Making Community Matter – One Cup at a Time

In this heartfelt and inspiring episode of On the Fly!, Joan Kaup sits down with Ruth Anne Wolfe, the passionate founder of Community Happens Here, a grassroots social enterprise proving that deep, meaningful community can’t be mass-produced—it must be built, cup by cup. ☕

From her unexpected path through Japan, law, and motherhood to founding a brick-and-mortar community space in Cincinnati, Ruth Anne shares the journey that led her to reimagine what local connection really looks like. Through hospitality, art, and conversation, Ruth Anne is cultivating a place where children, entrepreneurs, and neighbors meet, learn, and build trust across differences.

Listen to hear more about: 

• The origins of Community Happens Here and its mission to combat loneliness through radical localism.
• Ruth Anne’s experience in Flywheel’s accelerator and the “aha” moments that shaped her approach to social enterprise.
• How sliding-scale coworking, youth-led coffee service, and sidewalk tea transform a neighborhood block.
• The importance of being your own angel investor when your vision doesn't fit traditional funding models.
• Why “you can't be what you can't see”—and how that philosophy shapes everything from mentoring to measuring impact.

 Visit communityhappenshere.org to explore coworking options, attend an event, or stop by for free coffee on a Saturday from 11am–1pm at 6238 Montgomery Rd, Cincinnati.
Follow Community Happens Here on Facebook, Instagram, and LinkedIn.

 At Flywheel Social Enterprise Hub, we believe in the power of social entrepreneurs like Ruth Anne to drive equity and impact in our neighborhoods. Learn how Flywheel supports founders, invests in big ideas, and helps social enterprises thrive: flywheelcincinnati.org

On The Fly! is sponsored by First Financial Bank
Learn More at bankatfirst.com

Episode Transcript

Ruth Anne Wolfe (00:10):
You can't make community by a corporation. You
can't make community by agovernment. You have to make
community one person at a time.And I thought in that midnight
moment is I started a nonprofitcalled Community Happens Here.
Here means between you and me.That's the only place we could

(00:37):
make community.

Joan Kaup (00:40):
At Flywheel Social Enterprise Hub, we believe in
the power of social enterpriseto make a more sustainable and
equitable community. My name isJoan Kaup. I'm the host of On
the Fly. And today, I am inconversation with Ruth Ann
Wolff, founder of CommunityHappens Here. Ruth Ann totally

(01:04):
grasps how social enterprise ismaking community more equitable.
Hello, Ruth Ann, and welcome toOn the Fly.

Ruth Anne Wolfe (01:11):
Good morning. This is so wonderful to be here.
I'm always excited anytime Joanasks me to do anything.

Joan Kaup (01:17):
Well, it's always good to have a conversation with
you. Thank you so much forbringing your energy and your
smile and your expertise. Infact, you have quite an
interesting background. How didyou come to be a Flywheel
founder? Tell us a little bitabout that.

Ruth Anne Wolfe (01:31):
Well, there's the long story and there's the
short story. But the long storyis that I have had many
adventures in my life, and I hadalready been a Japanese
interpreter. I had lived inJapan, worked in Japanese
companies around Cincinnati.Then I became a lawyer, an event

(01:54):
planner. I had a child, whichwas a wonderful thing that
brought me a whole new adventureat age 40.
So at age 45 or six or so, Ifound myself at a Cincinnati
Public School. Cincinnati'sfirst neighborhood Montessori
elementary school, PleasantRidge Montessori. The most naive

(02:15):
person you ever thought youwould ever meet about public
school. And I hit the mostimportant work of my life, which
was to help a neighborhoodpublic school rise up. And in
that work in which I became thecofounder or co president of the

(02:37):
Pleasant Ridge Montessori ParentTeacher Association and the
founder of the foundation that Icreated, I realized how
important it was to createcommunity in a place where there
was nothing there.
And we were so excited and weworked so hard and my daughter
was in kindergarten and then wekept going, kept going, don't

(03:00):
give up, don't give up for allthose years, and we made it to
her in sixth grade. Oh, this wasgreat. Look at that. 250 people
in the auditorium, children onthe stage. Wonderful.
And then guess what? The nextyear when she went to high
school, poof, all of that wasgone because in Cincinnati we
have a very stratified society,socioeconomically and socially.

(03:26):
And all those children and allthat love that he had created
just dispersed into a place thatI just couldn't see it anymore.
And I said, where are thesechildren? They're still in the
neighborhood but they're gonefrom my life. And I became very
sad about that. And then oneday, was downtown and I was

(03:48):
paying for my parking atWashington Square and I got a I
saw this ad that was some large,utilities company saying, we
build community in Cincinnati.And I saw I got really mad. I
said, no. You don't. You can'tmake community by a corporation.

