In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Jerry, an entrepreneur who has built, bought, and sold over a dozen businesses, generating more than $450 million in revenue.

Jerry shares his journey from growing up in extreme poverty as one of nine children to building a life and career from nothing no degree, no safety net, and no shortcuts. Through it all, he built a mindset grounded in one powerful principle: total ownership of your life and outcomes.

This conversation goes beyond business. It’s about resilience, discipline, and rethinking what real success looks like.

We dive into why taking responsibility changes everything, how early life shapes long-term outcomes, and why a lot of popular business advice misses the mark. Jerry also opens up about imposter syndrome, leadership, and the reality behind building and sustaining success.

We also explore:

- Why responsibility is a superpower in business and life

- How adversity can shape your advantage

- Why “perfect” business personas are a myth

- Why common sense often beats formal education

- What most leadership advice gets wrong

- How to grow without losing yourself

This is a conversation about mindset, ownership, and what it really takes to build something meaningful.

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Website: https://www.kimmillerhershon.com
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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Michael Black, founder and CEO of Success Tutoring, one of Australia’s fastest-growing education franchises, and author of the bestselling book Millionaire Tutor.

Michael shares his journey from starting a tutoring business in a spare room as a teenager to building a global education brand with over 100 locations across multiple countries, all before the age of 30. Now expanding into the United States, his story challenges many assumptions about age, experience, and what it really takes to succeed in business.

Along the way, Michael realized that some of the most common advice entrepreneurs hear, like chasing “work-life balance” or diversifying too early, can actually slow growth. Instead, he built his success by focusing deeply on one thing, reinvesting consistently, and committing fully to a single vision without a backup plan.

We talk about what it means to build a business early in life, how to stay focused in the face of endless opportunities, and why execution matters more than perfection.

We explore:

Why work-life integration may matter more than work-life balance
The case for specialization before diversification
Why perfection can delay progress—and what to do instead
How reinvesting in your business fuels long-term growth
The reality of imposter syndrome at every stage of success
Why action, not just mindset, is the key to creating “luck.”

Michael also shares honest insights about navigating uncertainty as a young founder, from negotiating his first commercial lease to hiring his first team, and how pushing through discomfort helped him grow into his role as a leader.

This conversation is a reminder that success doesn’t come from having everything figured out—it comes from taking action, staying committed, and being willing to learn as you go.

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In this milestone episode of Unconventional Wisdom About Conventional Wisdom, I’m celebrating a moment that feels both exciting and a little surreal—Episode 50.

In less than a year, this podcast has grown into a space where leadership clichés come to retire and honest conversations about growth, business, and being human can actually take center stage. And while a podcast might look like a solo act from the outside, this episode is a reminder that it never really is.

This special episode is a pause—a moment to celebrate the guests, the listeners, and the behind-the-scenes team who have helped shape the conversations that make this show what it is today.

Along the way, I share a few reflections on what 50 episodes of challenging conventional thinking has taught me about leadership, growth, and the systems we often feel pressured to succeed within.

We explore:

Why conventional wisdom isn’t always wrong—but often incomplete
How questioning leadership “rules” can lead to better outcomes
The importance of honesty and vulnerability in real leadership conversations
Why many capable people struggle inside systems that weren’t designed for them
How curiosity and courage create space for better thinking
The power of community in building meaningful conversations

This episode is also a heartfelt thank-you to the incredible guests who brought their expertise and honesty to the show, the listeners who continue to share and support these conversations, and the production team who make sure each episode actually makes it from idea to published podcast.

Reaching 50 episodes isn’t just a milestone—it’s proof that people are hungry for conversations that go beyond motivational clichés and surface-level leadership advice.

If this podcast has helped you think differently, lead differently, or question the “shoulds” that shape the way we work and lead, consider sharing this episode with someone who might need the same reminder.

Because fresh thinking isn’t a one-time event—it’s a practice.

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Website: https://www.kimmillerhershon.com

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/kmillerhershon

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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Diane Wheeler, founder and CEO of Home Hub AI, a tech startup building an ecosystem that helps homeowners track, protect, and grow the value of their homes.

