Kansas City Leader Kyle J. Smith – The Penal System & Entrepreneurship

[00:00:00.000] – David Maples
Hello, and welcome back to another episode of the Kansas City Leaders Podcast. I’m one of your
hosts, David Maples. Today I’m here with Kyle J. Benson Smith, and we’re really excited to have him
on the show today. He runs a not-for-profit called Determination Incorporated. I want to just dive into
this today. I want you to tell me a little bit about your background and how you ended up in Kansas
City.

[00:00:39.640] – Kyle Smith
Sure. Thanks for having me. We’re glad to have you on the show. We’re glad to have you on the show.
At Determination Incorporated, we help formerly incarcerated people start and grow businesses. But
before I started the organization in 2018, I moved to Kansas City in 2014. I grew up in a small town in
Missouri called Mexico, Missouri. Did you know there was Mexico, Missouri?

[00:01:03.060] – David Maples
I was unaware that there was a Mexico, Missouri.

[00:01:04.790] – Kyle Smith
Now you know. We officially say Mexicoans. It’s outside of Colombia, which is where the University of
Missouri is, Go Mizzou. I grew up there and then went to school at Truman State University in
Northeast Missouri and got a degree in theater. I worked at a theater festival in Massachusetts one
summer and then followed a bunch of friends up to New York. I lived in New York for four years after
school. After spending four years in New York and really enjoying it, I wanted something in between
the biggest, best city in the world and tiny small town, Mexico, Missouri, and started to look around in
this area to be near family and started to hear about the entrepreneurship community in Kansas City.
At the time, I was working in fitness. I worked at a CrossFit gym in Manhattan, and I wanted to open a
gym of my own. I moved to Kansas City in 2014 with that goal, and I can share some of that story
later, one of my first entrepreneurial fails. But after I stopped working in fitness, I had an interest in the
entrepreneurship community and some experience in marketing and started working at KC
SourceLink, which is an organization based out of U.M.K.C, the University of Missouri, Kansas City
here. KC Source-Link acts as a central hub for all of the entrepreneurial support organizations
around Kansas City, of which there are over 260. I started working there and got interested in
entrepreneurship as a pathway out of poverty and started to look around for a community that I could
support and started to hear about reentry and people coming home from prison and took it from
there.

[00:02:45.660] – David Maples
You’ve had an interesting journey to get here, and I’ve read some about you a little bit and about your
journey. Let’s really dive into Determination, Incorporated. As I understand it, you help provide a path
in entrepreneurship to help formerly incarcerated individuals, lifting themselves up after they’ve been
released from a penal institution. Is that correct?

[00:03:08.700] – Kyle Smith
Yeah.

[00:03:09.270] – David Maples
Okay. Tell me a little bit about your role. What made you decide to start this? Then what do you find
most rewarding about it?

[00:03:19.840] – Kyle Smith
I’ll jump off from working at KC Source-Lank and being interested in entrepreneurship as a pathway
out of poverty. Started to look around for a community that I could support and started to hear about
reentry and how unnecessarily difficult it is for our brothers and sisters coming home from
incarceration to reacclimate into society. They face so many barriers. Some of the biggest are
housing. Having a place to live with a felony on your record can be very difficult. Transportation is
really difficult around Kansas City. We do have the bus system, but that is way harder than having a
car. Then, of course, getting a job can be difficult as well. In Missouri, the latest data I’ve seen is from
2020, and 45% of people on parole in Missouri are unemployed. When I was working in the
entrepreneurship community, I was interested in supporting folks in reentry, and so I started to get to
know nonprofits that work in that area and learned about organizations like Second Chance, like
Connections to Success, like Journey to New Life that provide help for people in terms of finding a
job. But I wasn’t hearing about any organizations that were helping people start and grow businesses.
I specifically remember sitting down at the desk of a probation and parole officer who had been in the
field for over 10 years and saying, Hey, I’m thinking about starting this business support group for
formerly incarcerated people. Do you have any clients who may be interested? He said, They’ve
always had people come to them interested in starting a business, but never knew where to send
them, and they had so many other things going on that they always had to back burner it. I said, Well,
here’s our flyer. We’re starting this group, and just took it from there. The second part of your question
was, what’s most rewarding about the work? I think it’s just getting the chance to work with people
one-on-one. As much as we’re able to share education or share resources or maybe help someone
feel inspired, I feel just as inspired by doing the work as well. Because seeing the resilience that
people have built up after being incarcerated and seeing them wanting to make a fresh start and
wanting to do something new and different with their life is really inspiring to me. I really like working
with people.

