Insight Out : Big Ideas for the Modern Entrepreneur
Every successful business journey begins with an insight—an idea, a unique approach, or an innovative solution. Insight Out explores these internal revelations and how they’ve been turned outward into actionable strategies, systems, and results. Through intimate conversations with elite business leaders, founders, and entrepreneurs, we unravel the insights that have driven their success and learn how they’ve transformed these insights into extraordinary business outcomes.
Episodes
May 1, 2026 • 65 mins
What if the janitor in your building knows more about your business than your CEO? What if the person you overlook the most holds the exact insight that could save your company millions?
And what if the only reason you have not heard it is because no one ever thought to ask?
According to sociologist Gary David, that is not a hypothetical but a pattern. In every organization, the people at the lowest point of the org chart often h...
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April 18, 2026 • 57 mins
Have you ever opened a package so beautiful you hesitated to even throw it away, or felt like it Have you ever bought something and immediately felt like the packaging itself changed how valuable it seemed? Like before you even used the product, your perception was already different?
That’s something Jason Wong talks about a lot. He’s the founder of Paking Duck, and he’s also built and scaled multiple product businesses before mov...
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Is your company optimizing for the wrong kind of success? Almost 90 percent of companies are focused on short term efficiency metrics when the real winners are playing a long term profitability game. The scary part is your numbers can look better than ever while your business is actually getting weaker.
In this episode of Insight Out, I sit down with Nicolas Darveau-Garneau, growth strategist, former Google Chief Evangelist, and a...
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March 6, 2026 • 68 mins
Investors spend 90 seconds on your pitch deck. Most founders waste the first 30. So how do you grab their attention fast? And what separates the startups that raise millions from the ones investors dismiss in the first 30 seconds?
In this episode of Insight Out, I sit down with Carl Fudge, founder of Presentation Mode, to break down the anatomy of pitch decks that raise capital. Carl combines psychology, strategy, and design, draw...
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February 20, 2026 • 61 mins
What does it take to build a global company that loses money for 23 of its first 25 years and still impacts tens of millions of lives?
In this episode of Insight Out, I sit down with Kurt Avery, founder of Sawyer Products, to explore the 40-year journey from a French snake bite kit to a global leader in water filtration and insect repellent. Sawyer has changed tens of millions of lives while giving away over 90% of its profits to ...
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February 13, 2026 • 58 mins
Did you know that toxic work environments are draining the global economy by a staggering $9 trillion every year? That’s the price tag of showing up to work and checking out emotionally.
My guest today, Phil Johnson, founder of the Master of Business Leadership Academy, joins me to explore why emotional intelligence (EQ) is more critical than ever, not just for us, but for the next generation. Phil explains why our kids will suffe...
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February 6, 2026 • 50 mins
In this episode of Insight Out, we sit down with Julie Colombino, the founder of Deme, a fair-trade fashion brand that creates living-wage jobs in Haiti. Julie shares her remarkable journey from providing immediate disaster relief after the 2010 earthquake to creating sustainable economic opportunities for the Haitian community.
Julie recounts the pivotal moment when a Haitian woman told her, "I don’t want water; I need a job," an...
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January 31, 2026 • 24 mins
What makes creators like Philip DeFranco so irresistible to audiences? Why do millions keep coming back to his content day after day? And what is he doing right that most creators completely miss?
In this episode of Insight Out, I sit down with Cat Shanu to break down exactly what draws viewers in and keeps them coming back. Using Philip DeFranco as a case study, we explore the habits, strategies, and small choices that build tru...
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January 16, 2026 • 50 mins
Brendan Kane is a New York Times bestselling author and one of the most influential minds of our time. He is the author of 1 Million Followers and Hook Point. He has helped the largest brands and celebrities in the world reverse engineer how to make content go viral.
In this episode, Brendan joins me to talk about what it takes to make content go viral. Brendan discusses how the world of content creation has changed in the last 2...
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January 2, 2026 • 54 mins
Disruption is everywhere. AI, careers, leadership, nothing stays the same. My guest today, Patrick Leddin, a leadership expert, former Army captain, and Vanderbilt professor, encountered that reality in a powerful way while sitting in a classroom listening to James Patterson share a deeply personal story. After losing his fiancée to cancer, Patterson transformed profound loss into a platform for impact. That moment reshaped Patrick...
