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Hitting The Ceiling

EOS Worldwide

Most entrepreneurs will tell you about the pivot, Hitting The Ceiling™ will tell you what happened the night before. Hitting The Ceiling, brought to you by EOS Worldwide is the perfect podcast for businesses, entrepreneurs, and key leaders and managers to talk about the moments they’ve never said out loud. 

Hitting the Ceiling is where business leaders and entrepreneurs talk about the moments they’ve never said out loud that often keep them from growing their businesses in healthy ways. These stories often happen behind closed doors, in the quiet, when the business was surviving, but the entrepreneur wondered if they were burning out. The cashflow ran out. The team walked. The personal life fell apart while the company kept going. 

Everyone hits a ceiling. On this show, host Mark O’Donnell helps guests identify the Five Leadership Disciplines that help leaders break through those seasons to realize the business and entrepreneurial success they were made for. 

New episodes drop weekly. Subscribe wherever you consume podcasts. 

In upcoming episodes of Hitting The Ceiling, you can expect to hear: 

  • What Happens When The Business Owner Is The System with Jill Young
  • The Power of Simplifying Business When Everything Collapses with Sue Hawkes
  • How Success Nearly Destroyed Their Friendship with Al Alexander and Ryan Loos of ConEquip
  • When You’re Forced To Lead Before You’re Ready with Avery Ward
  • When Growth Starts Stealing From Your Family with Ben Glass
  • Upcoming episodes with Patrick Lencioni, Gino Wickman, Kelly Knight and more on leadership, business growth, managing growing teams, and the Five Leadership Disciplines in business.  

Hitting The Ceiling is hosted by Mark O’Donnell, CEO and Visionary of EOS Worldwide™. The Entrepreneurial Operating System is a better way to run your business with tools that hundreds of thousands of business around the world are using to strengthen their businesses, 

New episodes drop weekly. Subscribe wherever you consume podcasts. 

To find out more about EOS Worldwide, visit www.EOSWorldwide.com 

To subscribe to Clarity Break Thoughts, visit www.ClarityBreakThoughts.com

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  • 22 episodes
  • weekly
  • Avg 50 min
  • English

Episodes 22

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  • S1 · E22
    Yesterday · 56 min

    The Private Jet Company That Nearly Crashed Before Takeoff

    What happens when the systems that helped you grow start becoming the very thing holding you back? Cory Bengtzen and Tommy Aoki have helped turn SkyShare from a small aviation brokerage into a fast-growing private jet company competing against some of the biggest names in the industry, but beneath the polished world of aircraft, owners, and luxury travel is a business entering a much harder stage of growth. As SkyShare pushes toward becoming a top 10 operator, Cory and Tommy face the pressure of limited systems, expensive talent, pilot retention, acquisition goals, AI disruption, capital needs, and a company that has outgrown the scrappy tools that got it here. You’ll hear how two lifelong friends are trying to preserve culture, simplify operations, align incentives, and build the discipline required to scale a high-stakes aviation business without losing what made it work in the first place. What you’ll learn in this episode: (01:48) How Cory went from barely graduating high school to selling cars, building dealerships, and launching an aviation company with no roadmap. (02:31) How SkyShare grew from a simple aircraft brokerage into a full-service private aviation company spanning FBOs, fractional ownership, charter, aircraft management, and more. (03:24) Why a painful business split made Cory swear off partners, and why he eventually trusted Tommy to help scale SkyShare. (04:06) How Tommy’s dream of becoming a Fortune 500 CEO took him through wireless, GameStop, and major operational leadership before bringing him back to building a company with his lifelong friend. (10:13) How one blunt conversation with a potential customer forced SkyShare to rethink its values, culture, and leadership from the ground up. (17:43) Why Tommy believes broken culture can be rebuilt, but only when leaders stop treating values like slogans and start living them every day. (22:24) Why SkyShare abandoned its goal of being “most loved” to pursue a top-10 operator ranking by 2030, and what that ambition will demand. (39:15) How systems, AI, pilot retention, office space, and access to capital are now standing between SkyShare and its leap from regional player to national contender. Learn more about Cory Bengtzen, Tommy Aoki, and SkyShare: https://www.skyshare.com/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E21
    August 25 · 51 min

