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June 21, 2025 24 mins

What does it take to guide a social entrepreneur from vision to venture? In this insightful episode of On the Fly!, host Joan Kaup sits down with seasoned Flywheel coaches Mishawn Styles and Paul Szydlowski to explore what coaching really looks like behind the scenes—and how empathy, active listening, and honest guidance can transform a founder’s journey.

Both coaches bring decades of leadership, business, and human insight to Flywheel’s social enterprise accelerator. But it’s their coaching mindset—not just their resumes—that truly supports founders as they balance passion and profitability.

💡 You’ll hear:

  • The difference between coaching and mentoring—and why both matter
  • How Flywheel coaches help founders refine their business model, develop their pitch, and face personal blocks
  • Why entrepreneurship is more about mindset than mechanics
  • Real stories from the front lines of startup growth, founder breakthroughs, and the power of team coaching
  • What it really means to “get out of your own way” as a founder

Whether you're launching your first social enterprise or guiding others to do so, this episode is packed with wisdom on how to stay grounded, focused, and supported through it all.

Learn more about Mishawn’s work: StylesHR.com

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 sponsored by First Financial Bank
Learn More at bankatfirst.com

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Paul Szydlowski (00:09):
I once heard money isn't the objective.
That's the scorecard. That tellsyou that your idea, your
service, your product is beingaccepted by the marketplace. And
so, he goes, if you believe inyour product and you're
delivering something that hasvalue, the money will come. But
if you just go out there for themoney, you're it's not going to

(00:31):
work. You have to be focused onthe customer and deliver
something of value. A coworkerof mine used to say that profit
is the result of successfullysatisfying your customers'
needs. And it really is true.

Joan Kaup (00:47):
To date, Flywheel has coordinated 5,242 coaching and
consulting hours withentrepreneurs dedicated to
social impact, and that numberincreases every month. Today, I
have the pleasure of talkingwith two of the Flywheel
certified coaches who have giventheir time and talent to work

(01:09):
closely with our selectedfounders of start up
organizations, those thatembrace the bottom double line
of purpose and profit. With meis Mishawn Styles and
Szydlowski. People are thecompany's most precious

(01:31):
resource. And as you say,Mishawn, pivoting and zigzagging
is a new norm. So tell us alittle more about that and about
your background, please.

Mishawn Styles (01:43):
Oh, my background is very vast. I
initially started in humanresources and mental health, and
then I just zigzagged over tohuman resources. And just
recently, my husband and Istarted Styles HR to help
individuals within organizationsto be their best, their best
selves. And it's been a joy.It's been a joy.

Joan Kaup (02:05):
Well, good for you. If our listeners want to know
more about StylesHR, where dothey find that information?

Mishawn Styles (02:11):
StylesHR.com.

Joan Kaup (02:12):
Oh, that's easy enough. Thank you. Paul, once
again, you are currently leadingan innovative company, one that
has only been around for abouttwenty years. You have a career
of leading organizations andreorganizing companies for new
growth, stability and brighterfutures. Tell us more about that

(02:34):
drive and certainty.

Paul Szydlowski (02:37):
That's a good question. It comes from seeing
how things could be done better.And my first entrepreneurial
endeavor was in the dry cleaningbusiness and it was after a dry
cleaner screwed up my pants. Isaid, I could do this better.
And I started a dry cleaningbusiness and did that for
fifteen years. And since then,it's just been a matter of

(02:59):
seeing processes, opportunities,just anything that could be
improved and finding better waysto do it. And I enjoy being in
the thick of things. I don'twant to be on the side watching
things happen. So it reallycomes from just wanting to make

(03:22):
things better and and takingcontrol of that situation.

Joan Kaup (03:27):
You just do it. You just go for it.

Paul Szydlowski (03:30):
Yep.

Joan Kaup (03:30):
Thank you. Tell us a little bit more about why you
decided to be a coach forFlywheel and how you bring the
strengths of your career intoconversation with the founders.

