Podcast
Measure Success Podcast
Hosted by Carl J. Cox · EN
This is the Measure Success Podcast, which features top leaders on how they measure success in their business and life. We talk with CEOs, entrepreneurs, authors, and extraordinary high achievers.
The host, Carl J. Cox, is the CEO of 40 Strategy. 40 Strategy guides leaders to take their organization to the next level by designing world-class strategic plans and keeping them accountable to get it done. Go to 40strategy.com to learn more. As an entrepreneur and executive, Carl has been with 7 different companies that have grown from 2x to 7x.
Carl is the author of Lost at CEO, An Entrepreneur's Guide to Strategy. This book reached #1 Amazon bestseller in 12 separate categories at launch, and a must-read for entrepreneurs and leaders.
43episodes
Episodes
Newest firstAll episodes
Tariffs, Energy, and AI: Economic Signals to Watch
Mar 1700:39:20Tap to summarizeEconomic headlines move fast. Strategy requires context. In this episode of the Measure Success Podcast, Carl J. Cox speaks with economist Dr. Bill Connerly 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 productivity gains will come from specialized tools built for specific problems, not just general AI chat systems. Carl and Bill also discuss energy disruption, global uncertainty, and what business leaders should watch as they plan for the next decade. Listen to the episode and consider how economic signals shape your strategy. Author of the book: The Flexible Stance: Thriving in a Boom/Bust Economy Website www.conerlyconsulting.com
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How to Build a Reputation in Business
Mar 1000:28:29Tap to summarizeIn 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 importance of respect and leadership on job sites • Why entrepreneurs must embrace visibility and personal branding Steve also shares lessons about hiring, leadership, and the importance of being present for family. Listen to the episode to learn how strong leadership and consistent execution build lasting success. Guest Assets: LinkedIn https://www.linkedin.com/in/stevegriggsdesign/ Facebook https://www.facebook.com/SteveGriggsDesign Instagram https://www.instagram.com/stevegriggsdesign/ Twitter https://twitter.com/stevegriggsdsgn Website https://stevegriggsdesign.com/
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Startup Strategy in an AI-Driven World
Mar 300:40:34Tap to summarizeAI 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 navigating innovation pressure. Listen now and rethink how you build for long-term value. Josh's LinkedIn https://www.linkedin.com/in/joshuajcarter/ Josh's Website http://upstartcollective.org
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The Truth About Business Valuation and Risk
Feb 2400:33:21Tap to summarizeSelling 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 essential listening for owners who want to understand their options before going to market. Listen now and start planning your exit with clarity. LinkedIn https://www.linkedin.com/in/gregory-kovsky-460aab7/ Website https://ibainc.com/
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How to Turn Around Strategy for Businesses
Feb 1700:31:10Tap to summarizeIn 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 entrepreneurs and operators who want alignment between strategy and execution. Listen now and start measuring your success. Guest Assets: LinkedIn https://www.linkedin.com/in/ashish-gup/ Website https://scaleupexec.com/
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Big Bet Leadership in the Age of AI
Feb 1000:42:03Tap to summarizeHigh-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. This episode is for executives, operators, and entrepreneurs responsible for leading real change. 🎧 Listen now and measure success differently. John Rossman Links: LinkedIn https://www.linkedin.com/in/john-rossman/ Facebook https://www.facebook.com/rossmanpartners Website http://rossmanpartners.com/
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Why Most AI Efforts Miss the Mark
Feb 300:34:58Tap to summarizeAI 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 a clear, practical conversation about AI, strategy, and modern business execution, this episode delivers. Listen now and learn how to apply AI with intention. https://www.linkedin.com/in/eliportnoy/ https://www.backengine.com/
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How To Scale Sales: Avoid Mistakes
Jan 2700:36:36Tap to summarizeThis episode is sponsored by Altezza Solutions, liberating entrepreneurs through fractional sales execution. Today, Steve helps growth-stage companies break through revenue barriers while giving founders the freedom to focus on building extraordinary businesses. Founder-led businesses often grow fast, then stall. In this episode of the Measure Success Podcast, Carl Cox sits down with Steve Caton, Founder and CEO of Altezza Solutions, to discuss why sales becomes the biggest bottleneck for growing companies. Steve shares why hiring salespeople often fails, how founders unintentionally trap themselves in the sales role, and what it takes to build repeatable, predictable sales systems. You'll learn: Why sales talent alone does not solve growth How systems and process drive consistency When fractional sales makes sense How founders can step out of the sales seat If sales depends on you, growth will too. Listen now and measure what success really looks like.
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The Real Truth About Private Equity Growth
Jan 2000:26:06Tap to summarizeSelling to private equity is not the end of the journey. It is the beginning of a new phase of growth. In this episode of the Measure Success Podcast, Carl J. Cox, CEO of 40 Strategy and 40 Accounting sits down with Neel Bhargava, founding partner at NB Group, to unpack how private equity partnerships really work for founder- and family-owned businesses. Neel shares how his firm approaches growth-focused investing, why rolling equity is critical, and how conservative use of debt protects long-term value. The conversation also explores what typically changes in the first 18 months after an investment, including finance, leadership structure, and strategic planning. This episode offers clear insight for founders thinking about private equity and operators preparing for their next stage of scale. Listen now and learn how to build a business that is ready for growth, partnership, and long-term success. https://www.linkedin.com/in/neelbhargava/ www.nbgroup.us
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The Funding Mistake That Kills Deals
Jan 1300:36:01Tap to summarizeIn this episode of the Measure Success Podcast, Carl J Cox sits down with real estate investor and educator Jay Conner to break down private money and why it has been the foundation of his business since 2009. Jay explains how private money works, who private lenders really are, and why having capital ready changes everything about deal execution. He shares a real world case study where preparation and access to funding made a fast, profitable exit possible when traditional financing would have failed. Listeners will learn why mindset matters as much as mechanics, how conservative strategy protects both sides, and why serious operators stop chasing money and start attracting it. If you want more control, less friction, and a cleaner path to growth, this episode delivers a practical framework worth studying. Listen now and learn how strategy shapes results.
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