David Dillon: Tech, Faith & City Transformation

David Dillon, tech entrepreneur and co-founder of Dillon Kane Group, shares how his faith shapes his approach to business, leadership, and innovation. He also discusses his work with Together Chicago and Redeemer City to City, exploring how Christians can pursue excellence, serve their cities, and integrate faith in everyday work.

On Good Work is a Lakelight Institute Production. 

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Transcript

Welcome to On Good Work, a production of Lake Life Institute. On this show,
we talk with people about the good work they do, what they love, what they wish
they could change, where they see hope, and where they meet God in their daily
work. My name is Ben Dockery. Thank you for learning with us.
Today, I have a chance to talk with David Dillon. I first met David in an event
in 2018. He was a breakout speaker. Tim Keller happened to be in town speaking at
this event and little did I know that David was on the board and eventually become
chairman of the board. For city to city, you'll hear a little bit about that in
the interview. But David spent more than 30 years in the world of technology,
creating software solutions and for the financial industry. He served in a number of
roles. Early on, he was CIO at a group in Chicago, a leading derivatives firm
called CRT. David led a global technology organization there that supported things
like real -time pricing, trade execution, risk management capabilities. They did all
sorts of different things. And eventually those efforts led to CRT being a success
and ultimately a sale to Nations Bank. And after that, David was a leader in the
global corporate and investment banking side of things, so he led teams to do
technology solutions for all sorts of complex corporate banking problems. That's been
the part of what he's done, leading teams to help people do that. He's a part of
Citadel Investment Group as well in Chicago. If you're from Chicago, you may know
that name. But he did that before he formed his own group with his partner, Don
Cain. So Dylan Cain became an organization in 2001. And we learned a little bit
about that in this interview as well. Excited for you to hear that. But they've
done a number of things over the past 24 years, acquiring, building, incubating
software -based businesses. It's a really impressive thing, and I loved learning about
ways that software, creating good software solutions for people, loves them, and
serves them as their neighbor in ways that David thinks about that as a way to
love God with his work. So I could say more about his resume. Let me get out of
the way and let you hear his story from him. I hope to enjoy this conversation as
much as I did. You'll learn not just about his work and his life, but also about
the amazing stuff he's doing through two nonprofits, one called Together Chicago, one
called City to City in New York. So here's my conversation with David Dillon.
- Well, David, thanks for joining me on the show today. Glad to have you with me.
- It's so good to be here with you, Ben. - Yeah, well, hey, well, before we jump
into even some of the questions we've discussed, Where are you coming from today?
You're driving here, we're recording this in studio in Lake Forest, but where'd you
drive in from today? I woke up this morning in Prospect Heights, Illinois. Okay. And
how far away is Prospect Heights? It's about a 27 -minute drive from Lake Forest,
northwest suburbs of Chicago. Yeah. We're recording this right before Memorial Day,
and it's a balmy, what, 38 outside? And rainy. Yeah, and rainy. So, I mean, it was
a lovely day to drive all the way up to Lake Forest. Yes. Lake Forest, but spring
in Chicago, what do you do? - Even in the rain, Lake Forest is beautiful. - Yeah,
that's true, that's true, that is a fair point. So, well, I wanted to start by
really asking where did you start your career? So take us back to, before we jump
into some of these other questions, where did you get going early on in your
profession and take us back to that spot? - Yeah, well, if I can, let me just
start the very beginning quickly 'cause it sets a good context for it. So, My first
17 years grew up in Japan. I'm a missionary kid My parents were career missionaries
from 1948 to 78 and that was a very formative experience for me. Yeah,
I am that yeah So I could say a lot about that but got to the United States in
73 Ended up doing my senior year of high school in Wheaton, Illinois, and then went
to Wheaton College. Okay, sure and just got fascinated by Frankly the financial
industry little by little and ended up getting my undergraduate degree at Northern
Illinois University in finance and that led to a job working for the largest bank
in Chicago at the time called Continental Illinois National Bank which for many years
it went away in the 80s and there's a personal story of mine that relates to that
it going away But at the time continental was a really good bank.
I mean very very influential in the whole Midwest and I got a good job there
working in the bond department in 81 and worked there for three plus years and
Really enjoyed it at first But then just frankly got kind of restless I'm sort of
one of these serial entrepreneurs who have to have a lot of things going on and
that was already starting Yeah, my early in my early career. So it's a long story,
but I started doing some research on options trading and the mathematics of options
and started building software for that. And that actually led me to a job in the
derivatives trading industry, working for this firm called Chicago Research and Trading
that turned into a rocket ship. It started with a small group of folks and turned
into the largest options trading firm in the whole country. And it was bought by
Nations Bank of North Carolina in 1993. So I started at CRT in '84,
started by a really interesting guy named Joe Ritchie, who is a missionary kid from
Afghanistan. Oh, wow, what a connection that is. Also really interesting. The whole
history of CRT is fascinating. And anyway, really enjoyed working there. And quickly,
the quick story is I stayed through the Nations acquisition, I had a lot of fun,
got to play at a much bigger stage then, because Nation's Bank was this very big
global business. And what was your role? I was working in the technology sector of
Nation's Bank, particularly in the corporate bank, and I did a pretty significant
part of the technology for the whole corporate bank. Okay, so the developing software
stuff early on was still part of this? Very much, yeah. And so at CRT, yeah, my
role had morphed. In fact, I should explain that a little bit. I became the Chief
Technology Officer at CRT, which was a big job, building all the trading systems.
