The Tale of Two Program Managers

I say this as lovingly as possible. It is like one of my favorite parts of this work. The crazier an entrepreneur is, the further they'll go. We have a lot of conversations in this ecosystem about betting on the jockey versus betting on the horse. And it always comes down to, you know, you wanna make sure that the horse is good enough, but ultimately, your jockey is what's going to see the idea through from good to great.

An entrepreneur that, again, I say this with all the praise in the world, that is stupidly passionate about solving a problem that they're working on, that is absolutely married to the impact that they wanna make or the gap that they wanna fill, that founder is going to do it no matter what, regardless of you, regardless of me, regardless of capital. And those are the opportunities that if we rally around them and take a little bit of time and energy and resources to invest, you'll see that multiplied so much.

80% of the for profit and nonprofit organizations that have interacted with Flywheel Social Enterprise Hub are still actively serving their communities. Through Flywheel, 187 social impact driven entrepreneurs have gathered in cohorts to improve their tools and skills needed to expand their impact through our programs. Today, Flywheel Executive Director Donna Zaring is in conversation with Josie Dalton, who originated the programs taught to our cohorts, and Samuel Baker, who is our current program director.

Hello. Hello.

It's like a tale of two program managers.

Well, thanks for being here today. Josie, when I first met you, I guess three years ago, you were leading the Sustainable Cincy cohort at Flywheel. And we bonded because we were both graduates of Miami University in Ohio. Tell us a little bit about your journey from Miami to Flywheel and to where you are now at the UC Center for Entrepreneurship.

I can't claim it was very planned. Miami, as anyone familiar with Flywheel knows, is a founding partner of Flywheel from its beginning. So the relationship had been there long before I entered the scene. But when I was in undergrad at Miami, I was a philosophy major and entrepreneurship minor. When I was getting close to graduation, I sort of came to the realization that I really needed to figure out what I was going to do.

There weren't really a lot of jobs at the philosophy factory. So I started to talk to my entrepreneurship professors and a good friend of flywheel, Brett Smith, introduced me to Bill Tucker, which is how I found my way into a internship with Bill my senior year. Jess Mabes was in my position before that through a relationship with AmeriCorps. So for those of you who know Jess from deep in the startup Sinsy lore, she was with Flywheel and then actually left Flywheel to work for Lesoups, which is one of Flywheel's first accelerator companies. We were very excited to see her go continue to develop their operations.

And then I stepped in, is how I got to know Bill and the Startup Cincy ecosystem. After graduation, I was able to take a position with a youth and family services organization called NECO that's actually based in Over The Rhine here in Cincinnati and again maintains a relationship with Flywheel to this day. So I worked there for about a year before Bill brought me back on full time in the program manager role in February. So that was in between our second and third cohorts of the accelerator, which at the time we were just calling Elevator. It was broadly social impact focused.

So none of the themes, none of the specific topics or impact areas that we were looking for. Social enterprise was kind of a new and emerging concept in the ecosystem. So our mission was really just to prove to the community that it could add value and be just as good of an investment as the other startups that were starting to coalesce in the ecosystem. So that was 2018. 2019 saw our first funded accelerator with cohort four.

And then we tumbled right into our other programs. I remember when I met you, I was super excited to hear about the work that Flywheel was doing and to see that you and Bill were you know, had had evolved from Elevator to a sustainability focused accelerator was really interesting to me. Samuel, you have been a program manager at Flywheel for a year and a half now.

Year and half. Yeah.

You've been doing tremendous work in a short It feels like you've been there longer. You are really experienced in the nonprofit world here in Cincinnati. For about a decade, you've been working in our community. Tell us a little bit about the work you've been doing and and how you found Flywheel and why you're excited to be in this role.

For sure. So when I went to college, I was a business major and an entrepreneurship minor, and my goal was to come out and be a founder, actually. And that was kind of my thought all the way up until the summer before my senior year. I did an internship at a small incubator called the Incline Incubator in Price Hill. Realized that I loved solving founder problems that I didn't have to take home with me. And so instead of being a founder, was like, oh, I just I wanna help founders. That'd be awesome.

That's so real.

And so I was curious about this and I was like, okay, let me see, like, is there anyone that's doing this kind of on a larger scale that I might be able to get in with? And it's actually my pre law professor took me to like a little like conference summit kind of event And guess who was speaking? None other than Josie Dalton. And that was the first time I heard of Flywheel. And I remember walking away being like, wow, she's so passionate about the work that they're doing.