[00:05:38.290] – David Maples
Just to chime in on one of the things you said here is that according to the statistic you quoted, 45%
of people who are formerly incarcerated do not have gain full employment right now. One of the
biggest challenges for someone is as they’re leaving the penal system, as I understand it, and I have a
personal story about that, I have a family who finished, they’ve done their time and done their part.
One of the biggest challenges when they come out, at least from what I understand, is that they said,
I’ve done my time, I’ve done my bit. I’m going to go out in the community and be involved. They
literally find, I mean, there’s that checkbox, have you ever been convicted of a felony before? In some
places people use it in housing applications. It makes it very, very difficult without a huge support
structure. It’s very difficult for these people to really get a leg up and really start their lives over. I’ve
always personally found that to be a bit unfair because you’ve done your bit, you’ve done your time,
and most people do. The stat that I know is that I think 90% of people who are formerly incarcerated
believe that they’ll have received some employment within about 90 days of exiting the penal system.
The reality of it is a year later, especially if you’re a man, it’s less than half. Then that contributes to
that cycle. It’s the recidivism thing. Ultimately, regardless of how people feel about the penal system, I
fundamentally think that it’s failing these people as they reenter our systems. We want these people
to have part of the community. These people have families. We want them to have jobs. We want
them on the tax rolls of nothing else. We want them to be contributing to community. One of the
biggest ways that I see that that can happen is by getting them gainful employment. I didn’t mean to
go off on the soapbox there. But that’s how I feel about it.

[00:07:38.970] – Kyle Smith
Yeah, and it’s totally true. It’s very much true. Having a felony on your record is really a scarlet letter
that can follow a person around for the rest of your life. I’m with you. You would like to think that
someone’s home and they’ve done their time and they get a fresh start. But as you said so well, that is
rarely ever the case. It is such a stigmatized part of our community. It’s really unfortunate because we
know that one of the biggest predictors of recidivism of returning to prison is poverty. Without
financial opportunity, that makes someone more desperate and they may be led back to what led
them to prison in the first place.

[00:08:19.710] – David Maples
Entrepreneurship is a leg up or way to move out of poverty. Because ultimately, if they have the ability
to get into one of these entrepreneurial type programs that you have, that means they get to chart
their own destiny in a way. They’re not necessarily relying on someone giving them a shot necessarily.
I guess that’s what your organization does, am I correct?

[00:08:42.970] – Kyle Smith
Yeah, that’s the goal. We know that entrepreneurship is not going to be everyone’s path. Data from the
Kaufman Foundation says that three out of 1,000 people will become entrepreneurs. But for those
who are pursuing entrepreneurship, and you’re right, perhaps there’s a higher percentage of formerly
incarcerated people because of the stigmas, because of wanting to be their own boss, because of not
wanting to have someone else give them the chance, are interested in entrepreneurship, those people
who do choose that path, I think it’s important that they get the support they need to succeed so that,
like you said earlier, they can make a living, they can provide for themselves and their family, they can
stay home, they can give back to the community. Whenever I first started the organization, I started to
hear about folks who were having success through entrepreneurship after incarceration. One of those
is Sarah Montine, and she’s still on our board. Whenever she got home from prison about a decade
ago, she was at that time living homeless in a shack, trying to figure out what she was going to do
next with her life. She decided while she was reading the newspaper and watching the movie Pursuit
of Happiness relentlessly, that she saw some opportunities for some cleaning jobs, cleaning on
construction sites. She decided that that is what she was going to focus on. She just started walking
on the construction sites and saying, Hey, I’m here, I’d love to clean, and I’m starting a business in this.
She just learned on the job. She made good relationships with people and actually learned from the
people that she was contracting with how to do the job and just built the business from there, where
over the course of years, she was able to grow into a business that has grossed hundreds of
thousands of dollars in revenue and has actually employed people who are home from incarceration
as well. She makes a really big focus to employ people who are in recovery or who are recently home
from incarceration, which is a part of our goal as well as an organization that folks would be able to
hire other people coming home from incarceration to provide them a chance.

[00:10:54.630] – David Maples
That’s actually really interesting. She’s actually doubling down on this by the fact that she not only
started her own company, but she’s actually giving other people who were in similar situations a
chance to move forward. To move the conversation a little bit beyond that, are there any things…
Because in my other life, in the Bucks Stop to Your Podcast, I do consulting for business owners, and
I’ve actually put business owners in touch with certain programs because there are certain programs
to help off… There are sometimes state grants and other things that these businesses can even avail
themselves to if they’re actually hiring people who were previously incarcerated. Do you know about
any of those programs? Is there a way that maybe we could shift the paradigm a little bit for business
owners? Why don’t we take a chance on these people?

[00:11:44.760] – Kyle Smith
Yeah. There’s a national tax credit available called the Workforce Opportunity. Workforce? Yes. I’m not
getting the acronym exactly right, but like you described, that’s a tax credit for people who hire
formerly incarcerated people. It is something that some businesses take advantage of. I remember
conversations with some of my friends who work in reentry that say it’s not a huge driver for the
actual employers, probably because it sounds like a bunch of paperwork. It doesn’t usually change the
conversation with that employer when it comes to, Will they hire formerly incarcerated people? Oh,
only if I get a tax credit. Instead, what those organizations lead with is, These are great employees.
These are driven people who, when given a chance, will be dependable for you and your business. I
think leading with that value is of more interest to the business owners and gives more dignity to
formerly incarcerated people as well.