And at that time, you couldn't buy all these systems. You had to build them. That
was back in the day, hardcore, working in the C programming language, and our team,
just incredible team. In fact, that's really one of the big reasons Nations Bank
bought CRT was for the technology. So it was a lot of fun to be in this big
sphere of Nations Bank with a great tech team working on all kinds of great
problems. And then in '98, Nations Bank and Bank of America merged. And it was
these two equal banks, both huge. And I went through that process for a couple
years. And that for me was kind of the beginning of the end, honestly. It was kind
of a soul -crushing experience to go through a merger of equals like that, where
there's just duplication of every function. Yeah, absolutely. - And so after a couple
years of it, I said, you know what, Lord, I think you have better plans for me.
So I moved on from there. So that's, but that's my quick history. - Yeah. And one
of the things you mentioned serial entrepreneur. So when did you, when did you
recognize that? Was that sort of something you knew from childhood or that's
something that once you got the itch and you were in the game, you started
realizing you needed more, more things to do. - I think I've always had this more
things to do from the time I was a kid. I mean, I've always been involved in many
different projects. My wife would laugh at she was here.
years of working in tech, kind of in the financial industry, led me to really
realize that there was a role for great software, really in any business, of course,
but particularly in the financial industry. And this was long before, you know,
there's been a lot of articles now, Mark Andreessen's obviously leader in the venture
capital world, and he's written great articles about how important software is. And
but we kind of realized we had a way of helping businesses, take their technology
spend and actually really do a better job with it. And that's one of the core
skills, frankly, of any business is how do you build a software infrastructure that
takes your platform and your practices and operations to another level. And any
business that can do that basically is going to win. It's a huge advantage. And you
see that now, of course, with all the major Amazon and all these huge companies.
But At the time, it wasn't so commonplace. People weren't thinking of it quite that
strategically. So anyway, we started a business in 2001, myself and a partner,
Don Kane. And there's a whole story of how that happened. It's too long to go
into, but it's a God story where God gave us the ability to kind of build this
business right in the beginning of a great relationship with a major insurance
company in the United States who we had a tremendous relationship with around
innovation. We got to work at the sea level with them and see other problems, and
that firm spent about $2 .5 billion a year in technology spend. So we got to really
help them with major things that they were trying to do, big parts of the claim
systems and underwriting and policy administration, and all these big things that
insurance companies have to do, we were able to help them with that. And then along
the way, we started seeing, hey, we actually have a little bit of skill at this.
And so we started offering that to other people and started growing our professional
services business. And then what happened along the way is we started-- So you're
scaling with that one company to get to 2 .5 billion or whatever you said the spend
was, and now scaling sort of outside of that? Scaling outside of that, going with
other companies. And then also, we started to realize, hey, let's actually start some
of our own businesses that are not just building software for other people, let's
launch our own tech companies, basically. So we started doing that and we did a
number of them and I take too long to go through all of them but we've had some
success and we also acquired some from some major tech companies that were getting
rid of some businesses. So between starting and acquiring, we've had about 18 tech
companies - Oh my goodness. - That we've acquired or started ourselves. We've shut
some down, we've sold some. We still have about six that we're really focused on
today. But it's been a God journey and super exciting. - Yeah, I can see why your
wife would be laughing earlier on, Tia. Like, yeah, it sounds like you do have to
have a couple irons in the fire at any given time. So, well, what do you love
about that work you get to do? And maybe that's at different stages, but what but
what really brings you joy in the work you get to do? - Yeah, it's a great
question. I think the biggest joy that I get, well, there's a few things. I think
one is just the people. It all comes down to people, right? And I just love seeing
people using their creativity powerfully and creating great innovation that makes a
difference in the world. That just jazzes me. And so I love creating teams that
work well together. Frankly, I love treating people well. And so to me, that means
a couple things. One is we've been able to do this for our whole history is we
pay 100 % of the health insurance premiums for our workers. And that's a pretty big
benefit. And but we've just felt like that's one way we can bless our team very
materially. So we've been able to do that for 24 years up to this point. And I
mean, I don't know if you can get back to the origin on that. It's both a
competitive advantage and a just value set that you guys brought to the table to
say we want to care for people this way. Precisely. Yeah, and it does retain
people. Not completely, of course, but it does help. It does help. The other thing
I just love to do is I just love to see innovation that works and actually makes
a difference in the daily world. So one of our companies is an incredible secure
communications platform That actually is being used by many parts of the US military
and it actually helps. I won't go into the details of it But it helps very
significantly the military do what it's trying to do right and I just love that I
mean, I love building software that actually makes a difference in someone's daily
work So all of our platforms do something really unique. We have a aviation safety
platform that calculates the friction coefficient of a plane as every plane as it
lands on a runway So the next plane that lands now knows how slippery the runway
is. Oh, wow Yeah, and we're the only company in the world that has that we have
the patents on it We created it and we have 20 million with commercial. Yeah, it's
with okay. Yeah, big big planes Yeah, big planes. Yeah, so we're working for all
the major airlines And I'll be at O 'Hare later today. Well, we'll try to keep you
safe. We'll try to keep you safe So it's been quite a journey, but I love things
like that. It's like over. That's a really hard physics problem You know, how do
you actually calculate the friction coefficient of a runway? That's a really hard
thing to figure out I didn't even know someone was doing that. Well now you do So
anyway, so we have a lot of different things. There are different spaces. We have
something in the telemedicine Um, one of our biggest software companies was sold to
another competitor actually two years ago, but it's kind of the back office data
integration space that just made operations more efficient for major corporations.
