Hitting The Ceiling

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

    5 hr ago

    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/

    53 min
  2. The Dark Side of Public Leadership | Paul TenHaken, Mayor of Sioux Falls, SD

    16 Jun

    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/

    1hr 2min
  3. The Twenty Days That Changed Everything | Lindsay Joss Iudicello, Owner & President of Botanie Soap

    9 Jun

    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/

    48 min
  4. The Problem AI Can Never Solve | Patrick Lencioni, founder of The Table Group

    2 Jun

    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/

    51 min
  5. When Growth Breaks Everything You Built | Rob Hughes, MBA, IMC CEO of Hughes Integrated

    26 May

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

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

    19 May

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

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

    12 May

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

    36 min
  8. When Growth Starts Stealing From Your Family | Ben Glass, Founder, CEO, BenGlassLaw

    5 May

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

    1hr 15min
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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
    2k
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © 2026 EOS Worldwide
  • Show Website
    Hitting The Ceiling

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