Why does it feel so hard to actually keep the money we earn?

In this episode, Bill is joined by bestselling author and entrepreneur Mike Michalowicz to explore the deeper patterns that shape our financial behavior. Mike shares insights from his upcoming book, The Money Habit, and offers an honest take on the emotional and psychological traps that sabotage even the most high-achieving business leaders. This conversation will change how you think about money.

Mike Michalowicz is the author of Profit First, The Pumpkin Plan, and Clockwork. His work has helped thousands of entrepreneurs grow healthier businesses, and his latest book, The Money Habit, dives into the behavioral finance side of entrepreneurship.

Topics explored in this episode:

(08:15) Why Smart People Still Struggle with Money

• Success doesn’t always equal financial security.
• Cutting your spending isn’t really the solution.

(12:40) The Lies We Tell Ourselves

• We will always find new ways to spend our ‘new money’.
• Mike explains Parkinson’s Law.

(20:30) Building Financial Habits That Stick

• Tiny habits are more powerful than massive overhauls.
• Mike shares how to “friction-proof” your financial systems.

(27:10) Different Life Stages Require Different Levels of Planning

• There are seasons to making money and spending money.
• No one wants to miss out on fun moments with their family because they're busy in the ‘earning’ stage.

(37:40) Relying on Will Power Does Not Work

• Mike wanted to exercise regularly; how did he make that happen?
• With money, find your daily practical pattern and then tact on a money-related action item on top of it.

Thanks to Mike Michalowicz for being on the show!

Connect with Mike on LinkedIn: Linkedin.com/in/mikemichalowicz/

Learn more about his work: Mikemichalowicz.com/

Preorder The Money Habit here: Mikemichalowicz.com/the-money-habit/

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

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Could your business survive a month without you or would it collapse the minute you left?

In this episode, Bill shares a personal story about stepping away from his company for a month-long family trip to Italy—and what it took to make that possible. It’s not just about systems and scorecards (though those matter), but about shifting your leadership style and truly empowering your team. This isn’t a fantasy. It’s a leadership strategy that can dramatically improve your life and business.

Topics explored in this episode:

(00:26) The Real Question: Can You Leave?

*Taking a month off wasn’t convenient, but it was necessary—and Bill committed to making it happen.

(03:40) The Leadership Problem

*Even with systems in place, Bill realized he was still the bottleneck. His team couldn’t step up if he didn’t let go.

(04:29) Training the Team, Slowly and Steadily

*How he rewired his leadership by handing off responsibility and asking, “What will you do when I’m gone?”

(08:03) The Result: A Month in Italy

*His team performed beautifully during a critical growth phase. No fire drills. Just updates and momentum.

(09:30) Stop Being the Hero

*If you always need to save the day, you’ll always surround yourself with people who need saving.

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

Subscribe via Spotify: https://spoti.fi/3PGhWPJ

Subscribe via Apple Podcasts: https://apple.co/3PKe00u

Bill on Facebook: https://www.facebook.com/billgall/

Bill on Twitter/X: https://x.com/billgall

How do you grow your business and your reputation without faking it?

In this episode, Bill sits down with Ramon Ray, entrepreneur, speaker, and author, to explore how authentic visibility fuels business growth. From meeting the President to selling three companies and pivoting during a pandemic, Ramon shares real stories about showing up, adding value, and becoming your own best brand asset. Whether you're building your first business or reinventing your voice, Ramon offers a masterclass in connection, resilience, and personal branding that actually works.

Ramon Ray is a five-time entrepreneur, best-selling author, and global keynote speaker known for his infectious energy and deeply human approach to business. He’s the founder of ZoneofGenius.com and has interviewed everyone from President Obama to the founders of major brands. Ramon’s mission? To help entrepreneurs build not just successful businesses, but joyful lives.

Topics explored in this episode:

(08:10) Meeting the President

• Meeting the President wasn’t a fluke, it was the result of years of showing up and serving with integrity.
• Visibility follows value. Recognition happens when you're focused on impact, not status.

(18:00) Lessons from Selling Three Companies

• An exit doesn’t have to be massive to be meaningful. Even modest acquisitions can be life-changing if they align with your goals.
• Reinvention is part of the entrepreneurial cycle. Each sale opened new creative and professional doors.

(29:45) The Power of Personal Brand

• How do you become a ‘celebrity’ CEO? Ramon shares his take on visibility, trust, and being the brand without being fake.
• Brand is resilience. Ramon’s reputation and authenticity made it easier to pivot to new avenues because people already trusted him.

