can we build this?” to “Should we build this?” and, in the AI era, “Can people trust the system when it makes or executes a decision?” The conversation then moves into AI-powered commerce, the evolution from machine learning to generative and agentic AI, and why adding AI to a fragmented customer journey does not automatically create an intelligent one. KJ and Hemang explore the foundations organizations need before scaling AI: reliable product data, capable platforms, clear business outcomes, appropriate governance, human oversight, and a deliberate approach to autonomy. Hemang also introduces his TRUST framework and explains why organizations should prioritize the data that matters most to the customer rather than allowing enterprise-wide cleanup efforts to delay experimentation indefinitely. The episode closes by widening the leadership question. As AI moves from recommending to acting, product and technology leaders must decide where automation creates value, where guardrails are necessary, and where human judgment must remain. In This Episode • Why Hemang moved from engineering into product leadership and how that changed the questions he asked. • Why AI initiatives should begin with customer and business problems rather than a desire to deploy AI. • How machine learning evolved into today’s generative and agentic AI landscape. • What AI-powered commerce actually means across discovery, decision-making, purchasing, fulfillment, and support. • How B2C and B2B AI-commerce journeys differ in complexity, stakeholders, rules, and accountability. • Why product data, existing platforms, and operational foundations matter before AI is scaled. • How to prioritize high-value data and use pilots instead of waiting for perfect enterprise readiness. • Hemang’s TRUST framework for governed data, consent, identity, safe boundaries, human oversight, traceability, recovery, and accountability. • How to think about AI autonomy based on risk and when humans should remain in the loop. • Why leadership is less about having every answer and more about creating clarity, ownership, and better decision-making systems. Key Takeaway AI capability alone does not create transformation. Organizations create value when capable technology is supported by trustworthy data, appropriate platforms, clear governance, measurable outcomes, and people who understand where automation should end and judgment should begin. About the Guest Hemang Upadhyay is a product leader and AI strategist with more than 16 years of experience spanning engineering, digital commerce, enterprise platforms, AI-powered customer experiences, and large-scale platform transformation. His work focuses on translating complex technology into meaningful customer and business outcomes. Related Reading Kumar, R., Pandey, C. P., & Upadhyay, H. (2026). The Future of Responsible Investment: AI, Automation, and Human Judgment. In AI and Automation in Green Investment Platforms: Next-Generation ESG. The Product Leader’s Edge Publication: “AI Is the Feature. Readiness Is the System.” This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 16: Executive Edge: Before You Scale AI — With Hemang Upadhyay
  2. 28 Sept

    Interlude — From Building to Leading

    The Builder’s Series is complete, and Season 1 of The Product Leader’s Edge is entering its final stretch. In this short interlude, KJ reflects on what emerged from conversations with seven founders building across beverage, travel, wellness, community and belonging, art, AI, and digital experiences—and how those conversations reinforced the Season 1 thesis that product leadership shows up everywhere. But the product itself is only one part of the build. Customer experience, capital, technology, operations, people, and the broader systems surrounding a product all shape whether an idea can become something valuable. KJ also reflects on a theme increasingly shaping his work: technology is ultimately built for people, and the human element is what amplifies technology—whether we’re talking about AI, cloud, cybersecurity, or the products built on top of them. With just three episodes remaining in Season 1, KJ also shares updates on The Product Leader’s Edge Medium publication, Inside Solo Star, and what’s ahead as Season 2 begins to take shape. In this interlude: * Why the product is only one part of the build * What seven founder conversations revealed about product leadership * The relationship between people, business, and technology * Why the human element matters across AI, cloud, and cybersecurity * The growing Product Leader’s Edge platform * A look ahead to the final three episodes of Season 1 and Season 2 🎙️ The Product Leader’s EdgeA Solo Star Media & Technology production. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Interlude — From Building to Leading
  3. 14 Sept

