Scaling Up Business with Bill Gallagher

Bill Gallagher
  • 4.8 (77)
  • Entrepreneurship
  • Updated Biweekly

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

  1. The Only Tailwind Is AI — Inside the CEO Business Barometer, with Paul Witkay

    1d ago

    The Only Tailwind Is AI — Inside the CEO Business Barometer, with Paul Witkay

    CEOs are calmer about the world — and twice as worried about their own companies. Paul Witkay has been sitting in confidential rooms with chief executives through every cycle since the dot-com era. He’s the founder of the Alliance of Chief Executives and publishes a quarterly Business Barometer that tracks what CEOs are actually thinking across industries and around the world. In this conversation with Bill Gallagher, Paul walks through four quarters of data — and the picture is striking. After eighteen months of uncertainty that left CEOs frozen like deer in headlights, the mood shifted to action. Not because they found answers, but because they couldn’t afford to stay frozen. And sixteen times more respondents now say that twelve months from now, things will be even more unpredictable than today. Unpredictability isn’t a phase — it’s the new constant. They dig into the inside-outside paradox, where CEOs are getting less negative about the global economy but more pessimistic about their own businesses. Paul shares the AI data — the only indicator that showed as a tailwind in a sea of headwinds. Sixty-one percent of CEOs are now building AI agents in-house, fifty percent have AI mandates, and the job numbers surprised everyone: twenty-nine percent are adding staff because of AI while only twelve percent are cutting. Bill shares how AI runs through every part of his coaching, book, and PhD work — and they talk about what happens to companies that decide AI isn’t for them. If you lead a company and you’re trying to figure out how to move forward when nobody has the answers, this one’s for you. Links: Alliance of Chief Executives: https://allianceofceos.com Paul Witkay on LinkedIn: https://www.linkedin.com/in/paulwitkay/ Q2 Barometer survey opens June — contact paulwitkay@allianceofceos.com Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it’s free. ScalingCoach.com/Q20 Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com

    51 min
  2. What Your Team Won't Tell You

    Jun 17

    What Your Team Won't Tell You

    Every CEO story gets told from the leader’s chair. Episode seven of the Busy Is Broken series flips the camera. Bill walks through four composite vignettes — anonymized but visceral — drawn from real teams he’s coached. Each one shows what a leader’s patterns look like from the other side of the table. If you manage people, those people have a version of one of these stories. They’ve probably stopped trying to tell you. The Chaotic Team: a chief of staff opens her phone at 5:30 AM to find 3 AM messages rearranging tomorrow’s priorities. Operational meddling and strategic absence at the same time — the leader is everywhere on detail and nowhere on direction. The Unsafe Team: meetings opened with problems, never connection. Every new book the CEO read triggered a new system. People tapped out alongside a leader who slept two hours a night. They were tired of sprinting after gusts of wind. The Resigned Team: “This is how it is.” They’d moved past hoping things would change. No one was angry anymore. That’s worse than anger. The Frozen Team: everything waited on the founder. A gentle, patient, permanent freeze. Lovely people making a lovely product. But they were helpers, not leaders. Their own potential sat on the shelf for decades. The hard truth is the gap. The gap between how you’d describe your leadership and how your team would describe it. Self-reflection has limited perspective. You need the outside-in view. This week’s invitation: ask one person on your team — someone you trust to be honest — this question: “What’s the one thing I do that makes your job harder?” Then listen. Don’t defend. Don’t explain. The answer is worth more than any consultant’s report. Links: Busy Is Broken book and free diagnostic: https://busyisbroken.com Q20 Growth Diagnostic: https://scalingcoach.com/Q20 Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    14 min
  3. Stop Dumping and Start Delengaging — A New Framework for Delegation, with Tess Fyalka

    Jun 10

    Stop Dumping and Start Delengaging — A New Framework for Delegation, with Tess Fyalka