[00:12:43.990] – David Maples
Absolutely. I can definitely see how that would be very attractive. I guess my question is that through
your organization, in what ways are you contributing to making Kansas City a better place to live, play,
and work? How do you see this as helping a rising tide lifts all boats? How does this help the
community overall?

[00:13:07.590] – Kyle Smith
Yeah, I would like to thank and do believe that by supporting our community of formerly incarcerated
entrepreneurs and them supporting one another and each other, lifting each other up, that we provide
help one person find more wellbeing, more satisfaction, more opportunity, feel more supportive, so
that that creates ripples in their family and in the broader community as well. I also know we publish a
twice-monthly, high-five-Thursday newsletter where we share about members of our community and
what they’re doing in their business. I know that’s really a positive beacon for people as well, helping
to change slowly, but helping to open people’s mindsets to formerly incarcerated people and what
people who have a felony record are up to. Yeah, It’s taken me a long time to learn it on a personal
level, because I definitely grew up in the generation of like, You can change the world. I’ve only really
recently adopted the idea that you can really only help one person at a time, but I believe that matters
too. That’s what we try to do through our organization.

[00:14:20.100] – David Maples
You mentioned them, changing the world. You mentioned the ripple effect. By changing one person,
how many people do they touch? At the end of the day, it’s a ripple effect. If you throw a rock in a
pond, it has… I don’t know. We may cut this out of the podcast. I don’t know. I’m thinking about it a
little bit. I was thinking about changing one life, you impact their community, you impact their kids,
you impact their loved ones. Just from my own standpoint, my own family, I was thinking about how
my brother, I went and visited him and I saw and he was in the penal system in Georgia. I saw state
institutions. I saw private prisons, which I thought were abhorrent. Like a guy in a cell next to him died
with appendicitis because they wouldn’t call the doctor because it costs too much after hours and he
was malingering. The guy was in there for cutting checks. He didn’t deserve to die in terrible pain.
Anyway, I’m not trying to… Is some of the stuff I saw was just really… It made you angry. You were
like, Dude, I mean, it’s prison. This is not supposed to be a gulag. The idea is that we’re supposed to
have a path. I don’t know, it’s funny. It made me get interested in the United States Penal System
anyway, because our prison system in the early 1900s, 1910 to 1920, was considered a model prison
system for the rest of the world. We paroled people into the army. We did a whole bunch of different
things. They were really considered, and Scandinavian countries do it now, Scandinavian look more
like college dorms in some cases. The recidivism rates are much lower. We’re talking at seven years,
they’re talking about recidivism rates for even heavy drug offenders and things like that. But people
with bad addiction things where the recidivism rates can be approached 70% at seven years. They’re
looking at 15. Even if you don’t care about people who went to prison, it’s like, dude, you don’t want to
pay taxes for them. Wouldn’t we be better off? I’m not trying to appeal to people like that. We’ll
probably cut all this out, but I’ve really thought about it.

[00:16:32.360] – Kyle Smith
No, it’s really important.

[00:16:33.400] – David Maples
How do you get to have a conversation with business owners like, Hey, man, dude, take a chance on
these people. Whisky, Tango, Foxtrot, mate. Is it just lock them up and throw away the key? What if it
was your kid? What if your son or daughter or your cousin or brother? It’s very different. Look, I get it.
We all make mistakes. I certainly don’t want to be judged by my worst day in life. How many of us
would in jail have we been caught doing something we weren’t allowed to do? I don’t know. Sorry, I
didn’t mean to go off on a tangent there. It’s stuff I think about sometimes. I’m like, How do we… I
don’t know.

[00:17:13.910] – Kyle Smith
It really matters. When it comes to the ripple effect, we know from data that the child of an
incarcerated parent is six times more likely to go to prison than their peers. By helping someone stay
home with their family, you reduce that chance and hopefully can break that intergenerational cycle. I
know the first time that I went into a prison, it was really shocking to me. It wasn’t even the worst
conditions, but just to come out and go, Oh, man, we treat people like that. We also call it
rehabilitative. We call that corrections. How can that setting, how can going from a terrible
circumstance to a terrible-er circumstance, equals something better? It just didn’t make sense to me.
You have described the different prison models that exist around the world that are more humane and
more dignified, I think, are really important to consider. We still, in America today, have a very
retributive justice mindset around people who have committed a crime. We’re still very much focused
on punishment. You see it every time you turn on the local news and they’re talking about the most
recent murder or the most recent terrible thing that went on in the community, we all reflexively go,
Well, get rid of them. We need to get rid of that person. Perhaps, and very likely, people do need to be
removed from society, especially if they are a risk to themselves or others. But that doesn’t solve all
the problems, and it certainly doesn’t get to the root issues that led to the problem in the first place,
which in a lot of cases can be mental health issues, can be substance abuse, and can be living in a
community that is impoverished and that is dangerous as well, where people don’t have the chance to
pursue other things. I do think it’s important that more people open their eyes to the problems that
exist around incarceration and mass incarceration in our society. That’s a whole other conversation
about how mass incarceration goes all the way back to slavery in the United States, was really
ramped up around the war on drugs, where you very much saw the numbers that increased. I believe
right now in the United States, there are 1.9 million people who are incarcerated. 95 or more % of
those are going to be home someday. In Kansas City, I’ve seen the number that 4,000 people come
home from prison every year in our area. I do believe that it’s important that we support those people
so that they don’t go back and we don’t keep wasting taxpayer dollars on things that aren’t working. In
Missouri, our recidivism rate, 46% of people return to prison within five years of release. If your
business was only 54% successful, you probably wouldn’t be in business anymore. There’s something
that we could be doing differently. That’s not to say that there’s not positive things going on within the
prison system, which I can talk more about that, but we need to keep an eye on this and constantly be
improving that system if we want our communities to get healthier and safer and more prosperous
for everybody.