Sure. Yeah. So, so needed. Yeah. So needed. So I just love that. I love seeing
innovation that actually works, that makes a difference and, and people's lives. And
I just, I really jazzed me. Yeah. Was there somebody early on that sort of steered
you that direction? Or was there a mentor or someone that played a role to help
you see that in your own life? What's the early influences in David Dillon's life?
Yeah, that's a great question. I have to say my dad, my dad was clearly an
influence. My dad was one of the, he had the most perseverance of anyone I've ever
met, like in missionary Yeah, exactly. In face of great obstacles,
he would kind of keep finding a way. And in fact, my dad passed 16 years ago.
We just observed the anniversary of his passing a couple days ago. So I was just
thinking about that, actually.
Yeah, but dad was very committed to his work and to the Lord,
and had just a tremendous amount of perseverance. So that impacted me deeply.
I think also just being in the companies that I was at, like so CRT was this
incredibly entrepreneurial place where if you had an idea and you could demonstrate
that it was a good idea, there was a way to do it.
So that was a real sort of learning experience for me to see that in practice on
an increasingly big scale, like hundreds of people and millions of dollars and a lot
of risk being taken. People trusting other people, you know, with very large scale
risks. And when you see that live down in practice, it's a real learning ground for
how to do that. - Yeah, I mean, it sounds like you saw that culture and brought it
to what you've been doing today. It's with the number of new tech products or tech
companies that you've started. - Yeah, yeah, exactly.
- So let me ask, let me the corner because I know we're going to shift from sort
of work and vocation life over to your faith life but before you even get to how
you're trying to integrate those, tell me a little bit about your faith story. I
mean we got a little bit about your biography so where did your where did your
faith sort of come alive and where did God meet you in the middle of those years?
Yeah, thanks Ben. Yeah well growing up on the mission field you know a lot of kids
and I have a lot of friends who of course grew up there. Some kids really kind of
run away from the work that their parents are doing. For me
I really felt called to be sort of part of this mission work that my parents were
doing so I actually got to play a bit of a Role and I'm a guitar player and a
bass player. Yeah, we were talking music right before. Yeah, exactly So I got to do
that in a missionary context in Japan and the Lord actually really blessed that I
could tell you some stories But some young people came to faith in Christ and one
powerful day at our church that my parents had started through some music We were
doing fine. Yeah, so but it really was part of my life, too. It wasn't just their
thing. It was my thing, too Um, I think what I'd say to wrap up, you know, I'm
68 years old now. So a lot of years have gone by And I did have a time of
rebellion for a few years in my like mid 20s that I regret I really wasn't living
the Christian life and did some things I really regret sure, but um But I'll tell
you what's been so powerful for me Just it's kind of coming back to the basics of
just the value of Scripture. I mean, I just love it I mean I read Scripture and
every day like just this morning, you know, I was reading several places and it
just it's it's amazing How the Holy Spirit uses Scripture uniquely almost every time,
you know, there's something powerful about it Yeah, and I've just found that that's
the spiritual practices, right just taking those seriously, like, you know, setting
aside time, there's no substitute for that. And that's the way God works, I think,
in our hearts. And he's worked in my heart that way. - Yeah, absolutely. And I
mean, I'm assuming that practice is ebbed and flowed given seasons of life and kids
and how busy our kids in different seasons. But right now you're, sounds like you're
reading a song. I mean, I see you have a Psalm open, so I'm guessing that. Tell
me just practically, what do you have? What does that look like right today? - Yeah,
thanks for asking. So I do this thing called the daily prayer project. It's actually
a thing that you can subscribe to it. And it's a website and they produce a
booklet. It goes through the different seasons of the year. And it follows the
church calendar. I should say that more truthfully. And in each calendar, you have
readings to do and they give you prayers to pray and things like that. So it's
like a little liturgy that you can do yourself every day would include scripture. So
I've been doing that for years and I just find that that really keeps me grounded.
And I like, I also like that it takes you through the whole scripture. Like, 'cause
the whole scripture is incredible, right? And there's parts of it that would be
really obscure that I wouldn't read naturally unless someone said you need to read
this today, you know? But then I'm blessed by it, you know? So I find that that
discipline really helps me. No, that's that's forcing someone to read Judges or
Leviticus or even parts of the song Exactly, exactly immediately make sense Exactly.
