Scaling Up Business with Bill Gallagher

Mike Chaput, an entrepreneur and CEO, shares his inspiring journey from bankruptcy to creating a multi-million-dollar IT services firm. He discusses how he initially struggled with financial literacy and faced severe stress during his darkest hours. Emphasizing the importance of strong personal relationships, Mike illustrates how collaboration and support helped him rise again. He also introduces the concept of 'return on luck,' highlighting how crises can unveil new opportunities when approached with the right mindset.

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 

In a captivating conversation, John Rossman, a former Amazon executive who launched the Amazon Marketplace, shares invaluable insights on scaling businesses. He discusses the importance of a 'betting bigger' mindset and reveals how Amazon handles risk through rapid experimentation. John emphasizes that high standards elevate scalability, while low standards hinder it. He also advocates for thoroughly testing solutions to customer problems before fully committing, offering practical strategies for leaders aiming to enhance their operational efficiency.

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: 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 This episode was produced by Story On Media: https://www.storyon.co/ 

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 

Elliott Kallen, founder and CEO of Prosperity Financial Group and co-founder of A Brighter Day charity, shares his journey of resilience after the tragic loss of his son. He discusses creating resources for teen mental health, including a crisis texting hotline. The conversation touches on the loneliness of the modern generation, fueled by social media, and how wealth doesn’t always equate to emotional security. Elliott emphasizes living with passion and making meaningful connections to foster a lasting legacy that truly matters.

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 

In this engaging conversation, Rick Crossland, a talent expert and founder of A Player Advantage, shares invaluable insights on building a team of high-performers, or 'A Players'. He discusses the importance of hiring based on coachability and the CART traits: Coachability, Accountability, Results, and Tenacity. Crossland also examines the role of AI in enhancing team performance while emphasizing that human intuition remains irreplaceable. With practical systems and tools, he outlines a path to elevate your organization's talent density and success.

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