[00:20:39.700] – David Maples
That’s a very interesting point. Let’s talk for a minute. Let’s talk about the initiatives you’ve seen going
on in the prison systems here that you think are bearing fruit, that are having a positive impact. What
do you see?

[00:20:53.000] – Kyle Smith
Yeah. Here in Kansas City, we straddle the state line, of course. We’ve done some work in the Kansas
prisons and more work on the Missouri side. In Kansas, the prison systems have strong partnerships
with private industry. They actually have businesses that are running inside of institutions or with
folks who are coming from the institutions. I’ve heard anecdotally that that’s a very positive program
for people because it gives them work skills, it allows them to work in a work environment, and they
also get a little bit bigger of a paycheck than they would with just a prison job. Of course, they also
build relationships with people who are on the outside so they have support when they come home.
There’s different nonprofit organizations that are doing good work on the Missouri and Kansas side
inside of the institutions. Two that we’ve partnered with on the Kansas side are Brothers in Blue
Reentry and Reaching Out from Within. Brothers in Blue Reentry is a faith-based program that actually
has a housing wing inside of a prison in Lansing and does personal and professional development
with people, does group therapy, does positive community building and helps people whenever they
get home as well. Reaching Out from Within is a support group that is led by currently incarcerated
people, where they study topics related to anger management and conflict resolution and traumainformed care and that thing. They also have a strong network on the outside. On the Missouri side,
there are good initiatives going on when it comes to education. This happens in prisons all over the
place. Many people get their GEDs while they’re inside of prisons. Here in Kansas City, there is a
correctional institution called the Transition Center of Kansas City, which before COVID was a
minimum security prison, and now it’s underneath probation and parole. It’s actually a place where
people who are finishing up their prison sentences and coming back to this area but don’t have a
home plan yet can land for a while while they’re getting reacclimated to the community. That
transition center of Kansas City is working closely with a nonprofit here in Kansas City called the
Center for Conflict Resolution on building a restorative justice community. They have circles every
morning where they meet with residents. They don’t call them offenders, they don’t call them felons,
they call them residents, and staff and talk about what’s going on in their area, what’s coming up,
what do they have going on. They’re working really hard to bring a lot of community partners down
there so that people have connections with organizations on the outside.

[00:23:39.850] – David Maples
A lot of what you said here, from my studies of the prison systems is a little bit, I’ve learned a little bit
about… They talk about one of the most important things for people who are incarcerated is to
engage in what they call cognitive behavioral therapy. The idea is it’s about reframing situations. For
example, anger management. When something happens, it’s to think about the situation, reframe it,
and figure out like, Okay, how do I need to handle this? For example, most of us, when we lose a job,
we think about like, I’m going to go up and get another job the next morning. If I’ve grown up in a
situation with poverty, I might have a different set of life choices that have been given to me. I’ve been
just like, Well, maybe how do I make my money or whatever I have to do? I might turn to crime for
that. But one of the things they said about one of these big things is by giving people new tools and
new ways to reframe things and think about things differently. For example, if your only opportunity to
make money is something that is not legal, then those are your choices that are presented to you.
Whereas when you go into these prison systems, and I think what you said there’s really interesting,
like reframing, they talk about re-housing these people. It’s like you don’t call them offenders or
anything else. They’re now people, they’re now residents. That sounds like a more inclusive model. If
you start thinking about yourself as a resident as opposed to a prisoner, I think that’s a very powerful
framework to operate under. I’m not trying to oversimplify either, but I know there’s a lot there. In
particular, in regards to the stuff you do, what you think opportunities or challenges do you see
coming from Kansas City in the coming few years? What do you see on the horizon?

[00:25:21.790] – Kyle Smith
A big challenge, and I’m far from the first person to say this, but is affordable housing. We feel that
really specifically and in really dire ways, whenever it comes to working in reentry and helping
formerly incarcerated people, because there’s already so many stigmas when it comes to renting to
formerly incarcerated people. A few years ago in Kansas City did in KC Moe pass ban the box, which
makes it a city statute that you can’t have or you’re convicted of a felony on the application for
housing and for employment, that ban the box measure is only as effective as it is enforced, and I’ve
heard from the communities that it may not be enforced as well as it could be. Also, just because
someone doesn’t ask on an initial application doesn’t mean that they’re not eventually going to do the
search and perhaps deny you housing. Affordable housing and safe and decent housing is a big
problem for a lot of people in Kansas City, but especially for people who have been incarcerated
before.

