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Win Win - An Entrepreneurial Community

Win Win - An Entrepreneurial Community

Released: 2025-04-08
© Copyright Fractional Leadership LLC
Win Win - An Entrepreneurial Community - QR Code
198 Episodes
Audio
Listen on Apple Podcasts
198 Episodes
Audio
Listen on Apple Podcasts
Released: 2025-04-08
© Copyright Fractional Leadership LLC
Most Recent Episode
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

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;
Time: 1:15:10
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!
Episode ID: 1000702712461
GUID: EBMSLY4-LSKU1H5M
Release Date: 08/04/2025, 19:50:49

Description

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.

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