Iconoclasting

Sarah Smith
  • 5.0 (2)
  • Entrepreneurship

The road not traveled can be rockier, but it also teaches you more. Hear from people who had unconventional and non-linear pathways into what they do now, how they got there, and why it matters that they rejected the norms and focused on how to build what fits for them.

  1. 9h ago

    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

  2. Oct 1

    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

  3. Sep 25

    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

  4. Sep 17

    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

  5. Sep 10

    EP 19 - Iconoclasting with Faith Morris

    What does it look like to run two businesses, raise two young kids, spend winters in Australia, and still show up as an operations expert for founders? Ask Faith Morris, because she's doing all of it. In this episode of Iconoclasting, I sit down with Faith Morris, operations strategist for agencies and coaches, who built her expertise over a decade of hands-on work in aged care, disability services, hospitality, and leadership, and then took that foundation and built a business around helping founders get out of their own way. Faith's story is self-taught, nonlinear, and deeply human, and her advice for entrepreneurs at every stage is some of the most grounded, practical wisdom I've heard on this show. This one felt like a conversation between two ops-obsessed founders who just happened to hit record. I think you're going to love it. Here's what we cover: ✅ Faith's background in health and human services and how it shaped her human-centered approach to operations ✅ What she actually does for founders and why most of them don't know what's wrong until someone looks at the whole picture ✅ Why she pilots everything in her life, including spending nine weeks in Australia every winter ✅ What entrepreneurship running in the family really looks like (her dad is a serial entrepreneur, bestselling author, and podcast host with millions of downloads) ✅ Why hospitality experience is one of the most underrated qualifications for any leader or business owner ✅ How to navigate dual roles when you're working with friends, family, or people you have a personal relationship with ✅ Her advice for anyone scared to take the leap into entrepreneurship or a nonlinear path 🔗 CONNECT WITH FAITH: 🧵 Threads: https://threads.net/@remote.ops.partner 🎙️ The Internet Lied Podcast: https://faith-morris.myflodesk.com/the-internet-lied 📸 Instagram DMs: @remote.ops.partner 📌 Subscribe to Iconoclasting 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:00 Introduction to Faith Morris and Her Background 02:56 Balancing Two Businesses and Motherhood 05:27 Health and Human Services to Human-Centered Ops 09:53 Entrepreneurship Runs in the Family 12:56 How Hospitality Work Informs Owning a Business 15:47 Navigating Dual Roles in Business Relationships 18:34 Faith's Advice for New Entrepreneurs 🔑 KEYWORDS: operations strategist for founders, online business operations, balancing business and family, non-traditional entrepreneurship, self-taught entrepreneur, hospitality and leadership, dual roles in business, living in the messy, women entrepreneurs, Iconoclasting podcast

  6. Sep 3

    EP 18 - Iconoclasting with Rachel Stewart

    What does data analytics have to do with revolutionizing face-to-face sales? If you're Rachel Stewart, the answer is everything. In this episode of Iconoclasting, I sit down with Rachel Stewart, founder of Listel.ai, who took a technical background, a series of intentional career pivots, and a deep commitment to authenticity and built an AI startup tackling one of the oldest challenges in business: understanding what actually tips the scale for a customer in a face-to-face sales interaction. Rachel breaks down the technology behind Listel.ai, what it's like to build in the Chicago startup ecosystem, and why core values are a survival strategy for founders. If you've ever wondered what it looks like to solve a real problem with technology — and do it with integrity — this episode is the blueprint. Here's what we cover: ✅ Rachel's journey from data analytics to founding an AI startup ✅ The origin story of Listel.ai and the real sales challenge it was built to solve ✅ How the technology behind Listel.ai actually works ✅ What it's like to navigate the Chicago startup ecosystem and leverage Midwest strengths ✅ Lessons from multiple career pivots, plus what each one added to her founder toolkit ✅ Why authenticity and integrity are non-negotiable for long-term startup success ✅ How diverse skills and experiences create unique advantages in entrepreneurship ✅ Practical advice for anyone on a nonlinear career path considering a leap into tech or founding The line I keep coming back to: "Guiding your startup with your core values." 🔗 CONNECT WITH RACHEL: 🌐 Listel.ai: https://listel.ai 💼 LinkedIn: https://www.linkedin.com/in/rachelstewart259 📌 Subscribe to Iconoclasting 📲 Follow me on Instagram: @iconoclast_innovations_llc 🎙️ Listen on your favorite podcast platform ⏱️ CHAPTERS: 00:00 Introduction to Rachel Stewart and Her Journey 02:47 From Data Analytics to AI in Sales 05:44 The Birth of Listel.ai: Solving Sales Challenges 08:26 The Technology Behind Listel.ai 11:19 Navigating the Startup Landscape in Chicago 14:04 Lessons from Previous Startup Experiences 16:51 The Importance of Values in Entrepreneurship 19:36 Advice for Nonlinear Career Paths 20:29 Connecting with Rachel and Listel.ai 🔑 KEYWORDS: AI startup founder, face-to-face sales technology, data analytics to entrepreneurship, Listel.ai, Chicago tech scene, nonlinear career path, startup values, sales AI, women in tech, Iconoclasting podcast