    He Sold His Company, Only to Buy it Right Back

    Are you building your company with a purpose, or because you need to prove someone wrong? Eric V. Holtzclaw built his career turning ideas into businesses: launching Liger Marketing (yes, that’s a Napoleon Dynamite reference), building a research company, and learning firsthand what happens when a founder’s ambition collides with a revenue ceiling. Having to figure out how to get out of a difficult partnership, while under serious pressure to keep growing, forced him to look inward and explore what it was he really wanted out of his business. So, Eric sold Liger. But then, he watched the acquiring company lose a major client and decided to buy the business back. Suddenly, he found himself rebuilding around the clients and relationships that made the company valuable in the first place. Along the way, he had to confront a harder question: how much of his business identity was tied to proving that he could make something bigger? In this episode, you’ll hear how Eric is learning to separate independence from isolation, ambition from identity, and business growth from growth at any cost. His story takes you inside the emotional reality of entrepreneurship, from walking away from a misaligned partnership to resisting the lure of private equity and building Liger Marketing into the kind of lasting, partner-led firm he actually wants. What you’ll learn in this episode: (01:11) Why Eric sold Liger, bought it back, and had to rebuild the company around its clients again. (02:06) How one major client loss inside the acquiring company forced Liger into a high-stakes reset. (05:21) Why revenue growth became Eric’s recurring ceiling, even when Liger could deliver at scale. (07:40) How misalignment between a growth-minded founder and a lifestyle-business partner can quietly stall a company for years. (08:22) Why Eric chose to sell his interest in his research business rather than force a broken partnership to continue. (13:06) Why entrepreneurs need to be brutally clear about whether they are building a lifestyle business or a growth business. (14:48) How Eric’s “rectify” and “magnify” framework reveals the emotional fuel behind many entrepreneurs and their founder identity. (23:53) Why Eric wants Liger Marketing to become a lasting, partner-led firm instead of another agency built for a private equity payday. Learn more about Eric V. Holtzclaw and Liger Marketing: https://www.ligerpartners.com/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E20
    August 18 · 53 min

    What the World Cup Taught Us About Workplace Culture

    When does the drive to grow become a cover for ego, fear, or the need for recognition? Jonathan Reynolds built Titus Talent Strategies around a simple belief: the right people in the right seats can change everything, but as the company grew, the cracks started showing inside the leader himself. The pressure to know everyone, stay central, get credit, protect the culture, and keep growing exposed a deeper fear: what if Titus became healthier when it needed him less? In this episode of Hitting the Ceiling, you’ll hear how Jonathan and Mark unpack founder ego, purpose, AI, automation, people-first leadership, and the Entrepreneurial Operating System®, a system for running your business or organization, as tools for becoming clear enough to lead without being the bottleneck. What you’ll learn in this episode: (01:18) When the leader’s own seat becomes the ceiling the company has to break through. (02:36) How scaling a people-first company can create anxiety when you can no longer personally know everyone. (04:23) What it feels like when the company starts making decisions without you, and why that can hit your ego. (06:01) How to celebrate leaders you’ve developed without needing credit for everything they accomplish. (08:33) Why the hunger for legacy, recognition, and significance can quietly shape your leadership behavior. (12:52) What purpose reveals about the way people join, leave, and contribute to a company’s story. (29:12) How hidden founder motives can break trust when leaders say one thing but are building for something else. (41:14) How AI and automation can either threaten people or free them up for the deeply human work only they can do. (48:10) Why clarity breaks, honest reflection, and the Entrepreneurial Operating System® tools matter when you feel ready to quit. (51:54) How your stress as a leader can change the atmosphere for everyone around you. Learn more about Jonathan Reynolds and Titus Talent Strategies: https://www.titustalent.com/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E19
    August 11 · 45 min

    The Family Business Nobody Wanted to Inherit

    What happens when the family business you spent your life building has no family member ready to take it over? Derek Volk spent decades turning his family's Maine packaging company into a $50 million operation. He worked hard to build it just the way his father and grandfather had before him. Then, three weeks from closing a sale that would have let him walk away clean, the deal fell apart. No buyer. No exit. Just Derek, still holding the debt, still on the hook for the personal guarantees, still responsible for 110 people who counted on him for a paycheck. And underneath all of it, he couldn’t stop thinking: he was still building something his own kids didn't want. That is what kept him up at night. Not the collapsed deal. Not even the debt. The realization that the name on the building didn’t really mean anything to the people who share his last name. In this episode of Hitting the Ceiling, you’ll hear how Derek is confronting succession, culture, debt, delegation, EOS, and the hard work of becoming less essential so the company’s legacy can survive beyond him. What you’ll learn in this episode: (00:16) What happened when Derek Volk was three weeks away from selling his family business and the buyer suddenly walked away. (03:25) How Derek wrestled with the realization that he may be the last family member inside a company that has carried his name since 1967. (07:25) What you lose when a key family leader exits and why it is so hard to replace someone who truly puts the business first. (10:18) The real burden of leadership when 110 employees, debt, personal guarantees, and company culture all rest on your shoulders. (18:54) Why an ESOP is considered after a failed sale and how existing debt can complicate the path to employee ownership. (21:52) How reading Traction can transform a leadership mindset, drive EOS adoption, and expose hidden people problems in your business. (37:58) Why learning to delegate and systemize is the key to making yourself as irrelevant as possible inside your own company. Learn more about Derek Volk and Volk Boxes: https://volkboxes.com/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E18
    August 4 · 31 min

