Scaling Up Business with Bill Gallagher

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 you at the end of your life?*Your purpose is your emotional center behind work, family, and community life.(4:15) What is Your Intuitive Power? *What comes easy to you? Do more of that! *Notice what drains you? What do you hate to do? Do less of that! (6:45) Schedule Time for Some Play*Bill showcases how he incorporates play into his life and the work he does. *You need to have fun in order to be fresh and sharp. (9:45) Bringing it Together: Purpose, Power, Play. *When all three align, even a packed schedule feels energizing.*All 3 don’t need to happen simultaneously, we just want to touch all of them throughout the week/month. 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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 embracing failure. Topics explored in this episode:(03:00) Mike’s Entrepreneurial Start*Banks and private equity lent him money at 24, but he didn’t understand what a profit/loss statement was.*With no experience, Mike is surprised how he survived during such an economically uncertain time. *After starting his second business, it still took Mike 8-9 years to have a stable business. (11:00) Life is a Fail Forward Thing*Mike filed for bankruptcy 6 months after his son was born and his wife had quit her job.*Mike didn’t have the skills to cope with that kind of stress and developed horrible heath side effects during that time. *In life, you need to struggle in order to learn the skills needed to survive and to ascend to new heights. (18:35) People are the Glue to Your Success*Despite these hardships, Mike is still married to his wife and he is still business partners with his college roommate. *There’s something to be said for really sitting down and working through the problems with those that are closest to you. To collaborate, to listen, and to problem solve. (21:15) After a Big Failure, How Do You Start Again?*After declaring bankruptcy, Mike was back at the drawing board for his next business idea.*Mike was on the ground looking for new opportunities, new inspiration.  *Mike knew how to sell and he knew how to network; Mike believes this is why he didn’t file for bankruptcy sooner. (38:25) No Matter What, Bad Luck Will Happen*Bad things will happen in your business, expect to play it out strategically. *Slowly, you’ll start banking on good luck because you have enough experience with bad luck.Thanks to Mike Chaput for being on the show!Learn more about Mike here: https://www.endsight.net/Connect with Mike: https://www.linkedin.com/in/michaelchaput/Free Ebook: https://get.endsight.net/hubfs/Endsight%20Ebook%20-%20Embrace%205%20Vital%20Steps%20to%20Upgrade%2C%20Mend%2C%20or%20Transform%20Your%20IT%20Service%20Partnerships%20(2).pdfBill 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/BillGallBill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoach Visit

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 realize you want to retire and there’s no one who can take on the business.(1:15) Client Case Study *When you untangle a founder from the business, the team suffers. *The founder and team have decades of ingrained habits that make a succession difficult. *It took this client 6 years to properly sell. (3:15) ‘Someday’ Timelines Hurt Everybody*You can think about exit plans as early as the first year of business.*This allows you to build a company culture around the ‘exit strategy’. *The team gets a chance to be excited about their individual ownership in the company. 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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 masterclass in customer obsession, high standards, and building mechanisms that scale.Topics explored in this episode:(02:00) Playing Bigger is Actually Safer*How John Rossman went from traditional consulting to shaping one of Amazon’s most successful platforms.*The unique operating tempo and mindset inside Amazon.*Why high standards are scalable, and low standards are not.(11:20) Scaling Is Just a Series of Experiments*You never want to have all your eggs in one basket. *If you’re trying to juice your business for -today’s profitability-, you’re setting yourself up for a big risk. *After being let down by Fedex during the holidays, Amazon knew they had to take their delivery network in-house. (19:00) Stay in the Problem-Solving Headspace a Little Longer*Find small ways to test solutions to big customer problems. *Don’t go all-in or spend big $$ on customer problems without testing the available options. *Study history and past patterns from other companies to understand how problems get solved in a smart way.  (31:15) Reinventing the Business Model: The Amazon Way*John shares examples of Fortune 500 companies and how they failed to scale. *How Amazon out-thought competitors with better models, not bigger teams.*The mindset shift leaders must make to scale.(39:15) Leadership Isn’t a Trait. It’s a System.*Don’t wait for a profit decline. Amazon doesn’t.*Don’t leave your leadership up to chance.*How to build culture by design, not by accident.Thanks to John Rossman for being on the show!Learn more about The Amazon Way: https://the-amazon-way.com/Connect with John: https://www.linkedin.com/in/john-rossman/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/BillGallBill 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 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. Leading*Constant doing keeps you reactive.*When you always work in the business, you stop working on it.(05:02) Trusting the Team*Getting away tests your systems and your people.*If things fall apart when you're gone, it's not a vacation problem.(08:03) Breaks Create Capacity*When you return, you’re sharper, more creative, and more useful.*Distance gives you perspective and perspective gives you power.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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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) Buying a Bankrupt Business*Working with a shady accountant, buying a bankrupt business, and the accidental M&A lesson.*Early inspiration from Zig Ziglar, Brian Tracy, and “What They Don’t Teach You at Harvard Business School.”(10:30) Turnarounds that Worked and One That Didn’t*Why Matt’s retail experiment failed.*The power of simply raising prices and boosting sales.*Preparing a business for exit with minor tweaks, not reinvention(20:20) Discovering the Digital Goldmine*Moving from bricks and mortar to passive digital income.*Why Matt avoided eCommerce and leaned into affiliate websites.*How his first $20k website changed everything.(26:00) Built to Sell: Why Your Exit Strategy Starts Now*Sell on the way up, not at the peak.*Most founders wait too long and lose their best valuation.(31:50) Equity, Earnouts, and Strategic Sales*PE vs. strategic buyers: which gets you the better multiple?*Stories of regret from entrepreneurs who sold equity too early.*How smart PE groups structure incentives for better exits.(41:55) Shared Ownership Isn’t Always a Bad Thing*Why giving shares to store managers and salespeople drives better performance.*A proven incentive structure from one of Matt’s mentors.Thanks to Matt Raad for being on the show!Learn more about Matt: https://www.ebusinessinstitute.com.au/Listen to Matt’s podcast: https://www.digitalinvestors.com/podcast/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/BillGallBill 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:

