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Iconoclasting Podcast

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  1. EP 24 - Iconoclasting with Shruti Gupta

    I sat down with Shruti Gupta, founder of Pollsee, to talk about one of the more unexpected founder journeys I've heard. She started as an engineer, ran into regulatory walls in crypto, and ended up building a synthetic political population engine that helps people propose laws and predict where they'll pass. Pollsee uses digital twins — simulations built from real consumer data — to test how people are likely to respond to a policy, a campaign, or an ad. And it's already been used to help pass a property tax proposal in Louisville in seven months with bipartisan support. We also got into the broader questions this kind of technology raises: why polling is broken, how regulation disproportionately hits small businesses, what it looks like when government processes finally catch up to how people actually use technology, and what AI agents doing side hustles means for how we think about work. In this conversation, we cover: What Pollsee is and how political digital twins actually work Why traditional polling has collapsed and what that means for representation How a 23-year-old used Pollsee to pass a Kentucky property tax law in seven months Why broad regulations can burden smaller businesses in ways that larger ones absorb easily The case for autonomous agents participating in economic activity online Shruti's advice for anyone thinking about taking the leap into entrepreneurship Connect with Shruti Gupta: Instagram: @itspollsee Website: itspollsee.org LinkedIn: https://www.linkedin.com/in/gupta-shruti/ 🎙️ Subscribe so you don't miss the next episode of Iconoclasting. Chapters 00:00 Meet Shruti Gupta and Pollsee 01:09 From engineering and crypto to political technology 02:26 Why polling needs a new approach 03:16 How political digital twins are built and used 05:12 Making policy participation more accessible 06:24 A property-tax proposal tested with Pollsee 11:54 How regulation shaped Gupta's founder journey 14:14 When policy costs can disadvantage startups 17:03 Digital participation across generations 20:05 Side hustles, agents, and shifting work 24:25 Gupta's advice: take the leap Keywords: Shruti Gupta, Pollsee, digital twins, political technology, civic technology, policy proposals, entrepreneurship, AI, founder story, nonlinear career, women in tech, Iconoclasting

  2. EVOLVE Applied with Deb Keltner: Value Translation

    I sat down with marketing consultant Deb Keltner to dig into one of the trickiest parts of the EVOLVE framework: value translation. Not just how you talk about your value, but whether you actually know what it is. Deb works with mid-sized professional services companies hitting growth ceilings, and the pattern she sees over and over is the same: companies that have lost the plot on why they exist. We get into the dysfunctions that show up when value gets misaligned, what to do about it, and why getting an outside perspective is usually what it actually takes to move forward. In this conversation, we cover: Why confusing activity with value is one of the most common (and costly) mistakes businesses make What it looks like when your value proposition has quietly collapsed How to use case studies, win/loss data, and client conversations to diagnose where you’ve gone off course Why niching down is not a limitation, it’s a clarity tool What Dyson, Microsoft, and Amazon can teach you about knowing your lane How mission, vision, and values work as a decision-making filter, not just a careers page filler What AI is doing to commoditize the differentiators companies relied on for years If you’ve been stuck at the same revenue ceiling, or you’re not sure why prospects aren’t choosing you, this one is worth your time. Connect with Deb Keltner: Website: https://debkeltner.com LinkedIn: https://linkedin.com/in/debkeltner Learn more about the EVOLVE Framework: https://sarahsmith.com Chapters 00:00 Introduction to the EVOLVE Framework 03:08 Understanding Value Translation 06:33 Dysfunctions in Value Communication 11:02 Identifying Core Value vs. Activity 15:44 The Importance of Niching Down 20:36 Case Studies: Success and Failure in Value Proposition 24:08 The Role of Trust in Value Translation 29:48 Creating Value in Technology Teams 32:01 Mission, Vision, and Values as Guiding Principles 35:04 Innovation in Professional Services 39:03 The Impact of AI on Value Perception 40:03 Understanding Client Value and Feedback 46:03 Defining Ideal Clients and Cultural Fit 50:30 The Importance of Clear Value Translation Keywords: value translation, organizational alignment, marketing strategy, business growth, professional services, brand messaging, value proposition, EVOLVE framework, Deb Keltner, niching down, innovation, AI in business

