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PODCAST

Scaling Up Business with Bill Gallagher

Do you dream of an easier way to scale and grow your business? Do you wish you didn’t have to work so hard and put in as many hours? Do you find growth too slow, or hard to sustain? This podcast—Scaling Up Business with Bill Gallagher—can help you achieve and maintain the growth you want. A message from your host: “I’ve been in your shoes as a founder, CEO, and executive leader. I’ve coached and trained many leaders just like you over more than 15 years to grow their businesses successfully and

business entrepreneurship

All Episodes

12:09

The Importance of Getting Away

Scaling Up Business with Bill Gallagher ·

2025/08/27

What if stepping away from your business is the most productive move you could make?In this solo episode, Bill Gallagher explores the strategic importance of taking time away from the business in order to work on the business. Drawing from his own experiences and the breakthroughs of top leaders. Topics explored in this episode:(02:03) The Brain Needs a Break*Breakthroughs happen after breaks.*Stories from clients who saw massive clarity after they stopped grinding.(03:42) Executing vs

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47:51

Buying, Flipping, and Exiting Businesses with Matt Raad

Scaling Up Business with Bill Gallagher ·

2025/08/20

Should You Build a Business from Scratch or Buy One that’s Already Working?In this episode, Bill sits down with Matt Raad, founder of the eBusiness Institute and veteran business buyer, to explore the world of digital acquisition, business turnarounds, and intentional exits. From a humble start in zoology and manufacturing to flipping multi-million dollar websites, Matt’s journey highlights how you can build wealth through strategic business acquisitions.Topics explored in this episode:(07:00)

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12:52

Too Busy or Not Busy Enough?

Scaling Up Business with Bill Gallagher ·

2025/08/13

Everyone’s busy but are you TOO busy?In this solo episode, Bill digs into a leadership trap many fall into: staying chronically busy as a way to avoid real obligations. Extreme busyness often masks poor delegation, insecure leadership, and personal habits that chip away at both your business and your health. Through real stories from his executive coaching work, Bill unpacks what good busy actually looks like, and what needs to shift if you want to lead strategically instead of reactively.Topics

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48:35

Legacy, Loss, and Living With Passion with Elliott...

Scaling Up Business with Bill Gallagher ·

2025/08/06

What really matters at the end of your life, and how do you make sure you’re living meaningfully now?In this episode, Bill sits down with Elliott Kallen, founder and CEO of Prosperity Financial Group and co-founder of A Brighter Day charity, to talk about building a meaningful legacy, the lessons that come from deep personal tragedy, and how to live with passion in both business and life. From preventing teen suicide to guiding families through financial and life planning, Elliott’s story is one of

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11:01

Strong Teams Don’t Need to Be Rescued

Scaling Up Business with Bill Gallagher ·

2025/07/30

What if being Superman is the very thing holding your business back?In this solo pod, Bill challenges a very common leadership trap: always being the one to save the day. He shares stories from clients, and his own career, about the hidden costs of hero-style leadership, and lays out a better path forward: building a team that doesn’t need rescuing. This is about self-awareness, systems, and stepping back so others can step up.Topics explored in this episode:(01:38) Let Go to Grow Up*Why real

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50:11

How to Build a Team of All A-Players with Rick Crossland

Scaling Up Business with Bill Gallagher ·

2025/07/23

What if 90% of your team were high-performers, and your revenue tripled?In this episode, Bill is joined by Rick Crossland to break down what it really takes to build a high-performance team. Rick shares his system for recruiting, coaching, and retaining A players who consistently outperform their peers and elevate your entire organization. From hiring secrets to accountability culture to a powerful new tool for talent evaluation, this conversation is packed with ways to truly cultivate an

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10:54

The Real Reason You Can’t Let Go and Delegate

Scaling Up Business with Bill Gallagher ·

2025/07/16

Why can’t you let go…even when you know you should?In this episode, Bill unpacks the emotional reason behind why you struggle to delegate or release control. Through sharing a personal story and a powerful CEO coaching insight, he reveals how early fears sneak into your leadership style and why confronting them is the key to unlocking trust, innovation, and real team growth.Topics explored in this episode:(0:15) What’s Really Running the Show?*It’s not strategy, it’s your fear.(1:20) When the Bank

