PodcastsRank #21926
Artwork for Win Win - An Entrepreneurial Community

Win Win - An Entrepreneurial Community

EntrepreneurshipPodcastsBusinessManagementENunited-statesDaily or near-daily
5 / 511 ratings
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
Top 43.9% by pitch volume (Rank #21926 of 50,000)Data updated Feb 10, 2026

Key Facts

Publishes
Daily or near-daily
Episodes
198
Founded
N/A
Category
Entrepreneurship
Number of listeners
Private
Hidden on public pages

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Public snapshot
Audience: Under 4K / month
Canonical: https://podpitch.com/podcasts/win-win-an-entrepreneurial-community
Cadence: Dormant
Reply rate: Under 2%

Latest Episodes

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

Tue Apr 08 2025

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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!

More

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!

Key Metrics

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Pitches sent
15
From PodPitch users
Rank
#21926
Top 43.9% by pitch volume (Rank #21926 of 50,000)
Average rating
5.0
From 11 ratings
Reviews
6
Written reviews (when available)
Publish cadence
Daily or near-daily
Dormant
Episode count
198
Data updated
Feb 10, 2026
Social followers
353

Public Snapshot

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Country
United States
Language
English
Language (ISO)
Release cadence
Daily or near-daily
Latest episode date
Tue Apr 08 2025

Audience & Outreach (Public)

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Audience range
Under 4K / month
Public band
Reply rate band
Under 2%
Public band
Response time band
Private
Hidden on public pages
Replies received
Private
Hidden on public pages

Public ranges are rounded for privacy. Unlock the full report for exact values.

Presence & Signals

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Social followers
353
Contact available
Yes
Masked on public pages
Sponsors detected
Private
Hidden on public pages
Guest format
Private
Hidden on public pages

Social links

No public profiles listed.

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Audience & Growth
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Monthly listeners49,360
Reply rate18.2%
Avg response4.1 days
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Sponsor signals
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Sponsor mentionsLikely
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5 / 511 ratings
Ratings11
Written reviews6

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Frequently Asked Questions About Win Win - An Entrepreneurial Community

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What is Win Win - An Entrepreneurial Community about?

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

How often does Win Win - An Entrepreneurial Community publish new episodes?

Daily or near-daily

How many listeners does Win Win - An Entrepreneurial Community get?

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