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 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/

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.

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/

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 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/