    The Nonprofit Built to Say Yes Fast

    How do you protect the people doing the work without taking resources away from the people you serve? Rachel Kuhn stepped into A Special Wish Foundation of Central Ohio carrying a promise her grandmother made in 1982: give children with life-threatening illnesses and their families a moment of joy when they need it most. But behind every Disney trip, private character meet-and-greet, airport sendoff, and carefully planned wish is a pediatric nonprofit racing against treatment schedules, poor prognoses, donor uncertainty, and the pressure to never let a qualifying child sit on a waitlist. You’ll hear how Rachel and Wish Director Rebecca Brown are learning to protect the heart of local wish-granting while building the structure, funding, accountability, and team capacity needed to keep saying yes to families who cannot afford to wait. What you’ll learn in this episode: (01:33) What no one sees between a child qualifying for a wish and the moment it goes viral. (03:13) Why a wish isn’t just a trip, it’s a deeply personal dream shaped by treatment, timing, and hope. (05:39) Why avoiding a waitlist matters and the intense financial and emotional pressure it creates. (07:24) How nonprofits balance two audiences: families in need and the donors who fund it all. (12:18) When staying lean to save donor dollars starts burning out your team. (15:02) Why passion alone won’t sustain a nonprofit without strong business fundamentals. (17:57) How a MrBeast-level opportunity brought massive exposure and overwhelming pressure. (27:07) Why are they rethinking leadership, delegation, and growth on the path to 50, then 100 wishes a year. Learn more about Rachel Kuhn & Rebecca Brown and A Special Wish Foundation: https://www.aspecialwishfoundation.org/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E17
    July 28 · 38 min

    How to Build an ESOP Company That Can Scale

    What happens when the company you helped build starts outgrowing the structure holding it together? Mike Mortensen started at ARG Industrial as a delivery driver in Anchorage, Alaska, and spent more than three decades working his way through nearly every part of the business. What began as a small, single-location distribution company eventually became an employee-owned organization with a much bigger future ahead of it. As the company grew, Mike could see what ARG Industrial was capable of. But the leadership structure, internal support, and shared vision were not keeping pace. After more than 25 years inside the business, he reached a breaking point where he was prepared to walk away from the company he loved because he couldn’t keep pushing its future uphill alone. Mike pulls back the curtain on why he stayed. From expanding beyond Alaska and changing the company’s name, to investing in digital transformation and building a more robust leadership team, he reveals what it takes to grow without losing the identity that made the business matter in the first place. Now, Mike is facing another ceiling: Scaling ARG into the company it has worked so hard to become through its team, systems, and ambition. And this time, the challenge is not whether he can carry the vision himself, but whether he can keep building a company strong enough for everyone else to carry it with him. What you’ll learn in this episode: (01:32) Why Mike Mortensen nearly walked away from the company he had spent more than 25 years helping build. (05:32) Why employee ownership changed the emotional stakes of leadership, growth, and customer service at ARG Industrial. (09:14) How frontline employees became part of a wealth-building ESOP story that most blue-collar workers never get to experience. (14:16) How ARG Industrial worked through the grief and necessity of letting go of legacy names to become one unified brand. (18:08) Why digital transformation became a major growth ceiling for an industrial company serving remote customers with ecommerce and complex product needs. (23:28) Why Mike believes AI can help industrial distributors move beyond the limits of traditional ERP systems. (31:17) How ARG is pushing authority and accountability deeper into the business so branch leaders can stop “running the store” and start “running the business.” Learn more about Mike Mortensen and ARG Industrial: https://www.teamarg.com/ Want to gain traction in your own company? As written about in the best-selling book, Traction by Gino Wickman, the Entrepreneurial Operating System (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E16
    July 21 · 44 min

    The Family Legacy They Had To Rebuild | Denise Hutchinson & Michael Fleck of Occasions Fine Jewelry

    What happens when the business you inherited starts falling apart before you have even found your footing? When Michael Fleck bought his family's Texas jewelry business in 2014, he thought he knew what came next. Instead, oil prices crashed, his right-hand leader died from cancer, and the future of the company was suddenly in question. Faced with shrinking revenue and impossible decisions, Michael and his sister, Denise Hutchinson, sat in a hotel room preparing a plan to downsize the business they loved. They cried over the people they might have to let go and wondered if simply surviving would have to be enough. It wasn't. In this episode of Hitting the Ceiling, Denise and Michael share the painful and powerful story of rebuilding Occasions Fine Jewelry—a family business that has grown into one of the top fine jewelry retailers in the country. From learning to embrace accountability and difficult conversations to redefining their roles as Visionary and Integrator, they've discovered that every new level of growth requires letting go of something that once made you successful. Now, they're facing another ceiling: opening a second Texas location, simplifying their business, and learning to lead through discomfort once again. What you’ll learn in this episode: (01:56) Why Michael’s 2014 purchase of Occasions turned into an immediate crisis when oil dropped, his right-hand person died, and the business started sliding. (05:50) How family-business transitions carry emotional weight because the buyer is often inheriting someone else’s identity, not just assets. (08:47) Why Michael and Denise built a plan to shrink the company, and what changed when Michael realized he did not want to merely survive. (12:03) How a loving, family-like culture can still fail when there is no accountability, no warning system, and no clear standard. (17:20) What it felt like to “win Midland,” hit an eight-figure showroom, and then realize the old playbook had reached its limit. (22:30) How Denise and Michael clarified their visionary and integrator roles so Michael could let go and Denise could build repeatable systems. (29:01) Why simplifying communication meant stopping constant problem-solving conversations and building a cleaner process for real issue resolution. (34:07) How the siblings are preparing for a second store by making the flagship stronger, delegating cleaner roles, and staying open to change. Learn more about Denise Hutchinson & Michael Fleck and Occasions Fine Jewelry: : https://occasionsfinejewelry.com/ Want to gain traction in your own company? As written about in the best-selling book, "Traction" by Gino Wickman, the Entrepreneurial Operating System (EOS®) helps entrepreneurial leadership teams clarify their vision, gain traction, and work together more effectively. Learn more at www.eosworldwide.com Want a little more clarity in your week? Sign up for Mark O'Donnell's Clarity Break Thoughts newsletter: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E15
    July 14 · 35 min