I would love to be passionate about that. And it was cool because I I had volunteered a lot of my life in high school and college. And so hearing that there was a world where entrepreneurship and community advancement could, like, be hand in hand, I was like, oh, that's like perfect for me. So I graduate college. Flywheel's not hiring.

And I look around, I was like, okay, cool. Where where else? Nowhere else is hiring in that kind of environment, which is kind of funny to think about. And so I was like, I don't really know what to do. And a door opened into the nonprofit world.

And so I ended up starting my career there working for City Gospel Mission. I was running a program called Rising Scholars. It's a career readiness program for high schoolers, and I ran that for around seven, eight years. During my time there, I also got involved with another local nonprofit called Sprouting Minds, and I'm on the board for them as their board chair. And then continued that theme throughout my life of kinda balancing, volunteering for other nonprofits, working in nonprofit, and kinda really growing my roots down there all the way up until I saw that Flywheel was hiring.

And I was like, oh, wow. Maybe I'm not the right fit now. Like, I'm kinda in this nonprofit space. I haven't looked at entrepreneurship in a while. But my wife held me at gunpoint and said, if you don't apply, like, I'll do it myself.

Because I had had stayed in connection with Flywheel, kinda just watching from afar, like, what they were doing and who they were working with. I was told her, like, if I ever left City Gospel Mission, Flywheel would be where I would want to work. And now I'm sitting here today.

Well, we're so we're so glad. Thanks for sharing that journey. Both of you touched on this a little bit in your intros, but Flywheel works with founders who are trying to make the world a better place. Right? Part of their business mission is that double bottom line of social and financial impact.

Josie, during your time with Flywheel, what were some of the main challenges you saw social entrepreneurs face in their startup journey?

So that's that's a really great question. Social entrepreneurs are in a really unique position that a lot of times works to their advantage, a lot of times works to their disadvantage. And that position at the intersection of social impact and market viability has this weird reverse impact for the opposite stakeholders, for a founder who's trying to build. And I'll explain that word salad by saying for somebody who's building something that is market driven, that has a business model behind it, but is also designed for social impact. When that person goes out seeking capital, right, assuming that they don't come from a background that enables them to bootstrap it solo as most entrepreneurs are not and especially most entrepreneurs in the social impact sector are not because they tend to come from backgrounds that make them passionate about some sort of, you know, impact area or community need or something like that.

They're building. They need capital. They need it from outside sources. Their options are traditional funders so they could look at a VC or an SBIR or a bank or a something who will look at them and say, oh, that's nice but that's a little more cushy than we usually fund. We don't know if that's necessarily as profitable as the things that we usually fund.

Maybe you should look more towards the nonprofit and charitable side of things. So the founder is like, okay, good point. I'll go I'll go looking for philanthropic dollars. Right? I'll go look for grants.

I'll go look for foundation dollars. I'll go try to seek impact focused capital. Those funders say, what you're doing is really nice and cool, but we really fund stuff that's more, you know, that is nonprofit or that is charity funded or that, you know, is a community driven model that is not, you know, they shy away from things like profit business model, revenue streams, market viability. So these founders are sort of left bereft in this middle area where they are very smartly using the principles of entrepreneurship to solve a problem. But the people at the opposite ends of that spectrum are too unwilling to meet in the middle.

Which is really the genesis of why Bill and I started pushing on advocacy for impact investing in this community and starting to train up the full entrepreneur network and really educate people on how if you both believe in entrepreneurship as a means of economic development and job creation and you believe in different social impact causes, there's a perfect investment opportunity here for you at this intersection. So hopefully we can shift that major challenge into an opportunity.

That's great. Along those lines, Samuel, what would you say are the most common questions that founders have?

The main question is where's the money?

Literally.

No. Like, I think Josie teed that up perfectly. They kind of are left in this middle ground and trying to navigate that is tough, especially if you are coming into the entrepreneurship ecosystem without prior connections, especially if you are coming from a background where entrepreneurship is not stressed. It's a different language. Asking that question of, like, where where do I go to, like, to actually find some funding for this to make this happen is a main question.

I also think, who should I know? Is another great question. Who are the people? Who are the players that I need to be in contact with to make this a reality? What kind of resources do I need?

A lot of my job as program manager is making those connections and putting them in contact with people that they might not even know that they need to know, especially in regards to, like, legal services and and what it takes to get your business legally founded. At the end of the program, you know, kinda helping them get their feet underneath them and think about how to scale their business, I think the the next question is, okay, cool. Like, this is super helpful. What do I do now? And and that's another opportunity that Flywheel has to be a resource for them.

