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
Nobody Is Coming to Save You
How do you stop carrying everything when being the reliable one has become part of your identity?
Clay Harris learned early not to wait for someone else to fix things. His father was mostly absent, his mother was raising him on her own, and one of the adults who believed in him most was a high school teacher who would simply point to a banner at the front of the classroom that read, “Look inside y
You Can't Save Your Team From Themselves
How do you keep leading when every new stage of growth exposes skills you don’t have yet
Shannon Badger helped grow Badger CPA from nothing into a 60-person firm, but behind the inspiring growth story was a founder learning in real time how much a business can take from your confidence, marriage, health, parenting, and sense of control. As the firm scaled, Shannon and her husband Jonathan remortga
When Your Dream Starts Depending on Your Name | Ryan Hawk of The Learning Leader Show
When does your personal brand become the ceiling on your company?
Ryan Hawk built his life around hard work, competition, and consistency, but losing the quarterback job to Ben Roethlisberger forced him to confront an uncomfortable truth: sometimes effort alone cannot change the outcome. Years later, he walked away from a successful corporate career to turn The Learning Leader Show into a business
When Your Business Starts Owning You
How long should you tolerate “growing pains” before admitting the way you are operating is not working?
Brock Beiersdoerfer and his wife Kimberly opened The Heavenly Donut Company hoping to build something meaningful, but the business soon had Brock working brutal hours, worrying about payroll, covering overnight shifts, and watching the freedom they wanted disappear. The pressure peaked in mome
How to Rewire Your Working-Class Mindset
How much of your business is actually being run by the eight-year-old version of you?
Kieran James built Stryde from the ground up, but the real story starts earlier than that: a working-class childhood where food got stretched with oats and money was never quite enough. That scarcity mindset didn't stay in his childhood home — it followed him into every pricing conversation, every hiring decision
This is What It Takes to be the "Hardest Worker"
What happens when the drive to succeed becomes the very thing holding you and your business back?
Glen Smith built GDS Wealth Management from relentless cold calls and early financial uncertainty into a firm managing roughly $1.8 billion. But behind that business growth was a fear of failure that shaped nearly every decision he made, pushing him to work harder, hold on tighter, and believe that
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
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 diffi
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 expos
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
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
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
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, Mic
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 create
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 e
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
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 day
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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