Yeah over time, especially can be deeply shaping. It really can. Yeah, so How does
that now when we want to try to combine this in conversation? So let's talk a
little bit about you know, we use the language of faith and work or yeah, whatever
phrase makes most sense in your world Yeah, when did you start seeing those
connections and when did you start trying to, was that a Wheaton College thing? Was
that earlier than that? When did you try to make those connections? - Yeah, it's a
great question. And for me, it's been an evolution. Like if someone would have asked
me in my 20s, what does faith and work mean to you? I really wouldn't have had an
answer to that. So it's been very much an evolution where really as my career
progressed, and I started to see the role that leaders have in the business
community, how they can impact their employees, how they can impact their customers,
how they can impact the wider community. I started to get a little bit of a vision
for this and then frankly, it's through the work of Tim Keller. You know, I'm a
huge Tim Keller fan and I know you've had many people on already talking about Tim,
but you know, he started influencing me through his preaching and podcasts and all
that. And you never spent time in New York. It was It was long distance. Yeah,
long distance and until you knew it personally, but until one day I got invited to
join the board. Okay. And so that's another part of my life we can get to but But
Tim was already influencing my journey in that way and I started to see this
holistic vision of like city You know city transformation. Maybe that's a good way
to say it and how business plays a role in that and so I'd won by the an
informative experience where a missionary to Japan came to me when I was in my
early 20s and kind of looked me in the eye and said, "You know, you know how many
cities there are in Japan that don't have a church? You need to go and be a
missionary in Japan." Okay. And it was kind of like, "This is a will of God for
you." Wow. It's quite forward. It was quite forward. And I was taking... I assume
they knew your family in the first place. Yeah, they knew my family. They knew I'd
grown up there. And and they're like, you know, there's not many missionary kids,
you know, the language, you know, the culture, this is clearly what God wants you
to do. And it was a moment where I was like, wow, I really have to take this
seriously, because he's right. I mean, I grew up there. I, you know, a lot about
it. And so I really thought enough, and I just thought, you know, Lord, is that
what you have for me? And I just felt confirmation that no, that wasn't the path
for me, that the path for me was more in in the marketplace. And I think that's
frankly where my gifts were more, you know? I mean, anyway. Did you have people
affirming that on the other side? Like once you chose the marketplace side, were
there anyone maybe specifically in a church or a Christian perspective that was
saying, hey, we see this in you and this is you're doing the right thing? Very
much. Very much. And I'd be on boards. I've been on many boards of very good
organizations over the years. And sometimes I'd say of them, hey, if I quit all my
work and came and did stuff for you full time as a volunteer, would that be better
for you? Or would you rather that I'd stay in this role on your board and also do
all this entrepreneurial stuff? All of them would say, no, stay in your work because
the insight you bring to your work on the board from the marketplace is actually a
significant contribution to what we're trying to do in that on profit. So, Yeah, I
did. I did feel a lot of confirmation in that, absolutely. And I really see that
the whole faith in a work movement has really matured a lot, obviously, over the
last 20 years. The way we were talking about it 20 years ago was not nearly as
complete and beautiful as I think it's being talked about now. And I do have to
plug this book, Missy Wallace, and I, of course, knew each other, and Lauren Gill,
of course, from city to city. Yeah, right. And you just had her on and I enjoyed
listening to her podcast and I've read her book and I do think that there's parts
of that book that are really extremely unique and insightful. It's one of the most
beautifully detailed picture of what sort of what they call the integrated leader, an
integrated church, and an integrated city. Right. Just those three diagrams alone are
worth the price of the book. Yeah, we could have spent the entire discussion
actually on just those. Exactly those images that they had and what they meant
exactly and those are very profound to me I mean, I think it's a beautiful picture
of how we as leaders can play a role and how our churches can play a role in
City transformation. Yeah, and you met Missy through Yeah, exactly.
I joined the board about 10 years ago now and Missy and I met somewhere along that
when she joined and Just right away hit it off I really enjoyed working with her.
- Yeah, 'cause that would've been right when she, she probably wasn't full -time or
she wasn't on staff yet. - Not at the beginning, yeah. - She was part of the Gotham
network. - She was part of the Gotham network from Nashville. - From Nashville. - And
then she joined full -time at one point, yeah. - Yeah, that makes a lot of sense.
Well, maybe after this, I'd love to hear more about just, you know, that jumping on
board at that point. So, well, one of the things I've heard you talk about is, and
I was trying to, I tried to write down where this was just to confirm it, but I
couldn't find So, it could have been in 2018 at the Chicago breakout because I was
there when Citi -Citi did something. Yes. I've also heard you interviewed on a couple
other things, but you were talking about the role of excellence and how that is
like a Christian value and ways that you were able to, whether it's directly or
explicitly, bring that into, you know, software stuff and tech and investment and
banking in those areas. So, what's behind that And if my memory serves me right,
was that you talking about excellence and talk to us a little bit more about that?
It was me. Yeah, guilty as charged. You got me. Yeah, for some reason I've always
had a passion about that. I just feel like the first order of a Christian worker
is to honor. What's the scriptures say, right? To basically honor God through your
work, right? And so the first order of what we do is to take our work very
seriously and do a great job. And I think part of why I'm passionate about it and
maybe talk about it is I've seen the opposite of that firsthand. And I've seen,
unfortunately, people who talk a lot about their faith, but some of their work
product leaves a lot to be desired. And look, we're all like that. I'm guilty of
charge. I'm not saying I don't do everything perfectly. But I just think it's a
high value that I have to say, whatever I do, I want to do really well. And I
think that that's just that creates credibility, frankly, for the message of faith
and even relational credibility. If people see you in an organization, whatever your
role is as owner or worker or whatever, that you're really serious about your work
that creates relational credibility. So anyway, that's just been a high value to me.
Okay. Yeah. And so when you, because I'm going to with the opposite direction now
next, but when you champion something like that, when you're talking about excellence,
I'm sure during some of these, you talk about one of the hard transitions, I'm sure
you've also hit your series of failures, or at least run into something that slowed
you down a little bit. So you value excellence, but tell us about the other side,
maybe when something doesn't go as well as it could, or in one of these big
investments, or one of these risks doesn't work workout, what would you learn in
failure? What's an example? - We've had plenty of that. Yeah, let me be the first
to say, it's not always up and to the right. - Yeah, that'd be nice. - I wish it
was.
- It may not be as much fun in that as we all think, but for a moment it feels
like it is. - But that's actually the beauty in having a little bit of diversity
across our platforms. It's sort of like a portfolio effect. If you have some that
do really well, then that pays for the that don't, right? So that's been our
experience. But we've had many times when we've realized, look, we worked as hard as
we could, we've made something great, we think it's better than the competition, but
we just can't sell the darn thing, you know, for whatever reason. And there's very
many examples of that. And so you know what, there's no shame in that, you know,
there's no shame in saying, okay, we failed. I mean, it's hard, you know, you lose
a lot of money, and you have to let people go sometimes. And, you know, Those are
all really hard personal decisions, but I think if you've done it with integrity,
you can look people in the eye and say, "Look, you know how hard we tried. We've
been on this journey for many years now. It's not happening. Unfortunately, we just
have to shut this thing down." Most people would say, "I understand." Is there one
failure or is there like a moment where you look back and think, "I really grew or
after we got on on the other side of all this. This was helpful in my career.
