How to Move from Employee to Business Owner
Measure Success Podcast
In this episode, Carl speaks with Jon Ostenson about franchising, business ownership, and the shift happening in today’s workforce. As AI reshapes jobs, many professionals are exploring ways to build their own income streams. Jon shares what he sees across the market and what separates successful business owners from those who struggle. Key takeaways include: • Why following a proven system matters • The role of mindset in business success • How “non-sexy” businesses can drive strong returns • What to expect when transitioning from employee to owner This episode gives a clear...
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Why Leaders Burn Out and How to Prevent It
Measure Success Podcast
In this episode of the Measure Success Podcast, Carl J. Cox speaks with Dr. Tracy Gapin, founder of the Gapin Institute and a leading expert in executive health and performance. After years of success in traditional medicine, Dr. Gapin realized that many high-performing professionals were neglecting their own health while pursuing business success. The conversation explores how stress, poor sleep, hormones, and lifestyle habits affect leadership performance and long-term health. Key takeaways include: • Why many entrepreneurs wait until health problems appear • How small daily habits...
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How to Actually Use AI to Scale Smarter
Measure Success Podcast
In this episode of the Measure Success Podcast, Carl J. Cox sits down with business strategist and performance coach Ashley Shaw. Ashley shares how she transitioned from the fitness industry into entrepreneurship and built a thriving business focused on helping entrepreneurs scale smarter through systems, recurring revenue, and AI-driven processes. Key insights from this episode include: • Why entrepreneurs must deeply understand their ideal customer • How recurring revenue creates financial freedom • The role mindset plays in scaling a business • How Ashley reduced marketing...
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Tariffs, Energy, and AI: Economic Signals to Watch
Measure Success Podcast
Economic headlines move fast. Strategy requires context. In this episode of the Measure Success Podcast, Carl J. Cox speaks with economist about the trends shaping business decisions today. The conversation covers tariffs, supply chain strategy, artificial intelligence, workforce shifts, and energy markets. Dr. Connerly explains why tariffs rarely trigger immediate recession but can reshape sourcing decisions across industries. Companies are shifting toward supply chain reliability after years of disruption. The episode also explores the real impact of AI in business. The greatest...
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How to Build a Reputation in Business
Measure Success Podcast
In this episode of the Measure Success Podcast, Carl J. Cox speaks with Steve Griggs, founder of Steve Griggs Design, one of New York City’s premier luxury landscape design-build firms. Steve shares how he built a successful company after starting in the lawn care business at age 16. With more than 30 years of experience, he explains what it takes to manage high expectations, lead construction teams, and deliver exceptional results. Key takeaways include: • Why successful clients value honesty and execution • How focusing on one project at a time improves outcomes • The...
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Startup Strategy in an AI-Driven World
Measure Success Podcast
AI is accelerating innovation—but it is not a substitute for strategy. In this episode, Carl J. Cox speaks with Josh Carter, co-founder of Upstart Collective, about what founders must understand to build sustainable companies. Josh shares insights from working with early-stage startups, including why chasing trends weakens businesses and how defensible value is created. The conversation covers AI misuse, founder blind spots, customer discovery, fundraising realities, and why execution still separates winners from noise. This episode is a must-listen for founders, operators, and leaders...
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The Truth About Business Valuation and Risk
Measure Success Podcast
Selling a business is not a simple transaction. It is a strategic event that often defines an owner’s financial future. In this episode, Carl J. Cox speaks with Gregory Kovsky, President and CEO of International Business Associates, about what it really takes to sell a privately held business. Gregory shares insights from more than three decades of deal experience, including why only a fraction of businesses ever sell and what separates those that do. The discussion covers buyer demand, valuation mistakes, financing hurdles, and the risks behind earn-outs and retained equity. This episode is...
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How to Turn Around Strategy for Businesses
Measure Success Podcast
In this episode, Carl sits down with Ashish Gupta, founder of ScaleUp Exec, to discuss business turnarounds, leadership decisions, and culture resets. Ashish shares how he acquired a struggling company, realized innovation had stopped, and eventually rebuilt the team to change the company’s trajectory. Key takeaways: Why the business must come first How to identify thinking leaders during interviews The role of systems before people and process When AI tools help — and when they fail How founders define success differently This episode offers practical insights for...
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Big Bet Leadership in the Age of AI
Measure Success Podcast
High-stakes initiatives fail more than 80% of the time, yet leaders still have to pursue them to grow. In this episode of the Measure Success Podcast, Carl J. Cox talks with John Rossman, former Amazon executive and author of Big Bet Leadership, about how leaders should approach bold, risky transformation efforts in the age of AI. John shares why leaders must stop chasing predictability, treat strategy as a set of hypotheses, and focus on one critical bet at a time. The discussion covers AI strategy, experimentation, leadership discipline, and how organizations avoid dilution of focus....
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Why Most AI Efforts Miss the Mark
Measure Success Podcast
AI is everywhere, but most businesses are using it the wrong way. In this episode of the Measure Success Podcast, Carl J. Cox sits down with Eli Portnoy, co-founder and CEO of BackEngine.ai, to talk about the real gap between AI hype and real-world results. Eli explains why generic AI outputs fail, why context matters more than tools, and how sales and go-to-market strategies must evolve in a crowded, low-trust environment. They also discuss how outbound sales has changed, why easy channels stop working, and what leaders can do today to build relevance, trust, and long-term growth. If you want...
info_outlineOn this episode of the Measure Success Podcast, Carl J. Cox sits down with Lubo Smid, co-founder and CEO of STRV, a tech company building digital products for renowned brands. Lubo shares his insights on the pivotal role of AI, Web3, and agile strategies in driving business growth.
Explore how STRV empowers clients, from startups to household names, to scale and succeed by focusing on impactful technology solutions. Learn why staying ahead with AI is critical in today’s market.
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📖 Read Carl’s book "Lost at CEO: An Entrepreneur’s Guide to Strategy": https://a.co/d/iMiZVf2