Scaling Up Business Podcast

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 fo

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 Mi

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 effec

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:

What if your addiction to hustle is the very thing holding your business back?In this episode, Bill unpacks the hidden addiction that plagues so many leaders: the need to feel busy. He explores how overworking, micromanaging, and always being “on” isn’t just unsustainable, but also a failure of effective leadership. Bill shares powerful stories of CEOs who broke the cycle and built stronger teams by stepping back, letting go, and empowering others to rise up to the occasion. Topics explored in this episode:(0:10) The Hidden Costs of Busyness*Being constantly busy feels productive, but it's actually a trap.*Imagine a world where you could step back and things don’t fall apart.(1:00) Case Study of a Fitness CEO*A thriving business, healthy personal life, and empowered team; you can do it all by doing less.*Why nudging, not rescuing, is the key to accountability and performance.(3:15) The Output is More Important Than ‘Busy’*Entrepreneurs love to glamorize their busyness, but true effectiveness is about res

How can leaders connect their personal purpose with their company's mission?In today’s episode, Bill talks with leadership coach Ben Renshaw about the importance of discovering your personal why. They also discuss how aligning personal and company purposes can lead to more meaningful leadership and a positive work environment.Ben Renshaw is a former classical violinist turned leadership coach who’s all about helping people find what truly lights them up. He’s worked with top global brands and execs, all while keeping his focus on one big question: what’s your why?Topics explored in this episode: (1:11) Discovering Your Why- Ben shares his journey from classical music to personal development.- Co-founded The Happiness Project in the skeptical UK of the 1990s.(7:45) Building Real Connection- Ben reflects on how different cultures respond to emotional authenticity.- How a company’s purpose can cascade into personal leadership development.(14:21) Transforming Leaders from the Inside Out- A reluctant CFO disc

What if your relentless hard work is actually costing your business more than it’s helping?In this episode, Bill explores the hidden costs of overwork, particularly when leaders confuse effort with effectiveness. He shares a cautionary tale of a CEO who pushed too hard, micromanaged excessively, and ultimately failed—highlighting how unchecked hustle undermines both personal well-being and team performance. Topics explored in this episode: (0:42) The Hidden Price of Hustle* Overwork has obvious personal costs, but its impact on the business is often overlooked.(2:40) The CEO Who Couldn’t Let Go* The story of a SaaS CEO who tried to control every part of the company, despite lacking expertise in many areas.* A promising company failed due to leadership that was anxious and overreaching.(5:27) From Hero to Enabler* True success comes not from doing everything, but from rallying a capable team.(6:38) The Real Cost of Doing It All* Personal sacrifices become habitual and ultimately unsustainable.* Overw

How can leaders create social contracts that foster true team accountability and shared success?In this episode, Bill and guest Keith Ferrazzi explore the importance of moving beyond traditional leadership towards a model of “teamship,” where teams hold themselves and each other accountable. Keith also shares insights about the power of vulnerability and candor, and practical exercises like the “stress test” to build high-performing teams. Keith Ferrazzi is a powerhouse thought leader and author who’s redefining how we connect and collaborate. His latest book is Never Lead Alone.Topics explored in this episode: (02:27) From Networking to Vulnerability* Vulnerability is the key to authentic relationships—even in business settings.(06:08) Building Co-Elevating Teams* The goal is not just psychological safety, but teams that push each other to succeed.(10:37) Practices That Change Culture* Teams need a social contract and regular “stress tests” to challenge each other productively.* Keith’s early expos

What are the hidden costs of micromanaging and overworking on team morale and business outcomes?This episode explores the main reasons why leaders often work too hard, including lack of trust, fear of failure, ego, habit, and being too busy to delegate. Bill argues that overworking is not a badge of honor but rather a sign of inadequate team building. Topics explored in this episode: (0:26) A Case Study in Micromanagement* A new CEO's micromanaging during a company sale led to longer transition times and negative impacts on team morale. (2:54) The Five Reasons Why Leaders Overwork* The five main reasons include lack of trust/perfectionism, fear of failure, ego/hero syndrome, habit (founder syndrome), and—you’ll have to listen to or watch the episode to find out the fifth! * Ego can drive leaders to seek out crises in which they can be the hero.  (6:59) The Impact of Overworking* Why overworking indicates a failure to build and empower a team. (8:22) Shifting Your Mindset* Id