[00:26:27.800] – David Maples
Are there any ways you think that there are things either conversation need to be had or the
organizations you’re working to make that mixed-use development? Is there anybody you see who’s
doing stuff in that to help in that aspect?

[00:26:39.710] – Kyle Smith
There’s definitely positive things going on. I don’t, off the top of my head, know the name of those
organizations, but housing is just a really tricky problem right now. I think it goes beyond one of the
things that gets the most air time in the news and stuff are the disputes that happen between tenants
and landlords. I think it is important to pay attention to those things, and it is important to
acknowledge the power dynamics that are at play there. But that’s far from the only problem going on
in housing. It’s not just greedy landlords and it’s not just bad tenants. I’m far from an Uber expert in
this area, but I’ve learned from people who have been home builders in our city for decades that a big
part of the problem is just available housing stock, is just how much housing is out there. There was a
big slump in building new housing in the Great Recession in 2008, and it hasn’t caught up. Cities like
ours and across the nation, we are hundreds of thousands of housing stock short in many, many
areas, and that will drive prices up. That’s just basic supply and demand. So that’s not an easy
problem to fix right now either, because if someone is going to decide to go into home building or if
someone is in home building, costs are really high when it comes to supply and labor. It’s not the
most lucrative thing to build affordable housing, it’s the most lucrative thing to build luxury housing.
Maybe, but not really. There could be a trickle down effect there because it opens up other housing
stock, but nothing happens quickly and it’s hard to make large enough things happen to make a really
big change happen. I’m glad that the problems around affordable housing are on more people’s
radars, but it’s not something that we’re going to be able to fix overnight. It’s something that we’ll have
to continue to pay attention to and make a top priority.

[00:28:44.200] – David Maples
This leads to my next question. You’re someone in the know based on what’s going on in this area,
not just affordable housing, but in incarceration, recidivism. You’re a community expert in a way. How
do you approach collaboration and fostering unity within your community or in your field? How do you
get people who are formerly incarcerated, how do you get people who were maybe sympathetic or
may be able to help bring these things together? How do you help foster that connection?

[00:29:21.900] – Kyle Smith
Community collaboration and working with other organizations is crucial. It’s essential to the work
that we do. Because I described earlier starting Determination Incorporated, and one of my first steps
was getting to know the reentry organizations that provide support in these other areas. We don’t do
the same things that they do. We refer to those organizations all the time, and they refer to us
whenever they have a client who’s interested in entrepreneurship. There are different coalitions that
exist in reentry to keep these organizations connected. I think that’s really important because we don’t
want to work in silos and we don’t want to recreate the wheel all over the place. I mentioned earlier
the organization Reaching Out From Within, they do a really awesome annual event called the
Courage to Change Symposium. I had the honor this year of serving as the chair of the committee
that put it together. They’ve been doing it for, I believe, seven years now. It’s an awesome event that
they have at a hotel in Kansas where they invite folks who work in Ranchary and they invite the staff
of the Department of Corrections and they invite people who are interested in the topic and they invite
formerly incarcerated people and they invite leadership from the Department of Corrections all to
come together to learn about what’s going on in the area, but also what, on a grander scale is going
on around the nation and even the world that could be brought here and improve our system here in
the area. One thing that really stuck out to me from that symposium, they have the top leadership
from the Missouri and the Kansas Prison. The head of the prison system in Kansas, his name is Jeff
Zmuda; in Missouri, her name is Anne Precythe, and they were on a panel together and they were
sharing about what’s going on in the prison systems and what they’re working on. I heard Anne say
something a couple of times and she’s from North Carolina, I believe. I don’t want to get that wrong
because she would say a snide, funny comment if I got her Carolina wrong, but she has a very sweet,
southern accent is why I bring it up.

[00:31:31.050] – David Maples
She’s from one of the Carolinas, either North or South. She’s from the best Carolina. She’s from the
best Carolina.

[00:31:38.490] – Kyle Smith
Yes, exactly.

[00:31:39.300] – David Maples
I’m glad that we could talk about her.

[00:31:41.610] – Kyle Smith
Sure. I had the mic and I said, Anne, I just want to make sure I heard you correctly. Did you just say
that when someone goes to prison, being removed from society is enough of a punishment, and
prison doesn’t need to be more of a punishment. She said, Yeah, that’s what I said. I knew I was going
to try and it wasn’t going to go that well. But yeah, that’s what she said. I just turned to everyone in the
crowd, all these Department of Corrections staff and reentry staff, and I just said to all my colleagues
like, This is our moment, folks. Do good work, because she is protecting you from the whims of the
legislature and other opinions that may be out there and she wants to create a more compassionate,
more restorative prison system. It takes time to change a big ship like that. But with leadership like
that, now is the time to try and make positive changes in the system. That was really heartening for
me.