    The Reckless Bet That Became A Legacy | Brenton Cloud, President of Greenhouse

    What parts of your business are you calling success simply because they look impressive from the outside? Brenton Cloud came from a pest control family that dated back to 1934, but building his own future meant selling a nearly paid-off house, leaving the family business, and betting everything on Greenhouse. The company exploded to about $10 million in roughly three years, but the growth created chaos: too many accounts, too many hires, too many trucks, and a painful realization that success was costing him time with his children. A fourth-generation pest control entrepreneur, Brenton Cloud is the founder and visionary of Greenhouse Termite and Pest Control, a Florida-based company serving homeowners across the state’s west coast. What you’ll learn in this episode: (01:13) What it feels like to risk a nearly paid-off house and a young family’s security to build a business from scratch. (02:03) Why Brenton saw opportunity where his father saw risk, responsibility, and more work. (03:25) How Greenhouse grew too fast without systems and why Brenton says the business almost swallowed him whole. (05:34) Why hiring anyone with a pulse became one of the most expensive mistakes of the early growth years. (08:34) How seasonal demand led Brenton to buy too many trucks and what that taught him about predicting capacity. (13:00) What the personal cost of building at all costs really looks like, including the bedtimes and childhood moments Brenton says he can never get back. (19:21) Why Brenton now says no to shiny opportunities, including acquisitions the old version of him would have chased. (20:53) Why Greenhouse’s next ceiling is not demand, but building enough managers to grow without recreating the chaos. Learn more about Brenton Cloud and Greenhouse Termite and Pest Control: https://mygreenhousepro.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts: www.eosworldwide.com/claritybreakthoughts Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E14
    July 7 · 1 hr 8 min

    The Ceiling Inside EOS Worldwide | Kelly Knight, President, EOS Worldwide

    What happens when someone else’s prediction for your future becomes the thing you spend your life refusing to accept? As Kelly Knight stepped into EOS Worldwide, she wasn’t just joining a company; she was inheriting a movement built on trust, community, and a system that people expected the business itself to live perfectly. Within 18 months, the founder was selling the company, private equity entered the picture, the culture felt exposed, and Kelly had to grow from new Integrator into steward of something much bigger than herself. You’ll hear how a childhood moment of defiance shaped her leadership, how EOS had to mature without losing its soul, and why the next ceiling is forcing the company back to simplicity, focus, and the five leadership abilities. What you’ll learn in this episode: (04:48) Why the same fighter instinct that helped Kelly as a child still shapes the way she protects the greater good at EOS Worldwide. (08:21) How Kelly became EOS Worldwide’s first full-time employee and stepped into the integrator seat without fully knowing the weight of the mission. (14:42) What Kelly noticed when she first encountered the EOS Implementer community and why the culture felt stronger than advertised. (20:26) Why direct feedback can feel uncomfortable at first, but becomes a gift when it comes from love, trust, and a desire to help people grow. (28:41) How Kelly navigated the pressure of Gino Wickman selling EOS Worldwide just 18 months after she joined the company. (39:45) Why Kelly believes scaling should not be about cold growth language, but about finding the most efficient way to bring your mission to the world. (56:44) How EOS Worldwide is hitting its current ceiling by returning to simplicity, clarifying its flywheel, and focusing on the five leadership abilities. Learn more about Kelly Knight and EOS Worldwide: https://www.eosworldwide.com/eos-history-team Get a grip on your business with Traction by Gino Wickman, the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts: www.claritybreakthoughts.com (https://www.eosworldwide.com/claritybreakthoughts) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E13
    June 30 · 59 min

    When Helping People Starts Hurting the Business | Chadwick & Michela Taylor of The Service Center

