Hitting The Ceiling
Hitting The Ceiling is a podcast for entrepreneurs and business leaders, hosted by Mark O'Donnell. It explores the untold stories behind business growth, focusing on the personal struggles and challenges that leaders face. The show discusses the Five Leadership Disciplines to help break through ceilings and achieve success. New episodes are released weekly.
Episodes
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 b
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 responsibilitie
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 b
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
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 expl
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
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 financia
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
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
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
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 tho
The Power of Simplifying When Everything Collapses | Sue Hawkes, CEO of YESS!
How do you keep showing up when you feel like a complete fraud?
As Sue Hawkes, CEO of YESS!, built a career helping leaders find clarity, her own life was quietly unraveling behind the scenes. Her businesses were struggling, her family was facing devastating loss, and a single unopened letter revealed she was about to lose her home. You’ll hear how she navigated that breaking point in real tim
What Happens When You Are the System | Jill Young, Creator of Coaching Magic
What signs are you ignoring before everything breaks?
As Jill Young’s accounting firm grew and won awards, the success masked a deeper issue: everything depended on her. When she lost her top employee and biggest client on the same day, the pressure didn’t just shake the business; it exposed a system that had never been built to run without her. You’ll hear how she faced that breaking point, cha
Welcome to Hitting The Ceiling, a Business Podcast from 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 th
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