212: Embracing Smart Risks, Casey Cheshire - The Entrepreneur Gene Series
Release Date: 08/26/2025
Succession Stories
"Exit planning is good business, not just about exits. Doing exit planning is going to help your business today." Too many founder CEOs pour years into scaling their company without ever building a plan for what comes next — and it costs them. Bruce Eckfeldt is a former Inc. 500 CEO who scaled, led, and exited his own company, and now coaches founder CEOs to do the same with intention. He faced the reality of an unplanned post-exit life firsthand — and what he discovered changed how he coaches everyone who comes after him. Key Insights: Exit planning improves your business today,...
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"The day you start your business, you should know your exit strategy." Host Laurie Barkman sits down with Amy Veltri, Co-Founder and CEO of NGE, an environmental and geotechnical engineering firm. Amy built the company with her brother nearly 20 years ago, and made the deliberate choice to transition to 100% employee ownership through an ESOP. Amy shares the personal journey of weighing a third-party sale, doing nothing, or choosing a path that protected the people who helped build the business. Celebrating 6 Years of Succession Stories This episode is part of a special...
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“Profitability rewards the founder. Transferability rewards the future.” In many founder-led businesses — especially those under $10 million — the owner is the strategy, the rainmaker, and the decision-maker. But what happens when the business can’t operate without you? In this episode of Succession Stories, Laurie Barkman is joined by Steve Preda, Founder, Summit OS Group, to explore the role of structural capital in succession planning and exit readiness. They unpack the difference between building a profitable business and building a transferable one — and why reducing owner...
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"No one's promised tomorrow." Host Laurie Barkman talks with Scott Arden, Chairman of Controllers Ltd and Managing Partner of Generational Wealth Solutions, about the intricacies of financial strategies for business owners. Controllers Limited focuses on advanced strategies for asset protection and generational wealth. Focusing on growth, succession planning, and the importance of legacy, Scott emphasizes the need for business owners to prepare for transitions, whether through exit strategies or succession planning, and highlights the significance of teaching financial literacy to future...
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🎙️ Business growth and succession planning start long before an exit. In this special Succession Stories swapcast, Laurie Barkman introduces the B.U.I.L.T.™ Method, a practical framework for building value and preparing for business transition. 🔓 This episode features Laurie’s guest appearance on The B2B Growth Podcast with Mark Osborne, where the mic is turned around and she shares the thinking behind the B.U.I.L.T.™ Method for Business Growth and Transition. Designed for founder-led and closely held companies, the framework helps owners reduce dependency on themselves,...
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In this episode, Laurie Barkman is joined by Dr. Brianna Rhue, optometrist, entrepreneur, and co-founder of Dr Contact Lens. Brianna shares her journey from a private practice owner to a tech maven, driven by the need to solve a critical "leaky bucket" problem: doctors losing contact lens sales to online retailers. She discusses the "entrepreneurial gene", the power of a "chip on your shoulder", and the lessons learned in building a full-blown tech platform from scratch. 💬 Quote from Brianna: “You have to get a really thick skin... as an entrepreneur, you are going to pave roads and...
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🎧 Tune in to learn the realities of entrepreneurship through acquisition, from the search process to surviving economic uncertainty in the first year. Laurie Barkman sits down with Aashay Kumar, owner of Tri-Form, Inc. Aashay shares his story of leaving a corporate career to buy an existing manufacturing business. He demystifies the process of entrepreneurship through acquisition. Listen in as Aashay reflects on his acquisition journey including stealth search process, securing an SBA loan, diligence misses, and the ups and downs of the first 15 months of ownership. 💬Quote from...
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What does it take to finance a business transition or acquisition? In this episode, Laurie Barkman sits down with David Miller, Executive Vice President at Enterprise Bank, to demystify lending for business owners — from SBA loans to insider buyouts. David shares how banks assess deals, why management continuity matters most, and how entrepreneurs can become “bankable” when it’s time to grow or exit. 💬 Quote from David Miller: “Don’t think you can’t buy a business just because you’re not personally wealthy. If you have the right skillset and knowledge of the industry, there...
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Host Laurie Barkman welcomes Brandon Stanchock, CEO of SWF Industrial Inc. Brandon discusses his journey to take the helm of a family business. He emphasizes the importance of leadership, employee development, and implementing innovative collaboration strategies in the industrial sector. The conversation also highlights Brandon's commitment to providing support for employees and internal promotion programs. Brandon shares how his personal interests in travel, gaming, and podcasting align with his broader mission to help people reach their full potential both inside and outside the workplace....
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Host Laurie Barkman welcomes Larry Whiteside Jr., an expert in information security, risk management, and entrepreneurship. Larry discusses his journey from cybersecurity to becoming the Co-Owner of Lifesaver Pool Fence of Tampa and Co-Founder of Confide. Larry emphasizes the importance of passion, operational efficiency, and overcoming challenges in business. They delve into key trends in cybersecurity, focusing on AI and automation’s growing influence. The conversation also highlights Larry’s commitment to promoting diversity in the cybersecurity field and how his military...
info_outline“ 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:
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Focus on creating meaningful relationships through various mediums to foster long-term success.
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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.
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Take calculated, smart risks rather than reckless ones.
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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 Casey Cheshire:
LinkedIn: in/caseycheshire
Website: ringmaster.com