(39:10) Nobody Wants Boring

• It’s okay to tweak your content depending on your audience. The key is to stay engaging.
• Show up where you’re wanted. Look for strategic opportunities that align with your voice and values.

(45:40) Best Way to Build Your Unique Voice

• Use social media as a low-stakes way to develop and express your personal brand.
• Don’t hide behind the company logo, add to it with your personality.

Thanks to Ramon Ray for being on the show!

Connect with Ramon on LinkedIn: https://www.linkedin.com/in/ramonraysmallbiz/

Learn more about his work: ZoneofGenius.com

Get his book: The Celebrity CEO: How Entrepreneurs Can Thrive by Building a Community and a Strong Personal Brand - https://a.co/d/aeJ0eQm

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning,...

What if your obsession with “getting it right” is actually making everything harder?

In this short solo episode, Bill unpacks why leaders often resist simplicity, even when the evidence shows that simpler rhythms like daily huddles and weekly meetings drive better execution. He shares a cautionary tale of a team that struggled to implement Scaling Up habits because they were too focused on customizing and controlling every detail. The lesson? Stop overcomplicating. Embrace ease.

Topics explored in this episode:

(00:05) Easy Isn’t Lazy

*Why simplifying operations is a mark of strong leadership; not weakness or laziness.

(01:10) A Team That Overcomplicated Everything

*A client’s resistance to basic practices like daily huddles and weekly meetings derailed their growth.

(02:45) The Cost of Not Trusting the Process

*Each team member wanted to “get it right” their own way, which led to silos, stalled execution, and no progress on quarterly priorities.

(04:15) The Cure for Overthinking

*How great leaders build predictable rhythms and make execution feel frictionless.

(05:25) The Case for Easy

*From customer experience to vendor and team interactions, ease is the ultimate scaling advantage.

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

Subscribe via Spotify: https://spoti.fi/3PGhWPJ

Subscribe via Apple Podcasts: https://apple.co/3PKe00u

Bill on Facebook: https://www.facebook.com/billgall/

Bill on Twitter/X: https://x.com/billgall

What makes an in-person event truly unforgettable and value-packed for the attendees?

In this episode, Bill sits down with Eric Rozenberg to explore how the best companies use live meetings to create culture, drive alignment, and build momentum. Eric shares insights from producing events for Fortune 500 companies and global brands, and explains how thoughtful, strategic meetings aren’t a luxury, but a very important growth tool. If you're wondering whether to gather your team in person this year, this episode will help you make the call.

Eric Rozenberg is an international event strategist, author of Before It’s Too Late, and founder of Event Business Formula. With more than two decades of experience creating events across six continents, Eric teaches leaders how to design live experiences that actually move the needle.

Topics explored in this episode:

(06:00) The Real ROI of In-Person Events

• Why meetings and conferences aren’t just about the content.
• The power of shared physical space to build trust and alignment

(15:30) Avoiding the “Event as Expense” Mindset

• How to justify and structure meetings so they deliver real business value
• Time spent with the right people is where the true business magic happens

(25:00) From Tactical to Transformational

• What separates logistics-focused events from culture-shaping ones
• How to build events that fuel strategic clarity and team momentum

(32:00) Leading Through Live Experiences

• Why your leadership presence matters more in person
• Mindset over Mishaps: When there’s a will there’s a way
• When things go wrong, focus on creating memories

(37:45) The 7 Steps to a Successful Event

• Map out the main objectives with the client
• Then you craft the unique experience around these objectives

Thanks to Eric Rozenberg for being on the show!

Connect with Eric on LinkedIn:https://www.linkedin.com/in/ericrozenberg/

Learn more about his work:https://eventbusinessformula.com/

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

Subscribe via Spotify:

What if working harder is actually a lie that’s making your business worse?

In this episode, Bill shares a story of a billion-dollar company brought to its knees by a CEO who hustled too hard. What once starts as ambition can quickly turn into micromanagement and business confusion. Bill breaks down why hustle culture is a lie, what it’s really costing you, and how to shift out of this chaotic mode and into something much more sustainable.

Topics explored in this episode:

(0:15) The Billion-Dollar Crashout

*The story of an ad tech CEO who lost 90% of company value by trying to do everything.

*Why over-involvement, scattered priorities, and non-stop hustle backfired.

