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★★★★★

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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.

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Check latest episodes from Win Win - An Entrepreneurial Community podcast

199 - Replacing Your #2 Leader the Right Way - Mark Mahoney, Cyndi Gave, and April Stercula

2025/04/08

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!

198 - How Fractional CFOs and COOs Work Together to Scale Businesses - Kevin Mayo

2025/03/11

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!

197 - How to 10x a Business Internationally (Without Costly Mistakes!) - Pete Palermo

2025/02/18

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!

196 - How to Build a Leadership Team That Runs Without You - April Stercula

2025/02/04

In this episode of the Win-Win Podcast, April Stercula, #2 leader and part of the Wolf's Edge Integrators team, joined us to discuss 10x’ing the quality of your leadership team. With a background spanning Fortune 100 companies, high-growth SaaS, and entrepreneurial ventures, April shares insights on what it really takes to build a leadership team that drives the business forward—without being driven. April and Ben explore: ✅ The signs your leadership team is holding back growth (and how to fix it) ✅ Why having the right people in the right seats is the foundation of scaling ✅ The brutal honesty required to elevate—or replace—leaders who aren’t growing ✅ A real-world approach to mentoring, measuring, and developing leaders If you’re an entrepreneur looking to scale beyond yourself, this conversation is packed with practical takeaways for transforming your leadership team into high-performing, independent business drivers. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

195 - Smart Scaling: Leveraging Process to Grow 10x - Joanne Giordano

2025/01/21

In this episode of the Win-Win Podcast, Ben Wolf welcomes Joanne Giordano, COO and Integrator of Wolf’s Edge Integrators, to discuss 10x’ing process in your business. With extensive experience in operations and crisis management across corporate and small business environments, Joanne shares powerful insights on how businesses can scale efficiently without burning out their teams. Joanne delves into the difference between 2x and 10x thinking, and how creativity—not just effort—fuels scalable growth.If you're ready to scale your business the smart way, this episode is packed with actionable takeaways to help you implement processes that support exponential growth. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

194 - How to 10x Your Leadership Team - Thomas Hoover

2025/01/07

In this episode of the Win-Win Podcast, Ben Wolf is joined by Thomas Hoover, a seasoned business leader and Fractional Integrator at Wolf’s Edge Integrators, to explore how to 10x the quality of your leadership team. With decades of experience in owning, operating, and scaling businesses, Thomas shares actionable insights on empowering leaders, fostering growth, and driving organizational success. Thomas discusses real-world examples of leadership transformations, including helping teams improve focus, achieve 100% goal completion rates, and surpass three-year targets in just two years. He emphasizes the importance of clear expectations, intentional leadership development, and building a culture where everyone strives to make those around them better. 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), your favorite podcast platform, or stream directly at https://winwin.cast.rocks/.

193 - From Chaos to Clarity: 10x Process Transformation - Kevin Hooiveld

2024/12/17

In this episode of the Win-Win Podcast, Ben Wolf welcomes back Walt Brown, a renowned EOS Implementer and author of the upcoming book Attract or Repel: Seven Keys to Magnetize Your Company and Build the Culture of Your Dreams. With over 1,400 sessions and 188 clients under his belt, Walt shares insights on building a workplace culture that fosters belonging and belief, ensuring team members are aligned with your company’s mission and values. Walt explains his framework for identifying critical needs in organizations, the importance of role clarity, and how businesses can create environments where employees thrive or self-select out. Learn how the right tools, like Walt’s “Flower Power” exercise, can transform accountability and engagement while magnetizing your company for growth. Whether you're an EOS enthusiast or a business leader, this conversation offers actionable takeaways for cultivating a high-performing team and achieving cultural alignment. 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), your favorite podcast platform, or stream directly at https://winwin.cast.rocks/.

192 - How to Build a Magnetic Company Culture - Walt Brown

2024/11/26

191 - From Vision to Execution: Qlarity Access’s Journey - Colson Steber and Joanne Giordano

2024/11/12

In this episode of the Win-Win Podcast, Colson Steber, Co-CEO of Qlarity Access, and Joanne Giordano, Fractional Integrator from Wolf’s Edge Integrators, share their journey of collaboration as Qlarity Access's Visionary and Fractional Integrator (#2 leader) to guide the business through its transition to the Scale stage. Colson reflects on the evolution of his company—from facing recurring operational challenges to creating a leadership team that fully owns their functions. Joanne discusses the key strategies she implemented to develop internal leaders, transition Colson and his business partner Curtis out of day-to-day roles, and prepare the company for a 10x growth trajectory. 🎧 Listen now on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), your favorite podcast platform, or stream directly at https://winwin.cast.rocks/.

