On The Fly!

Flywheel Social Enterprise Hub
  • 5.0 (7)
  • Non-Profit

Certified Flywheel Coach Joan Kaup, an accomplished business woman, shares interesting and friendly conversations with entrepreneurs and those who support them. Each episode is a conversation with a business coach, an entrepreneur, or an expert in the social impact ecosystem. ON THE FLY! features the community of Flywheel Social Enterprise Hub, located in Cincinnati Ohio, who have supported more than 35 founders and generated more than $5,000,000 in revenues. Flywheel is fostering innovation, building stronger communities, and creating meaningful change. ON THE FLY! highlights businesses that have the double bottom line - both a return on investment and a positive social impact. This podcast will give you reason to smile and think. It aims to motivate you to act on ideas and personal passions. Welcome to ON THE FLY! and our community where business drives change. Listen in!

  1. 5d ago

    What Are Investors Really Looking For? Jonathan Preedom on Storytelling, Risk & Entrepreneurship

    What are investors really looking for when they evaluate an early-stage venture? In this episode of On The Fly!, Dr. Jonathan Preedom explores what happens when entrepreneurs pitch their ideas to investors, how storytelling shapes investor decision-making, and why a great pitch is really about earning the next conversation, not walking away with a check. Jonathan brings both academic research and firsthand entrepreneurial experience to the conversation. His research focuses on investor decision-making, entrepreneurial storytelling, market emergence, and how entrepreneurs and investors make sense of uncertain situations. Before pursuing his PhD, Jonathan founded two ventures of his own, giving him a firsthand perspective on the challenges founders face. Jonathan and Joan talk about why entrepreneurs should think of themselves as risk managers rather than simply risk takers, how founders can distinguish the size of a problem from the size of their actual market, and why investors, employees, and other stakeholders are ultimately investing in the future they can envision. They also dig into what larger companies can learn from smaller, more nimble businesses, why rural entrepreneurship deserves more attention, the role communities play in creating an environment where social enterprises can grow, and why social ventures don't have to choose between doing good and making money. Jonathan was also part of Flywheel's 2026 Impact Catalyst Midwest event, where he coached purpose-driven entrepreneurs through their pitches and led the Elevator Pitch Showcase. Learn more about Jonathan Preedom and his research:https://www.lsu.edu/business/directory/employee-profiles/preedom-jonathan-sdeis.php Learn more about Flywheel Social Enterprise Hub:https://flywheelcincinnati.org/ At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit https://flywheelcincinnati.org/ to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Ha

  2. Oct 24

    The Work Is Hard, But It’s Not Impossible: Denisha Porter on Changing Systems

    Denisha Porter believes the work is hard, but it’s not impossible. As the founder and Executive Director of All In Cincinnati, Denisha has spent years bringing people together to tackle some of the biggest challenges facing the community, from health and housing to education, economic mobility, and justice. Her approach is rooted in systems change: bringing the right people to the table, finding common ground, and turning conversation into action. In this episode of On The Fly!, Denisha talks about growing up in Avondale, finding her voice, building All In Cincinnati from a team of one, and what happens when a community decides it’s not enough to simply talk about the problems. She also shares how a Flywheel business plan helped connect her work with George Washington University and ultimately helped All In Cincinnati become part of a national conversation around systems change. Denisha is also featured in America’s Truth: Cincinnati, a documentary produced by the Center for Community Resilience at George Washington University. The film examines how structural racism in policies, practices, and programs creates and sustains racial inequity, and follows Cincinnati’s efforts to address those systems through truth, healing, and equity. Watch America’s Truth: Cincinnati:https://ccr.publichealth.gwu.edu/americas-truth#americas-truth-stream Learn more about All In Cincinnati:https://allincincinnati.org/ Learn more about the George Washington University Institute for Socioeconomic Opportunity:https://socioeconomicopportunity.gwu.edu/ At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit https://flywheelcincinnati.org/ to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  3. Oct 17

    Circular Fashion & Social Impact: Sherwood MacVeigh of Goodwill

    What if waste wasn't waste? In this episode of On The Fly!, Sherwood MacVeigh, Vice President of Marketing at Ohio Valley Goodwill, takes us inside CIRCLE, a collaboration bringing together Goodwill, UC DAAP, Standard Textile, Sew Valley and Flywheel to rethink what happens to textiles after they're no longer wanted. What started with a big idea and a bale of clothing has grown into a broader exploration of circular fashion, sustainable design, manufacturing, workforce development and social enterprise. Sherwood talks about why she didn't want to simply do another fashion show, and how a group of partners began asking a bigger question: how can we use creativity, education and collaboration to actually solve the problems created by textile waste? • The surprising scale of textile waste• Why designers can help solve sustainability problems, not just create products• Turning reclaimed materials into new designs and scalable products• The CIRCLE initiative and its growing network of partners• Circular fashion and the future of textile recycling• The connection between environmental sustainability and workforce development• How Goodwill has evolved for more than a century by listening to community needs• Why sustainable communities aren't just about sustainable materials, but about building people and opportunity Sherwood's philosophy is simple: think big, start small, bring the right people together, and keep moving. Connect with Ohio Valley Goodwill: https://www.cincinnatigoodwill.org/ Learn more about CIRCLE: https://www.cincinnatigoodwill.org/humanity-in-fashion/ At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit https://flywheelcincinnati.org/ to learn how you can get involved. On The Fly! explores the people, ideas and organizations working to create positive social impact through entrepreneurship, innovation and community. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  4. Oct 10