- There's several.
There's one that I'll highlight that's fairly recent. When we sold our biggest
company to a private equity firm two years ago, I wouldn't call it a failure
because financially it was a good thing. But what was disappointing to me,
very disappointing is we had a lot of discussions with the private equity firm about
how they're gonna treat the company that they're acquiring. How they're gonna treat
the people and the platform we built and all that. And they made a lot of promises
about doing that, that they're gonna invest in it and all that. And that's really
not what happened. And so that was really hard for me because you know you lose
control. Yeah. Misexpectations on those are. Exactly. So I'm still kind of frankly
reeling from that a little bit because there were people that I cared for a lot
that got hurt by that. And I really feel sad about that. And also just to say,
I'm one of three partners, so I don't get 100 % vote on everything. So yeah, so we
as a group made a decision to do some things and it hurt some people. And so I,
those kinds of things happen, you know? And I regret that. - Right. Well, back to
your spiritual practices, and that's where you hit the songs on the right day, and
it really does help you walk through some of those feelings or that sense of regret
or whatever frustration you might have. - Absolutely, absolutely. - Yeah, well, thanks
for sharing that. - Yeah. - Let me change gears just a little bit. You have done a
lot of work outside of tech and outside of investment and helping on that side.
One of them is with Together Chicago. So for those who don't know,
tell us a little bit about Together Chicago goals, initiatives, how big is it,
what's the team? Just give us like an introduction to what you're doing there.
- Sure. Yeah, and let me take it back again, time -wise just to set the context
quickly, 'cause I think it makes a difference. - Yeah, sure. - But my own personal
journey in that was I was on boards of great organizations. I was on Sunshine
Gospel Ministries Board, which is a hundred year ministry and Chicago, tremendous
ministry, and learned a lot through that actually, learned a tremendous amount about
why Chicago is the way it is. And in 2016, Chicago had this spike in violence
that's well known that shootings and homicides, you know, we had over 800 homicides,
4 ,200 shootings in one year. And God was just working on me that whole year about,
is there a place for the body of Christ to come together to work on some aspect
of this problem, because it seems like each part of our society, police and mayor's
office, government, they have a role to play, but the faith community has a big
role too, and that we need to be part of this picture. And are we, are we really
looking at this holistically and saying, hey, here in Chicago, we have thousands of
churches, hundreds of thousands of Christians, and there's this terrible thing
happening in our midst. What are we doing about this, what can we do? And so that
question just wouldn't stop. I thought about it all the time. - Yeah, that's one of
the questions in Missy's book. I mean, actually that tribes. - Exactly. - Yeah,
tribes, thanks for it. - Exactly. And so I was able to convene 12 leaders together
who were just amazing leaders, who were doing great things already in different
organizations across the city. And we just gathered to pray and to talk for months
about that question. And long story short, it led to a weekend retreat where we've
gathered some pastors and at that weekend we just felt like kind of this Holy
Spirit moment where there was a oneness across a group of serious leaders in Chicago
and we said there is something more we could do together and this is still 2016
that was it that weekend was early 2017 okay yeah by that time and so then that
launched what's now together Chicago and together Chicago has just been wow what a
blessing and and what a ride. To answer some of your questions, it's over a hundred
people now working across five areas. I've been watching from a distance but didn't
realize I'd grown that. Yeah, it's very significant in size and scale. We work
across five areas of work, quickly their economic development. So trying to create
opportunities for people, whether jobs, job training, creating businesses, homeownership,
all sorts of things in that category. education, trying to improve the Chicago Public
School system with partnerships with churches, mentoring, and all sorts of things. We
have a love your school initiative there. We have a lot of churches have now
adopted schools. It's a beautiful thing. Yeah, it's really wonderful. We have a
Gospel Justice Center ministry. We have 23 legal aid clinics operating out of
churches on the south and west sides. We can go on a Saturday morning and get high
quality legal advice. So that's really cool. We have what we call faith community
mobilization, which is training churches to kind of what we call get out of the
streets and get out of the seats into the streets. And so we train pastors and
leaders to say, what could our church do in our community to actually make a
difference in our community? And so we do the spring training thing. We have an
annual rhythms thing that we pray in the winter. It's one of my favorite things. We
get like 2 ,000 to 3 ,000 people together in the winter time to pray, right? And
it's a beautiful thing. And then we train and then we do the work. A lot of the
summer work is particularly important because that's when the violence spikes in the
city. So we're trying to be really visible. We actually have a hands across Chicago
thing coming up Memorial Day weekend. There's always a day of, yeah, exactly. So
there's always something to do. But yeah, so So the other thing's the big area
biggest area in terms of people is our violence prevention area and by God's grace
We were able to get to know and bring on to our team an incredible Man named
Lovanna's troop who was ahead of one of the largest gangs in Chicago and he came
to faith in Christ in this amazing way Wow, and he's now preaching the gospel
everywhere. He goes and other gang leaders have come to faith And we have actually
over 50 people who are in gangs, gang affiliated, who now work for us, who are
trying to get people out of the gang lifestyle. - Yeah, I haven't heard that story,
so that's amazing. - Yeah, it's a beautiful story. And so yeah, we just feel it,
and it all started with just asking questions. Like we didn't start saying we knew
what this plan was, we just started asking people questions, like what could we do
that would help? And we took one thing at a time and just kind of through into
these five areas. - Yeah, well, I'd written down the question and you may have just
answered it. So I had written down because I remember hearing about this, and I
think, again, it was back in 2018 when I heard you give a presentation and then on
your website as well, that Collective Impact is sort of driving that. But is that
essentially those five areas coming together or what is Collective Impact? - Yeah,
it's a great question. Collective Impact is really, I didn't come up with it by the
way, I at the SSIR periodical, who published a story in 2014,
which describes collective impact, what it is. It's on our website, by the way.
