Dan Sullivan of Strategic Coach And Steve Krein of StartUp Health
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What is a Free Zone Frontier? You enter into a Free Zone when you increasingly create unique collaborative possibilities and payoffs that are amazingly free of competition. Join Dan Sullivan of Strategic Coach and Steve Krein of StartUp Health as they launch the Free Zone Frontier podcast. Learn the concepts as they relate to their own companies, and how this transformative mindset is the future of entrepreneurial growth.
Based on 6 episodes we listened to · September 2026
Dan Sullivan and Steve Krein make entrepreneurial frameworks concrete through questioning, company examples and sustained attention to how operators think.
Free Zone Frontier turns entrepreneurial frameworks into working conversations. Dan Sullivan and Steve Krein test ideas against company growth, team incentives, long-range planning and decision-making under uncertainty.
A 25-year ambition gets quarterly checkpoints, if you're ready to stop treating goals like New Year's decorations.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A longevity conversation that treats aging as a business problem as much as a medical one.
Stephen Krein and Dan Sullivan frame age reversal as a practical business question: how can entrepreneurs keep performing at a high level well past the usual retirement script?
A clear reminder that strong messaging holds up best when it matches what people actually experience.
The piece draws a clean line between what someone says they do and what others can point to after the fact. Dan Sullivan and Steve use Strategic Coach's When Are You Great?
Capitalism is framed as a system of flywheels, accountability, and following talent.
The episode treats capitalism as something to pick apart, not just praise or condemn. Stephen Krein and Dan Sullivan use Capitalism and Everything Else to talk through flywheels, accountability, and how entrepreneurial effort gets organized inside a company or a network.
A business conversation about ambition, technology, envy, and building around unique ability.
The episode frames ambition as something tested by pressure: new technology keeps opening doors, while envy, the pull of the past, and status thinking keep tugging in the opposite direction.
A thoughtful look at values, fit, and the decisions they shape.
The episode treats core values as a working tool, not a slogan. Steven Krein and Dan Sullivan keep coming back to how those values shape hiring, firing, customer choices, product calls, and the smaller decisions that keep an organization lined up.
A grounded AI-and-entrepreneurship conversation about leverage, speed, and staying relevant.
Free Zone Frontier treats AI as a practical lever for entrepreneurship rather than a shiny add-on. It centers on Lior Weinstein, the warning that being good at everything can turn into a weakness, and a framework built around "Your Life as a Single Project" and the questions…
A loose but useful discussion of how communities keep people engaged.
Free Zone Frontier uses Barry Manilow's concert as a starting point for a practical talk about community. Dan Sullivan and Steve Krein move from entertainers and entrepreneurs to the wider circles around EO, YPO, Scaling Up, Tony Robbins events, and Michael Gerber's E-myth.
A clear reminder that easy offers usually beat better arguments.
Steven Krein and Dan Sullivan use this episode to make a simple point: convincing arguments matter less than offers people can actually say yes to. They ground that idea in FreeZone workshop talk, then make it concrete with Apple Watch rings and Insight Tracker.
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
Naval Ravikant on epistemology, startups, and crypto, from David Deutsch to Vitalik Buterin.
Alex Theuma interviews SaaS founders and investors on scaling to $10M-plus ARR.
Guy Raz traces founders' origin stories and fields live advice-line calls from entrepreneurs.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
Twenty-five years turns into a planning horizon you can actually hold.
Stephen Krein opens the conversation with Dan Sullivan around a simple but loaded question: why age reversal now, and why should entrepreneurs care?
Dan Sullivan says Strategic Coach’s thinking tools came out of 50 years of coaching entrepreneurs, not theory, and he traces one tool to a London hotel break-in that forced him to rewrite a book in one week.
Dan Sullivan links entrepreneurial hiring to theater casting, saying the shift is from “a new cost item on their balance sheet” to building a cast that works together.
Stephen Crine and Dan Sullivan frame FreeZone Frontiering as “collaborative” and “competition-free,” then use Apple, Amazon, and the U.S.
Dan Sullivan says the core of his work is a VOTA pattern — vision, obstacles, transformation, and action — and he credits Catherine Nomura with helping name it during a walk on the beach in Carmel, California.
Dan Sullivan and Steve Krein explore how entrepreneurs can cultivate ambition through innovative time systems and resilience.
Ambition is a muscle that grows stronger with challenge, not a depleting tank
Stephen Krein and Dan Sullivan talk through CoachCon, a first-time conference built around Strategic Coach’s 35th company anniversary, Sullivan’s 50 years of coaching, and his 80th birthday year.
Steven Krein starts with a laid-back update after getting away with college friends to a beautiful lake outside Atlanta.
Dan Sullivan opens by framing Free Zone Frontier around entrepreneurial collaboration.
Dan Sullivan opens with Steve Krein and a 4x4 casting tool.
Stephen Krein opens with Dan Sullivan on ambition, technology, and the idea that the future should keep stretching what entrepreneurs believe is possible.
Dan Sullivan and Steve Krein explore the power of shared language in building entrepreneurial communities, drawing parallels from Barry Manilow's concert engagement.
Key insight from segment 5
Dan Sullivan and Steve Prine discuss how to approach annual planning by leveraging the best of your past experiences and consistent successes to build a predictable future.
Key insight from segment 5
Dan Sullivan and Steve Krein discuss the pushback against digital incursions, exploring how hybrid models in work, education, and daily life offer better optionality.
Dan Sullivan and Steve Krein keep circling back to Lior Weinstein’s habit of being good at nearly everything he tries.
Dan Sullivan and Steve open with a tool called When Are You Great?.
Dan Sullivan and Steve Krein sit down with Lior Weinstein for a grounded conversation about how growth actually happens.
Dan Sullivan and Steve Krein discuss the 'When Are You Great?' tool, which helps entrepreneurs distinguish between telling clients what they do (good) and sharing what clients say about their impact (great).
Dan Sullivan and Steve Krein explore the future of entrepreneurship, discussing how technological shifts like microchips and AI have empowered founders.
Stephen Krein opens by framing Dan Sullivan's new book, *Capitalism and Everything Else*.
Dan Sullivan opens by describing a world that feels economically, politically, and culturally unsettled.
The episode opens at the shore.
Steven Krein opens by saying he has been thinking hard about core values in his organization and his family.