182 episodes

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.WolfsEdgeConsulting.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.

Win Win - An Entrepreneurial Community Fractional Leadership LLC

    • Business

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.WolfsEdgeConsulting.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.

    184 - Avoid Trust-Breaker Behaviors - Kim Baker

    184 - Avoid Trust-Breaker Behaviors - Kim Baker

    Struggling with trust issues in your team? Kim Baker, an expert in team dynamics, shares how to rebuild trust in your organization.

    In this episode, Kim explains how unclear roles and poor communication can break trust, and how to fix it. She talks about her process, which includes conducting trust assessments and identifying behaviors that build or break trust.

    Our guest shares a real-life example of an engineering team plagued by trust issues due to ambiguous roles and lack of clear expectations. Kim’s structured approach, which involves clarifying roles and improving communication, helped the team move from mistrust to effective collaboration.

    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/.

    • 38 min
    183 - Help Your Team Find Purpose In The Workplace - Brandon West

    183 - Help Your Team Find Purpose In The Workplace - Brandon West

    How can you help your team to find purpose in the workplace? Join us on this episode of the Win Win Podcast as we explore the crucial role of purpose in business with Brandon West, founder and Chief Purpose Officer at Phos Creative.

    Discover how aligning your team's work with a deeper mission can transform everyday tasks into impactful contributions.

    Brandon shares invaluable insights from his journey at Phos Creative, illustrating how purpose can drive business success and personal fulfillment, to cultivate a culture of purpose that resonates through every level of your organization.

    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/.

    • 29 min
    182 - Being open and honest. Is it worth it? - Ben Kogard

    182 - Being open and honest. Is it worth it? - Ben Kogard

    Is being open and honest with others worth it? Embracing these values can build meaningful connections and drive personal and professional growth.

    Ken Bogard, an Expert EOS Implementer®, founder of Know Honesty, and co-founder of The Visionary Forum, sheds light on the effects of “West Michigan nice,” a culture that can stifle genuine dialogue.

    This episode is packed with valuable lessons on building genuine connections and achieving meaningful communication, whether you’re leading a team or nurturing personal relationships. Ken brings his extensive experience working with over 300 leaders across 60 companies, focusing on fostering openness and honesty for better leadership.

    Discover the insights from Ken’s upcoming book, ‘Know Honesty’, and learn how you can take the honesty assessment (knowhonesty.com) to measure your levels of openness in various aspects of your professional and personal life.

    Listen to the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/win-win-an-entrepreneurial-community/id1465488607), or wherever you normally get your podcasts. You can also listen on the web at winwin.cast.rocks.

    • 38 min
    181 - Profit as a Habit, Not a Result - Chris White & Jason Petro

    181 - Profit as a Habit, Not a Result - Chris White & Jason Petro

    So many business owners got tired of never having any profit left after day-to-day business and then had their minds blown by Mike Michalowicz's book, Profit First.

    The problem is that just from reading the book, many people can't successfully implement the framework and take advantage of all of its "take your profit first" promises.

    This episode features two guests who talk about the solution they came up with for that problem. The first is Jason Petro, a 3X entrepreneur, certified Profit First coach, and co-founder of ProfitPro.app.

    Our other guest is also a co-founder of ProfitPro.app, Chris White, a 7x entrepreneur, co-founded Ninety.io, former Expert EOS Implementer, and co-founder of the System and Soul BOS coaching system.

    Chris and Jason share how the software system they created, ProfitPro.app, solves that and how business owners can maximally utilize the Profit First Model.

    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/.

    • 32 min
    180 - Interrogate Your Business - Daniel Hammond

    180 - Interrogate Your Business - Daniel Hammond

    How can you interrogate your own business to fulfill its potential? Veteran military intelligence and interrogation instructor Daniel Hammond teaches how to ask the hard questions so you can take immediate action to optimize your business.

    Daniel is the Founder and President of Business Interrogation LLC (www.BusinessInterrogation.com). He leverages 30 years of military intelligence experience, including as an interrogator and interrogation instructor and his 20 years of business experience. Daniel is also the author of Customer-Driven Leadership: How to Win with Entrepreneurial Servant Leadership, Responsiveness to Client Data, and Constant Creativity (https://www.amazon.com/Customer-Driven-Leadership-Entrepreneurial-Responsiveness-Creativity/dp/B0CB1QW1NN).

    Using stories and examples, Daniel shares the main principles he learned in the military of interrogation, shares how he realized their applicability in business once he entered the entrepreneurial world, and teaches us how to apply those principles to our own businesses. 

    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/. 

    • 27 min
    179 - Founder/COO Relationship Insight You've Never Heard - Rachel Lebowitz

    179 - Founder/COO Relationship Insight You've Never Heard - Rachel Lebowitz

    How similar are codependents and Visionaries/CEOs with their COO/Integrator?

    Our guest, Rachel Lebowitz (https://www.rachel-lebowitz.com/empoweredcoo), is a Professional EOS Implementer and is the author of the forthcoming book Empowered COO: A Guide to Restoring Confidence in the Second in Command / Integrator Role. 

    Rachel shares a unique insight that she came to after studying addiction, codependency, being part of a fast-growing entrepreneurial business married to its founder, and learning from scores of sessions with leadership teams as a Professional EOS Implementer. 

    She shares where those dynamics come from and what strategies COOs/Integrators can use to become less enmeshed, more effective, happier, more successful, and less burned out.

    COOs/Integrators can also take this assessment Rachel developed to determine how empowered and healthy of a 2IC they are: https://www.rachel-lebowitz.com/assessment.

    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/. 

    • 37 min

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