(04:11):
You can't make community by agovernment. You have to make
community one person at a time.And I thought in that midnight
moment when if you're a lawyer,you can do things uninadvisedly
is I started a nonprofit calledCommunity Happens Here. Here
means between you and me. That'sthe only place we could make

(04:36):
community. Then hopefully, itbuilds and builds and builds,
but it has to happen here inthis hyper local moment of two
people talking and slowing downenough. So I got that idea and
then didn't know what to do withit. My financial adviser had
told us about a thing called adonor advised fund in the

(04:57):
Greater Cincinnati Foundation.And for tax reasons, we had put
a chunk of stock over there.
And so then suddenly, had whatto me seemed like a huge amount
of money, like $50,000. I coulddo something with this. And I
started taking classes with thisthing I found. Bill Tucker was
teaching on social enterprise.And he gave me a name for the

(05:21):
thing I was thinking about. Andeventually, it came around to
be, me taking that Flywheelclass.

Joan Kaup (05:31):
Oh, good. Bill Tucker was one of the first executive
directors of Flywheel SocialEnterprise Hub. He's the one
that pulled all of thistogether. Ruth Ann is sitting
here, and she's got on a prettylittle shirt that has two coffee
cups on it. They're facing eachother, and they have the x
between them. Tell us about yourcoffee cups.

Ruth Anne Wolfe (05:53):
So it is embroidered with a repair
technique called sashiko, andthey are the two cups with x
because I came to understandthat the way I could do this
work was cup by cup. That means,in my mind, we repair the world
one person and one talk and onecup at a time. And that was

(06:17):
building on a program that I hadstarted many years before that
when Amelia was in fifth gradecalled Coffee Cup Entrepreneurs
at Pleasant Ridge Montessori andit was to teach
entrepreneurship. So in the end,these two threads have come
together where I teach fourth,fifth, and sixth graders the
principles of hosting and ofbusiness and of how to see their

(06:39):
life in dream big ink terms andthen keep those kids and
encourage those kids to come tomy now building that I own
called Community Happens Hereand become the hosts of this
hopeful new world that we aretrying to build cup by cup.

(07:01):
Because every time a child makesa cup of coffee, asks an adult
what's their name, what wouldthey like in their coffee, and
then is literally teaching theadult how to interact with
humans. And, of course, we'rereinforcing for the children,
don't be afraid, speak yourvoice, tell people that this is

(07:26):
the job you're doing, be thewelcomer, and be the host. So
those two threads have pulledtogether and, become what is now
making community cup by cup.

Joan Kaup (07:39):
That is excellent. Many of the founders who come to
Flywheel, they have a a greatconcept but little experience or
financial support to get it offthe ground. That was not exactly
the scenario for you. Like yousaid, you had $50,000. Oh my
goodness. Can't I just changethe world with that? So tell us
what you were looking to gainfrom your time and training at

(08:01):
Flywheel.

Ruth Anne Wolfe (08:03):
As with so many things, you get more much more
than you ever think you willget. I the first thing I got was
to sit with a mentor. And Joan,you were amazing because you
totally understood from themoment we started talking what I
was trying to envision and bringinto reality. That explanation

(08:29):
is the hardest part of CommunityHappens Here's mission from to
connect people acrossdifference. Well, what do you
mean? "What's your goal?" Why?"Who cares?" "Why is that social
enterprise?" "What are you gonnado with it?" All of those things
in those fifteen weeks, I reallystruggled because you and all

(08:54):
the people the program isdesigned to make you answer
those questions. Some peoplecome in saying, how am I going
to get money, investment? What Ilearned, one of the biggest
pieces that I took away from itwas that there's a big
difference between running anonprofit and running a
business. And social enterprisetries to pull those together,

(09:17):
but you don't always have theskills. One person doesn't
necessarily always have theskills. And so trying to make a
nonprofit into a business is areally big lift, and Bill
pressured me on that. The onlythe other thing that I really
learned was having come from alaw background and a lot of

(09:41):
school, school, school, school,I needed to get my A. Right? I
wanted to get all my homeworkand get an A. And they kept
saying to me, no. You need toget the best, the minimum viable
product. The best you can dodoesn't have to be an a. It
needs to be, B, get as muchinformation as you can and move

(10:01):
forward. Figure it out as bestas you can and move forward.
Those were some of the greatchallenges and, learnings that I
got at Flywheel.

Joan Kaup (10:10):
Oh, that's interesting to hear. It is about
momentum and keeping themomentum. And at, Flywheel, we
often talk about the doublebottom line. It is where passion
and profit comes together. Andyou certainly have the passion.
But if you didn't have a littlebit of the scratch, it wasn't
gonna go anywhere. And nowCommunity Happens Here is not

(10:31):
just a concept. It is actuallybricks and mortar. It is
property, and you operate it asa coworking site. So you have a
revenue from those professionalswho use your space for workspace
and those professionals interactwith the young students who run

(10:51):
the little coffee cafe in thelobby so that those young
students interact with theprofessionals and both sides
benefit from that interaction,from that community experience.
Did I summarize that prettywell?