    Ep 15: Building Belonging with Whitney Pollard of homii

    Builder’s Series: Building Belonging with Whitney Da'Gail of homii Global What does it actually take to feel like you belong somewhere new? After a layoff, Whitney Da’Gail spent a year traveling through South America and Southeast Asia before settling in Vietnam. That journey eventually led her to build homii Global, a community platform focused on helping people find trusted communities, experiences, and spaces where they can feel connected. In this Builder’s Series conversation, Whitney joins KJ Green to talk about how homii evolved from a travel concept into a broader community platform, what she learned from building community in Vietnam, and why belonging can be just as important as logistics when entering a new city or culture. They also discuss MVP testing, cultural context, trust and safety, founder sacrifice, choosing the right co-founder, and balancing a long-term vision with what needs to happen in the next 30, 60, and 90 days. In this episode: * Building homii from lived experience * Why belonging became bigger than travel * Testing community ideas before turning them into technology * Trust, safety, and cultural awareness * Founder tradeoffs and sacrifice * Choosing the right co-founder * Why founders have to make the decision and show up Connect with Whitney Da’Gail LinkedIn: Whitney Pollard Instagram: Whitney Da’Gail homii Global Instagram: @homi.global This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 15: Building Belonging with Whitney Pollard of homii
  4. 31 Aug

    Ep 14: Building a Creative Life That Takes Up Space with Olivia Brown

    What happens when creativity becomes more than a talent—and begins to shape a business, a healing practice, and a platform for community? In this Builder’s Series episode of The Product Leader’s Edge, KJ Green sits down with Olivia Brown, founder of OliviaGeorgette Studios and a multidisciplinary artist, designer, instructor, and community builder. Olivia shares how she evolved from working primarily in graphic design to embracing traditional art, painting, engraving, teaching, and live creative experiences. She explains why her work became more resonant when she stopped creating what she thought people wanted and began sharing art that felt personal and authentic. The conversation also explores what happened when Olivia realized she had outgrown exhibiting inside spaces created by other people. That realization led her to host her own art shows, design complete OliviaGeorgette experiences, and confidently take up space as an artist and founder. KJ and Olivia also discuss art as a source of healing, the importance of representation, the opportunities and concerns surrounding AI-generated design, and how Olivia used her creative platform to mobilize support for families in Jamaica following Hurricane Melissa. As Olivia looks toward the next stage of her business, she reflects on the challenges of being the owner, artist, marketer, and event coordinator—and why building a strong team will be essential to scaling OliviaGeorgette Studios. In This Episode * Becoming a multidisciplinary artist * Moving between digital design and traditional art * Creating authentically instead of chasing social media expectations * How art can support healing and emotional release * Representation and creating art that feels like a “visual hug” * The impact of AI on artists, designers, and creative ownership * Recognizing when you have outgrown someone else’s space * Building immersive art shows and community experiences * Using creativity to mobilize support for Jamaica * The realities of scaling a founder-led creative business * Defining success through impact, collaboration, and reach * Taking up space in creative and corporate environments About Olivia Brown Olivia Brown is the founder of OliviaGeorgette Studios and a Caribbean-American multidisciplinary artist, engraver, designer, entrepreneur, and creative facilitator based in New York. Through vibrant artwork and immersive creative experiences, Olivia celebrates self-love, body positivity, culture, and the beauty of Black and Brown communities. Her creative practice includes hand-painted canvases, custom apparel and accessories, murals, engraved keepsakes, and her signature Plant & Paint workshops. Her work is grounded in a belief that art can help people feel seen, create space for healing, and bring communities together. Episode Chapters 00:00 – Introducing Olivia Brown 02:10 – What it means to be a multidisciplinary artist 02:55 – From graphic design back to traditional art 05:46 – Making the personal communal 08:09 – Continued learning, creative evolution, and AI 11:37 – Outgrowing other people’s spaces 14:10 – Representation and art as a visual hug 16:06 – Painting as healing and emotional release 18:45 – Making creative experiences accessible 21:31 – Using art to support Jamaica 28:12 – The challenges of building a founder-led business 30:07 – Olivia’s definition of success 32:44 – Create, Teach, or Exhibit 35:03 – What it means to take up space 39:08 – Where to connect with Olivia Learn More About OliviaGeorgette Studios If you’d like to explore Olivia’s artwork, attend one of her creative experiences, or learn more about OliviaGeorgette Studios, you can connect with her below. 🌐 OliviaGeorgette Studios Website📸 Instagram🎨 Artwork, Workshops & Custom Creations About The Product Leader’s Edge The Product Leader’s Edge is a podcast and publication by KJ Green exploring how founders, operators, and product leaders build products, companies, and careers in the age of AI. Through conversations with builders across technology, startups, media, and consumer brands, each episode uncovers the decisions, tradeoffs, and lessons behind building something that lasts. Continue the conversation: 📬 Solo Star Newsletter 🎙️ The Product Leader’s Edge Podcast 💼 LinkedIn 📺 YouTube 📬 The Product Leader’s Edge Publication This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 14: Building a Creative Life That Takes Up Space with Olivia Brown
  5. 17 Aug