    What does it cost when generosity turns into enabling? Chadwick and Michela Taylor built Service Center Pro from a simple phone-answering problem into a growing virtual team, but beneath the success was a business stuck at the same employee count, the same revenue range, and the same exhausting cycle of turnover and client pressure. Every time they got close to scaling, people left, expectations broke down, and the couple had to confront whether their own leadership, generosity, and communication patterns were keeping the ceiling in place. You’ll hear how they turned painful feedback, kind candor, better delegation, and a clearer culture into a path forward for a company still fighting to become what they believe it can be. What you’ll learn in this episode: (00:18) How Chadwick and Michela turned a recurring small-business problem into the idea behind Service Center Pro. (02:38) Why their company has stayed stuck around 24 to 30 employees and what that ceiling revealed about their capacity to scale. (04:11) How Chadwick’s imposter syndrome shows up as he tries to grow from self-employed operator into a true people leader. (05:05) Why Michela realized her impossible expectations were creating resentment and limiting the people around her. (13:50) How high standards can drive a business forward, but also become destructive when leaders do not know how to coach through them. (18:59) Why the Taylors’ culture changed when they stopped hiring out of desperation and started filtering employees and clients through core values. (22:40) How “kind candor” helps their team tell the truth, hold people accountable, and still leave people feeling supported. (51:18) Why Chadwick believes entrepreneurs grow faster when they automate, integrate, delegate, or eliminate the work that keeps them stuck. Learn more about Chadwick & Michela Taylor and The Service Center: https://www.servicecenterpro.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts: www.claritybreakthoughts.com Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E12
    June 23 · 52 min

    The Moment Hustle Stops Being Enough | Chase Calhoun, CEO of Apex Real Estate Investments

    How do you build a company that can keep growing without constantly pulling you back in? As Chase Calhoun grew from buying a foreclosure sight unseen to running a real estate and construction operation with more than 130 units under management, the pressure didn’t stem from a lack of opportunity; it came from becoming the bottleneck in the business. Capital constraints, scattered responsibilities, market cycles, and the need to hire before he felt ready forced him to confront the limits of doing too much himself. You’ll hear how Chase is learning to simplify the work, delegate real ownership, build systems from painful experience, and turn a founder-led hustle into a business that can scale beyond him. Chase Calhoun is a real estate investor, developer, and owner of Apex Real Estate Investments in Little Rock, Arkansas. After leaving law enforcement and moving from the San Francisco Bay Area, Chase bought a foreclosure sight unseen and turned that first risky bet into a growing portfolio of rental properties, construction projects, and real estate ventures. What you’ll learn in this episode: (02:57) How a single investment became the foundation for a much larger real estate and construction business. (04:40) What it looks like to build multiple businesses that work together under one growing operation. (07:03) Why ambitious founders set long-term growth targets and how larger projects can accelerate that vision. (09:26) Why delegation becomes one of the biggest growth ceilings and why the next level requires leaders who can own decisions, not just tasks. (11:38) How capital, market cycles, and changing economic conditions can shape a company’s growth trajectory. (14:59) Why some operators are shifting away from complex renovations and toward more scalable development strategies. (30:25) How founders can transfer hard-won experience out of their own heads and into the organization through training, systems, and accountability. Learn more about Chase Calhoun and his companies: https://linktr.ee/ChaseCalhoun Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts: www.claritybreakthoughts.com Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E11
    June 16 · 1 hr 2 min

    The Dark Side of Public Leadership | Paul TenHaken, Mayor of Sioux Falls, SD

    What does a crisis reveal about the way you make decisions under pressure? As Paul TenHaken built a thriving digital agency and later became mayor of Sioux Falls, the outside story looked like momentum, influence, and achievement, but underneath it were cash flow panic, purpose stagnation, and the cost of stepping into public leadership. A diner conversation with his wife, a political smear days before an election, and the chaos of leading through COVID forced him to confront what leadership costs when the money, reputation, and answers are no longer guaranteed. You’ll hear how Paul moved from success to significance, learned to lead without control, and rebuilt his view of work around calling, people, and the greater good. Paul TenHaken is an entrepreneur, public servant, and leadership speaker who served as mayor of Sioux Falls, South Dakota. Before entering public office, he founded and grew a successful digital marketing agency, where he experienced the highs and pressures of entrepreneurship firsthand. As mayor, Paul brought a business-minded but people-first approach to city government, using EOS principles to improve accountability, meeting structure, and team alignment. What you’ll learn in this episode: (00:01:30) Why fast growth can still leave an entrepreneur wondering if it is time to quit and go back to a salary. (00:04:23) How one billing mistake turned Paul’s digital agency into the bank for his clients. (00:05:18) Why success, income, and flexibility still left Paul feeling unfulfilled. (00:07:31) How writing his own obituary helped Paul confront the difference between success and significance. (00:10:49) Why your job title can change while your calling stays the same. (00:15:18) Why entrepreneurs are ultimately remembered for people and relationships more than profit or performance. (00:22:51) How Paul brought EOS into city government to create clearer goals, stronger meetings, and real accountability. (00:38:07) What Paul learned when public attacks, COVID, and crisis leadership pushed him to the edge. Learn more about Paul TenHaken: https://www.siouxfalls.gov/government/council/council-members/paul-tenhaken Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E10
    June 9 · 47 min

    The Twenty Days That Changed Everything | Lindsay Joss Iudicello, Owner & President of Botanie Soap