    Thinking Like a Social Designer: Michael O’Bryan on Creativity & Social Design

    What happens when you stop editing an idea before it has a chance to become something? On this episode of On The Fly!, Joan Kaup talks with Michael O’Bryan, founder and CEO of humanature and founder of The Wealth + Work Futures Lab, about social design, human potential, creativity, economic opportunity, and the importance of giving big ideas room to develop. Michael's path is anything but conventional. Growing up in Hartford, Connecticut, he went from selling ICEEs as a kid to studying music and performing professionally before his work in art, public health, mental health, workforce development, and social design eventually led him to focus on the economic conditions underneath many of the challenges people face. He shares lessons on entrepreneurship, delegation, hiring, leadership, AI, long-term thinking, and the importance of keeping people at the center of technological change. And then there's the Purple Dragon. Michael explains why brainstorming requires us to resist the urge to edit too early — because sometimes the idea that comes several steps after the “ridiculous” one is exactly the idea we needed. In this episode: Michael's unconventional path from music and theater to social designWhy economic conditions are often underneath the problems we try to solveBuilding humanature and The Wealth + Work Futures LabLearning to delegate and giving yourself grace as an entrepreneurWhat makes a good hiring processWhy defining failure can be as important as defining successKeeping humans at the center of AI and technologyCathedral thinking and planning across generationsHuman ecology and the systems that shape our livesWhy you can't edit while you're brainstorming“Riding the Purple Dragon to the Moon”Curiosity, critical thinking, and informed intuitionBuilding a future around human potential and well-beingConnect with Michael humanatureThe Wealth + Work Futures LabMichael O’Bryan on FlywheelMichael O’BryanAbout On The Fly!On The Fly! celebrates social enterprises and the people who build them, along with the organizations and communities that support them. Each episode explores the ideas, challenges, and people working to create meaningful change. At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit https://flywheelcincinnati.org/ to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  5. Oct 3

    Don’t Let Your Zip Code Dictate Your Future: Moira Weir from United Way

    What does it take to move from responding to community crises to changing the systems that create them? On this episode of On The Fly!, Donna Zaring sits down with Moira Weir, President & CEO of United Way of Greater Cincinnati, to talk about what it means to think beyond immediate needs and build long-term solutions for families and communities. After more than 25 years with Hamilton County Job and Family Services, Moira brought a deeply practical understanding of community needs to United Way. She talks about the shift from crisis response to systems change, why lived experience and community voice need to be at the center of decision-making, and how data can help organizations understand what a community actually needs. The conversation explores United Way’s 211 system, housing stabilization and eviction prevention, financial empowerment, free tax preparation, workforce development, and the Future of Manufacturing Fund. Moira also shares why collaboration matters so much — and why, in her words, “you can’t opt out of your community.” In this episode: Moving from crisis response to long-term systems changeWhy community voice and lived experience matterUsing 211 data to understand community needsHousing stabilization and eviction preventionFinancial empowerment and free tax preparationCreating pathways into manufacturing careersUsing technology without losing the human connectionWhy collaboration and collective ownership are essentialThe idea that your zip code shouldn't determine your futureConnect with Moira & United Way of Greater Cincinnati United Way of Greater Cincinnati: https://www.uwgc.org/ About On The Fly! On The Fly! celebrates social enterprises and the people who build them, along with the organizations and communities that support them. Each episode explores the ideas, challenges, and people working to create meaningful change. At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit https://flywheelcincinnati.org/ to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  6. Sep 26

    "Friend-Raising", Not Fundraising: Dom Peebles of Brick Gardens

    What happens when a childhood spent working on a family farm comes full circle in the heart of Cincinnati? For Domonique Peebles, it started with tomatoes, neighbors, and a lesson from his dad: if you have food, make sure your neighbors do too. That instinct eventually became Brick Gardens, a Cincinnati social enterprise using urban agriculture to grow food, create jobs, and build community. In this episode of On The Fly!, Dom talks about the unexpected path from a job at Fidelity Investments to farming, the grant application that launched Brick Gardens, and why he believes friend raising—not fundraising—is what really builds an organization. He also shares what he's learned about food insecurity, why growing food is only part of the solution, how young people can become leaders—not just workers, and why Cincinnati's parks could play a much bigger role in food access. At the heart of it all is a simple idea: sometimes you don't need to wait for the perfect resources. You just need to start doing the work—and bring your friends along. Learn more: Brick Gardens: https://www.brickgardens.com/World Resource Institute: https://www.wri.org/profile/carla-d-walker About On The Fly! On The Fly! is a podcast from Flywheel Social Enterprise Hub featuring conversations with entrepreneurs, coaches, investors, and community leaders working to create meaningful social impact. At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit flywheelcincinnati.org to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  7. Sep 19