  3. EP 23 - Iconoclasting with Megan Flanagan

    What if you stopped thinking about your career as a ladder and started treating it like a pie chart? In this episode of Iconoclasting, I sit down with Megan Flanagan, fractional B2B health tech strategist, ultra runner, and host of the Evolve Your Path podcast, who has spent her career doing exactly that. Megan brings a genuinely multifaceted background across workforce wellness, health systems, organizational culture, and go-to-market strategy — and she makes a compelling case that a portfolio career is not a lack of direction. It is a deliberate choice to pursue fulfillment alongside income. This one is practical, honest, and packed with the kind of nuance that healthcare and systems work actually require. Here's what we cover: ✅ What a portfolio career really means — and why Megan describes hers as a pie chart, not a ladder ✅ Health and wellness as a whole-person system, not just a benefits package ✅ How her background as an athlete shaped her professional values and long-game thinking ✅ What fractional B2B health tech work actually involves — from pipeline audits to leaky bucket diagnostics ✅ The parallels between ultra running and long sales cycles, entrepreneurship, and systems change ✅ Why organizational culture and psychological safety are not soft skills — they are business infrastructure ✅ How she designs career experiments using a minimum effective dose approach ✅ Why she designed her own college major and what that taught her about nonlinear paths ✅ Practical advice for trying on new roles without blowing up what you have built ✅ Her upcoming Evolve Women Summit in Denver for women in transition or building on their own terms The line I keep coming back to: "Try on a different hat — be okay with experimentation." From someone who has tried on more hats than most people own, that is advice with real weight behind it. 🔗 CONNECT WITH MEGAN: 🌐 Website: https://evolvedpotential.co 🎙️ Podcast: Evolve Your Path - https://open.spotify.com/show/3cI11hM7lwQ5xev6BsNFdk?si=65ba96233e45449f 📅 Evolve Women Summit — Denver, November 2026: https://www.eventbrite.com/e/the-evolve-womens-summit-tickets-1999223324782 📌 Subscribe to Iconoclasting 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:06 Introduction to Megan Flanagan and Her Multifaceted Career 02:56 Health and Wellness as a Whole-Person System 05:44 How Megan's Athlete Background Shaped Her Values 09:13 Fractional B2B Health Tech: What It Is and How It Works 12:52 Megan's Nontraditional Journey and Advice for Nonlinear Pathways 🔑 KEYWORDS: portfolio career, fractional health tech, systems change healthcare, organizational culture, career experimentation, workforce wellness, ultra running and business, Evolved Potential, nonlinear career path, Iconoclasting podcast

  4. EP 22 - Iconoclasting with Nina Lubarsky

    What does working in professional kitchens and on farms have to do with building brands for purpose-driven small businesses? For Nina Lubarsky, it turns out everything. In this episode of Iconoclasting, I sit down with Nina Lubarsky, founder of Humm House, who took a deeply nonlinear path through environmental science, farming, and professional cooking before landing in branding and visual identity work. Nina helps purpose-driven entrepreneurs build brands rooted in their values, and her approach starts from the inside out: who you are, what you stand for, and how that translates visually to the people you actually want to reach. This is one of those conversations that made me rethink what branding really means, and why the most authentic brands are never built from a template. Here's what we cover: ✅ Nina's journey from chef and farmer to brand strategist and founder of Humm House ✅ Why the physical realities of kitchen and farm work shaped how she thinks about creative work ✅ What handcrafted branding looks like in a world increasingly dominated by AI-generated design ✅ How Nina finds and represents the many facets of a founder's identity visually ✅ Why aligning your clients with your core values is a business strategy, not just a philosophy ✅ Her four core values at Humm House: care, communication, connection, and integrity ✅ How to differentiate yourself in a crowded market by understanding your industry landscape ✅ Her work with female founders and what authentic personal branding actually requires ✅ Why experimentation and systems are both necessary for sustainable creative growth ✅ Nina's brand clarity session offer — 25% off for Iconoclasting listeners The line I keep coming back to: "Developing the brand personality starts inward." 🔗 CONNECT WITH NINA: 🌐 Website: https://hummhouse.com 📸 Instagram: https://instagram.com/humm.house ✨ Brand Clarity Session (25% off for listeners): https://hummhouse.com/brand-clarity 📌 Subscribe to Iconoclasting 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:00 Introduction to Nina Lubarski 01:57 Nina's Journey from Chef to Branding 06:29 Handcrafted Branding in an AI World 09:40 Finding Identities and Representing Those Visually 15:27 The Importance of Aligning Your Clients with Your Values 18:03 Nina's Advice for Nontraditional Pathways 🔑 KEYWORDS: purpose-driven branding, visual identity for small business, handcrafted branding, brand strategy for female founders, AI and creative industries, authentic personal branding, Humm House, brand clarity, values-based business, Iconoclasting podcast