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December 26, 2025 • 54 mins
If you’re in the creative space, you already know this tension: the pressure to create never really shuts off. Content still needs to go out, even when your ideas dry up. So what happens when your mind stalls? How do you get unstuck without forcing it or burning out and still create ideas your audience actually cares about when life is full and inspiration feels miles away?
In this episode, I sit down with Cat Shanu to tackle thos...
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December 12, 2025 • 62 mins
Are you feeling stuck in life, like a pumpkin in a jar? You’re not alone. Many people suffer from a “mistaken identity”, not realizing their true potential or the power of their own dreams. This week on Insight Out, Doug Dane is here to show us how to use the Mistaken Identity Model to get self-discovery, freedom, and success. He's been able to beat the odds and find success in his own life, despite the trauma of physical, emotiona...
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December 5, 2025 • 49 mins
Just like every great recipe, captivating communication requires some spice! And who better to teach us that than world-renowned communication and public speaking expert, David JP Phillips?
David has spent his career researching and building a business on the art of communication and presentation, but his expertise goes beyond these practical skills that allow us to succeed in professional settings. He’s also dedicated to helping...
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November 28, 2025 • 47 mins
What keeps a digital business moving and thriving, and what makes it truly valuable?
Blake Hutchison, CEO of Flippa, is joining me on this episode of Insight Out to break down his role at Flippa, his experience over the last 20 years, and the variables that influence the value of businesses in the market. He touches on the importance of looking at growth, average order value, refund rate, cost base, etc., when evaluating how much...
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November 21, 2025 • 63 mins
After starting as a barista in 1996 to becoming the co-founder, owner, and Co-CEO of Biggby Coffee, this week’s guest on Insight Out is Mike McFall, a growth-minded entrepreneur that believes in the power of self-awareness, positivity, and conscious capitalism as the core values of a successful business.
His book, Grind: A No-Bullshit Approach to Take Your Business from Concept to Cash Flow, focuses on the importance of revenue a...
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November 7, 2025 • 59 mins
In this episode, Will shared his experience and how the far-reaching consequences of trivial acts, and self-awareness have shaped his goals and mindset. and the positive effects of not being afraid to do crazy things.
Will is an avid learner and has earned certifications as a Stockbroker, Flight Instructor, Certified Product Manager, Technical Trainer, Commercial Pilot, Microsoft Certified Systems Engineer, Cisco Certified Netwo...
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October 24, 2025 • 49 mins
How can we shift our thinking in order to break a pattern? And how can we take positive action to make transformative changes in our lives?
That’s the focus of Scott Miller’s new book, “Master Mentors Vol. 2.” It examines key insights from 30 of the world’s most transformational leadership thinkers – including Seth Godin, Susan Cain, General Stanley McChrystal and more – and provides simple steps to implement the same insights in ...
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October 18, 2025 • 57 mins
Who do you look up to the most? Is it a superhero from a comic book, a famous athlete, or a historical figure? We often forget the everyday heroes who quietly make a big impact on our lives. Our dads, the real-life heroes in our families, shape who we become, teach us important values, and help us navigate life's twists and turns.
In today’s episode of the Insight Out podcast, I have the pleasure of having a conversation with Paul...
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October 10, 2025 • 77 mins
George J. Chanos is a lawyer and a former attorney general with both eyes on the future. His foresight led him to write the books Seize Your Destiny: A Roadmap to Success and Millennial Samurai: A Mindset for the 21st Century.
However, creating thought-provoking books isn’t his only talent. George has recently been hard at work on an NFT art project called People Reign.
In this episode, George shared his predictions for the futu...
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October 3, 2025 • 64 mins
This isn’t your typical family business story.
Bobby started in finance, swore he’d never work with family, then life forced a pivot. Stepping in reluctantly, he helped scale the business to 40 locations and $50M, but success came at a cost: resentment, burnout, and the realization that growth without alignment is a trap.
So, he walked away.
Bobby went on to build Greenridge Wealth, a firm built on values, systems, and a team-fi...
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