    Predicting Homelessness Before It Happens: Kevin Finn on Prevention, Data & Impact

    What if you could identify a family at risk of homelessness before they lose their home — and intervene early enough to keep them there? On this episode of On The Fly!, Joan Kaup talks with Kevin Finn, President and CEO of Strategies to End Homelessness in Cincinnati, about a radically different approach to preventing homelessness: using data to identify families at the highest risk of eviction and reaching them before they become homeless. Kevin shares his journey from working with homeless teenagers to leading a coordinated community effort involving dozens of organizations across Greater Cincinnati. He explains how Cincinnati's unusually comprehensive homelessness data helped make predictive analytics possible, and how a Flywheel innovation lab and housing stability hackathon helped lead to the creation of Tenant Guard, a tool that allows people to identify themselves as being at risk of losing their housing. The results are striking. Kevin explains why helping a family remain in their apartment can cost about $3,600, compared with an average of $22,500 after a family enters a homeless shelter. while also producing better outcomes. The conversation also explores the role of 84.51º, the City of Cincinnati's Impact Award, research with Notre Dame, the potential to take Cincinnati's model to other communities, and the policy changes Kevin hopes could shift more resources toward prevention. Most importantly, Kevin talks about what those numbers mean for real families, especially children who can avoid the disruption of homelessness, including repeatedly changing homes and schools. Learn more Strategies to End Homelessness: strategiestoendhomelessness.orgTenant Guard: tenantguard.orgAbout On The Fly!On The Fly! is a podcast from Flywheel Social Enterprise Hub featuring conversations with entrepreneurs, coaches, investors, and community leaders working to create meaningful social impact. At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit flywheelcincinnati.org to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

  8. Sep 12

    Can Purpose and Profit Coexist? Jenna Nicholas on Impact Investing

    What if financial success and social impact aren’t competing goals? On this episode of On The Fly!, Donna Zaring talks with Jenna Nicholas, a social entrepreneur, investor, founder, and author whose career has focused on bringing purpose and financial models together. Jenna shares the personal experiences that led her toward social entrepreneurship, from growing up in London to studying at Stanford and discovering the work of pioneers like Muhammad Yunus and Bill Drayton. She talks about her work with Calvert Funds, the World Bank, One Planet VC, Impact Experience, and her current work with Lightpost Capital. The conversation explores one of the biggest misconceptions in impact investing: that you have to choose between financial returns and social and environmental impact. Jenna shares examples of companies demonstrating that both can reinforce one another, and explains what investors look for when evaluating purpose-driven founders. Jenna also introduces the HEAL framework — Hope, Empathy, Abundance and Legacy — and explains how these ideas can become practical guideposts for entrepreneurs, investors, and organizations. From building strong founder communities to thinking seven generations into the future, this conversation asks a bigger question: What does it look like to build businesses around a deeper sense of purpose and meaning? Connect with Jenna 🌐Jenna-Nicholas.com 🎧Enlightened Bottom Line Podcast  📖Enlightened Bottom Line Book ✏️Jenna’s Substack  About On The Fly!On The Fly! is a podcast from Flywheel Social Enterprise Hub featuring conversations with entrepreneurs, coaches, investors, and community leaders working to create meaningful social impact. At Flywheel Social Enterprise Hub, we pair experienced professionals with purpose-driven founders to make a real difference in our communities. Interested in coaching, mentoring, or starting your own social venture? Visit flywheelcincinnati.org to learn how you can get involved. On The Fly! is produced by Joan Kaup and Joey Scarillo, with support from Gianna DiMona. Music by Ben Hammer. It is recorded at 1819 Innovation Hub, courtesy of the University of Cincinnati.

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5
out of 5
7 Ratings

About

Certified Flywheel Coach Joan Kaup, an accomplished business woman, shares interesting and friendly conversations with entrepreneurs and those who support them. Each episode is a conversation with a business coach, an entrepreneur, or an expert in the social impact ecosystem. ON THE FLY! features the community of Flywheel Social Enterprise Hub, located in Cincinnati Ohio, who have supported more than 35 founders and generated more than $5,000,000 in revenues. Flywheel is fostering innovation, building stronger communities, and creating meaningful change. ON THE FLY! highlights businesses that have the double bottom line - both a return on investment and a positive social impact. This podcast will give you reason to smile and think. It aims to motivate you to act on ideas and personal passions. Welcome to ON THE FLY! and our community where business drives change. Listen in!

Information

  • Creator
    Flywheel Social Enterprise Hub
  • Years Active
    2025 - 2026
  • Episodes
    32
  • Rating
    Clean
  • Copyright
    © 2026 Flywheel Social Enterprise Hub
  • Show Website
    On The Fly!