I love that last one because by the time they're asking that question, you've seen what they can do in such a short amount of time. And you're like, alright, let's go. What is your next thing?

100%.

Bill Tucker was one of the early executive directors of Flywheel and responsible for building out much of the programming that we see active today designed to help entrepreneurs who want to create social impact. What was Bill trying to accomplish all those years ago and how is that applicable today?

Right around February, I wanna say 1516 when the start up Sinsy ecosystem really started to crystallize. When Union Hall opened up to start ups and co working, when Centrifuge really started to actively recruit capital from outside this region. A lot of those things started to coalesce. Bill very wisely saw the opportunity to harness some of that energy and explore the principles of social enterprise and, you know, pursuing startup and for profit entrepreneurship as a vehicle for social impact, which led to that very first social impact summit to help educate the community about the opportunity that we have, led to the very first social impact accelerator that Flywheel hosted, which was actually under a brand label called Social Enterprise Cinci. And really just sort of snowballed from there.

Between the real need in the community, the financial gap for impact organizations, and the sort of very timely uptick in startup activity in this ecosystem, It's sort of what we tell our startups all the time. Luck is a combination of preparation and timing. Like, it just came together at just the right time. And he did an excellent job positioning how the principles of entrepreneurship can marry with impact by highlighting this first batch of companies that we had where we said, look, these are people who are doing real work in this community, making real impact and you can invest dollars in them that will actually generate a market rate of return and everyone is the better for it.

What makes social entrepreneurs uniquely positioned to drive impact in our community?

So having spent so much time in nonprofit, I met very passionate people. But the limitations of nonprofit is that you are beholden to ownership, and you can have as many dreams as you want to be able to execute. And there are nonprofits that execute on an incredible level and make some really valuable changes in levels of impact in our community. I think social impact entrepreneurs kind of sit outside of that. It gives them a really unique vantage point.

They can go where certain nonprofits can't and can look at an issue from a different perspective. They're a lot quicker and more agile because a lot of them are are smaller. Right? They can respond to community needs in a decisive and very powerful way. The other element that I would say is that for entrepreneurship, there's kind of a creative out of the box thinking that's required.

Hence, these issues that we're looking at, environmental sustainability, racial and gender equity, socioeconomic equity, these are problems that have existed for millennia. Being able to look at it from an entrepreneurial standpoint to come up with some kind of new strategy or approach to it brings creativity to the solutions that ultimately we're yearning for and looking for as a community.

Yeah. Yeah. And if I if I flip that around, Josie, my question, follow-up question for you is what is it about being mission and impact driven that that makes a better entrepreneur? Because you work with startup founders every day at the UC Center for Entrepreneurship now. So what is what is it about a mission driven entrepreneur that makes them a better entrepreneur?

I say this as lovingly as possible. It is like one of my favorite parts of this work. The crazier an entrepreneur is, the further they'll go. We have a lot of conversations in this ecosystem about betting on the jockey versus betting on the horse. And it always comes down to, you know, you wanna make sure that the horse is good enough.

But ultimately, your jockey is what's going to see the idea through from good to great. An entrepreneur world, that is stupidly passionate about solving a problem that they're working on, that is absolutely married to the impact that they want to make or the gap that they want to fill or whatever, that founder is going to do it no matter what, regardless of you, regardless of me, regardless of capital. And those are the opportunities that if we rally around them and take a little bit of time and energy and resources to invest, you'll see that multiplied so much.

I couldn't agree more. I mean, I come from a I'm in a family of entrepreneurs and I would say without a doubt the number one quality that this that makes success is just never quitting.

Right. We get founders all the time. I mean every founder or aspiring founder is really excited about their idea. Right? Whether it's, you know, a product or a service that they want to introduce to the market or a segment that they want to serve or whatever it may be.

They they come in jazzed. And we're like, cool. We love it. You love it. Are you gonna love it just as much a year from now when it's two in the morning and you don't know how you're gonna make payroll and you're freaking out or whatever.

The ones who say yes, we're like, let's go. We're all in.

The only thing that I will add to that I think is for mission driven founders. They're working towards something that's bigger than them.

Exactly.

