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

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

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

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

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

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

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

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

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

What does it actually look like to take your public health expertise and build a consulting business around it?

In this episode of Iconoclasting, I sit down with Alexandra (Allie) Piatkowski, founder and CEO of Piat Public Health, who made the leap from public health professional to entrepreneur, working across both Canada and the US. Allie breaks down the role data and project management play in driving real community health outcomes, how COVID-19 reshaped her career path, and why consulting was the answer for someone who needed variety, independence, and the freedom to think differently about health.

If you've ever wondered whether there's a non-traditional lane in public health or healthcare, this conversation will open your eyes to what's possible.

Here's what we cover:

Allie's journey from public health professional to founder and CEO of Hyatt Public Health

How data and project management intersect with community health work

The key differences between navigating public health in Canada vs. the US

How COVID-19 became a turning point in her career path

Why consulting offers the variety and independence traditional roles often can't

The social and societal factors that have an outsized impact on health outcomes

Practical advice for aspiring public health professionals exploring non-traditional paths

Allie's advice that stuck with me most: "Think outside the box and explore different pathways." In a field as broad and impactful as public health, that's not just encouragement — it's a strategy.

🔗 CONNECT WITH ALLIE:

🌐 Website: www.piatpublichealth.ca

💼 LinkedIn: https://www.linkedin.com/in/alliepiatkowski/

📲 Follow me on Instagram: @iconoclast_innovations

⏱️ CHAPTERS:

00:00 Introduction to Public Health Consulting

03:05 The Role of Data in Public Health

05:31 Navigating Different Healthcare Systems

07:27 The Impact of COVID-19 on Career Paths

10:00 Embracing Project Management in Public Health

10:48 Building a Consulting Business

16:36 Advice for Aspiring Public Health Professionals

🔑 KEYWORDS: public health consulting, public health entrepreneurship, community health, data in public health, project management in healthcare, MPH careers, healthcare innovation, non-traditional career paths, Iconoclasting podcast