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 create environments where people feel valued. Topics explored in this episode: (02:15) The Science of Mattering* How mattering influences employee performance and well-being.* Why recognition alone isn’t enough to make people feel valued.(10:40) Workplace Disconnection* The hidden costs of employees feeling like they don’t matter.(18:55) The Role of Leaders in Creating Mattering* Mattering shouldn’t be just an HR initiative—it’s a leadership responsibility.(28:30) Purpose vs. Mattering* Why having a sense of mattering is more foundational than purpose.* Case studies of compan

What leadership habits can help your team take more ownership and solve their own problems? In other words, how can you step back in a way that actually makes your business stronger?In this episode, Bill challenges the hustle culture myth and shares how stepping back, empowering your team, and embracing balance can actually strengthen your company.Topics explored in this episode: (00:16) The Myth of Hustle Culture* The real cost of hustle culture and why it can harm your company.* Bill’s story of taking a month-long family trip to Italy while his business thrived.(01:51) Leadership That Empowers, Not Micromanages* The power of asking the right questions instead of providing immediate answers.(04:17) Making Work More Fun * The benefits of hobbies and interests outside of work.* How compartmentalizing time helps maintain balance.(06:23) Embracing Challenges Without Unnecessary Suffering* The key difference between unavoidable problems and optional suffering.* Shifting your mindset to tackle obstacles

How can anyone, regardless of their background, develop lasting confidence?Confidence isn’t something you’re born with—it’s a skill you build, and Dr. Nate Zinsser has spent his career helping elite athletes, military leaders, and business professionals master it. In this episode, he shares lessons from his work with NFL star Eli Manning, Olympic athletes, and West Point cadets, revealing how anyone can develop unshakable self-belief.Dr. Nate Zinsser is a mental performance coach, author The Confident Mind, and a longtime director at West Point’s Performance Psychology Program. Topics explored in this episode: (02:00) The Foundation of Confidence- Why some people embrace coaching while others resist it.(10:30) The Making of a Performance Psychologist- How wrestling and martial arts shaped Nate’s approach to confidence.(20:45) Training the Mind - How the military and top athletes develop mental resilience.- The story of Olympic bobsledder Jill Bakken and her confidence breakthrough.(30:20) The E

What are the two most important factors for scaling a business?Scaling a business comes down to two key elements: focus and differentiation. Companies that maintain a clear customer and product focus while emphasizing what sets them apart are more likely to achieve sustainable growth. Topics Bill explores in this episode: (0:30) Two Critical Factors- The importance of focus and differentiation in scaling a business.    (4:47) Identifying Your Ideal Customer and Maintaining Focus- Focusing on one primary customer type, even for large companies.    - The importance of staying in your lane and not deviating from your focus.    (5:59) Focusing on Core Products and Services- The example of Steve Jobs' return to Apple and his focus on a simplified product matrix.    - Identifying and focusing on the profitable, growth-oriented parts of your business.    (7:15) Differentiating Your Business from Competitors-

What are some practical ways that businesses can optimize their operations with AI?Scaling a business is tough, but scaling by 300% while dealing with fraud and financial chaos is next-level challenging. In this episode, Gerard Murtagh shares how AI helped his company, MouldMen, navigate rapid growth, uncover fraud, and optimize operations. This conversation is packed with real-world AI applications, leadership lessons, and practical strategies for business owners looking to stay ahead.Gerard Murtagh doesn’t do business the conventional way. From launching his first venture at 17 to flying across the world to learn mold remediation firsthand, he’s built his success on innovation, grit, and a whole lot of AI-powered problem-solving.Topics explored in this episode: (2:00) The Unexpected Crisis* Gerard discovers a staggering $1.4M in fraud and financial mismanagement.(10:54) Turning to AI for Answers* Using AI to analyze company financials and expose fraudulent expenses.* Early AI wins convince Gerard to di

When growing your business, how can you differentiate between good advice and bad advice?In this episode, Bill shares a personal story about taking bad advice that cost him millions. He also explores the importance of timing when raising capital and the difference between surface-level advice and experience-based guidance. Topics explored in this episode: - Why a “good story” is an opportune time to bring in investors or partners.- The danger of waiting too long to reach revenue milestones before seeking investment.- How greed and the desire for control can cloud business judgment.- Questioning an advisor’s experience behind their recommendations.- How confirmation bias can lead you to seek advice that validates your preferences.Chapters in this episode: (00:20) The Danger of Bad Advice (03:45) The Costly Decision to Wait for a Revenue Milestone(05:32) Missing the Perfect Timing to Raise Capital(07:04) Aligning with Company Values and Goals(08:11) Learning to Probe for Experience Behind Ad