    Ep 13: Building in the Age of AI with Nick & Laura Rackley of Vibe Otter

    What happens when the barrier to building starts to disappear? In this special episode of The Builder’s Series, KJ sits down with Nick and Laura Rackley, co-founders of Vibe Otter, to explore what it means to build products and businesses in an era where AI is making creation faster and more accessible. Nick and Laura share their journey from corporate careers into entrepreneurship, how early customer feedback helped shape Vibe Otter, and why they’re focused on making AI-powered building accessible beyond traditional technical audiences. The conversation explores rapid experimentation, finding early customers, building as a co-founder couple, and the growing importance of distribution when launching a product becomes easier. The episode also goes under the hood of Vibe Otter, including how AI, system prompts, APIs, and cloud infrastructure come together to power the platform. Then, rather than simply talking about building, KJ, Nick, and Laura put the idea to the test by attempting to build an AI-powered church finder live during the episode, glitches and all. Later, the conversation flips as Nick and Laura ask KJ about his own journey into podcasting, why he created The Product Leader’s Edge, and what he has learned from documenting builders while building a media platform of his own. Throughout the conversation, one question keeps resurfacing: If everyone can build, what actually matters? The answer may increasingly lie beyond the technology itself—in understanding the customer, choosing the right problem, earning distribution and trust, and having the judgment to know what is worth building. In this episode: * Building and testing an MVP before everything is perfect * Going from corporate careers to entrepreneurship * Designing AI products for everyday users * Using customer feedback to shape the product * Building Vibe Otter as a co-founder couple * Why distribution still matters when AI makes building easier * What AI is actually doing underneath modern applications * The cloud infrastructure behind the AI era * Building an AI church finder live * Why websites alone don’t create customers * Bootstrapping versus venture capital * KJ’s journey into podcasting and The Product Leader’s Edge * What becomes valuable when everyone has the ability to build The Builder’s Series explores the people, decisions, experiments, and lessons behind building companies, products, communities, and new ideas. This episode also serves as a bridge into Applied AI Foundations, coming in Season 2 of The Product Leader’s Edge. Learn More About Vibe Otter 🌐 Vibe Otter 📸 Instagram 🦦 If You Can Text, You Can Build a Website — or a whole app. Tell the Otter what you want: pages, booking, customer logins, hosting, and more — then turn the idea into something live. About The Product Leader’s Edge The Product Leader’s Edge is a podcast and publication by KJ Green exploring how founders, operators, and product leaders build products, companies, and careers in the age of AI. Through conversations with builders across technology, startups, media, and consumer brands, each episode uncovers the decisions, tradeoffs, and lessons behind building something that lasts. Continue the conversation: 📬 Solo Star Newsletter 🎙️ The Product Leader’s Edge Podcast 💼 LinkedIn 📺 YouTube 📬Medium Publication This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 13: Building in the Age of AI with Nick & Laura Rackley of Vibe Otter
  6. 3 Aug

