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212: Embracing Smart Risks, Casey Cheshire - The Entrepreneur Gene Series

Author
Laurie Barkman
Published
Tue 26 Aug 2025
Episode Link
https://successionstories.libsyn.com/212-embracing-smart-risks-casey-cheshire-the-entrepreneur-gene-series

“ The flip of one-to-one communication to a one-to-few communication is going to become priceless. It's all about connection.” - Casey Cheshire

What kinds of risks are the ones worth taking when it comes to entrepreneurship? Casey Cheshire, CEO of Ringmaster Conversational Marketing, believes smart risks are the key to success. 

Host Laurie Barkman talks with Casey about the importance of risk tolerance, learning from failures, and the need for smart risk-taking in business. They also explore the future of marketing with the advent of AI and the significance of maintaining human connections in an increasingly automated world.

Casey's military background, personal entrepreneurial journey, and passion for authentic marketing strategies provide a rich and engaging discussion on what it truly means to be an entrepreneur.

 Takeaways:

  • Focus on creating meaningful relationships through various mediums to foster long-term success.

  • View entrepreneurship as a muscle that can be developed with practice and effort. Engage in activities that build skills necessary for entrepreneurship, such as problem-solving and risk management.

  • Take calculated, smart risks rather than reckless ones.

  • Although challenging, niching down can lead to better targeting and business efficiency. Test narrow focuses to see if they drive better results without betting the farm.

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 _________________________________________________________________   Connect with Laurie Barkman:  Email: [email protected] LinkedIn: in/lauriebarkman Book: Free Download YouTube: @TheBusinessTransitionSherpa  Connect with Casey Cheshire:

LinkedIn: in/caseycheshire

Website: ringmaster.com 

 

 

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