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.

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

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

Connect with me on LinkedIn:
/kmillerhershon

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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.

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

Connect with me on LinkedIn:
/kmillerhershon

Subscribe to newsletter:
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