- Sure, yeah. - And I really like it a lot. And it talks about that change in our
society, if it's gonna happen, it's gonna have to happen through different parts of
our society working together. So this idea that any one church, any on profit,
working by itself can do a lot of good, but to really make a material change in
our society will take involving the mayor's office and the police and the school
systems and the leadership and all the different segments of society, businesses, et
cetera. And there's five ingredients to that. It won't take the time to go through
all of them, but one of them is what's called a backbone organization. So this idea
that someone gets up every day thinking about this notion of collective impact? And
how do we work together? How do we get to know each other? And so we saw kind of
white space in that area in Chicago that there were some people doing similar
things, but not in the faith community so much. And so we're like, we really want
to connect the faith community together to work on these things. So that's what
we're trying to do is be a backbone, support organization across many facets of work
in the city, across the faith organizations. Yeah, I mean, it makes a ton of as
you say it. And I can see how the reason, I mean, it's not necessarily the first
thing people step out to do. So the reason that there was white space, the reason
is that no one says I want to be a vertebrae, like, or we know, like, I want to
hear what I want to do would be the spinal column. Exactly. For all these other
organizations. Because a lot of people are doing really good things. I mean, they're
good at those things. They are. And there's hundreds of them. They love it. Their
life was changed. And we work with them and we love them and they're partners of
ours. But someone trying to connect it all together is also helpful. - Yeah,
absolutely, I can see that. Now you just had some leadership change. - Yeah,
yeah. - So quick update on that. - Yeah, so Pastor Michael and Alan and I started
Together Chicago back in 2017, and we've led it since then until January 1st of
2025, when we were grateful to hand the leadership off to two younger, smarter,
better looking guys. And so Mark O 'Halloran, who's a great guy,
a great background in business, and also a serial entrepreneur, he and I have become
very close friends and he has tons of gifts. And then also Pastor Jonathan Banks,
an African -American pastor, leader, also from the marketplace, incredible, amazing set
of skills. Those two young men are now co -CEOs of Together Chicago. So We just had
our board meeting yesterday and got to celebrate them. - Oh, fun. - And so, yeah,
and we're constantly working on getting better, you know. Yesterday we talked a lot
about economic development. How can we do more? Like there's much more we wanna do.
And there are some phenomenal things happening, by the way, if I can, take a second
on that. - Yeah, I was gonna ask you for, I mean, we were down in the city a
few, maybe it's a month ago now, and heard some stats specifically on crime. I
didn't know if you have any of those new stats. There were really There were really
positive that people I have a ton of stats. I'm so glad you asked. Yeah, they
brought some charts You just had a board meeting. Yeah. Yeah. Yeah. Yeah, so yeah,
there's some amazing I mean if you just go online, so I'm showing you here. There's
a Headline here. Chicago's homicide told in April was its lowest of any month in a
decade. I didn't see that and actually Any in April of 25.
It was the lowest homicides with any month in more than 60 years. - Oh my goodness.
- So yeah, homicides are down significantly. Now, the summer of course is always the
hardest time, but we're still considering April of '25 versus all the other April's,
you know? So anyway, we are making a difference and it's not just together Chicago,
it's 15 organizations in this thing called CP4P, Communities Partnering for Peace.
So we're one of many organizations doing this work, but we are making a difference.
Yeah, I mean, it's exciting for the city. Yeah, obviously any homicide is awful, but
exactly to reduce that scale is significant. Absolutely. The other thing that's really
exciting is there are some really great things happening in the economic development
space. So some good friends of mine, again, in Cliff Barber, I'll call him out.
He's a phenomenal African -American leader. He's the CEO of something called the
Fillmore Linen service, which is a commercial laundry for most of the major hospitals
in Chicago. And it was backed by a wonderful family in Chicago who put up the
money for this. But now it's creating good jobs in Laundale, like more than 100
good jobs cleaning the linens from all these hospitals. A constant need. A constant
need. And they have a high quality product. They're making money. They're paying
people well. I mean, it's the win, win, win story, right? - Well, my first job
arguably was linen service. I was at a camp, I had a college, but they weren't
paying me well, I would say that. But that was my first job. I mean, I was
really, really just doing a bunch of people laundry from the crazy camp kids all
summer. - So I love this story. This is our heartbeat is how do we create real
opportunity for people that's a commercial success, right? It's not hand out. You
have to show for work every day. It's hard work, but you're rewarded for that. And
it's a it's a personal discipleship and growth opportunity, right? And by the way,
we learned a lot from a guy named Dan Meyer, who I can't say enough good about.