Paul Szydlowski (03:46):
Well, it was interesting. I was putting
together working with P and G ontheir global alumni Convention
here in Cincinnati. And I wasputting together the Small
Business Symposium. And while Iwas doing that, I was introduced
to Bill Tucker. And they'resaying, I think you should get
involved with this. And I waslooking for something that was

(04:09):
more than just another job. Iwas at that point where you want
to start to give back. And thisjust fit perfectly with that.
And I got involved. I didn'tknow how it was going to work. I
had never coached in a formalcoaching setting. I worked with
Peggy Zink and her team fromWorkforce Connection. They were
actually Cincinnati Works, butthey were starting this

(04:31):
Workforce Connection. And it wasjust fascinating to watch it go
from idea to demo day andwatching the pitches, you know,
over time. And and I've juststayed with it ever since.

Joan Kaup (04:46):
So Bill Tucker is one of the original directors of
Flywheel Social Enterprise Hub.He's the one who kind of got it
up and running in thatcommunity. And he was very busy
with his outreach, gatheringexperienced business people and
qualified folks to come in ascoaches. Yeah, that was his
bailiwick. And I think over theyears you have coached, what, a

(05:09):
half dozen different startupcompanies?

Paul Szydlowski (05:11):
Well, I think it's seven.

Joan Kaup (05:12):
It's seven Yeah. Yeah. Excellent.

Paul Szydlowski (05:15):
And I mean, a diverse, truly diverse set of
businesses and ideas and people.It's been fascinating.

Joan Kaup (05:24):
You mentioned demo day. So at Flywheel, we work
with a founder for a series ofmonths covering various topics
that are important to abusiness. And then that
culminates with an opportunityfor them to stand up in front of
an audience of interested folks.It could be their cheerleaders.

(05:44):
It could be possible investors.It could be media. And that is
what we call demo day. So that'show we get to that term. So,
Mishan, how about you? How didyou become a coach, and how do
you integrate your yourbackground and experience?

Mishawn Styles (05:59):
Actually, it was through Michael Moore through
Cincinnati Black Achievers. Iwas volunteering with his
organization as a mentor and wasalso volunteering with local
colleges and universities as amentor. And he said, I think
that this will be something goodfor you to do. And I said,
Michael, I'm too busy. I can'tdo that. And a year later, he
said, I think this is somethingyou really should do. And I came

(06:22):
on board and was partnering withBill and with Paul. And I said,
I I think this would be helpful.I thought that I brought a
different perspective toFlywheel because my husband has
started so many differentconcepts, small businesses. I
thought that my take would behelpful to the different

(06:43):
founders that were trying tostart their companies.

Joan Kaup (06:46):
You do bring a different perspective. I've had
the joy of coaching with you.And I love the way you will
remind the founders kinda like,just breathe. How does this make
you feel? How does this fit intothe big puzzle of your life in
general? I mean, there's more toit than just go, go, go. It also
has to fit and resonate with youas a human being. And I think

(07:08):
that's a really importantreminder when you are coaching.
Tell me in your mind thedifference between mentoring and
coaching.

Mishawn Styles (07:18):
Mentoring. Well, it's not too big of a
difference. The most importantthing to remember is that when
you're mentoring or coaching,you're not trying to make that
person be a mini me of you or todo the things that you want.
When you're coaching, you'rebringing forth the best of that
individual to realize their bestpotential. Mentoring, you're

(07:41):
coaching in a way, but you'rehelping that individual to
navigate life. And when you'recoaching, you're helping them to
navigate a product, a service,something, a tangible something.

Joan Kaup (07:55):
When you are coaching, what do you find
yourselves repeating from onegroup to another? Paul, what are
your key points forentrepreneurship? Or what do you
find yourselves teaching?

Paul Szydlowski (08:06):
You know, there are a couple of traits that
every successful entrepreneurhas. One of those is focus. They
understand the value of time sothat they're not doing
everything. And third is thatthey act. But the focus is
really probably the first thingthat are the most important
thing with these folks as theycome in to the program because
they've got these ideas. They'vegot these grand dreams. And a

(08:30):
lot of times, it's just the seedof an idea and a desire to
deliver this good, this service.And it's a matter of, Okay, how
are we going to do that? Andreally helping them narrow it
down to what are you focusingon? How is this going to work in
the marketplace? And as you seethat kind of it's an iterative