    What happens when the person holding the business together is suddenly gone? Botanie had grown from a tiny kitchen-based soap operation into Montana’s largest natural soap manufacturer, but behind that growth was a founder carrying too many seats and a wife who never expected to lead the company without him. Then Tim was diagnosed with an aggressive cancer and gone within weeks, leaving Lindsay Joss Iudicello to face grief, motherhood, ownership, and a 25-person company she had only touched part-time. You’ll hear how Lindsay chose to grow instead of freeze, leaned on the structure already built through EOS, and learned to lead the business forward without becoming the founder she lost. Lindsay Joss Iudicello is the owner, president, and visionary of Botanie, a Montana-based contract manufacturer that creates natural soap, body care, and solid hair care products for values-driven brands. After the sudden loss of her husband and the company‘s founder, Tim, Lindsay stepped into the leadership of a company she never expected to run. Today, she leads alongside a strong executive team, using EOS principles, clear structure, and a deep commitment to Tim’s legacy to grow the business without carrying it alone. What you’ll learn in this episode: (00:01:15) What Botanie does as a contract manufacturer and how the family business grew into a company serving hundreds of partners. (00:02:22) How Lindsay stepped back into a business she never intended to run after years of being only lightly involved. (00:05:19) Why Tim began looking for an operating system once the company grew beyond what he could hold together himself. (00:09:50) How Botanie’s three-year picture helped the team see what they had predicted, planned, and actually accomplished. (00:13:31) What happened when Tim was diagnosed with aggressive cancer, and Lindsay and Tim had to step away from the business almost immediately. (00:15:29) How Lindsay faced the internal choice between freezing and growing after suddenly becoming responsible for the company. (00:17:46) Why Lindsay did not try to run everything herself and instead stepped into the visionary seat while elevating leaders around her. (00:27:56) How financial systems, outside experts, and the willingness to ask for help allowed Lindsay and the leadership team to get up to speed quickly. Learn more about Lindsay Joss Iudicello and Botanie Soap: https://botaniesoap.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts: www.claritybreakthoughts.com Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E9
    June 2 · 51 min

    The Problem AI Can Never Solve | Patrick Lencioni, founder of The Table Group

    Are you building success while quietly losing peace? Pat built one of the most influential leadership movements in modern business, but beneath the bestselling books and global influence was a growing realization that success had become tangled with anxiety, people-pleasing, and the fear of never being enough. As companies chase growth, AI acceleration, and performance at all costs, Pat explains how avoidance, artificial harmony, and unhealthy ambition quietly erode trust, relationships, and even the leaders themselves. You’ll hear how he learned to confront discomfort instead of outrun it, why vulnerable trust changes everything inside an organization, and what it really takes to build a company where people genuinely love coming to work. Patrick Lencioni is the founder of The Table Group and the author of bestselling books including “The Five Dysfunctions of a Team,” “The Advantage,” and “The Ideal Team Player.” For nearly three decades, he’s helped leaders build healthier organizations. In this conversation, he opens up about the anxiety, fear of failure, and pressure beneath the success that shaped his work. What you’ll learn in this episode: (00:02:17) Why success driven by fear and insecurity can still leave you feeling like nothing is ever enough. (00:04:25) How Patrick’s childhood view of miserable workplaces shaped his mission to build healthier organizations. (00:06:41) Why trust-building is never “finished” and how healthy teams keep returning to it over and over again. (00:08:35) What vulnerability-based trust actually looks like inside high-performing leadership teams. (00:11:28) Why avoiding difficult conversations creates more damage than conflict ever will. (00:16:27) How AI could quietly weaken organizational health when leaders stop thinking critically for themselves. (00:21:44) What anxious leadership looks like behind the scenes and how false urgency can damage both leaders and teams. (00:42:54) How Working Genius helped reveal that an underperforming employee was simply sitting in the wrong role. Thank you to Patrick for being on our show! Learn more about Patrick Lencioni and The Table Group: https://www.tablegroup.com/ Read The Five Dysfunctions of a Team (https://www.tablegroup.com/topics-and-resources/teamwork-5-dysfunctions/) to better understand organizational health and team trust. Explore the Working Genius assessment to better understand the type of work that gives your team energy versus frustration. Use code “CEILING” for 20% off your Working Genius Assessment at https://www.workinggenius.com/ Listen to Patrick Lencioni’s podcasts, including At The Table with Patrick Lencioni (https://www.tablegroup.com/pat/#podcast) and The Working Genius Podcast (https://www.workinggenius.com/wg-podcast-post), for practical insights into leadership and organizational health. Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc Apply now to sponsor Hitting the Ceiling: https://www.eosworldwide.com/podcast-sponsor-inquiry This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E8
    May 26 · 47 min

    When Growth Breaks Everything You Built | Rob Hughes, MBA, IMC CEO of Hughes Integrated