And I think that they kinda hold that in a different way. And and again, that's not to say that non, quote unquote, mission driven founders aren't. But I think when you are working on something, but you're constantly contextualizing yourself within a much larger narrative, I think that gives you that extra oomph to to say, okay, cool. Like, I I'm struggling or or I I'm not feeling it at 2AM this morning, but this is bigger than me. And I've seen that in the founders that I've had the privilege to work with in my short time here at Flywheel and and continuously inspired by it.

Yeah. The urgency that, like, the world needs this.

Yeah.

That's amazing. That's why I love Flywheel.

Me too, man.

Okay. Well, since we're talking about the founders that you've encountered along your journey, what what are some funny stories that you have from from different engagements with founders at Flywheel? Oh, funny can share.

Know. Right?

It's a great caveat.

Honestly, the first the first thing that comes to mind is that we were about halfway through our fourth elevator cohort. I think our cohort meetings, we did like a Tuesday, Wednesday, Thursday sort of vibe. So our cohort meetings were on Tuesday morning and we all got in and the vibes were just like kind of off. Like everyone was tired, like nobody was really into like the discussion we were having. Everyone seemed like they were kind of dragging.

And Bill and I kind of looked at each other and we were like, alright, Let's table whatever this discussion is, whatever it was at the time and just like, let's go around and just talk about like what is eating at you guys, what's keeping you up, like let's have like campfire conversation. Right? Let's just talk. And the way those founders blossomed and we were able to just sit back and be like, okay, you guys are having similar challenges. Talk to each other about it.

Okay. You were just talking to us in a meeting the other day about how you solve that problem you're having. Talk to each other about it. And that like the realization that, okay, sometimes founders don't need programming. Sometimes they just need community.

We were like, oh my god. We it was it was funny to us in a way because we were like, it can really be that simple for especially mission driven founders who they tend to be on an island with their passion and they're usually getting discounted by everybody around them. But that little juice of like sometimes they just need like friends who understand what they're going through. That's something that we could have been providing from the get go. So that was a little bit of like a kick ourselves moment but it was you know.

That is so awesome to see that happen. Samuel, do you have a funny story to share?

Yeah. This was my first cohort. So we did an Elevate Equity cohort. It was focused on health equity. And so I'm getting the hang of everything, you know, and connecting with coaches and founders.

And I had one particular coach and founder pair. And they were feeling each other out and kinda getting connected and just different forms of communication. I remember it was a Tuesday. I'm not an early riser at all. And so the fact that I was awake enough to even have this conversation is a miracle in and of itself.

I wake up cause my phone is buzzing at 07:30. And I look in and I see, oh, it's a it's a founder. And I pick up and I'm like, "oh, hey, like, what's going on?" And the founder just launches. Boom.

Straight into the conversation. Ah, like, it's blah blah blah. And I don't think that this is working with my coach and blah blah blah. And she did this and I said this and blah blah blah. And I was like, oh, snap.

Okay. What what what's going on? And so I talked with her for about an hour and I was able to kinda like talk her off the ledge and I was like, hey, you know, you gotta understand. She's here to help you. I'm sure that there's a miscommunication here.

Like, let's talk about it. And was able to successfully like kinda talk her down. It was great. And so I get off the phone at, like like, 08:20. Ten minutes later, coach calls me.

Oh.

And so on the phone with the coach, and the coach is like, have you heard from the founder? And I was like, yeah. And she was like, well, this happened and this happened and everything. And then I was able to kinda, like, talk with the coach and we came to a point of, like, agreement. And it was funny because they're both super passionate.

You know, the founder is passionate about their idea, you know, and kinda like you were saying, comes from a place where people have been discounting her and her idea and and the viability of it. And so she's super protective and territorial about it. And then you have this coach that just wants the best for them and is trying to help them, believes fully in their idea and wants to see it blossom. And so it was funny to kinda be in the middle of that and ultimately help come together. But I remember hanging up from talking to that coach and being like, what did I sign up for?

Seven thirty calls. I don't know.

I think that's a great story because it highlights a bit about the type of work that you do every As program managers, you all work with coaches, with founders, and run our nine week cohorts of accelerators with different workshops and speakers come in. There's a lot of education going on with founders, but there's a lot of the emotional piece too. And I think sometimes that's the part that goes unseen, is just the amount of energy that goes into making sure founders are feeling heard, understood, that coaches are able to give the best of what they have to offer and that the environment is right for everybody participating in the cohort and that support is 24/7. And I know that's the case at Flywheel. I know Josie now at UC Center for Entrepreneurship.