He's the founder of Nehemiah Manufacturing in Cincinnati. Just if anyone goes to the
web, type in Nehemiah Manufacturing. It's an unbelievable story of what they've
accomplished. So we just want to be like little Dan Meyers in Chicago. - Yeah, we
can add that to the show notes so people can hit that link. - Yeah, please, there's
Harvard Business Studies on it. It's a remarkable story. And Dan's been so kind,
he's come to Chicago more than once to kind of mentor us and teach us. And so
he's just a phenomenal leader. And his story is exactly the kind of story we're
trying to do here in Chicago. And we have some pieces of that now happening which
we're very excited about. - So you're on the board for the organization still, you're
gonna stay on a leadership role on that. - Yes, very much. - Yeah, okay, great. And
you said, I mean, kind of shifting away from that, you said you served on the
board at City of City. Are you still active on that board? - I am very active on
that board. - Okay, that's what I thought. - In fact, yeah, more and more and more.
And in fact, when Tim Keller, our dear friend, passed a few years ago, they asked
me to be the chairman of the board. So I'm on the board chair. And yeah, I cannot
say enough. - I introduced you as the board chair. So I was hoping that that was
an accurate introduction. - That is accurate. - That is you.
Redeemer, Presbyterian Church. He was a reluctant church planner. He thought someone
else should do it. And finally they said, "No, Tim, you're the guy." And God just
blessed it incredibly. And within a few years, thousands of people were coming to
church. And it grew so much, it was on the Upper East Side, Upper West Side, and
downtown. And people like you and me listening to sermons. 100 % podcast. And, you
know, before they called it podcast, right? Cassette tapes, right? Yeah, it was
tapes. I did a lot of those, but now gospel and life, you know, has hundreds of
thousands of listeners and it's a beautiful ministry. But yeah, so I heard about
that, of course, from those days and then what happened was people from around the
world started coming and saying, what's going on here in New York? Like this is
remarkable. This is unique. It's never happened quite like this before. So how can
we learn from this? And So they started helping people understand the model and it
turned into what was called the church planting center. Then that grew and grew and
grew 'cause they couldn't run their church and try to train everyone at the same
time, right? It was too much. - Yeah, no way. - There were people coming literally
internationally from all around the world. So then that church planting center grew
so much, they said this has to be its own 501 to C3. So they made that separate
and that's when it really started taking off in an even bigger way. And God's
really blessed it amazingly in every continent of the world now, except Antarctica,
because there's very few people in Antarctica, but every other continent. More
missionaries in Japan than in America. Yeah, that's right. That's right. But God's
really blessing this affiliate -based church planting model. So every continent has its
own leaders, all the writings have been translated into the local languages in many,
not every country yet, but we're working on that. - AI man, I mean, one of the
amazing things we can do is - We're diligently, diligently working on that. I can
tell you a lot about that. - Yeah. - Absolutely, we say AI has a huge help in the
ministry we're trying to do. But we've actually, just to give you a number, so if
you look at the website, Redeemer City of Cities website, it's 2 ,156 churches have
been planted and helped in some way through the city -city. - So say that number
again, 2 ,156. - Wow, yeah. - And that's, and that-- - The short amount of time.
- The short amount of time. And what's really encouraging is the pace of church
planning is growing significantly, particularly in the non -Western world. So if you
look at Asia, I mean, in Indonesia, and I mean, literally hundreds of churches
springing up in Indonesia, in Latin America, and Africa, in South America. - And the
new needs you're seeing, obviously, translation in Bible-- - Training, mentoring,
discipleship. - Educational for pastors and those-- - All that, right, exactly. 'Cause
we want them not just to be churches, but healthy churches, with the DNA of a
church that cares about its community and that kind of thing. So, and centered one
with humility and repentance and, you know, there's a lot of characteristics of that
that we try to model. And by the way, Steve Shackleford is the CEO, great business
guy, tremendous friend and colleague. And we talk all the time that it's really
beautiful to see sort of his skills as a business guy, I guess my skills as a
business guy, but entering into this work of church planning around the world in a
big scale, you know, it's really, and we have a great board. I could, you know,
people from all kinds of backgrounds, but God's really using it powerfully. So yeah,
I'm super. Yeah, that's exciting to hear that you get to see that perspective
because not, I mean, oftentimes when you get involved as deeply as you are locally,
the chance to serve outside of that and another, another role is not always, you
know, not always the same. And so I went to, I think it was 2021, 2020, 2021 it
was it was I want to say it was right after COVID but now that I'm saying that
none of us were wearing masks so maybe it was maybe it was early 2020 January 2020
went to one of the faith and work training oh great events that they did yeah and
half the room which was thing I wasn't expecting half the room we're not Americans
I mean it was and so when we were comparing stories about what you're doing and
how you're trying to you know do training and create some of these marketplace
groups and leadership things or run fellows programs in your church. The contexts
were vastly different, which is something before I got there, I wasn't ready for
that. But it was really helpful. Well, the things, I love so many things about Tim
Keller, of course, but he really coined this phrase contextualization, right? And
everything like the gospel, gospel is just one gospel, but the way it's integrated
into that community or church or society or life is going to be highly
contextualized, contextualize, right? Absolutely. And it's so powerful. He'll tell you
the four missionaries in quote and foot and off the top of his head, you know, who
came up with that phrase and said first and second and third. And yeah, he's, I
mean, exactly. That's amazing that he could do that. So yeah, his vision for,
as you said earlier, role that, I mean, the book Every Good Endeavor that spun out
into what Catherine was doing with faith and work stuff was and got them together
was you know was a lot of fun a lot of fun to see so well hey I've asked you a
lot of questions I've got a handful more sure I'm gonna go to what we call the
speed round okay sure we just start trying to you know grab a few tips yeah life
hacks yeah from David Dylan so you know so I'll run through these short answers if
that works for you yeah is if you're gonna you know talk to a young employee or
somebody you're mentoring, you can answer questions like that. So for people
listening. So, number one, what is one or maybe two specific resources that have
helped you navigate life? So we've already talked about Keller being one of those.