[00:32:48.540] – David Maples
I want you to… Can you share a personal experience or a lesson or maybe one of the people you’ve
worked with that has significantly shaped your perspective on things? It could be personal or it could
be somebody you’ve worked with, etc. How has your perspective changed based on either being in the
system, working with people in the system, or based on the work you’re doing now?

[00:33:13.050] – Kyle Smith
What’s first coming to mind—and I can share more about people that we’ve worked with as well who
have inspired me—but what’s first coming to mind is when we think about people who are in prison
and we think about it in a political way, maybe on the right side of the aisle, there can be too much of
the, Look what they did. They deserve to be punished. Throw them in prison. Then on the left side of
the aisle, there can be a lot of, But look at the environment that they’re in. Look at the issues that
they’re dealing with. We need to have more compassion. I think one of the things that’s become really
solidified for me in doing this work is that it seems to me that the answer is really somewhere in the
gray area, in the middle of those two things, is really in the messy middle. Because you don’t want to
lean too far and say, We just need to have endless compassion for people because things were so
difficult, because that really steals the agency from someone. They were a human being who made a
decision and who hopefully want to make better decisions later on in life. But we also just can’t say,
Hey, look at the terrible decision they made, without looking the environments that people are coming
from. I think it’s important to spend more time in that gray area because at the end of the day, it is a
human being who got put in prison and it is a human being who’s going to come home from prison,
and they have to do what’s best for them and what’s best for their family, and they have to believe that
that’s possible. They have to choose to do the right thing. They have to choose to be on the positive
side of life instead of taking from others. In order for them to believe that about themselves, it’s
important that we believe that about them as well. When it comes to folks who we’ve worked with
who have inspired me, I’m really moved by whenever you meet someone who’s been to prison and
who has made it through that experience and is starting a business now, who’s just the kindest,
gentlest, sweetest person that you’ve ever met. Because I think it can even imagine myself just getting
really bitter in that situation. But there’s a gentleman who, his name is Ricky Kidd, and Ricky was in
prison for over 20 years for a crime he didn’t commit. Now Ricky is out and he does great work with
the Innocence Project, and he also does great work leading seminars about resiliency. Ricky says, Get
better, not bitter. I think when people are able to achieve that, that’s really inspiring. I had an
experience that’s coming to mind now. There’s a gentleman in our community named Richard who,
when he was in prison, he was a part of an intensive therapeutic community where they had certain
rules and customs that they used in their housing unit to help people follow the rules and to really
create, instead of a top-down, here are the rules, because that’s what the staff member said, it was
actually the people in the community reinforcing the values and the rules of that community. They
called it their… We called it Circle Up. He had a slightly different name to it that’s not occurring to me
right now, but just an opportunity for people to encourage one another to do the right thing. We
actually ended up taking what he learned from that community and adapting it into ways that our
entrepreneurs could use to lead crews in their businesses so that people could help their employees,
the people that they’re working with, create a more positive environment and create a good culture. To
take something that came from prison and to adapt it to make your business better, I think, is really
remarkable.

[00:37:16.140] – David Maples
You said it’s getting better, not bitter, or getting better, not bitter. That’s a pretty powerful message.
Beyond that, are any of the local leaders in the Kansas City community who you look up to right now,
who inspire you in determination and corporate right now? You said, This person really makes me
realize that we’re doing good work, or This person makes me want to do more.

[00:37:45.530] – Kyle Smith
I’m really inspired by… I mentioned the Transition Center for Kansas City, and two of the leaders there
who are running that program are Michelle Tippey, who is the head of the Transition Center of Kansas
City. She works for the Department of Corrections. Then Greg Winship works with the Center for
Conflict Resolution, which is the nonprofit that they’re working with to create the restorative justice
community. I’m very inspired by both of them because they’re in the trenches doing the work, but they
also have a big perspective, a wide angle lens for the work that they’re doing as well. Michelle,
creating a brand new program and working through all the bureaucracy of working with the state and
working with the prison system, and also working with an entirely new crew and having to find the
right people to be in those positions, I think is just remarkable work. She’s so positive every time I talk
to her, and she just realizes that you just have to move it one step at a time. Things will never be
perfect, but you can always be heading in the right direction. Then Greg is actually a formerly
incarcerated person of himself who has dedicated his life to restorative justice and has really worked
tirelessly to bring more compassionate practices to Kansas City and specifically to the transition
center of Kansas City that I think is instilling a lot of new ideas in people’s minds. You mentioned
earlier how it’s remarkable to even call someone in a correctional institution a resident instead of an
offender. That would be the usual language, an offender. I think that’s a seemingly small thing, but like
you said, creates a big mindset shift. Also, when you start to think about all the ramifications of what
does it mean for someone to be a resident and what positive support would you provide to someone,
how would you be hospitable instead of punishing someone creates a lot of changes as well. That
just makes me think of the people who work in the Department of Corrections, which I want to point
out, we’ve been talking about the system and how much there is to improve. The staff members of
the Department of Corrections are rarely the problem. Can they sometimes be the problem? Sure. But
also these are very hardworking public servants who have one of the most difficult jobs in our state,
who are doing their best to do something positive with the work that they’re doing and be a positive
influence on the people who they serve, which are currently incarcerated people. We shouldn’t just
assume that because someone is a correction staff member that they’re on the wrong side, that
they’re working for the man. That’s very much not the case. These are people who are really trying to
do something better and make changes, and they’re doing it in the hardest, dirtiest, most difficult way,
which is actually just being on the ground, working in the system every day.

