Hitting The Ceiling

EOS Worldwide
  • 4.5 (11)
  • Entrepreneurship
  • Updated Weekly

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

  1. 1d ago

    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: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  2. Jul 14

    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: https://claritybreakthoughts.com/ Follow the show on your favorite platform: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  3. Jul 7

    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? 🔔  New episodes every week! Subscribe so you don't miss one: http://lnk.to/hittingtheceiling 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 (https://claritybreakthoughts.com/) This episode was produced by Story On Media: https://www.storyon.co/

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

  4. Jun 30

    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 Follow the show on your favorite platform: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  5. Jun 23

    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 Follow the show on your favorite platform: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  6. Jun 16

    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: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  7. Jun 9

    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 Follow the show on your favorite platform: http://lnk.to/hittingtheceiling This episode was produced by Story On Media: https://www.storyon.co/

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

  8. Jun 2

    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: http://lnk.to/hittingtheceiling 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/

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

4.5
out of 5
11 Ratings

About

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

Information

  • Creator
    EOS Worldwide
  • Years Active
    2026
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © 2026 EOS Worldwide
  • Show Website
    Hitting The Ceiling

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