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Win Win - An Entrepreneurial Community

Win Win - An Entrepreneurial Community

Written by: Fractional Leadership LLC
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 Win Win - An Entrepreneurial Community is where successful entrepreneurs share how they accomplish the tricky parts of growing their business so everyone in the community (that’s you!) can do the same. Topics range from how to hire good people in a scalable way, branding, marketing, baking your values and culture into the whole team, to learning how to scale the business. Whether your business is a startup or multi-million dollar business, our host and guests teach tools you can use in every episode. Your host is Ben Wolf, a native Nashvillian currently living in Long Island, NY. Ben practiced industrial real estate brokerage and then went on to go to law school at night and practice as a corporate restructuring and bankruptcy attorney for five years in New York City. He then joined a visionary entrepreneur to help him create a mission-driven, technology powered healthcare startup in the home care space. Using the principles and tools of the Entrepreneurial Operating System (EOS®), he was the company’s Chief Development Officer, building up the majority of its operational divisions and leading a variety of projects until, after three years, it was the largest and fastest growing organization of its type in the State. Now, as Chief Integration Officer at Wolf’s Edge Consulting, Ben liberates founders of entrepreneurial businesses (“trapped Visionaries”) to help them return to the parts of the business they love while executing on their vision using EOS tools. You can read more about that at www.wolfsedgeintegrators.com. The Win Win podcast creates a venue where successful entrepreneurs can pay it forward by sharing actionable information, tools, and knowledge that other members of the entrepreneurial community can immediately put into action in their own businesses.Copyright Fractional Leadership LLC Economics Leadership Management Management & Leadership Politics & Government
Episodes
  • 199 - Replacing Your #2 Leader the Right Way - Mark Mahoney, Cyndi Gave, and April Stercula

    199 - Replacing Your #2 Leader the Right Way - Mark Mahoney, Cyndi Gave, and April Stercula
    Apr 8 2025
    What happens when a visionary hits a wall—and decides it’s time to hand off the reins? In this powerful episode of Win-Win, Ben Wolf sits down with Mark Mahoney, co-founder and CEO of Jackrabbit Technologies; Cyndi Gave, founder of The Metis Group; and April Stercula, Fractional COO at Wolf’s Edge Integrators, to unpack the full story of Jackrabbit’s transition through two Integrator hires. From Mark’s early burnout and the fear of changing reporting structures, to the processes that helped define the visionary and integrator roles clearly, this conversation dives into what it really takes to scale a company without losing its soul. You’ll learn how Jackrabbit used EOS, behavioral science, and fractional leadership to gain clarity, maintain culture, and move forward with confidence. Whether you’re navigating a leadership transition or wondering if a fractional integrator could help your team, this one’s packed with hard-earned insights and inspiration. 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607) or your favorite podcast platform!
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    1 hr and 15 mins
  • 198 - How Fractional CFOs and COOs Work Together to Scale Businesses - Kevin Mayo

    198 - How Fractional CFOs and COOs Work Together to Scale Businesses - Kevin Mayo
    Mar 11 2025
    Scaling a business requires financial clarity and operational execution, but what happens when both are led by fractional executives? In this episode of The Win-Win Podcast, Kevin Mayo, Partner at Fintech Partners, joins Ben Wolf to uncover how fractional CFOs, CIOs, and COOs work together to create financial stability, operational alignment, and strategic growth. Kevin shares how finance and operations need to function in sync to drive business success, the biggest financial mistakes business owners make, and why implementing a structured operating system like EOS® changes everything. They also discuss the hidden role of data in connecting leadership, sales, and manufacturing, and how businesses can scale efficiently without hiring full-time executives. If you’re considering fractional leadership, struggling with financial clarity, or want to understand how finance and operations work together, this episode is packed with insights you can’t afford to miss. 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607) or your favorite podcast platform!
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    33 mins
  • 197 - How to 10x a Business Internationally (Without Costly Mistakes!) - Pete Palermo

    197 - How to 10x a Business Internationally (Without Costly Mistakes!) - Pete Palermo
    Feb 18 2025
    In this episode of the Win-Win Podcast, Ben Wolf sits down with Pete Palermo, Fractional Integrator at Wolf’s Edge Integrators, to discuss the complexities of scaling a global business. Pete brings decades of experience working in Fortune 25 companies and helping businesses expand across international markets. 🌍 In this episode, Pete talks about: ✅ The biggest mistakes companies make when expanding internationally ✅ How to maintain company culture and core values across different countries ✅ Why the right local leadership makes or breaks global success ✅ How to adapt operations for different economic and political landscapes Pete shares real-world experiences from working in Japan, China, and Europe, highlighting how cultural norms affect decision-making, leadership styles, and business strategy. Whether you’re expanding into new markets or managing a multinational team, this episode is packed with insights! 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607) or your favorite podcast platform!
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    35 mins
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