Episodes

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.

Eric V. Holtzclaw built his career turning ideas into businesses: launching Liger Partners (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 leave 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.

Jonathan Reynolds built Titus Talent Strategies on a simple, stubborn belief: Get the Right People in the Right Seats, and genuinely care about them, and everything else will follow. But as the company grew past what just one person could hold, that belief started to crack under its own weight. The pressure to personally know everyone, stay central to every decision, protect a culture he built, and keep proving his worth exposed something harder to face: What if the healthiest version of Titus Talent needed him… less?

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.

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.

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.

What happens when the business you inherited starts falling apart before you’ve 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 passed away from cancer, and the future of the company was suddenly in question.

Pest control has been in Brenton Cloud’s family since 1934, but building something of his own meant leaving the family business, selling a nearly paid-off house, and betting everything on Greenhouse. The company exploded to about $10 million in roughly three years, but the growth created new problems: too many accounts, too many hires, too many trucks, and a painful realization that success was costing him time with his children.

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.

Chad 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.

As Chase Calhoun went 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.

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 lay cash flow panic, purpose stagnation, and the weight of stepping into public leadership. A meaningful conversation with his wife, a political smear days before an election, and the uncertainty 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, community, and the greater good.

Botanie Soap 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 once 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.

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 Robert Hughes scaled his company 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 volatility 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 resilient leadership actually requires.

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?

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 implosion, 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.

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.

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.

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.

As Sue Hawkes 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 time, simplified everything down to what truly mattered, and rebuilt her life and leadership from the ground up.

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, challenged everything she thought she knew about leadership, and rebuilt the business around systems instead of herself.