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46:17

The Money Habit with Mike Michalowicz

Scaling Up Business with Bill Gallagher ·

2025/07/09

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

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11:04

Build a Business That Runs Without You

Scaling Up Business with Bill Gallagher ·

2025/07/02

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

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53:28

Becoming the Celebrity CEO With Ramon Ray

Scaling Up Business with Bill Gallagher ·

2025/06/25

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

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07:01

Easy Isn’t Lazy: Simplicity Is the Ultimate...

Scaling Up Business with Bill Gallagher ·

2025/06/18

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

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50:54

Cultivate Valuable In-Person Meetings and Events with...

Scaling Up Business with Bill Gallagher ·

2025/06/11

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,

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11:25

The Hustle Culture Mousetrap: More Isn’t Better

Scaling Up Business with Bill Gallagher ·

2025/06/04

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

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47:16

Unlocking Curiosity at Work with Dr. Diane Hamilton

Scaling Up Business with Bill Gallagher ·

2025/05/28

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

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11:31

Can You Scale AND Have It All?

Scaling Up Business with Bill Gallagher ·

2025/05/21

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

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52:31

Design Yourself Out of the Business with Michael E....

Scaling Up Business with Bill Gallagher ·

2025/05/14

What if the most powerful move you could make as a founder is to stop being the one doing it all?Today’s episode explores the mindset shift that turns your business from a job into a scalable, valuable system. Bill is joined by legendary entrepreneur and author Michael E. Gerber to discuss why strategically working on the business, not in it, is the single most important shift a founder can make. From designing scripts to building systems that run without you, Michael shares what it truly means to

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11:36

Are You Addicted to Being Busy?

Scaling Up Business with Bill Gallagher ·

2025/05/07

What if your addiction to hustle is the very thing holding your business back?In this episode, Bill unpacks the hidden addiction that plagues so many leaders: the need to feel busy. He explores how overworking, micromanaging, and always being “on” isn’t just unsustainable, but also a failure of effective leadership. Bill shares powerful stories of CEOs who broke the cycle and built stronger teams by stepping back, letting go, and empowering others to rise up to the occasion.Topics explored in this

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47:49

Why Every CEO Needs a Personal “Why” with Ben Renshaw

Scaling Up Business with Bill Gallagher ·

2025/04/30

How can leaders connect their personal purpose with their company's mission?In today’s episode, Bill talks with leadership coach Ben Renshaw about the importance of discovering your personal why. They also discuss how aligning personal and company purposes can lead to more meaningful leadership and a positive work environment.Ben Renshaw is a former classical violinist turned leadership coach who’s all about helping people find what truly lights them up. He’s worked with top global brands and execs,

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11:11

What are the Hidden Costs of Overwork?

Scaling Up Business with Bill Gallagher ·

2025/04/23

What if your relentless hard work is actually costing your business more than it’s helping?In this episode, Bill explores the hidden costs of overwork, particularly when leaders confuse effort with effectiveness. He shares a cautionary tale of a CEO who pushed too hard, micromanaged excessively, and ultimately failed—highlighting how unchecked hustle undermines both personal well-being and team performance.Topics explored in this episode:(0:42) The Hidden Price of Hustle* Overwork has obvious

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44:09

Never Lead Alone with Keith Ferrazzi

Scaling Up Business with Bill Gallagher ·

2025/04/16

How can leaders create social contracts that foster true team accountability and shared success?In this episode, Bill and guest Keith Ferrazzi explore the importance of moving beyond traditional leadership towards a model of “teamship,” where teams hold themselves and each other accountable. Keith also shares insights about the power of vulnerability and candor, and practical exercises like the “stress test” to build high-performing teams.Keith Ferrazzi is a powerhouse thought leader and author

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139 results

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