190 - Managing Explosive Business Growth - Elise Buie

2024/09/24

In this episode of the Win-Win Podcast, we welcome Elise Buie, founder and CEO of Elise Buie Family Law, to discuss how her firm navigated explosive growth and overcame significant challenges with the help of a fractional COO from Wolf's Edge Integrators. Through her experience, Elise shares valuable insights on scaling a business, fostering leadership growth, and creating a balanced work environment for long-term success. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

189 - When is the right time to onboard an integrator? - Conrad Saam

2024/09/10

When is the right time to onboard an integrator? In this episode, Conrad Saam from Mockingbird Marketing joins us to share his journey from self-implementing EOS to bringing in an integrator from Wolf's Edge Integrators as his second in command. Conrad delves into his decision to hire a fractional COO and how her leadership significantly improved the company’s performance by introducing accountability and structure. He also discusses overcoming the challenges of running an agency in a rapidly changing digital landscape. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

188 - Right-People Alignment: Pelletier MS Story - Gary Pelletier, Ralph Riccio, and Tom Hoover

2024/08/27

In this episode of the Win Win Podcast, we'll share the growth story of Pelletier MS, after months of working with Thomas Hoover from the Wolf's Edge Team. We'll discuss the challenges the company faced before bringing in an integrator. This episode highlights the significant changes and improvements after the visionary Gaty Pelletier, began working with Ralph Riccio (EOSi) and Tom Hoover (WEI FI). Visionaries with second thoughts on whether to get an integrator will find this episode very helpful. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

187 - What Is a Great Integrator? - Jim Coyle

2024/08/13

What does a great integrator look like? In this episode of the Win Win Podcast, EOS Implementer Jim Coyle shares his insights on what makes a great integrator and their critical role in a company's success. Drawing from his journey of owning and running 12 businesses, Jim shares valuable insights on overcoming common leadership challenges and achieving sustainable growth. Whether you're a business owner, leader, or aspiring entrepreneur, this episode offers useful advice for taking your business to the next level. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

Special Edition of the Win/Win Podcast with my Fractional Executive Integrator - Joanne G

2024/08/01

The big day is here! Check out our special episode of the Win Win Podcast where we dive into Project MOAA, our new assessment that's going to change the way Implemeters, Visionaries and the EOS community perceives the role of the integrator. Small business owners deserve tools to make better decisions on their most important hire. This tool is the HOW to find the WHO.

186 - Why Process Alignment is Crucial for your Business - Lisa Gonzalez

2024/07/09

Processes are the backbone of any successful business. Are you investing enough time in keeping your processes updated? Join us for this episode of the Win-Win Podcast with Lisa Gonzalez, certified EOS Implementer and co-author of the book Process! - where we dive into the importance of processes in building invincible strategies for our business growth. Lisa also reveals the critical role of Integrators in ensuring these processes are documented, followed, and applied seamlessly across leadership teams. Listen to the show on Apple podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), wherever you normally get your podcasts or listen on the web at https://winwin.cast.rocks/.

Podcast reviews

Read Win Win - An Entrepreneurial Community podcast reviews

5 out of 5

14 reviews

★★★★★

jewishshiksa 2024/04/09

Always great takeaways from this show!

Ben always brings on meaningful guest that have powerful takeaways! Win win podcast is one of the only few podcasts I listen to because the content i...

★★★★★

TFEtim 2023/12/21

Great actionable conversations

The host Ben is so good at asking a pointed question and then letting the guest just share their wisdom and knowledge. It is amazing that mini podcast...

★★★★★

Chris W in Texas 2023/09/19

Win-Win help-first attitude brings value to everyone!

Ben’s help-first attitude drives value for everyone he impacts.

★★★★★

David Shriner-Cahn 2021/11/15

Ideal for Executives Exiting Employment

If you want to be self-employed after years of experience as an executive, the process of getting enough of the right kind of business can seem daunti...

★★★★★

ascension7 2020/08/14

Great show with valuable content

Great show with valuable content! I enjoy listening to this show. Ben asks really great questions. I highly recommend for leaders in organizations. ...

★★★★★

Daniel Orlansky 2020/01/16

Fascinating show, great guests

I like how each episode brings something unique that actually offer a practical benefit to business owners. Each guest brings a particular expertise a...

★★★★★

becky-lewis 2019/07/25

Small business leaders tune in!

Great content to help a small business leaders stay laser focused on what it takes to grow and thrive!

★★★★★

Lovefreeapps1234567 2019/05/29

This podcast is a MUST for all entrepreneurs!

Great content! Looking forward to hearing more!

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