Ruth Anne Wolfe (11:06):
You did. And there are some Saturdays when
our, especially during taxseason, when the woman who runs
her tax business out ofcommunity happens here has to
ask her clients to park aroundthe corner because we have a
full blown sidewalk hospitalitygoing, and they have to sort of

(11:28):
wend their way through maybesome Jenga or, you know, things
happening like that. And thatmakes some people put off or
they don't know how to do it. Sowe ask a lot of our coworkers,
and we also give to ourcoworkers. The other side of

(11:50):
that is that we have a slidingscale. And so, for example, we
have one of our favoritecoworkers, and she was vaguely
trying to figure out her life.Now she has her business doing
notary, and and she's a realtor.And we gave her that soft place
to start. And so she becomes thewelcomer because that's a very

(12:16):
important thing that they're notjust seeing my gray haired old
lady face. She's an up andcoming entrepreneur. And of
course, as we say so often, youcan't be what you can't see.
This gives all the people thatare working in our space and our
children, the girl scouts comingin, they see that work and

(12:36):
ideals and life and children arenot all separate things. I tried
to create a space where it wasokay for all of those to go
together. And we we have to beaccommodating to each other to
make a new world of work thatactually works for everybody.

Joan Kaup (12:55):
As long as we're talking about it, why don't you
tell the listeners how they canaccess you, contact you, learn
more about Community HappensHere?

Ruth Anne Wolfe (13:03):
Well, we are, of course, on the web at
www.communityhappenshere.org.And on that site, you can find
out how to rent our space, howto become a coworker, what the
events are that are coming up.We have large public events, and
then we have smaller classes andthings that happen there. We're
also on Facebook at @6238, oryou can search for Community

(13:27):
Happens Here, and we're onInstagram at Community Happens
Here. So we even have twoTikToks.
I'm not so good at that one.And, of course, LinkedIn. We
have a LinkedIn, and I'm on thatas well. So all the places that
you're used to finding stuff.

Joan Kaup (13:42):
Okay. Thank you. So you are less than 10 years old.
Can you tell us, are youcomfortable sharing with us how
many employees you have, whatyour annual budget is now?

Ruth Anne Wolfe (13:53):
That's such an interesting question because, of
course, when I first started, Iwas– I had two interns and I had
a director of development and apart time but a COO type person
and all of these things. It wasso much and I was so in the
messy middle and I spent so muchmoney. And since then, I have

(14:20):
gotten way leaner and I have oneamazing person that I work with.
His name is Tyler Chernesky andhe's the grant manager but also
a person who can really helpwith the guiding. And he's a
hundred and ten hours a month,so that's not very much.
He's paid some. Luckily, he hasanother gig that he can help

(14:42):
support himself with, and Idon't get paid. Some I tried
that for a little while. Itdidn't really work because I'd
shovel the money in one end andtake it out the other and then
have to pay tax on. But I'mworking towards that ideal where
I will be able to pass it onwith a space for another person
who could be me. That's the theholy grail, isn't it? We have

(15:04):
about a hundred and $70,000 ayear of budget. And we I funded
it. I funded this last yearabout 56,000 from my donor
advised fund. Let's be realabout that. But we're heading
towards the day when we'rereplacing that 50,000 with other

(15:28):
donors. We have small donorsthat have monthly. They give us
$10 a month. We have coworkersat $100 a month. We have $350 a
month businesses.
So we have this wide range. Andthen we have a number of a good
bit of income from othernonprofits renting our space

(15:50):
four times. We don't do a lot ofbirthday parties because that is
more work than income, but we dorent the space quite often for
small retreats. We can do about25 to 30 people. We can do a
lovely party for that, foradults, or wine tastings and

(16:10):
things like this. So we havethat mix, and we're working
towards bringing the 50,000, 60thousand that I have been
putting in, bringing that up tosnuff, and then filling the
bucket further so that we couldhave more employees. Because the
more you can do, the more peopleyou have to run things, the more

(16:35):
you can do. But then having apayroll is very difficult, You
know, tricky because as we allknow, you have to come up with
that money every month whetherthey do anything or not.

Joan Kaup (16:47):
And your board, your board is engaged or is it an
advisory board?

Ruth Anne Wolfe (16:53):
That's a wonderful question. They are
engaged as long as I ask themfor help. They are always
willing to step up to help. Ihave a long history with many as
you said, Josie Dalton is on myboard. She was the program
director at Flywheel, she isalways pressuring me to say,

(17:13):
what is the impact measurement?We hope very much to be able to
get a data for equity grant thisyear. And whether we get it or
not, our focus this year is ongathering that data so that we
can press forward with thosebigger grants. As you know, the

(17:35):
surgeon general determined thatthere is an actual epidemic of
loneliness in America. And weare a health care organization
in our community. And we need toget the health care people we've
been talking more interact withhealth, children's hospital.