[00:41:05.390] – David Maples
I want to thank you for even just acknowledging that. I think a lot of times the narrative we get on the
outside of these things is that the prison guards. You’re right. Invariably, you’re going to have some
people who are part of the problem, but most of these people are in the system and are trying to
make positive change. I think that’s something a lot of us lose perspective of, just like we lose
perspective of people when they end up in the system. Another thing I really like that you said earlier
is how there’s a balanced approach. There can be too much red meat on the right wing of the aisle. At
the same time, there can be too much, and I don’t want to say Kumbaya because that sounds real
derogatory as well, but you can end up with extremes and the messy middle is where a lot of the work
gets done. There are reasons prisons exist and there are consequences to actions. I think it’s
important that you said that. That was interesting. It was a refreshing perspective, I think we don’t
always get we ask these questions. As you continue to work with Determination Incorporated and in
your own journey, what role do you hope to play in the future of Kansas City?

[00:42:15.740] – Kyle Smith
I’m just trying to help people one person at a time. I think that being a social entrepreneur and I’ve
been working on Determination Incorporated for five years now. I started off with a lot of idealism and
a lot of big ideas and a lot of, We can change the world. I’ve come back to reality in a lot of ways.
That’s actually been really tangible for our organization. I have this shirt on that says Visioneer, which
we give to folks who participate in our program because they’re engineering our vision. Our original
vision for Determination Incorporated, the first time I ever wrote it down, was that formerly
incarcerated people by starting viable hiring businesses will help to solve the problem of recidivism
and ultimately end mass incarceration. It’s such a great line. It gets so many claps and pat’s on the
back, but it’s really not realistic. I think if you had told me that five years ago, and specifically, I mean
the end of it, end mass incarceration is not realistic. That has a lot… That is a much bigger scope than
one small organization helping formerly incarcerated entrepreneurs can feasibly touch. But if you had
told me that when I first started the organization, I would have said, But you’re not dreaming big
enough. There’s something beautiful about that, but I think there’s also something beautiful and
important about the change that we’ve made to that vision statement, where now it reads that
formerly incarcerated people by starting viable hiring businesses help to solve the problem of
recidivism, create financial freedom, and build intergenerational wealth. That’s much more tangible
and much more focused for our organization and the work that we do with people. I just want to share
that just as a lesson that I’ve learned as a social entrepreneur because it’s very, very easy to
experience burnout in this area. You got to say the serenity prayer every day and just try and focus on
the stuff that you can control and have the courage to deal with the things that are out of your control.
I just think that’s an important lesson that I’ve learned along the way.

[00:44:45.080] – David Maples
Got it. To that point, though, building generational wealth, ending the cycle of recidivism, if you
multiply that out, you could have a future, but we can’t… We’re only part of that. We’ll never live to see
the end of this. Mass incarceration, well, probably it’s been with humans since we came down from
the trees. There’s been something, some part of that that’s always been part of the situation. I see
what you’re saying too about burnout, though, because definitely if you feel responsible for that, it’s
like, have I not done enough? You know what I mean? I think that could be very toxic at some level.
You could end up with a situation where you feel like even though you’ve accomplished these great
tangible things with a lot of these individuals. I mean, your numbers for 2022, I read some stuff about
you before the interview today, and I was like, Man, that’s great. We worked with I think you had nine
different individuals that you helped in the process in 2022. Is that correct?

[00:45:48.170] – Kyle Smith
Well, through our Rise Up Get Started program, on average in 2022, we served 50 formerly
incarcerated people a month. What you’re speaking of specifically is the data that we collected for our
second chance entrepreneur dashboard, which we started doing a couple of years ago, where we
looked at people who went through our Rise Up Get Started Matching Grant program and saw that the
average annual revenue for the businesses, these are businesses that are under three years old, were
$54,000, with one outlier grossing over $400,000 in her business. These folks created seven full-time
jobs and supported, I believe, 45 contract positions so that they’re creating work. Most of the folks
gave back to the community by volunteering. Importantly to us, there was a 0% recidivism rate. Those
folks did not return to prison. Those are the sorts of impact measures that we try and keep track of.

[00:46:44.090] – David Maples
I think that’s laudable and that’s really cool. For people listening to this show, how can our listeners
get involved to either support you or support your initiatives?