(08:51):
process and you see them narrowit down, narrow it down, that's
really probably what I spendmost of my time trying to help
them with. I would agree. Justsitting here listening to you,
when we're working with thefounders, getting them to focus.
When you're talking aboutcoaching, getting them to be
open to other ideals. Not ideas,but ideals. That what you've

(09:15):
dreamed and what you've birthedall of this time, there are
other avenues and there areother aspects that I think that
you should consider to make youridea better and to give you
exposure to more. Becausesometimes our founders can be so
laser focused on what they dreamthat they're missing other

(09:36):
opportunities. I have seen that.
A lot of Joan, you and I mayhave worked on it on one of the
where we had to get the founderto really get outside of their
own head to see the opportunityand see what was important to
their potential clients andcustomers rather than a lot of
times you go in and you want tosell. This is what we have. Look

(09:59):
at this. And it's, well, that'snot what's really important to
the customer. And sometimesthey're so focused on this great
little widget that they havethat they're not thinking, well,
how does that impact? What'sthat mean to the customer? It is
a great widget, but you need tosell why that's important to the
customer. Sometimes you have toget them to get outside their

(10:21):
own head. And that's that's abig part of it.

Joan Kaup (10:25):
It's equally challenging because the founders
that we work with, theseorganizations, they have a dual
bottom line. They are bothwanting to make a big difference
in the world through theirsocial impact, but they also
need a few dollars. They need afew coins at the end of the day
to keep things running. Talk tome about that dual bottom line,

(10:48):
what it means to you and what itmeans to your coaching
experience with founders?

Mishawn Styles (10:54):
When I was thinking about that dual bottom
line, I'm always thinking aboutin corporate America, what are
you giving back to the communitywhile making a profit? And I
think that sometimes with thefounders, there was this one
founder that we were workingwith that was so laser focused
on finances, income, making aliving, being rich. And I'm

(11:17):
thinking about what are yougiving back? What are you giving
back? And is there going to bebalance?
Because at some point in time,what if you're not earning that
income or gaining the clients?Or what if it's just so
one-sided that it no longer isthat joy for you? That's a great
point. I once heard onesuccessful business person say

(11:41):
that money isn't the objective.That's the scorecard. That tells
you that your idea, yourservice, your product is being
accepted by the marketplace. Andso he goes, if you believe in
your product and you'redelivering something that has
value, the money will come. Butif you just go out there for the
money, it's not going to work.You have to be focused on the

(12:06):
customer and deliver somethingof value.

Paul Szydlowski (12:08):
A coworker of mine used to say that profit is
the result of successfullysatisfying your customers' And
it really is true. And what'sgreat about Flywheel is that
we're not just satisfying acustomer's needs, but we're
satisfying a societal need anddesire as well. I shouldn't say
we are. We're helping ourfounders do that. But that's

(12:31):
what's so gratifying about it.And it is really truly doing
well by doing good. And you'vegot to have the proper mix
because you can't just sitthere, I'm going to do this and
not think about the bottom linebecause you're gonna do it for
six months, run out of money,and then you're gonna be back at
your old job. And so there hasto be a mix. And that's really

(12:52):
where I think the coaches comein. It's keeping keeping that
balance for them.

Mishawn Styles (12:55):
For sure.

Joan Kaup (12:57):
I love when you talk about anecdotes and stories. Are
there other stories that come tomind? Moments working with
founders or whether it was anmoment for you or for the
founders sitting across the deskfrom you that you can share with
us?

Mishawn Styles (13:13):
There was one founder that we were working
with, not this Paul, but anotherPaul within Flywheel. And we we
talk about founders getting outof their own way. And regardless
of how much insight and coachingPaul was providing to this one
founder, I kept hearing thisfounder say that they could not

(13:36):
do something. They could not dothis. It was always a day. And I
asked Paul, I said, do you mindus pausing for just a moment?
And I asked the founder, are youafraid to leave your home? It
was during COVID. And thefounder was afraid to leave, and
that was in direct conflict withwhat they were wanting to do.
Their role, they needed to beout and about networking with

(14:00):
their customers, with theirclients, with the population.
But if the founder was afraid toleave home, there was no way
that the business was going tomove forward. The moment for me
was sometimes we're so focusedon doing good and moving a
business forward that we areliterally in our own way. We
don't realize it.