How did Eugene Tutunikov grow SwissWatchExpo from a local storefront to a $90M+ e-commerce business?In this episode, Bill talks with the CEO of SwissWatchExpo, a retailer of certified authentic luxury Swiss watches, about how he scaled his family business. Eugene shares insights on the importance of timing, customer experience, and focusing on sustainable growth. The conversation dives into lessons learned from pivoting careers, working with family, and navigating market disruptions.Eugene Tutunikov (pronounced “Too-Too-Nikoff”) is a former Wall Street pro who traded spreadsheets for Swiss watches. Topics explored in this episode: - The pivotal role of timing in scaling a luxury e-commerce business.- Offering a personalized, video-based shopping experience.- Building trust through in-house authentication and servicing of watches.- Why compounding growth is more sustainable than hyper-growth.- The impact of super-fake watches on the luxury market and how SwissWatchExpo counters it.- Why focusing on o

What are the essential elements of an effective morning routine for executives, entrepreneurs, and business owners?In this episode, Bill breaks down the elements of a powerful morning routine for business professionals. He shares his personal approach to starting the day with mindfulness, gratitude, reading, and planning, while emphasizing the importance of flexibility. Topics explored in this episode: - Creating a morning routine that aligns with your natural rhythm.- Why flexibility in your morning routine leads to better long-term success.- The role of gratitude and mindfulness in setting a positive tone for the day.- How reading and "grazing" on diverse topics can spark creativity and fresh ideas.- The impact of nighttime preparation on a smooth, productive morning.- The importance of balancing productivity with relaxation, such as incorporating a hot tub ritual.- Why a great morning routine isn’t about copying someone else’s formula.Chapters in this episode: (02:30) Why Every CEO Needs a P

Why do visionary entrepreneurs like Steve Jobs and Elon Musk need strong operational counterparts like Tim Cook and Gwynne Shotwell? Successful businesses don’t just need visionaries. They need strong operational leaders to turn big ideas into reality. This episode highlights the crucial roles of Tim Cook at Apple and Gwynne Shotwell at SpaceX—leaders who ensured consistent execution behind the scenes. Topics explored in this episode: - The myth that a single visionary leader drives business success—why execution matters just as much.- How Steve Jobs relied on Tim Cook to scale Apple into a global powerhouse.- The critical role Gwynne Shotwell plays in running SpaceX while Elon Musk drives innovation.- Characteristics of great second-in-command leaders: consistency, reliability, and people management.- Why hiring a COO or operational leader is not about cloning the CEO but complementing them.- The risks of hiring externally vs. developing leadership talent from within the company.- Strateg

How can teachers bring their unique styles and passions into the classroom while staying effective?In this episode, Jeff Gargas shares his unexpected journey from musician and college dropout to education innovator. Host Bill Gallagher and Jeff explore the intersections of creativity, resilience, and education, with a focus on engaging audiences and scaling impactful solutions. Jeff Gargas is a four-time college dropout who turned his love of music and creative energy into a thriving career in education. As the co-founder of Teach Better, Jeff helps educators across the country improve their craft with passion, flexibility, and a touch of rock ‘n’ roll flair.Topics explored in this episode: - Jeff’s journey from being a record label owner to co-founding Teach Better.- Engaging students by capturing their interest right from the start.- How a mastery learning framework empowers teachers to adapt to their unique classrooms.- The challenges of scaling a business, from cash flow issues to team adjustmen

“What is the lesson you want to teach our kids?” “Who do you want to be for our kids?” My wife asked me these questions during a particularly stressful time in my career. They grounded me. Refocused me. Made me prioritize what kind of person—both a dad and a business owner—I wanted to be. In this episode, I explore the following lesson: honesty and vulnerability in leadership can be far stronger than having specific business plans. Topics explored in this episode: - The emotional toll of leading a business through financial uncertainty.- How a supportive family dynamic can provide clarity and motivation.- Asking for help and involving others in problem-solving.- Why vulnerability and honesty strengthen leadership.- How to inspire loyalty and commitment from a team during tough times.- Parents teaching resilience and determination to our children.(00:00) Bill’s Personal Story of Challenge(02:13) Facing the Fear of Losing Everything(03:10) A Heartfelt Conversation with My Wife(04:42) Asking for H