[00:46:53.880] – Kyle Smith
Yeah, definitely follow us on social media and @determinationincorporated on Facebook, Instagram,
and LinkedIn. Be sure to go to our website, which is here on my shirt, unlockeship.org. That’s short for
entrepreneurship, by the way. It’s also determinationincorporated. Org as well. Sign up for a High Five
Thursday newsletter so that you can hear and read stories about the entrepreneurs that we’re working
with and consider doing business with them. We have folks all the time who reach out and say, Hey,
do you know an electrician? Do you have a painter? Do you know anyone who does catering? I know
all those folks and many others. Always happy to answer those questions and make referrals. Then
lastly, I would invite people to invest in our mission as well. We invite people to invest at a level of $20
a month or $250 once, which allows us to keep doing this work and supporting second chance
entrepreneurs. Folks who invest at that level get a T-shirt that looks like this, but it says, Investor on
the front of it. They know that they’re a part of our community as well.

[00:47:56.950] – David Maples
I’ve got to ask, best barbecue in Kansas City? What is it? Where is it?

[00:48:03.590] – Kyle Smith
I hesitate to say best barbecue in Kansas City because I don’t want to pretend like I’ve tried them all
out and I had some rubric and I was really judging what was the best. All I can say is that when I have
friends visiting from out of town, this actually happened this past Sunday, and they say they want
barbecue, I always take them to Char Bar in Westport. It has very delicious barbecue. I love their
sandwiches. There’s fun stuff you can do outside, like play cornhole and enjoy the sun. I usually take
people to Char Bar in Westport.

[00:48:40.700] – David Maples
Do they have any standout dish or anything you say, Man, this is really good there?

[00:48:47.680] – Kyle Smith
I’m not going to remember the name of their sandwiches off the top of my head, but I always look at
their sandwich section because it’s a fun combination of meat. I prefer the sandwiches because you
could throw a pickle or some jalapeño or something a little bit different in there to mix it up a little bit.
I also think their appetizers are really good. They have some grits and some cornbread that’s
delicious. The last time I was there, when I was there on Sunday, I actually got their grilled pinto
cheese sandwich and added pulled pork, and that was really delicious. So yeah.

[00:49:31.020] – David Maples
It’s a Char Bar in Westport. Yes. We’ll have to check that out. And that’s the first time I’ve heard
anybody mention grits since I’ve been in Kansas City. So I’m going to definitely have to check that out.
I was born and raised in, well, not born in, but I was raised in Georgia. So grits are part and parcel.

[00:49:46.780] – Kyle Smith
Well, you know them better than me, but I’m a sucker for anything with lots of butter and cheese in it.

[00:49:50.290] – David Maples
Hey, that’s the only way to have them, right? Okay, so I have a few more questions just to finish up
here. What is one actionable piece of advice you’d like to share with our listeners if they either want to
get involved or be involved, what is something you would tell them that they want to take action or get
involved? What would they do?

[00:50:06.430] – Kyle Smith
I think that if people believe that it is important that employers consider formerly incarcerated people,
that one of the most powerful things that they can do is go to their HR department and ask, Do we
hire formerly incarcerated people? Do we have anything that’s on our books that stop us from hiring
formally incarcerated people? If they do have those things on their books, really taking a look at them
and saying like, Is this of benefit to us or is it just exclusionary for the sake of being exclusionary. Like
really thinking about why is this here, and should someone having a criminal record really preclude
them from working in our environment? I think that’s something that people can do that could make a
meaningful difference in our community.

[00:51:02.890] – David Maples
What do you love most about Kansas City and what makes it stand out from other cities?

[00:51:09.170] – Kyle Smith
What I love most about Kansas City is that there are a lot of people here who are taking care of each
other. I think we can see that at the very top. I’m thinking about the chiefs. I’m thinking about the
positive relationship that Patrick Mahomes and Travis Kelsey have. I’ve been a really big fan of Travis
Kelsey’s podcast with his brother, Jason Kelsey, and hearing about how things are on the locker room
and the really close relationships that they have. I think it’s cool that these champions, world
champions that bring such a great spotlight to Kansas City, just the great relationships that they have
with each other and how much they prioritize taking care of their team members. We see it all the way
up there and I see it every day in the work that we do and in the colleagues that I have the chance to
work with. I think if we’re all able to, through the years, just expand that circle of compassion, that will
help make us better and also make our city better. That takes time because it’s easier to just be in our
own little bubbles. Kansas City was built on segregation, and that’s a whole other topic, redlining,
leading to the suburbs being built and stuff. That segregation is still very much a part of how the city
operates. But if you realize that, then you can start to take small steps to grow your network and to
reach out to different people and people with different experiences and different backgrounds and
different lives than yourself. That’s when good things start to happen.

[00:52:52.860] – David Maples
Absolutely. Well, I want to thank you for being on the show. This has been Kyle J. Benson Smith with
Determination Incorporated. I just want to give you a heartfelt thanks for coming on the show today. I
really appreciate it.

[00:53:07.010] – Kyle Smith
Yeah, David, thank you so much for having me. This has been a great conversation.

[00:53:11.190] – David Maples
It’s been a lot of fun.

[00:53:12.390] – Producer
Thank you for listening to the KC Leaders Podcast. Please remember to like, share, subscribe and
leave a review wherever you listen. For more information about this podcast, you can visit
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