Joan Kaup (14:21):
That was really introspective that you could
figure out just from havingthese conversations. And during
that time, all of our coachingwas done online.

Mishawn Styles (14:30):
Especially during COVID, visually, we're
having these conversations,these virtual meetings, and we
didn't have the the benefit ofworking with our founders face
to face. But to just pick up onthe hesitancy and to see the
pauses and to see the diversionsand how the founder was

(14:52):
deflecting different questionsand coming up, I'm thinking,
wait a minute, something's notright here. Let me just listen
and pay attention. And I allowedPaul, through his leadership, to
lead the conversation. And Ijust paid attention to what the
founder was doing and what thefounder was saying. And then
that allowed me an opportunityto just ask the question out

(15:13):
loud. And then the tears came.It's like, okay, we're dealing
with something else here. It'snot about starting the business.
It's not about growing thebusiness. It's about you
receiving the support that youneed so that you can be healthy
for your business. Mhmm. And asa founder, if you're not healthy
for your business, when we'retalking about that double bottom

(15:36):
line, you're not going to behealthy for the society. You're
going to turn bitter. And yourcustomers are going to see that.

Joan Kaup (15:43):
They will know.

Mishawn Styles (15:44):
They will know. And then everything that you
fought so hard to grow, todevelop, to cultivate is going
to be for naught because youdidn't take care of yourself.

Joan Kaup (15:53):
Good point.

Mishawn Styles (15:54):
And it became a bitter love for this company
that I'm trying to birth. Andthe founder at that time stepped
back and put their dreams onpause for a moment.

Joan Kaup (16:07):
Brilliant. And you also remind me. When we coach,
we coach in a team of two orthree, which allows the coaches
to do active listening. I thinkit's a critical part of
coaching. So there may be oneconversation where you're taking
the lead of asking, exploring,directing, and I have the luxury

(16:29):
of observing and activelylistening and vice versa. And I
think that's a real strength ofcoaching with teams as we do at
Flywheel. Paul, do you have anstory that you want to share?

Paul Szydlowski (16:43):
You know, it's interesting. Mine is really
simple. With my first team andit was again with Peggy at
Workforce Connection. And duringpitch practice, I would just
kind of watch as she was talkingand nod and nod and kind of
smile. And I thought nothing ofit. And then on demo day, she

(17:04):
gave her pitch. And during thepitch, she kept looking over and
I'm just sitting there nodding.Afterwards she came up and she
said, she says, you know, Ididn't think I could do this.
And every time I started to getnervous, I would just look over
at you and you're just noddingand smiling. I was doing nothing
but nodding and smiling, but Irealized Peggy was accomplished
and a great leader. And yet,just being able to provide that

(17:28):
support, and I realized there'sso much more. I was still in the
thought of, I've got thisentrepreneurial background. I'm
going come in and tell them howthey have to do this and do that
and do this. And I realized thatit is about providing support,
guidance, and really being partof that support system that
these founders and theseentrepreneurs have. And that was

(17:49):
when I realized I'm not there topush so much as to assist.

Joan Kaup (17:55):
I think it's fun to see the names of the companies
crop up. And it's it's such ajoy as a flywheel coach to go,
yeah, baby. I know them orthat's one of ours.

Mishawn Styles (18:08):
I don't intentionally go out to support
the founders, but I do. And Ididn't realize that I did.
Because when I'm out and aboutin the community and may
someone's name come up or theirorganization come up or I'm
making references or referralsor advising them. Have you

(18:30):
considered Flywheel? Have youthought about Flywheel?
I do support and keep incontact. I just realized just
sitting here, yes, I do. I getsocial media contacts. "Hey,
Mishawn. I'm paying attention".I remember when you said this,
and I didn't give myself creditfor that.

Joan Kaup (18:47):
Absolutely. Take credit. And and your you said
you and your husband havelaunched a couple other
innovative creative things. Isthere something that you've
picked up through the flywheelcontacts that have been helpful
in those endeavors?