After spending more than 25 years in banking, Diane took an unexpected turn into entrepreneurship when she realized how little support homeowners receive after purchasing a home. Inspired by her own experience buying a house and feeling “ghosted” once the transaction was complete, she set out to build a smarter solution, one that puts the homeowner at the center.

The result is Home Hub AI, an app designed to help homeowners organize documents, track maintenance, receive reminders, and make better decisions about their homes. With the help of an AI assistant named Val, the platform turns what can often feel like guesswork into a clear, organized system for managing one of the biggest investments people make.

You can find the Home Hub AI app on the App Store, and Diane shared a special offer for listeners. If you download the app and message her to let her know you came from the podcast, she’ll give you a special deal.

Along the way, Diane discovered that many of the traditional assumptions about technology founders, like needing to be a coder or technical expert, simply aren’t true. Instead, her strength lies in understanding real problems and designing solutions around the people experiencing them.

We explore:

• Why you don’t have to be a technical expert to build a tech company
• How traditional corporate hierarchy can slow innovation and decision-making
• The importance of designing solutions around real customer problems
• Why working smarter, not longer, often produces better results
• How creativity and downtime can actually improve productivity
• What it means to lead with trust rather than control

Diane also shares candid insights about imposter syndrome, navigating gender bias in both banking and tech, and learning to trust her voice as a founder. Her journey is a powerful example of how innovation often comes from asking simple questions and refusing to accept that “this is just how things are done.”

This conversation is a reminder that entrepreneurship isn’t reserved for technical experts or Silicon Valley insiders. Sometimes the most meaningful innovation comes from someone who sees a problem clearly and has the courage to solve it.

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Website: https://www.kimmillerhershon.com

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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Tori Barker, founder of Creative Marketing, a digital marketing agency focused on helping coaches, consultants, and entrepreneurs increase their visibility and grow their businesses.

Tori shares her journey from spending 15 years in corporate marketing to accidentally becoming an entrepreneur in 2019. What started as freelance work quickly evolved into a full-fledged agency built around helping “best-kept secret” business owners become seen, heard, and recognized in their industries.

Along the way, Tori realized that many of the beliefs she carried from her corporate career—like the idea that simply working hard will lead to recognition and advancement—didn’t always hold true. Instead, she discovered that success often requires adaptability, visibility, and the willingness to rethink long-held assumptions about work and leadership.

We talk about how shifting perspective, challenging internal narratives, and embracing growth can transform both business and personal confidence.

We explore:

- Why hard work alone doesn’t always lead to recognition
- How perspective shapes what we believe is “hard” in business
- The reality of imposter syndrome—even after years of experience
- Why leadership works better when you individualize how you work with people
- The dangers of micromanaging and becoming the bottleneck in your own company
- How slowing down can actually create more clarity and better decision-making

Tori also shares how changing the way she starts her day—moving away from the constant urgency of email and task lists—helped her show up more intentionally as a business owner and leader. By giving herself time to pause, reflect, and reconnect with her purpose, she found a healthier and more effective way to grow her business.

This conversation is a reminder that entrepreneurship isn’t about following someone else’s formula for success. Sometimes the most powerful shift is simply giving yourself permission to slow down, trust your experience, and build a business that works for you.

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Website: https://www.kimmillerhershon.com

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/kmillerhershon

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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Evelyn Ackah, founder of Ackah Business Immigration Law, a cross-border immigration law firm supporting professionals and businesses across Canada and the United States.

Evelyn shares her journey from starting her legal career at major firms in Toronto to building her own practice while adopting twins as a single parent. What began as a need for flexibility turned into a thriving firm focused on helping people and businesses grow beyond borders through compassionate, proactive immigration support.

Along the way, Evelyn realized that much of the conventional advice she heard early in her career like keeping your head down and working endless hours wasn’t the path to the kind of leadership or life she wanted. Instead, she built success through relationships, visibility, and embracing what made her different.

We talk about how redefining success helped her grow a firm of nearly twenty people across multiple countries while staying grounded in authenticity and service.