    Every company promotes its best people into leadership, then sets them adrift with zero tools to actually lead. Tess Fyalka has spent 25 years cleaning up that mess. She's the founder of Angle Coaching & Communication, author of Walking the Leadership Ledge, and spent nearly a decade building leadership development infrastructure inside a mid-size commercial construction company before going independent. Two thousand ghostwritten articles and white papers later, she pulled the patterns into a book. In this conversation, Bill and Tess take on the promotion trap that quietly wrecks teams, the lie new leaders tell themselves to avoid hard conversations, and what it actually takes for a star individual contributor to become a real leader of people. Tess walks through "Betsy" — the kind of high-performer companies promote because they assume excellence is transferable, then watch flame out when the wheels come off the bus. She names the Big Lie directly: when a leader avoids a difficult conversation to "protect" their team member, they're really protecting themselves. And the cost of that avoidance compounds. They get into the inside-out nature of leadership development: you can't lead others well until you know your own values, your triggers, and what you're choosing to be in the role. Tess shares her BRRR framework for difficult conversations and why the imaginary scenarios in your head are almost never how the conversation actually plays out. Bill brings his own moments of getting it wrong, including the time he caught himself reflexively defending micromanagement. They close on the metaphor that gives the book its title: when you step into a new leadership role, you're standing on a ledge, and you don't know yet whether the drop is ten inches or ten thousand feet. In This Episode: Why the skills that earn a promotion actively work against you as a managerThe "Big Lie" ineffective leaders tell themselves to avoid hard conversations"Delengaging" — Tess's framework for delegating through genuine engagementThe Betsy problem: what happens when companies promote excellence and expect it to transferHow nearly a decade in commercial construction proved leadership development works anywhereWhy most delegation is really just dumping — and how to tell the difference About the Book: Walking the Leadership Ledge: The "New" Leaders' Guide to Building Resilience and Confidence at Every Step. Hybrid Global Publishing, 2025. Connect with Tess: Angle Coaching: anglecoaching.comBook: walkingtheleadershipledge.comLinkedIn: linkedin.com/in/tess-fyalka-cpcc-pccFree assessment — "NEW" Leader's Reality Check: walkingtheleadershipledge.com Connect with Bill: Website: ScalingCoach.comLinkedIn: linkedin.com/in/billgallagherFree Q20 Growth Diagnostic: ScalingCoach.com/Q20 Busy is Broken — Bill's new book, coming September 2026. Sign up at busyisbroken.com Keep scaling.

    41 min
  4. I Made All the Big Events. That's About It.

    Jun 3

    I Made All the Big Events. That's About It.

    This is the most personal episode in the Busy Is Broken series. Bill made all the big events — the graduations, the performances, the big games, the Bar and Bat Mitzvahs. He has the photos. He was in the right seat at the right time for every moment that had a date on a calendar and a crowd in the room. That’s about it. What he missed was everything that led up to those moments. The practices before the big game. The rehearsals before the play. The meetings with the rabbi in the weeks before the Bar and Bat Mitzvahs. The ordinary Tuesday nights and Saturday mornings that, strung together, make up the actual texture of a childhood. Nobody sends you a calendar invite for “the night your daughter told a funny story at dinner that became a family legend you’ll never know.” You just look up one day and the kids are grown. Bill’s engine was adrenaline. He loved being needed. Every rescue was a hit of proof that he mattered. And it was also what kept him on a plane when his kids were at practice and in a hotel when they were doing homework at the kitchen table. This isn’t self-pity and it isn’t a pitch to feel sorry for the host. It’s recognition. Bill tells the story because he sees himself in the leaders he coaches now — the founder who can’t leave the office before seven, the CEO who hasn’t taken a real vacation in three years, the leader checking Slack during their kid’s soccer game. The question underneath isn’t “why are you working hard?” That’s obvious. It’s why the specific pattern. Why the midnight emails. Why the inability to let go of decisions your team could make. Why the thing that costs you more than it earns. This week’s invitation is small and concrete: tonight, put your phone in another room during dinner. Not on silent. In another room. Be present for thirty minutes with the people you love. The moments that haven’t happened yet are still available. Links: Busy Is Broken book and free diagnostic: https://busyisbroken.com Q20 Growth Diagnostic: https://scalingcoach.com/Q20 Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    13 min
  5. From IPO to Bankruptcy and Back: Scaling Across Full Lifecycles with Mike Krupit