Mishawn Styles (19:00):
One thing that has been the benefit, I'm the
extrovert, the introvert that isoperating in an extroverted
world. I truly am the extrovertin our marriage. My husband is
extremely introverted. And fromFlywheel, we speak about the
pitch contest and being innetworking. And that is not a
strong point for either of us.It really is not. And just

(19:22):
working through and withFlywheel and the different
founders and learning theimportance of the network and
collaborating and gettingyourself out there and putting
yourself out there and beinguncomfortable. That has been the
greatest value that I've takenaway from Flywheel. Just put
yourself out there. We don'tknow everything. Our founders

(19:43):
don't know everything, but it'sthe collective of being in the
space with so many creativeindividuals that have different
ideas and different ventures anddifferent spaces that they're
occupying in this vast ecosystemthat we're all we have the
pleasure of working together in.And that's what we talk about

(20:03):
all the time, that we have toget outside of ourselves and to
be uncomfortable in thisextroverted space.

Joan Kaup (20:11):
Yep. Well said. What about you, Paul?

Paul Szydlowski (20:13):
Well, it's interesting because we spend the
bulk of our time seems to behelping these entrepreneurs
develop their pitch. And really,that's all about developing
their business idea and theirbusiness model and putting it
into a presentable form. And sowe're constantly working on
their pitches. And it'sfascinating to watch them

(20:35):
develop over time. But then, andyou know this because in my own
world, I've got this companythat may need some investment.
And our owners said, hey, putsomething together. And I'm
walking down the sidewalk atBlink and I run across Joe and I
say, hey, I may need to call youbecause I may need some pitch.

(20:57):
Help with a pitch. I need somepitch practice. But the thing is
is that shows, again, that'skind of an moment too that even
though we teach this, we helpthese people with that, when you
have to do it yourself, you needoutside help. And so it really
is something where we all needeach other. And it's truly an

(21:17):
ecosystem. And that's what I'vetaken from this that nobody
knows it all. And we all needhelp from somewhere else. And
everybody has something to give.

Joan Kaup (21:29):
And it's great to have a community like Flywheel
where we can find one another,reach out, support each other. I
often think thatentrepreneurship is not so much
a discipline as it is a mindset.I find myself shopping local,
supporting the independent,whether that's a restaurant or a
boutique shop. Anything else youwanna offer to our listeners

(21:50):
about your experience as a coachabout Flywheel?

Mishawn Styles (21:54):
I think that there will always be a need for
Flywheel. When Sterling and Iwere first starting our first
company, I wished there was aflywheel. I I just wish there
was. Just as we have all ofthese different generational
categories and groupings ofpeople, There will always be an
entrepreneur out there that isin need of the services that

(22:14):
Flywheel provides. And thatthey're needing to ask. They're
wanting to ask. You know,sometimes you can ask family and
friends, and family and friendsare not going to give you their
best. And there is always goingto be that intersection of an
opinion. However, through theservices of Flywheel, Flywheel
is going to prepare you. It'sgoing to prepare you for that

(22:36):
great big world out there as anentrepreneur that they are. And
I I just think that because ofthe resources and the coaches
and the financial advice or thefinancial guidance that Flywheel
provides to these entrepreneurs,that they have a better stake in
the game and they have a betteropportunity of their dream come

(22:58):
into fruition than in my yearspast. In my years past, it was
just a concept. It was just adream. I didn't have that coach
to encourage me forward or topoint me in the right direction
or to tell me, no. We're notgonna tell you no, but maybe now
is not the best time. ButFlywheel, everything that I've

(23:21):
learned since I've beenvolunteering for almost five
years now, wow. I wish that Iwould have known for myself.

Joan Kaup (23:31):
Thank you. Thank you both very much for showing your
time, your expertise, and thefun that we have as Flywheel
coaches.

Mishawn Styles (23:39):
Thank you, Joan.

Joan Kaup (23:40):
Thank you, Mishawn.

Paul Szydlowski (23:41):
Thank you.

Joan Kaup (23:41):
Thank you, Paul.
On the Fly is produced by JoeyScorilla with music composed by
Ben Hammer. Recorded at 1819Innovation Hub in Cincinnati,
Ohio, courtesy of the Universityof Cincinnati.
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