We explore:

- Why working harder isn’t always the key to success
- How building relationships can matter more than long hours
- The pressure many leaders feel to appear perfect
- Why vulnerability can strengthen leadership and team culture
- How personal growth directly impacts business success
- The importance of creating a workplace where people feel supported

Evelyn also shares how her perspective on leadership has evolved over the past 15 years from trying to be the “perfect boss” to embracing authenticity, openness, and trust. Her story is a powerful reminder that leadership isn’t about fitting into someone else’s mold. It’s about creating an environment where people can do their best work while still being fully human.

This conversation is a thoughtful look at what it really takes to lead a successful business while staying aligned with your values and the life you want to build.

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Website: https://www.kimmillerhershon.com

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/kmillerhershon

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Evelyn's Social Links:

Website: https://www.ackahlaw.com

LinkedIn: https://www.linkedin.com/company/ackah-business-immigration-law/

Youtube: https://www.youtube.com/channel/UCw7M2pQKwsRteq-nThuaELQ

Facebook: https://www.facebook.com/AckahBusinessImmigrationLaw/

Instagram: https://www.instagram.com/ackahlaw/

X: https://twitter.com/Ackahlaw/

TikTok: https://www.tiktok.com/@evelynackahlawyer

Apple Podcasts: https://podcasts.apple.com/us/podcast/ask-canada-immigration-lawyer-evelyn-ackah/id1461504289

#podcast #leadership #businessgrowth #unconventionalwisdom #personaldevelopment #UnconventionalWisdomAboutConventionalWisdomPodcast

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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Maitjian Welke, founder and co-owner of CMI Solutions, a Silicon Valley based managed IT services and cybersecurity company she founded in 2008.

Maitjian shares her journey from growing up in Indonesia to becoming a software engineer in Silicon Valley, leading global engineering teams at companies like IBM, Cisco, and VMware, and eventually building her own business alongside her husband. Along the way, she learned that some of the most common business advice, like “you must be a natural salesperson to succeed,” simply wasn’t true for her.

Instead, Majun built her company by leaning into her real strength: solving problems and helping people. We talk about why trying to fit into someone else’s leadership mold can backfire, and how staying authentic can lead to stronger teams, better decisions, and more sustainable growth.

We explore:

- Why networking doesn’t have to mean working the room

- How focusing on service can outperform chasing revenue

- The difference between optics and real leadership

- Why accuracy and overthinking can slow decision-making

- How imposter syndrome shows up even after success

- What it takes to lead without losing yourself

Maitjian also shares how cybersecurity and AI are reshaping small businesses, why education and prevention matter more than panic, and what leaders need to understand about protecting their organizations in an increasingly digital world.

This conversation is a reminder that leadership isn’t about following someone else’s formula; it’s about knowing your strengths, listening to your instincts, and building a business that reflects your values.

Connect with me here: Website: https://www.kimmillerhershon.com
Connect with me on LinkedIn: /kmillerhershon
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#podcast #businessgrowth #unconventionalwisdom #personaldevelopment #businesscoaching

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In this episode of Unconventional Wisdom About Conventional Wisdom, I sit down with Arash Shokouh, founder and managing principal of Off Tech, a managed IT services company supporting small businesses across the West Coast.

Arash shares how cybersecurity has become one of the most urgent priorities for modern businesses and why “zero trust” is no longer optional. From business email compromise to AI-powered scams, we talk about how threats are evolving and what leaders can do to protect their organizations without becoming paranoid or frozen by fear.

But this conversation goes far beyond technology.

Arash opens up about leaving corporate life after watching his division disappear overnight, what it was like to start a business with no revenue, and how persistence — not perfection — helped him build a team of eight and a thriving company culture.

We explore:

- Why writing a business plan can be less useful than talking to real people

- How networking is really a crash course in learning how to sell

- The hidden cost of saying yes to the wrong clients

- Why leading from the front matters more than delegating too fast

- How imposter syndrome is something you move through, not around

- The systems and habits that help leaders stay organized in a noisy world

Arash also challenges the idea that “the customer is always right,” arguing instead that the right customers are the ones who fit your values, your culture, and the way you want to grow.

This episode is a reminder that leadership isn’t about avoiding problems; it’s about building the confidence to face them, learning from them, and choosing progress over panic.

Connect with me here:
Website: https://www.kimmillerhershon.com
Connect with me on Linkedin: / kmillerhershon
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