Scaling Up Business with Bill Gallagher

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 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 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 

Mike Michalowicz, bestselling author and entrepreneur, shares insights from his latest work, The Money Habit. He tackles why even the smartest individuals struggle with money and the emotional traps that hinder financial success. Michalowicz emphasizes the power of small habits over drastic changes and discusses how different life stages impact financial planning. He also shares personal strategies to 'friction-proof' financial systems and the significance of aligning financial management with personal well-being.

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, 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 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 

In this conversation, Eric Rozenberg, an international event strategist and author, shares how live meetings can drive company culture and alignment. He highlights that in-person events should be seen as strategic growth tools rather than expenses. Eric emphasizes the importance of thoughtful planning to create transformative experiences that foster connection and trust. With insights from high-profile events, he discusses how to craft memorable interactions that yield business value, making a strong case for gathering teams physically.

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