Scaling Up Business with Bill Gallagher

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 c...

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 strategi...

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 ...

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 fam...

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.

Topi...

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, t...

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 Runni...

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 h...

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 strate...

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 busine...

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. T...

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 ...

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 susta...

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 ques...

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 harde...

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 ...

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 e...

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 wha...

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 ...