    What happens when your business grows faster than your ability to lead it? As Robert Hughes scaled his business through explosive growth, the success didn’t bring stability; it exposed cracks in leadership, systems, and control that had been building beneath the surface. Revenue surged, but chaos followed: overhiring, financial strain, toxic culture, and the gut-wrenching discovery that someone on his team was stealing from him while everything else was already unraveling. You’ll hear how he faced the moment he broke his own business, rebuilt from the ground up, and redefined what real leadership actually requires. Robert Hughes is an international keynote speaker and the CEO of Hughes Integrated, a relationship-driven marketing agency. After launching his first business from scratch and navigating seasons of financial strain, rapid growth, and internal breakdown, he now helps organizations build scalable marketing systems rooted in trust and long-term relationships. His work blends strategic frameworks with hard-earned leadership lessons from the moments that tested him most. What you’ll learn in this episode: (00:01:55) What it actually looks like to go 18 months without revenue while building a business from scratch. (00:03:42) Why having an idea means nothing until someone is willing to pay for it. (00:08:15) How isolation and self-doubt can quietly shape your decisions as an entrepreneur. (00:19:34) What happens when rapid growth outpaces your systems, structure, and hiring discipline. (00:20:26) How a lack of accountability creates internal chaos and opens the door for deeper problems. (00:21:21) What it feels like to discover someone inside your company has been stealing from you. (00:29:26) Why reinvesting everything back into your business can quietly become destructive. (00:34:48) How the “hero complex” turns founders into bottlenecks and limits long-term growth. Learn more about Rob Hughes and Hughes Integrated: https://hughesintegrated.com/ Get a grip on your business with Traction by Gino Wickman - the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E7
    May 19 · 57 min

    When Success Turns Into an Identity Crisis | Mary Nisi, Owner of Toast & Jam, Inc

    Are you prepared for the identity shift that comes after success? As Mary Nisi built Toast & Jam, Inc into a thriving company, the success created distance from the day-to-day, until the pandemic wiped out 564 weddings and exposed how little control she actually had. The pressure escalated as she was forced back into a business she no longer understood, managing chaos, team tension, and financial strain, and realizing that her leadership style was breaking under stress. You’ll hear how she rebuilt the company from the ground up, let go of control piece by piece, and ultimately faced the unexpected question that comes after survival: if the business doesn’t need you anymore, who are you? Mary Nisi is the founder of Toast & Jam, a Chicago-based DJ company known for redefining the wedding industry with its high-energy, non-traditional approach. Over the past two decades, she’s built a team that performs hundreds of events each year and has even DJed for President Barack Obama. Today, she’s navigating what comes next after stepping out of the day-to-day operations of the business she built. What you’ll learn in this episode: (00:01:22) How a fully booked year with 564 weddings collapsed almost overnight, and what that revealed about business fragility. (00:03:10) What it feels like to face overwhelming customer pressure and crisis communication at scale. (00:08:30) Why missing a personal milestone became the emotional breaking point that forced change. (00:12:43) How people-pleasing leadership creates hidden expectations that can backfire under stress. (00:15:46) What happens when your team expects more, even when the business is losing money. (00:19:58) Why keeping the wrong people too long can quietly damage your entire company. (00:32:41) How losing visibility into your systems leads to culture breakdown and declining performance. (00:43:58) What it means to step away from your business and confront an identity beyond it. Learn more about Mary Nisi and Toast & Jam, Inc: https://toastandjamdjs.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E6
    May 12 · 35 min

    The Hidden Cost of Avoiding Hard Conversations | Kara Roberts Founder, Pepper’s Personal Assistants

    What signals are you ignoring because you hope things will “work out”? As Kara Roberts built a thriving 30-person company, the systems worked for everyone, except her own leadership, where misalignment and avoided conversations quietly stacked beneath the surface. In a single week, one firing triggered a chain reaction: her business manager was gone, her HR leader quit, and another key operator walked out, all while her personal life was unraveling and a three-month trip loomed. You’ll hear how she navigated the chaos, rebuilt her team from scratch, and discovered that the collapse wasn’t the failure; it was the turning point that finally forced her to build the business the right way. Kara Roberts is the founder of Pepper’s Personal Assistants, a Seattle-based household management company she built from a side hustle into a 30-person business. Known for her honest leadership style and people-first approach, Kara has spent the last 14 years navigating the realities of entrepreneurship, from burnout and leadership breakdowns to rebuilding a stronger team and creating a business designed to support both growth and life outside of work. What you’ll learn in this episode: (00:01:57) How one leadership decision triggered a chain reaction that led to an entire team walking out. (00:03:28) What Kara would have done differently when firing a key employee and why it mattered. (00:04:59) Why lack of communication can quietly build toward a full leadership breakdown. (00:07:30) How to stabilize your business when everything is falling apart at once. (00:08:50) What it really means when your business can operate without key team members. (00:09:35) How the wrong team can cut your profitability in half, and the impact of fixing it. (00:11:51) Why investing in the right people is often the decision you can’t afford to avoid. (00:20:12) The hidden personal cost of building a business without the right support system. Learn more about Kara Roberts and Pepper's Personal Assistants: https://paseattle.com/ Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E5
    May 5 · 56 min

    When Growth Starts Stealing From Your Family | Ben Glass, Founder, CEO, BenGlassLaw