  7. Aug 27

    EP 17 - Iconoclasting with Darell Brown

    What does a media arts background have to do with bookkeeping? More than you'd think...and Darell Brown is living proof. In this episode of Iconoclasting, I sit down with Darell Brown, founder of ProProject Bookkeeping, who built a thriving bookkeeping and financial systems business by way of a path nobody would have predicted. Darell breaks down the early mistakes, the systems that saved her, the clients that shaped her, and why embracing a non-traditional route isn't a liability — it's a competitive advantage. This is one of those conversations that's equal parts practical and perspective-shifting, whether you're a founder, a freelancer, or just someone trying to figure out how to build something sustainable without burning out along the way. Here's what we cover:  ✅ Darell's journey from media arts to founding ProProject Bookkeeping  ✅ The systems and workflows she built to avoid burnout and inefficiency — and why she wishes she'd built them sooner  ✅ What her first client — a marketing agency grossing millions — taught her about client management and expectations  ✅ How to connect the dots between cash flow and profitability in a way that actually makes sense  ✅ Why business coaching was a turning point in how she runs her company  ✅ The value of prioritizing clients who align with your values (and how to have honest conversations when they don't)  ✅ How technology can streamline operations for small and growing businesses  ✅ Her take on non-traditional paths in entrepreneurship — and why the "wrong" background might be exactly right  ✅ Practical advice for aspiring entrepreneurs just getting started The line that stuck with me most: "Connecting the dots between cash flow and profitability."  🔗 CONNECT WITH DARELL:  🌐 ProProject Bookkeeping: https://www.linkedin.com/company/proprojectbookkeeping/  💼 LinkedIn: https://www.linkedin.com/in/darellbrown/ 📚 RESOURCES MENTIONED:  Build the Damn Thing by Kathryn Finney: https://www.amazon.com/Build-Damn-Thing-Successful-Business/dp/0593329260 📲 Follow me on Instagram: @iconoclast_innovations_llc 🎙️ Listen on your favorite podcast platform ⏱️ CHAPTERS:  00:00 Introduction to Iconoclasting and Darell Brown  02:39 The Journey of ProProject Bookkeeping  05:49 Navigating Challenges and Building Systems  08:38 From Media Arts to Accounting  11:26 The Importance of Business Coaching  14:23 Embracing Non-Traditional Paths in Entrepreneurship  17:06 Advice for Aspiring Entrepreneurs 🔑 KEYWORDS: bookkeeping for small business, ProProject Bookkeeping, non-traditional entrepreneurship, business systems and workflows, cash flow and profitability, client management, startup bookkeeping, women entrepreneurs, Iconoclasting podcast, build the damn thing

  8. Aug 20

    EP 16 - Iconoclasting with Alicia Wong

    What if fear wasn't a reason to stop, but instead a signal that you're pointed in exactly the right direction? In this episode of Iconoclasting, I sit down with Alicia Wong, a product manager and AI innovator, who took a business education and pointed it directly into the deep end of tech, startups, and artificial intelligence. Alicia breaks down what it actually looks like to navigate funding stages (and what the heck the difference between Series A and Series F is), how to build products in an AI-first world, and what it looks like to use uncertainty as a growth strategy instead of a reason to play it safe. This conversation is equal parts practical and perspective-shifting, and if you've ever felt behind on AI, Alicia has something important to say about that, too. Here's what we cover: ✅ Alicia's journey from business school to product management and AI innovation ✅ Startup funding stages explained — from seed rounds to Series F and what each one actually means ✅ How education shapes career choices in unexpected ways ✅ Why fear is a signal to move toward a challenge, not away from it ✅ How AI is making previously impossible things not just possible, but scalable ✅ The role of adaptability and continuous learning in a fast-moving tech landscape ✅ Why almost everyone feels insecure about their AI knowledge — and what to do about it ✅ The future of work and what AI's impact really looks like on the ground ✅ Practical advice for aspiring professionals trying to break into tech and AI The line I keep coming back to: "AI makes what was impossible now possible." 🔗 CONNECT WITH ALICIA: 💼 LinkedIn: https://linkedin.com/in/aliciawong 🐦 Twitter: https://twitter.com/aliciawong 📚 RESOURCES MENTIONED: AI and Product Management Substack: https://substack.com/ 📲 Follow me on Instagram: @iconoclast_innovations_llc 🎙️ Listen on your favorite podcast platform ⏱️ CHAPTERS: 00:00 Introduction to Alicia Wong and Her Journey 03:40 Understanding Startup Funding Stages 06:35 Education and Its Impact on Career Choices 09:35 Navigating Career Paths in Tech and AI 12:25 The Importance of Challenging Yourself 15:19 AI's Role in Innovation and Product Management 18:58 The Future of Work and AI's Impact 21:52 Advice for Aspiring Professionals 🔑 KEYWORDS: AI product management, startup funding stages, AI innovation, career development in tech, personal growth strategies, product manager career, embracing uncertainty, AI and the future of work, Iconoclasting podcast, women in tech

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Ratings & Reviews

5
out of 5
2 Ratings

About

The road not traveled can be rockier, but it also teaches you more. Hear from people who had unconventional and non-linear pathways into what they do now, how they got there, and why it matters that they rejected the norms and focused on how to build what fits for them.

Information

  • Creator
    Sarah Smith
  • Years Active
    2026
  • Episodes
    23
  • Rating
    Explicit
  • Copyright
    © 2026 Sarah Smith
  • Show Website
    Iconoclasting