    Ep 12: Building Wellness as Infrastructure | Joi James, Founder of finding joi

    What happens when care is treated as optional instead of foundational? In this episode of The Product Leader’s Edge, KJ Green sits down with Joi James, founder of finding joi, a holistic wellness platform creating psychologically and physically safe spaces for Black womxn and femmes navigating institutional environments. Joi shares how her experience with burnout, wellness coaching, somatic healing, and Pilates shaped the foundation of finding joi. What began as a personal healing journey has evolved into a growing wellness technology platform connecting Black womxn and femmes with culturally responsive resources, practitioners, workshops, coaching, and community. Together, KJ and Joi explore what it means to design care as infrastructure—not simply as a workplace benefit. They discuss how institutions can create safer systems, why trust breaks when leaders fail to model care, and how community-engaged design can produce solutions grounded in the lived experiences of the people they serve. Joi also opens up about building a business as an act of self-trust, protecting her own capacity while supporting others, and becoming both the builder and the first user of her product. In this episode, we discuss: * Why care and psychological safety should be treated as infrastructure * The institutional responsibility to create safer environments * How chronic stress affects Black womxn and femmes * Why trust is often the first thing to break when care becomes optional * Designing safety as an experience rather than simply stating it as a value * The role of discovery, accessibility, movement, and community in healing * Turning lived experience into a scalable wellness platform * The productivity paradox and its connection to burnout * Why organizations must co-create solutions with the people they serve * Building a business from a place of self-trust * Protecting your capacity while doing care-centered work * Why leaders must model the wellness practices they encourage About Joi James Joi James is the founder of finding joi, a stress recovery coach, Pilates instructor, and community-engaged designer. Her work sits at the intersection of wellness, social impact, racial justice, philanthropy, and systems design. Through finding joi, Joi is building an ecosystem of leadership coaching, workshops, movement practices, live experiences, and digital wellness resources designed for Black womxn and femmes. Learn More About finding joi If you’re interested in holistic wellness, leadership coaching, or learning more about Joi’s work creating safer and more restorative spaces for Black womxn and femmes, you can connect with finding joi below. 🌐 finding joi Website📸 Instagram💼 LinkedIn✨ Wellness Services and Experiences Follow the finding joi by Joi James on substack! About The Product Leader’s Edge The Product Leader’s Edge is a podcast and publication by KJ Green exploring how founders, operators, and product leaders build products, companies, and careers in the age of AI. Through conversations with builders across technology, startups, media, and consumer brands, each episode uncovers the decisions, tradeoffs, and lessons behind building something that lasts. Continue the conversation: 📬 Solo Star Newsletter 🎙️ The Product Leader’s Edge Podcast 💼 LinkedIn 📺 YouTube 📬 Medium This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 12: Building Wellness as Infrastructure | Joi James, Founder of finding joi
  7. 20 Jul

    Ep 11: Building Trust Through Travel with Tabetha Taylor-Cintorino

    What does it take to build a business people trust with life’s biggest moments? In this episode of The Product Leader’s Edge, I sit down with Tabetha Taylor-Cintorino, founder of Travel with Tab , to explore how she built an award-winning travel business rooted in trust, customer experience, and thoughtful service. We discuss entrepreneurship, building a service-based business, the evolving role of AI in travel, creating memorable customer experiences, and why product leadership extends far beyond technology. Whether you’re a founder, product leader, consultant, or service professional, this conversation offers practical lessons on building businesses that people trust. In this episode we discuss: * The journey behind building Travel with Tab * Why trust is the ultimate competitive advantage * How AI is changing the travel industry * Building a personal brand and finding product-market fit * Entrepreneurship, resilience, and continuous learning * Creating exceptional customer experiences * Why product leadership exists beyond technology Learn More About Travel with Tab Planning your next vacation, celebrating a milestone, or looking for expert guidance on your next adventure? Connect with Tabetha and explore how Travel With Tab can help bring your travel plans to life. 🌐 Travel With Tab Website 📸 Instagram ✈️ Schedule a Discovery Call About The Product Leader’s Edge The Product Leader’s Edge is a podcast and publication by KJ Green exploring how founders, operators, and product leaders build products, companies, and careers in the age of AI. Each episode uncovers the frameworks, decisions, and lessons behind building something that lasts. Continue the Conversation 📬 Solo Star Newsletter 🎙️ The Product Leader’s Edge Podcast 💼 LinkedIn 📺 YouTube This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit solostarbykjg.substack.com

    Ep 11: Building Trust Through Travel with Tabetha Taylor-Cintorino

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About

The New York–based flagship publication and broadcast of Solo Star, exploring enterprise cloud architecture, applied AI, platform governance, and product leadership for a global audience. Hosted by KJ Green, each episode delivers practical frameworks, technical blueprints, and conversations for leaders building what lasts. solostarbykjg.substack.com