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. 5d ago

    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

  2. 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

  3. 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

  4. 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

  5. Aug 14

    EP 15 - Iconoclasting with Kirsten Co

    What do Megadeath, four continents, two Masters’ degrees, and enterprise sales have in common? Kirsten Co. And yes, this episode is as fascinating as that sentence sounds. In this episode of Iconoclasting, I sit down with Kirsten Co, founder of K and Co Leadership Consulting, who built a career that spans continents, industries, and genres, literally. From managing international metal bands to navigating enterprise procurement at tech companies across e-commerce, AI, and cybersecurity, Kirsten has built one of the most unique founder stories I've ever heard. Just as you’d expect from this kind of diverse background, Kirsten’s philosophy is refreshingly grounded: take calculated risks, keep learning, and build real relationships. Here's what we cover: ✅ How Kirsten’s journey from the Philippines to New York (and two other continents) led her to global entrepreneurship ✅ Why her last name became her company name, and what that means for her brand identity ✅ The family influence and early experiences that shaped her entrepreneurial instincts ✅ Her educational journey through two Masters’ degrees ✅ What managing metal bands like Lacuna Coil and Megadeth taught her about business, risk, and relationships ✅ How diverse tech experience across e-commerce, AI, and cybersecurity made her a sharper consultant ✅ The role of cultural fluency and multilingual competence in global business ✅ What enterprise sales actually requires, and why old-school relationship-building is still the name of the game ✅ How to bridge the startup and corporate worlds without losing what makes you effective in either ✅ Advice for aspiring founders on calculated risk and applying past skills to new ventures My favorite line from this whole conversation: "Continuous learning is a treasure." Coming from someone who has lived and worked across multiple countries, industries, and cultures, that wisdom is grounded in experience. 🔗 CONNECT WITH KIRSTEN: 🌐 K and Co Leadership Consulting: https://kandco.ai 💼 LinkedIn: https://linkedin.com/in/kirstenco 📲 Follow me on Instagram: @iconoclast_innovations_llc 🎙️ Listen on your favorite podcast platform ⏱️ CHAPTERS: 00:00 Introduction and Kirsten Co's Background 01:59 Origin of the Company Name and Entrepreneurial Roots 03:09 Family Influence and Early Entrepreneurial Experiences 04:13 Cultural Background and International Living Experience 05:50 Deciding to Become a Founder and Move to New York 07:31 Language Skills and Multicultural Competence 08:37 Educational Journey: MBA and MS Degrees 10:35 Transition from Corporate to Entrepreneurship 11:44 Managing a Metal Band and Applying Business Skills 14:14 Expanding into the Music Industry and International Gigs 16:45 Lessons from Managing a Metal Band and Risk Management 18:59 Diverse Tech Experience: E-Commerce, AI, Cybersecurity 21:19 Building Relationships and Understanding Enterprise Sales 23:20 Bridging Startup and Corporate Worlds 25:48 Advice for Aspiring Founders and Risk Assessment 28:12 Applying Past Skills to New Business Ventures 28:58 Closing Remarks and How to Connect with Kirsten Co 🔑 KEYWORDS: leadership consulting, enterprise sales strategy, founder story, risk management entrepreneurship, continuous learning, global entrepreneurship, K Co consulting, metal band business lessons, multicultural business, Iconoclasting podcast

  6. Aug 6

    EP 14 - Iconoclasting with Hazel Jones

    What does Abercrombie & Fitch have to do with building a copywriting business? More than you'd think, as I learned on this episode of Iconoclasting with Hazel Jones. In this episode of Iconoclasting, I sit down with Hazel Jones, founder of Hazel Jones Copywriting, who went from retail to government work to a copywriter serving female founders by focusing on the opportunities in front of her and unlearning what being a “good employee” looks like. Hazel breaks down the real difference between SEO, AEO, and GEO (yes, there's a third one now), what it actually takes to unlearn the employee mindset, and why niching down to work with the people you actually want to serve changes everything about how you run a business. Here's what we cover: ✅ Hazel's winding path from working on the floor at Abercrombie & Fitch to navigating government bureaucracy to finding her creativity as a copywriting entrepreneur ✅ What SEO, AEO, and GEO actually mean, and why the distinction matters more than ever as AI changes search ✅ Why copywriters have to be marketers and ongoing learners to stay relevant ✅ How filling your creative well makes you a better writer and a better business owner ✅ Why the mindset of "I need money, but I don't need your money" protects your niche and your energy ✅ What unlearning the employee mindset really looks like in practice ✅ Why niching down to female founders was the turning point for her business ✅ Practical advice for entrepreneurs who are still figuring it out "I Need Money, But I Don't Need Your Money" is one of my favorite mantras I’ve ever heard on the podcast. If you’re in the middle of chasing clients and building something that excites you creatively, this episode is a must-listen. 🔗 CONNECT WITH HAZEL: 📲 Instagram: @hazeljonescopywriting 🌐 Website: https://hazeljonescopywriting.com 💼 LinkedIn: https://linkedin.com/in/hazeljones 📚 RESOURCES MENTIONED: Write Your Way to Freedom Course: https://copywritingcourse.com 📌 Take the EVOLVE Assessment: https://iconoclast-evolve.lovable.app/ 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:06 Introduction to Hazel Jones and Her Background 01:22 What SEO, AEO, and GEO All Really Mean 04:20 Abercrombie to Government to Copywriting: Hazel's Career Journey 09:02 Copywriters Have to Be Marketers and Ongoing Learners 14:24 From Government Bureaucracy to Filling Your Creative Well 16:54 "I Need Money, But I Don't Need Your Money" and Niching Down 20:08 Unlearning the Employee Mindset 23:29 Hazel's Advice for Entrepreneurs 🔑 KEYWORDS: copywriting for female founders, SEO AEO GEO explained, copywriting business, entrepreneur mindset, niche selection, freelance copywriter, email marketing, women entrepreneurs, career transition, Iconoclasting podcast