    May 27

    From IPO to Bankruptcy and Back: Scaling Across Full Lifecycles with Mike Krupit

    What does it take to go from startup all the way to exit, multiple times, across different sectors? Mike Krupit has done it. He's been part of three IPOs, including CDNOW, where he served as COO and helped take the company public. He's also been through the harder side: building, growing, and winding down companies when the math stopped working. In this conversation, Bill and Mike dig into what 30 years of building companies actually teaches you. The most surprising lesson, in Mike's words: it's not about the idea, the product, or the timing. It's about having the right people in the right seats. And in the AI era, that hasn't changed; AI is a multiplier on top of people, not a replacement for them. They get into the founder-to-CEO transition Mike has lived multiple times, the four accountabilities a real CEO holds (vision, fiduciary, people, outside face) and why everything else needs to be someone else's job. Mike shares the CDNOW story straight: a planned merger with Columbia House that fell through at the last minute, the dot-com bust hitting at the same time, preparing for Chapter 11 while also running a sale process, and a late acquisition by Bertelsmann at $3 a share when the stock had once peaked near $39. He also opens up about his last startup, where he chose to return capital and shut it down rather than take more money and put a team in greater jeopardy. In This Episode: Why people — not ideas or products — are the real driver of company successThe four accountabilities that define a real CEOThe CDNOW story: from IPO to near-bankruptcy and a last-minute acquisitionWhat bankruptcy and shutting down a startup teach you that winning never willWhy most companies have a comfort problem, not a culture problemHow AI multiplies great people but doesn't replace the need for them Connect with Mike: Trajectify: trajectify.comLinkedIn: linkedin.com/in/mkrupitYouTube: Building Better Businesses Connect with Bill: Website: ScalingCoach.comLinkedIn: linkedin.com/in/billgallagherFree Q20 Growth Diagnostic: ScalingCoach.com/Q20 Busy is Broken — Bill's new book, coming September 2026. Sign up at busyisbroken.com Keep scaling. Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    46 min
  6. The Eighth-Grade Reflex

    May 20

    The Eighth-Grade Reflex

    There's a healthcare CEO Bill coached — smart, driven, impeccable résumé — who ran a national company the same way they ran eighth-grade group projects: by doing everyone else's work. Episode five of the Busy Is Broken series is about the moment that reflex stops being a strength and starts being the bottleneck. The overachiever who took over the group project in middle school got praised for it. Decades later, the same instinct shows up at the C-suite, and it doesn't scale — it suffocates. Lee came into a healthcare empire valued in the hundreds of millions. From the start, Lee second-guessed the leadership team, reworked slide decks at midnight, edited marketing copy mid-flight, and jumped into facilitation exercises Bill was running — not to collaborate, but to control. Not cruel. Not incompetent. Just an overachiever reflex from school that had never been updated. The result: people stopped presenting detailed plans because they knew Lee would reshuffle them. They stopped proposing creative solutions because Lee would override them. They learned helplessness. The best ones left. The gap is the giveaway. If you asked Lee, Lee was "protecting the company." If you asked the team, Lee was suffocating it. That gap — between how the leader describes the behavior and how the team experiences it — is the micromanager's blind spot. Lee eventually got it. Replaced wrong hires with right ones, stopped covering for empty seats, started letting go. The company stabilized. But it took years of damage and talent loss before the reflex broke. This week's invitation: when someone brings you a draft, a plan, a decision, notice the impulse to edit. Before you touch it, ask: "Is this good enough to ship, even if I'd do it differently?" If yes, let it go. Links: Busy Is Broken book and free diagnostic: https://busyisbroken.com Q20 Growth Diagnostic: https://scalingcoach.com/Q20 Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    14 min

  7. May 13

    Suneet Agarwal

    Suneet Agarwal joins Bill Gallagher on the Scaling Up Business podcast. Tune in to hear Suneet share insights on growth, leadership, and building scalable businesses. Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    47 min

  8. May 6

    Two Ways to Run a Castle

    What kind of castle are you running? In this solo episode, Bill Gallagher breaks down two fundamentally different leadership styles: command-driven and culture-driven. One scales. The other burns people out. Most founders default to the command style because it feels productive. You tell people what to do, they do it, problems get solved. But as your company grows, that approach becomes a bottleneck — and a trap. Culture-driven leadership is harder to build but far more powerful at scale. It means creating systems where people make great decisions without you in the room. In This Episode: This episode is drawn from Bill's upcoming book Busy Is Broken. Connect with Bill: Mentioned in this episode: Busy is Broken book Our new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com Q20 Diagnostic Offer Stuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

    14 min
See All (692)

4.8
out of 5
77 Ratings

About

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

Information

You Might Also Like