You're still doing this kind of work in a different way. Talk a little bit about the emotional piece, if you don't mind. Why is that important to consider when you're helping entrepreneurs?

For me, it's almost as simple as like, if they're showing up 24/7, how can I give them anything less than that? Right? There's a lot of fulfillment in seeing somebody who not only achieves like a strategic goal that they've set out for themselves or reaches a milestone or whatever, but reaches a level of impact that you know that they were so personally striving for because of how meaningful it is to them. Because you're like, listen, they're on a mission that I know is quite literally to make the world a better place and seeing them achieve their goals is like, yes, that is one little step towards that. And we were able to be a part of that and help them.

And that development of the founder as a person is just as impactful to our community as the development of those ventures, for sure. Because even if that venture or that idea or whatever ends up you know, not developing any further, you know that founder is gonna keep hustling on that mission. Mhmm.

Yeah. I think for me, there's there's two elements. I think the first one is that I have such a deep respect and admiration for the founders because they're rolling up their sleeves and they're they're pursuing solutions that not only are necessary, but people have been working on these things for millennia. And so they're taking on this huge challenge of, you know, applying themselves to situations and challenges that are daunting. And so for me, having an opportunity to be a resource for them along that journey and help them, I think, is an incredibly fulfilling thing for me.

But it also, like, prompts me, you know, and here's the second thing. Think because they are people first, they kind of need that space to kind of flex a little bit and and decompress a little bit and to just dialogue, like Josie was saying, with people who get it, people who see the the need for what they're doing. And I think the being able to provide that that safe space, that, you know, smile, that conversation, that call at 07:30AM, I think goes a long way with them for sure. And so those are the kind of the two things for me, I think, emotionally, We're dealing with people. We're dealing with people who are trying to solve problems for people.

I just thought of another funny story that's not about a founder, but if you guys wanna capture a little bit of goofy flywheel lore. Okay. Sure. I'll make it very quick.

I love goofy lore.

And again, with apologies to Bill, who's not here to stop me from telling this story, fall of twenty twenty, our first sustainable Cincy accelerator. It got to be our demo day and fall twenty twenty things were still like 99% online. We were running the demo day entirely streamed on Zoom over YouTube. First time we'd ever done anything like that. Right?

So we're like, Oh man, we had eight teams, which is crazy. We got everybody synced up. We got everybody in the Zoom. We made sure everybody's presentations were rigged up. We were like, Okay, this is solid.

Our keynote speaker was in our little breakout. We were feeling real good. So we were on the fourth floor of Union Hall in a little conference room and we were like, Okay, we got ten minutes of showtime. Let's step out on the pad, the rooftop patio, get some fresh air and just get our heads in the game. I know.

You know where this is going. So we step out on the patio, we're like, this is gonna be great, great cohort, great speaker, like, let's rock and roll. We have no tech issues like manifesting. We go back to grab the door to go inside. It's locked.

I'm like, Do you have your phone? He goes, No. Do you have your phone? I go, No. So neither of us have a way to get back into the building.

Everyone is online inside ready to go. We're like, oh my god, there's like 100 people on the stream. Oh my god. So we're like, all right, let's not panic, as we're both completely panicking. We're running up and down the stairs, looking in windows, trying to figure out.

Bill down the street. So Bill runs down to Kruger's or maybe Quanhapa uses their phone to call his wife Eileen, says, Can you call Eric Weissman and get him to let us in the building? She's like, I don't know how to contact Eric Weissman. What do you want me to do? He's like, Okay.

He runs back to the front door. Finally, somebody's coming out the front door, lets him in, he comes and gets me, and we literally sit down to like go live on our demo day with like a minute to spare. Wow. If you want like a little inside baseball on how things happen at Flywheel in the era of Josie and Bill, that was a pretty good little microcosm. Oh my gosh.

I love it. What a great story. Okay. We're going to wrap things up with one final question. If you had one piece of advice for a social entrepreneur, what would that be? Mine was don't quit.

Know your story.

I would say don't schlub on the details.

That's good.

I like it. Schlub?

Yeah.

It's an industry term.

Okay. Very good advice. Well, thank you both for sharing your stories and your insights and your perspectives. And thanks for all you do for our ecosystem.

Thanks for having us.

Yeah. Thank you.

Go Flywheel.

Go Flywheel.

On the Fly! is produced by Joey Scarillo with music composed by Ben Hammer. Recorded at 1819 Innovation Hub in Cincinnati, Ohio, courtesy of the University of Cincinnati.