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 explored in this episode:(03:12) Case Study: When Your Patterns Tank the Business*A tech CEO worked on 3 hours of sleep for years*Company collapsed due to his micromanagement and poor health*Being needed by everyone = a failure of leadership, not a strength(07:47) If You Don’t Look in the Mirror, You Can’t Grow*Refusing to be coached is a huge red flag*Great leaders change themselves before trying to change others*The most important transformation is personal(08:51) Let Go of Low-Tier Work*Stop obsessing over small-dollar decisions*Identify what only you can do—and give away the rest*Shift your identity from operator to visionary(10:57) Sprinting Is Fine, but Strategic Rest Is Key*It’s okay to have intense moments*But if every week is chaos, something’s broken*You don’t scale by sacrificing yourselfBill 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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 resilience, purpose, and intentional living.Topics Explored in This Episode:(03:05) Building a Business & Facing TragedyElliott’s entrepreneurial path and buying out his partner.The devastating loss of his youngest son three weeks later.(08:00) Founding A Brighter Day CharityCreating resources for teens on stress and depression.Launching a nationwide crisis texting hotline.Why so many teens feel isolated despite being “more connected” than ever.(16:00) The Loneliest GenerationComparing today’s teen mental health crisis to the Great Depression era.How social media fuels feelings of inadequacy.Elliott’s “six-sided box” metaphor for mental health.(18:50) Stories of Loss Beyond Money and SuccessHow pressure and expectations in wealthy communities create risk.Per capita suicide rates in affluent vs. low-income areas.Why financial security doesn’t guarantee emotional well-being.Personal stories from Bill and Elliott.(23:45) Living With PassionThe “love, like, give up” exercise Elliott uses with clients.Why most retirees spend 6+ hours/day watching TV.Creating a life that your next generation admires.(39:50) How to Teach without Raising Their Defenses Timing is important when you express your concern to your children. How you frame the question to your loved one can make a night and day difference in how they receive it.Why “I’m worried” works better than “You should.”Thanks to Rick Crossland for being on the show!Prosperity Financial Group: https://prosperityfinancialgroup.comGet the Book: Driven by Elliott Kallen: https://a.co/d/26gb8eNA Brighter Day Charity: https://abrighterday.infoConnect with Elliott: https://www.linkedin.com/in/elliotkallenBill 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/BillGallBill 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...

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 leaders coach, empower, and replace when necessary(04:27) It Starts with the Mirror*Your patterns are the problem*Pull back, empower others, and design a business that runs without you(07:37) Simple Framework, Hard Truths*The important trio: self-awareness, strong team, good systems*Become strategic again(08:41) You Can’t Scale Without Evolving*Why self-awareness must precede transformation*Without change in the leader, everything else stays the same*Execution habits matter…but only when you get out of the wayBill 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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 extraordinary team. Rick Crossland is a talent expert, the founder of A Player Advantage and the author of The A Player: The Definitive Playbook. He’s worked with brands like Johnson & Johnson, Ford, and Lifesavers, and now helps companies of all sizes build talent-dense organizations using proven systems and playbooks.  Topics explored in this episode:(10:05) How to Test for CoachabilityWhy hypotheticals don’t workUsing real-life stories and hobbies to find the truth for ‘true’ coachability The red flags of performative coachability(18:00) How to Move to an All A Player TeamA normal business typically has only about 30% A Players. How clear roles, accountability, and merit-based playbooks outperform “relational management”Stop tolerating C players—they demoralize your top talent(27:00) Can You Replace People with AI? Can you use AI to enhance your team and your people’s performance? Why top grading alone isn’t enough; you need a system and great recruiters(33:15) The A Player Talent AnalyzerHow to measure A player percentage accuratelyMonthly evaluation: effort, results, and coaching logsWhy 50% of Bs can become As—but only if they want to(44:30) Purpose Magnets and Coin-Operated PlayersWhy end-user-focused purpose matters mostHow purpose-driven teams outperform paycheck-driven onesAligning personal purpose with company missionThanks to Rick Crossland for being on the show!Learn more at: https://aplayeradvantage.com/Get the book: The A PlayerConnect with Rick on LinkedIn: https://www.linkedin.com/in/rickcrossland/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/BillGallBill 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...