  7. Jul 30

    EP 13 - Iconoclasting with Morgan Abreu

    What do biology, Hawaii, and referral technology have in common? Morgan Abreu. In this episode of Iconoclasting, I sit down with Morgan Abreu, founder of Melia Strategy and Referral Reef, who went from biology to sales to building two businesses rooted in relationship-first thinking, ocean-inspired philosophy, and a refreshingly anti-bro approach to entrepreneurship. Morgan breaks down what a referral ecosystem actually looks like when it's built with intention, why sales doesn't have to feel gross, and how embracing your unique founder magic is the strategy most people overlook. This one is packed with practical insights and the kind of perspective shift that sticks with you. Here's what we cover: ✅ Morgan's journey from biologist to sales strategy queen to founder ✅ The origin story behind Referral Reef and Melia Strategy, including how Morgan honors her Hawaiian home ✅ What an anti-bro, relationship-based sales culture actually looks like ✅ How to build scalable referral processes that don't require complicated technology ✅ Why networking is only as powerful as your willingness to expand it ✅ The role of experimentation, data, and process in sales success ✅ How living and building a business in Hawaii shaped her philosophy ✅ The concept of Ikigai and how it can help you find your tribe and your purpose ✅ Tips for new consultants and aspiring entrepreneurs just getting started My favorite line from this conversation: "Referral Reef is about taking care of your ecosystem." 🔗 CONNECT WITH MORGAN: 🌐 Melia Strategy: https://meliastrategy.com 🪸 Referral Reef: https://referralreef.com 💼 LinkedIn: https://linkedin.com/in/morganabreu 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:00 Introduction to Morgan and Referral Reef 02:03 Building a Referral Network with Fractionals 05:44 Anti-Bro Culture Sales Strategy 06:48 Biologist to Sales Queen: Morgan's Path 10:00 Building a Life and Business in Hawaii 11:29 Finding the Hidden Entrepreneurs in Family 14:33 Why a Referral Network Is a Natural Extension of Sales 17:47 Sales Processes Are Science 19:58 Morgan's Tips for New Consultants 🔑 KEYWORDS: referral network, referral marketing, relationship-based sales, anti-sales culture, Melia Strategy, Referral Reef, founder magic, entrepreneurship Hawaii, sales process, Iconoclasting podcast

  8. Jul 23

    EP 12 - Iconoclasting with Michelle Collier

    What happens when a single day changes everything and eventually leads you to the work you were always meant to do? In this episode of Iconoclasting, I sit down with Michelle Collier, founder of Collier Connects, whose path has varied from law to education to nonprofit leadership to personal and professional development coaching. Michelle's path was shaped by life-altering moments, including the events of 9/11 and her own health challenges, that pushed her to ask harder questions about purpose, identity, and what it truly means to help others thrive. This is one of those conversations that reminds you why the winding road is almost always worth it. Here's what we cover: ✅ How Michelle went from law and education to founding Collier Connects ✅ What personal and professional development coaching actually looks like in practice ✅ How 9/11 shaped her career trajectory in ways she couldn't have predicted ✅ Teaching in alternative education: the challenges, the rewards, and the lessons ✅ What nonprofit leadership during COVID really looked like on the inside ✅ Why organizations that invest in employee coaching see better outcomes ✅ How health challenges forced her to reflect on identity and what matters most ✅ Why a growth mindset isn't optional ✅ What it means to listen to your inner voice when making big career decisions My favorite line from this episode: "It was always about the why." That's the through-line for Michelle's entire journey…and it might be for yours too. 🔗 CONNECT WITH MICHELLE: 🌐 Collier Connects: https://collierconnects.com/ 📲: https://www.instagram.com/collierconnects 👔: https://www.linkedin.com/company/collier-connects-llc 📲 Follow me on Instagram: @iconoclast_innovations_llc ⏱️ CHAPTERS: 00:00 Introduction to Michelle Collier and Collier Connects 03:00 Personal and Professional Development Explained 06:02 Navigating Life Changes and Identity 08:59 The Impact of 9/11 on Career Choices 12:01 Transitioning to Education and Leadership Roles 15:02 Challenges of Nonprofit Leadership During COVID-19 18:01 Overcoming Personal Health Challenges 21:02 Finding Purpose and Helping Others Thrive 🔑 KEYWORDS: personal development coaching, professional development, leadership coaching, growth mindset, career transition, nonprofit leadership, life changes and identity, Iconoclasting podcast, women in leadership

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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
    19
  • Rating
    Explicit
  • Copyright
    © 2026 Sarah Smith
  • Show Website
    Iconoclasting