    How do you know when your business is stealing from your life? As Ben Glass built a thriving law firm through relentless marketing and reputation, the success didn’t just grow the business; it trapped him inside it, consuming his time and pulling him away from his family. The pressure escalated as more clients poured in, chaos multiplied, and every decision bottlenecked at his desk, forcing him to confront the reality that he had built something that couldn’t scale without breaking him. You’ll hear how he rebuilt the firm from the inside out, handing off control, restructuring leadership, and ultimately proving the system worked when a life-threatening surgery forced him out, and the business didn’t miss him. Ben Glass is a longtime personal injury attorney who’s spent over 40 years in the courtroom, but his real focus has been learning how to build a business that doesn’t consume your life. He started out on his own, made plenty of mistakes along the way, and eventually figured out how to grow a firm that can run without him at the center of everything. Today, he not only leads Ben Glass Law but also helps other lawyers step out of survival mode and build businesses that actually support their lives, not take them over. What you’ll learn in this episode: (00:01:36) How early success exposed a lack of business knowledge and created hidden fragility. (00:04:36) Why mastering marketing first can create an entirely new operational crisis. (00:09:01) How growth forced impossible tradeoffs and began stealing time from family. (00:11:20) Why trying to self-implement systems often fails without outside help. (00:14:05) How bringing in the right operators can turn chaos into structure. (00:18:39) What it really takes to give up control—even to your own family. (00:27:38) Why holding onto the wrong people can quietly stall your company’s growth. (00:40:04) How a sudden health crisis proved whether the business could survive without you. Learn more about Ben Glass and Ben Glass Law: https://www.benglasslaw.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E4
    April 28 · 47 min

    When You’re Forced to Lead Before You’re Ready | Avery Ward, CEO of Little Italy Ristorante

    How do you step into leadership when you’re completely unprepared? As Avery Ward stepped back into his family’s restaurant, what looked like a beloved community staple was quietly unraveling beneath the surface. With his father incapacitated, no systems in place, and the business spiraling toward collapse, Avery found himself working 80-hour weeks just to keep the doors open while questioning if any of it was sustainable. You’ll hear how that breaking point forced him to rebuild everything from leadership to systems to trust and transform a fragile operation into a scalable business. What you’ll learn in this episode: (00:02:45) Why a lack of systems left the company facing bankruptcy, sale, or closure. (00:04:45) How stepping into leadership at 21 revealed deeper operational failures. (00:07:20) What happens when culture breaks down, and standards disappear. (00:10:30) Why doing everything yourself creates a ceiling you can’t escape. (00:12:30) How simple systems like checklists can radically improve consistency and training. (00:17:50) The mindset shift required to move from operator to true leader. (00:21:30) Why learning to let go and build structure is the key to sustainable growth. Thank you to Avery for being on our show! Learn more about Avery Ward and Little Italy Ristorante: https://www.littleitalygroveport.com/ Get a grip on your business with Traction by Gino Wickman—the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library Tap into the ENRG of entrepreneurs growing together. Join a local chapter (75+ cities + virtual) and gain connections, community, and access to the EOS Conference to help your business thrive. Get connected here: https://enrg.life/locations/ Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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  • S1 · E3
    April 21 · 57 min

    How Success Nearly Destroyed Their Friendship | Al Alexander & Ryan Loos of ConEquip

    How do you handle resentment when your partners aren’t carrying the same weight? As ConEquip scaled into a nine-figure company, the pressure didn’t just grow the business; it exposed cracks in control, communication, and trust. One founder was ready to walk away, the partnership was strained, and the weight of leadership started bleeding into their personal lives. You’ll hear how they faced those moments head-on, brought in outside help, and rebuilt not just the business, but their relationship with each other. Al Alexander is a co-founder of ConEquip, a leading supplier of heavy equipment parts. He leads the company’s vision, marketing, and culture, and has played a key role in scaling the business from a small startup into a nine-figure company. Al is passionate about building people, developing leaders, and creating a workplace where core values actually drive decisions. Ryan Loos is a co-founder of ConEquip and leads the company’s financial strategy and operational structure. Originally brought in as a consultant, Ryan became a partner and helped bring the discipline, systems, and accountability needed to scale the business. He’s known for turning ideas into executable processes and helping teams move from chaos to clarity. What you’ll learn in this episode: (00:04:57) How shifting from working in the business to working on it unlocked scalable growth. (00:06:20) Why delegation feels risky at first and how hiring your first employee changes everything. (00:10:50) The moment a consultant became a full-time partner and transformed the company’s trajectory. (00:16:13) What it looks like when each founder hits their personal ceiling and tension starts to build. (00:19:17) How refusing to let go of control can become the biggest obstacle to growth. (00:24:36) Why making decisions at 60–75% certainty can accelerate growth faster than waiting for perfection. (00:35:37) How outside counsel and hard conversations rebuilt trust and saved the partnership. Learn more about ConEquip: https://conequip.com Get a grip on your business with Traction by Gino Wickman, the proven system to help you gain clarity, accountability, and results. Learn more: https://www.eosworldwide.com/traction-library This episode was sponsored by ENRG, the community where leaders like you find connection—and the who’s and the how’s—to make your businesses thrive. Tap into the ENRG of entrepreneurs growing together by joining a local chapter (75+ cities + virtual) and gain connections, community, access to the EOS Conference, and more. Get connected here: https://enrg.life/locations/ Subscribe to Clarity Break Thoughts (https://claritybreakthoughts.com/) Follow the show on your favorite platform: www.eosworldwide.com/htc This episode was produced by Story On Media: https://www.storyon.co/

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