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 Came for My House*Bill shares the story of nearly losing his business and his home.*How voicing the real fear changed everything.(8:10) You’re Not the Problem: Your Fear Is*Fear of not being enough gets projected onto your team.*You’re surrounded by capable people, but fear blinds you.(9:25) Want to Scale? Look in the Mirror*Personal growth precedes team growth.*Break old patterns. Create space for new fears AND new breakthroughs.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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 MoneySuccess doesn’t always equal financial security. Cutting your spending isn’t really the solution.(12:40) The Lies We Tell OurselvesWe will always find new ways to spend our ‘new money’. Mike explains Parkinson’s Law.(20:30) Building Financial Habits That StickTiny 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 PlanningThere 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 WorkMike 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/BillGallBill 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:

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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill 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 PresidentMeeting 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 CompaniesAn 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 BrandHow 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 BoringIt’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 VoiceUse 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.comGet his book: The Celebrity CEO: How Entrepreneurs Can Thrive by Building a Community and a Strong Personal Brand - https://a.co/d/aeJ0eQmBill 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/BillGallBill 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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill 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 EventsWhy 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” MindsetHow to justify and structure meetings so they deliver real business valueTime spent with the right people is where the true business magic happens(25:00) From Tactical to TransformationalWhat separates logistics-focused events from culture-shaping onesHow to build events that fuel strategic clarity and team momentum(32:00) Leading Through Live ExperiencesWhy your leadership presence matters more in personMindset over Mishaps: When there’s a will there’s a wayWhen things go wrong, focus on creating memories  (37:45) The 7 Steps to a Successful EventMap out the main objectives with the client Then you craft the unique experience around these objectivesThanks 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/BillGallBill 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 HustleGet Clear: Define a breakthrough BHAG and long-term strategy.Build the Culture: Hire well, clarify roles, coach continuously.Execute Intentionally: Prioritize, track key metrics, and meet with rhythm.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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill 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-bookBill 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/BillGallBill 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 BetterSet a BHAG (Big Hairy Audacious Goal): Anchor your strategy in a long-term, purpose-driven outcome.Invest in People & Culture: Hire well, coach continuously, and create strong values-based accountability.Execute with Rhythm: Align priorities, metrics, and meetings to stay focused and effective.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/BillGallBill 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/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/ Bill on Twitter/X: https://x.com/billgall 

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 scale with intention.Michael E. Gerber is the author of the best-selling E-Myth Revisited and with over 28 other books, Michael has spent decades helping entrepreneurs turn chaos into structure and systems. His latest creation is The Dreaming Room, an immersive experience designed to help business owners redefine their business vision and create a roadmap for success.Topics explored in this episode:(02:45) The Origin of the E-Myth*How a chance encounter led Michael to uncover the hidden flaw in small businesses.(08:05) Systems Are the Brand*Why the DNA of a brand lives in its systems and not in its logo or marketing.(11:45) From Script to Soul*How do you express the same message over and over with intention and passion?(14:15) Why McDonald’s Gets It*What entrepreneurs can learn from Founder Ray Kroc about scaling through consistency.(18:20) Sarah’s Pie Shop and the Power of Working On It*An impactful story about a small business owner’s transformation from technician to entrepreneur.(27:40) The Dreaming Room and the Eightfold Path*The dreamer, the thinker, the storyteller, the leader, the designer, the builder, the launcher, and the grower.(31:25) The Business Is the Product*Don’t let the business become your boss.*You have to create something of value in your business, or else you will go out of business.*Most Small businesses are doing the wrong type of work. (40:45) From NuCo to Scale*Why scaling means letting go of “OldCo” and creating something that lives beyond you.Thanks to Michael E. Gerber for being on the show!Learn more about The Dreaming Room: https://www.michaelegerbercompanies.comContact Michael directly: michael@michaelegerbercompanies.comConnect with Michael on LinkedIn: https://www.linkedin.com/in/michaelegerberBill 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/BillGallBill 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...