(17:55):
Those places, we need to helpunderstand help them understand
who we are so that we can getfunding around this idea that
loneliness is a health careproblem and that we can help
alleviate it with our work.

Joan Kaup (18:12):
But you do touch on something that is a challenge
for any social impactenterprise, which is
measurement, measurement,measurement, and what is your
social impact, and how do youprove it?

Ruth Anne Wolfe (18:22):
Yes. I would say that is always the challenge
because one woman over fiveyears having grown a business in
our space because I didn't askher for more than $10. Now she's
busily working in our space.What number is that? Yes. That

(18:45):
number is one, and it is amillion. Right? Because the the
overall impact of her is soimportant. And besides, she's a,
mentor for her children.

Joan Kaup (19:03):
It's the ripple effect with not just her, but
her children and the youngpeople she interacts with at
your facility and her neighborsand friends and melting through
that loneliness. So it is a itis a huge ripple effect, and it
is such a challenge for you tograsp that in numbers. And for

(19:23):
many funders and grantors,that's that's as been expected.

Ruth Anne Wolfe (19:28):
Right. And it was a very it still is a big
question or why I tried manytimes to get the, investor group
to understand what I was doingand feel it was worth investing
in, and I didn't succeed. Itdoesn't have that direct line

(19:52):
that a angel investor is lookingfor. So I became my own angel
investor. I bought my own housein Florida here in Cincinnati,
because I feel it's important toprove the concept.

Joan Kaup (20:06):
So long term, have you painted that vision yet?

Ruth Anne Wolfe (20:11):
That's a everyday– 2025 is definitely a
turning year for us. We've setthat as the year in which we
create the explanation, theclarity of of of conversation
around this, and we identifywhere those funding sources can

(20:32):
be. We have a challenge in thatcoworking looks on paper like a
great way. More coworkers, moreincome, no problem. But the more
coworkers, the more frictionwith the Girl Scouts and the
afternoon programming and thekids coming in and out. So

(20:54):
there's a delicate balancethere. And it's not just any
coworker. It has to be someonewho is flexible that way. So a
lot of things that are just on apiece of paper in an Excel
spreadsheet don't fullycalculate out. But, we are
always with our eyes open to theright, person who can bridge,

(21:18):
like Tyler and I are able to do,all kinds of people from the
community, and then walk thatvision forward. So we're
thinking about our ourexplanation and then how to

(21:39):
bring this to the attention of,say, the bigger people. We're
becoming trying to become expertin loneliness and the expert in
this methodology that we'vecreated and prove to others. We
have talked to a lot of otherpeople in Cincinnati that that
it is actually possible to haveneighborhoods that talk to each

(22:03):
other. I mean, that's animportant thing. And a place to
work that isn't super fancy andisn't super expensive and is
welcoming, all of those thingsare part of what we're proving.
And I hope and I imagine thatthere will be the next person
who I can pass this on to thatwill bring the work to the next

(22:26):
level.

Joan Kaup (22:27):
Your conversation reminds me how different it is
to think and expand and grow andmeasure a social impact
enterprise versus a pure forprofit business. So thank you
for sharing that a little bit. Idon't want to put you on the
spot, but can you recite yourpitch or your mission statement?

Ruth Anne Wolfe (22:51):
Well, I have actually narrowed it back down
further and further. So westrive to connect people across
difference, and we usehospitality and art to slow
people down and create a momentin which they can connect with

(23:13):
each other.

Joan Kaup (23:16):
Is there anything else you want to share with our
listeners about CommunityHappens Here, about your
background, about Flywheel?

Ruth Anne Wolfe (23:23):
I would like to tell everyone that every
Saturday from eleven to one, weare at 6238 Montgomery Road
across from the library, and weare either physically or
metaphorically on the sidewalk.We have our free coffee, tea,
and hot chocolate. We have ourlittle bit of art. We have our
themes, and it is literally opento all ages of people. Every

(23:48):
single person can stop by andhave a glass of lemonade or a
cup of tea and try out what itis to just be there to talk. So
the most wonderful thing you cando for your community right now
is to stop by between eleven andone on a Saturday and talk to
somebody.

Joan Kaup (24:08):
That is so nice. Thank you. You really grasp
social impact and making adifference in the community in
the world. So more good wishesand continued success. Thank you
very much.

Ruth Anne Wolfe (24:20):
Thank you, Joan, for being the mentor that
helped all of this be launched.

Joan Kaup (24:27):
On the Fly is produced by Joey Scarillo with
music composed by Ben Hammer.Recorded at 1819 Innovation Hub
in Cincinnati, Ohio, courtesy ofthe University of Cincinnati.