On The Fly!

About On The Fly!

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!

Publisher

Flywheel Social Enterprise Hub

Category

business · business

Language

en

Explicit

No

First episode

31 May 2025

Latest episode

24 Oct 2026

Latest episodes

1 of 31 episodes have a transcript.

1. 

   24 Oct 2026

   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 (https://ccr.publichealth.gwu.edu/americas-truth#americas-truth-stream) Learn more about All In Cincinnati: https://allincincinnati.org/ (https://allincincinnati.org/) Learn more about the George Washington University Institute for Socioeconomic Opportunity: https://socioeconomicopportunity.gwu.edu/ (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/ (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.

2. 

   17 Oct 2026

   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/ (https://www.cincinnatigoodwill.org/) Learn more about CIRCLE: https://www.cincinnatigoodwill.org/humanity-in-fashion/ (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/ (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.

3. 

   10 Oct 2026

   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 design Why economic conditions are often underneath the problems we try to solve Building humanature and The Wealth + Work Futures Lab Learning to delegate and giving yourself grace as an entrepreneur What makes a good hiring process Why defining failure can be as important as defining success Keeping humans at the center of AI and technology Cathedral thinking and planning across generations Human ecology and the systems that shape our lives Why you can't edit while you're brainstorming “Riding the Purple Dragon to the Moon” Curiosity, critical thinking, and informed intuition Building a future around human potential and well-being Connect with Michael humanature (https://www.humanature.works/) The Wealth + Work Futures Lab (https://wealthworkfutures.org/) Michael O’Bryan on Flywheel (https://www.flywheelcincinnati.org/michael-obryan) Michael O’Bryan (https://www.mikeobimagines.com/) 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/ (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.

Inside a recent episode

How to Soar with Angel Investing

Published 21 Jun 2025 · Transcript excerpt

[…] Well, usually a startup is considered. It's a private company for the most part. And it's a company that is usually small. They're working on something. However, there's a scalability aspect to it. So there are a lot of small businesses out there in the US. We hear about all different types of businesses from your dry cleaner, a bank, something like that. But a startup is something that is usually involved with either some type of technology, maybe something around life sciences. And there's a scalability factor, meaning that the company has the potential to actually get much larger. And if there are investors that end up investing in a startup, there's a potential for them to get a nice financial return. […]

Who has been a guest on On The Fly!

Names identified in recent episode analyses. Showing up to five guests.

• Marcia Dawood
• Sue Bevan Baggott
• Mishawn Styles
• Paul Szydlowski
• Ruth Anne Wolfe

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

6 ratings

Spotify

5.0 / 5

1 ratings

Podcast Authority Score: 52 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

91

Social presence

0

YouTube

0

Engagement

32

Contact On The Fly!

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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