  5. EP 21 - Iconoclasting with Alyssa Moorhead

    Marketing gets all the attention, but sales is what actually keeps your business alive. And nobody makes that case better than Alyssa Moorhead. In this episode of Iconoclasting, I sit down with Alyssa Moorhead, lead generation strategist and host of The DM Sales Gal podcast, who built a done-for-you lead generation business after leaving corporate life and navigating a deeply personal journey through sobriety. Alyssa breaks down the real difference between marketing and sales, why ethical practices in lead generation are non-negotiable, and what it actually looks like to hand someone else the keys to your personal brand without losing what makes it yours. This conversation goes places most business podcasts won't. And I think that's exactly why it's worth your time. Here's what we cover: ✅ The difference between marketing and sales, and why conflating them is costing you revenue ✅ What done-for-you lead generation actually involves and who it is right for ✅ Why trusting someone else with your personal brand does not have to be scary ✅ Alyssa's path from corporate life to entrepreneurship and what pushed her to make the leap ✅ Her ten-year sobriety journey and how it shaped the way she runs her business ✅ How to build trust through content and visibility before you ever pitch anything ✅ Why impersonating clients in DMs is a hard no, and what ethical lead generation looks like instead ✅ Managing leads at scale without overwhelming yourself or your pipeline ✅ The role of face-to-camera content in building real connection with your audience ✅ Advice for anyone on a nonlinear path who has not given up on what they really want to do The line I keep coming back to: "Don't give up on what you really want to do." 🔗 CONNECT WITH ALYSSA: 📸 Instagram: https://www.instagram.com/alyssa_l_moorhead/ 🎙️ The DM Sales Gal Podcast: https://podcasts.apple.com/us/podcast/the-dm-sales-gal/id1551234567 📌 Subscribe to Iconoclasting 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:00 Introduction and Alyssa's Background 01:55 The Difference Between Marketing and Sales 06:44 Trusting Someone Else With Your Personal Brand Doesn't Have to Be Scary 11:38 Alyssa's Journey to Entrepreneurship 14:23 Alyssa's Ten-Year Sobriety Journey 19:19 Alyssa's Advice on Nonlinear Pathways 🔑 KEYWORDS: done-for-you lead generation, marketing vs sales, personal branding, authentic content strategy, DM sales strategy, ethical lead generation, sobriety and entrepreneurship, women in business, nonlinear career path, Iconoclasting podcast

  6. EP 20 - Iconoclasting with Jenn Smukler

    If your body is sending you signals you keep ignoring, this episode is the one to listen to. In this episode of Iconoclasting, I sit down with Jenn Smukler, holistic health coach and founder of Alive Unlocked, who left corporate America after her body started telling her something was deeply wrong. Jenn breaks down what burnout actually looks like before it becomes a crisis, why so many high-achieving women miss the early warning signs, and what a multifaceted, strategic approach to wellness really means in practice. This is not a conversation about bubble baths and taking more vacations. This is about learning to read your body before it forces you to stop. Here's what we cover: ✅ Jenn's journey from corporate America to holistic health coaching ✅ What burnout really looks like — and why it sneaks up on you slowly ✅ The physical signs your body gives you long before rock bottom arrives ✅ How to learn your body's specific responses to stress before they become serious ✅ How to recognize burnout in the people around you — not just yourself ✅ Why disconnecting is not optional if you want to sustain long-term performance ✅ The role of immigrant experience and cultural background in how we process stress ✅ Why strategic boundaries and self-awareness are the foundation of real wellness ✅ Jenn's advice for anyone on a nonlinear career path considering a pivot toward purpose The soundbite I cannot stop thinking about: "Burnout is a slow trickle, not an overnight event." 🔗 CONNECT WITH JENN: 🌐 Website: https://aliveunlocked.com 📝 Substack: https://aliveunlocked.substack.com 📸 Instagram: https://instagram.com/alive.unlocked 💼 LinkedIn: https://linkedin.com/in/jensmukler ⏱️ CHAPTERS: 00:00 Introduction to Jenn Smukler and Her Journey 06:13 What Burnout Really Looks Like 11:35 Learning Your Body's Responses (Before Rock Bottom) 15:14 How to Recognize Burnout in Your Loved Ones 20:27 The Importance of Disconnecting 23:03 Jenn's Advice on Nonlinear Pathways 🔑 KEYWORDS: burnout recovery, holistic health coaching, corporate burnout, stress management for women, recognizing burnout signs, wellness coach, career pivot to wellness, mental health for entrepreneurs, Alive Unlocked, Iconoclasting podcast