(3:50) The Myth of More ‘Hustle’

*Hustle culture is a lie!!!

(6:10) It’s Time to Shift Out of the Hustle

1. Get Clear: Define a breakthrough BHAG and long-term strategy.
2. Build the Culture: Hire well, clarify roles, coach continuously.
3. Execute Intentionally: Prioritize, track key metrics, and meet with rhythm.
4. Get a Life: Really make conscious time for what’s important to you.

(9:00) Integration Over Sacrifice

*It’s all connected: You bring your life into work, and work into life.

*Create a system that supports both.

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

Subscribe via Spotify: https://spoti.fi/3PGhWPJ

Subscribe via Apple Podcasts: https://apple.co/3PKe00u

Bill on Facebook: https://www.facebook.com/billgall/

Bill on Twitter/X: https://x.com/billgall

What’s really stopping your team from being more innovative, and how do you fix it?

In this episode, Bill is joined by Dr. Diane Hamilton, author of Cracking the Curiosity Code, to explore why curiosity, not just intelligence or skills, is the real key for innovation, engagement, and performance. Together, they dig into the hidden habits that stifle curiosity in leaders and teams, and how to cultivate a culture that asks better questions and solves better problems.

Dr. Diane Hamilton is a behavioral expert, researcher, and speaker whose groundbreaking work on curiosity has helped transform how companies approach culture, communication, and leadership. She’s the creator of the Curiosity Code Index and a leading voice on the future of work.

Topics explored in this episode:

(05:10) The Curiosity Crisis

*Why curiosity declines as we age

*How lack of curiosity hurts innovation at work

*The four fear-based factors that suppress curiosity: fear, assumptions, tech, and environment

(12:50) Formula 1 Efficiency vs. Hospital Mismanagement

*What happens when you bring in outside perspectives to improve your broken systems

*How far would people go to blindly follow rules?

(16:50) How Leaders Kill Curiosity

*Common leadership habits that discourage curiosity without realizing it

*The difference between curiosity and chaos: structure still matters

(31:30) Can Curiosity Be Measured?

*There is science behind measuring curiosity with the Curiosity Code Index

(35:10) Coaching Curiosity into Leadership

*Practical ways to coach and develop more curious thinking

*The link between curiosity and emotional intelligence

(40:50) The ROI of Curiosity

*Curiosity isn’t just nice to have, it brings in real revenue growth.

Thanks to Dr. Diane Hamilton for being on the show!

Connect with Diane on LinkedIn: https://www.linkedin.com/in/drdianehamilton

Learn more about her work: https://drdianehamilton.com

Get her book: Cracking the Curiosity Code – https://drdianehamilton.com/cracking-the-curiosity-code-book

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up...

What if scaling didn’t have to come at the cost of your health, your family, or your sanity?

In this episode, Bill challenges the common held belief that sacrifice is a rite of passage in entrepreneurship, especially during the growth phase. He shares the story of a tech CEO building a $200M company and outlines a four-part framework for scaling your business while also building a life you love. Spoiler: It's not about working harder. It's about rethinking your approach.

Topics explored in this episode:

(0:26) Can You Really Have It All?

*A thriving business and a healthy life are not mutually exclusive.

*The story of a CEO who’s grown a $200M company while staying balanced and grounded.

(2:30) Four Steps to Scale Better

1. Set a BHAG (Big Hairy Audacious Goal): Anchor your strategy in a long-term, purpose-driven outcome.
2. Invest in People & Culture: Hire well, coach continuously, and create strong values-based accountability.
3. Execute with Rhythm: Align priorities, metrics, and meetings to stay focused and effective.
4. Get a Life: Create time for family, health, and the things you love.

(7:50) You’re Not Supposed to Work 1,000x Harder

*The CEO of a billion-dollar company doesn’t work 1,000 times more than you, they have to work differently.

*Scaling means evolving how you lead, not just doing more.

(9:40) What’s The First Step?

*What do you need to redesign first?

*Who can help you shift your leadership style and strategy?

Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.

Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshop

Bill on LinkedIn: https://www.LinkedIn.com/in/BillGall

Bill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach

Visit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.

Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.

Subscribe via Spotify: https://spoti.fi/3PGhWPJ

Subscribe via Apple Podcasts: https://apple.co/3PKe00u

Bill on Facebook: https://www.facebook.com/billgall/

Bill on Twitter/X: https://x.com/billgall