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 profitably. But more than that, I’ve helped give them their time and sanity back. My core strength is making the growth process easier, faster, and way more fun.” A dynamic thought leader, Bill talks with fascinating and brilliant guests each week, including visionary CEOs, trailblazing entrepreneurs, best-selling authors, renowned business strategists, and more. Broadly, each episode focuses on one of the four major decision areas every entrepreneur and company must get right: People, Strategy, Execution, and Cash. More specifically, the show explores topics such as: * Business Growth & Scaling. * Customer Experience & Marketing. * Innovation & Differentiation. * Leadership Development. * Delegation & Accountability. * Vision & Strategy. * Team Dynamics. * Hiring & Talent Management. * Company Culture. * Employee Engagement. * Crisis Management. * Effective Communication. * Influence & Persuasion. * Business Strategies. Running a business is ultimately about freedom. Subscribe to this podcast to learn how leaders like you can get your organizations moving in sync, create something significant, and still enjoy the ride. Subscribe if you want to elevate your business to unprecedented heights by tuning in to a masterclass in business excellence. For information on Bill Gallagher’s coaching and training programs, and Scaling Up Workshops, visit www.ScalingCoach.com
Episodes
What would your future self thank you for starting today?
In this solo episode, Bill walks you through his personal strategy for designing a fulfilling and productive year before the new year hits. He shares how carving out time between Thanksgiving and mid-December creates the perfect window to slow down, reflect, and set intentional direction for the coming year.
Topics explored in this episode:
(01:00) Create Space Before the N...
How do you run a year-end strategy offsite that’s focused, fun, and actually gets results
In this episode, Bill is joined by strategic advisor Dan Clifford to walk you through how to plan and execute a high-impact annual strategy session offsite. From pre-planning to post-event execution, Dan shares his years of business knowledge with the audience today. Whether you’re a founder, CEO, or senior leader, this conversation will help y...
What if chasing “having it all” is exactly what’s making you miserable?
In this episode, Bill challenges what “having it all” means and explores what actually creates sustainable happiness for high-performing leaders. He shares moments from when he had money, success, and recognition, but still felt empty, and explains why joy often comes from subtraction of things.
Topics explored in this episode:
(03:40) Success Without Jo...
What does it really mean for people to feel like they matter in the workplace?
In this episode, Zach Mercurio unpacks why mattering is the missing piece in most workplace cultures and how leaders can foster it. He also explores how a sense of value and contribution drives engagement, innovation, and retention.
Zach is on a mission to make work and life more meaningful. As an author, researcher, and speaker, he helps leaders cre...
Are you planning time off or avoiding the truth about your team?
In this solo episode, Bill explores how the holiday season acts as a diagnostic tool for your business. Are you building a company that thrives without you or one that collapses the second you unplug? He shares why most founders avoid taking time off and how strategically stepping away can highlight leadership gaps, capacity issues, and trust breakdowns. If you're feel...
What does it really take to lead powerfully and why does knowing yourself matter more than sounding confident?
In this episode, Bill sits down with Susan Power, Founder and CEO of PowerUp Leadership, for a conversation about what it takes to lead well in today’s world. Susan shares her personal evolution as a leader, from trying to “do it all” to embracing emotional intelligence, slowing down, and showing up as her full self.
The...
What do you do when everything feels like it's falling apart?
In this solo episode, Bill explores why “feeling groovy” isn’t just a quirky phrase; it’s a powerful tool for high-performing CEOs. Drawing inspiration from Simon & Garfunkel’s 59th Street Bridge Song, Bill breaks down the connection between presence, creativity, luck, and leadership effectiveness.
Topics explored in this episode:
(01:15) Why CEOs Need to Feel Groovy
*Wh...
What happens when the hardest workers on your team start burning out?
In this episode, Bill is joined by Paul Austin-Menear for a conversation about the unseen toll of hustle culture on your team, your operations, and your long-term performance. Together, they explore the red flags leaders often miss, from rising sick days to unchecked overachievement, and offer practical ways to build smarter, more resilient companies. You’ll hear ...
What do you do when everything feels like it's falling apart?
In this solo episode, Bill talks openly about when things just don’t go according to plan. When life hits harder than expected, and when the most reliable tools seem to stop working, there are still ways out of it. He reflects on his recent client experience and how he coaches his clients out of hardship and being stuck.
Topics explored in this episode:
(03:45...
What if the real reason you’re not closing deals has nothing to do with your leads and everything to do with your process?
In this episode, Sean Samson breaks down the myths around what makes someone great at sales, and why most people fail. Sean shares how he went from average to top 1% by mastering the process, not his ‘sales’ personality. He reveals why decent leads don’t matter if your close rate is broken, how to adjust pricing...
What if real leadership isn’t about being louder, but about being more present?
In this solo episode, Bill Gallagher explores a different lens on leadership: mindful power. Instead of dominating a room with volume or charisma, Bill shares how the most effective CEOs lead through presence, clarity, and intention.
Topics explored in this episode:
(00:00) Power Isn’t Loud
*Real power doesn’t come from dominating the room.
*Before performan...
What would change in your business if you built it to support people; not just profits?
In this episode, Dean Mathews joins Bill to share how solving one simple, overlooked problem turned into a business serving over 200,000 users a month. As the founder of OnTheClock, Dean opens up about the early scrappy days, how he learned to build a team-first company from the ground up, and why fast learning was his biggest edge. He also refle...
What if your schedule isn’t the problem, but the way you’re living it is?
In this solo episode, Bill Gallagher explores the energizing trifecta of Purpose, Power, and Play, and how aligning with all three can transform your leadership, reduce stress, and make even the busiest weeks feel fulfilling.
Topics explored in this episode:
(1:20) What is Your Purpose?
*What’s the most important thing you want people to say about...
How Do You Rebuild After Everything Crashes Down?
In this episode, Mike Chaput joins Bill to share the raw, unfiltered story of what it really takes to recover from business failure. From filing bankruptcy just six months after his son was born to eventually building a stable, resilient business, Mike opens up about the toll stress took on his health, the importance of strong relationships, and how every step forward came from embra...
What if your exit plan never arrives?
Most founders treat their exit like a far-off dream; something they’ll figure out someday. But that vague timeline sabotages your team, your business, and your freedom. In this solo episode, Bill breaks down the real cost of waiting too long to plan your exit.
Topics explored in this episode:
(0:25) The Exit Date is Uncertain
*Time creeps up on you faster than you think.
*One day, you’ll reali...
What Can You Learn About Scaling from the Very Early Days of Amazon?
In this episode, Bill sits down with John Rossman, former Amazon executive, author, and expert in leadership strategy, to uncover the secrets behind Amazon’s remarkable scalability. From launching the Amazon Marketplace in 2002 to writing The Amazon Way, John shares leadership lessons and operational principles that any business can adopt. This conversation is a ma...
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...
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