So I won't repeat that. Yeah. So one thing is I'm part of this group called the
Chicago Fellowship and it's a group of business guys who get together, ministry guys
too. And we've been doing it for, I've been part of it for almost 18 years now
maybe. We get together downtown Chicago to study the Bible, but more importantly, as
importantly, share life together. And it's been a wonderful thing for me. In fact, I
don't know that together Chicago probably would have happened in the same way without
those relationships. It was a really formative time for me. So doing life together
with other believers is just such a key thing, just in general. But it keeps us
grounded, keeps us humble, keeps us encouraged, you know, and all those things are
so important. Yeah, most people don't think about community or about relationships
when this question is asked. They always go to some sort of book or magazine, which
maybe you're going there a second as well, but I love that you started with
community. That's exciting. A lot of people don't have it. It's been one of the
most important things in my life, you know, and I'm in a small group. I've got
various ways of people speaking into my life, which I need. I mean, I desperately
need that. Also there's great materials. I'm a big fan of John Ortberg, so all his
podcasts and writings. Yeah, he was actually just here. He was sitting at this
table. I saw that. I saw that. You guys have all the best here.
John Mark Comer, of course, Tyler Staten, all their sermons, books, podcasts. Those
young guys are killing it. They're amazing. They're amazing. Of course, Dallas Willard
and all the legacy that he's, you know, so there's So many great resources around
all that material.
There's one that a completely different vein of life is about business,
which I find super interesting. It's a podcast called Acquired. Okay. Yeah. And I
love it. I'm kind of a junkie. I'm listening to the Epic episode right now, which
is just, I mean, it's like four hours long. It's so long, but I'm learning a ton.
There's a board member at our church, someone Someone who's on the board at Epic is
a member of Christchurch and so when I was talking with him and anyway So it is a
great They do a great job and our software integrates with Epic of course, so I
know it from that. Oh, yeah Yeah, so that's that epic story is an amazing story,
but she seems amazing I don't know her at all, but her yeah, but if you go back
through all the episodes It's like a it's like going to MBA school I mean you
learn their origin story of all the biggest businesses in our country. Yeah, and
it's just so I find it fascinating Yeah, you got no
I'll be biking and I'll listen to a podcast while I'm biking like multitasking. Yep,
but I find it super interesting As an entrepreneur, I'm just always interested in
other entrepreneurs, right? Yeah, and I just I feel like a kinship with them So
anyway, I just love hearing their stories and so yeah, well that one's has been
pretty new to me pretty recent So I'm glad glad to know that there's a lot more I
can dive into. Yeah, it's great Like some of the like the Microsoft Facility is
incredible. I mean they have multiple ones on that. There's so many that are good.
Okay, I'll have to check it out. Alright, let's let's move toward managing your
time. So everybody does this differently. How do you, whether it's organized a day,
organized a week, organized a month, how do you systematize or prioritize your time
right now? It's a great question and I say I'm not an expert. My wife would
definitely say I'm not an expert.
That's the real question. - Yeah, don't please do not do that.
Now I'd say I try to, one thing I've learned over the years is to try to not let
any day or week or month, whatever overwhelm you, you know?
Like so what I mean by that is like pacing. Like you have to have pacing. I think
as a younger man sometimes, sometimes it was just forced upon me, but it still is
sometimes to this day, but I try to avoid it as much as possible. Don't think,
let things bunch up so much that you kind of lose yourself. And so when I'm
looking at my calendar for any given day or week or month, I try to have a pacing
aspect to it, but I've got a variety of different things going on. So in my world,
as you can tell, it's very different in terms of business things, very spaces,
missions work around the world, Together Chicago, violence, businesses. So I try to
pace it so that I've got some of all that stuff coming in on any given season.
And that keeps me fresh and keeps me, you know, interested in the world. If I only
did one thing back to my, you know, I get kind of bored. Yeah, the way you're
wired. Yeah, it just, I find that for me, that kind of, I call it context
switching. I can switch context pretty quickly. And I find it invigorating to to do
that, but also not to do too much of it in any one day. So, at the end of the
day, you want to end up back home with your wife and your family wanting to engage
with them, right? That's the key, right? You don't want to be so stressed at the
end of the day, you can't function. - So this is a similar question, but how do
you limit your work? Are there things you do you maybe have a hard deadline or
maybe you practice Sabbath or I don't know, but are there ways in which you
intentionally try to limit? 'Cause I mean, you've got a lot going online, so I I
don't know how you put guardrails up. - It's really just by what I say yes to,
essentially. So, you know, just like you, it's like a lot of people I get asked to
do a lot of different things. And I do say no to a lot of things. - Well, thanks
for being here, it's great, yeah. - Yeah, no, I mean, and you have to, you have to
make choices in your life. So I say no to things. That's the primary way I do it,
is just say, look, How does this stack up with the other things I'm working on new
thing enters and it's not it's hard to say no You know, I'm not wired to say no
I'm always wired to say yes and my wife would agree with that but I've learned I
have to say no and so I do that more Yeah, well, we'll thank Tom Terrell if he's
listening for making this work out. So Okay, let's move to hiring you've hired a
lot of people. We've had some big teams I mean you started off early by saying
people it's one of the things you love about your job Building teams being with
teams. Do you have a sort of a life hack for hiring? Is there something in an
interview or maybe a practice in which really helps you sort out candidates or know
who you're looking for? I have a perfect thing I want to tell you about. Oh,
great. I've told a few people about this. So we do all the usual evaluations,
right? Technical skills, business. So whatever the role is, you know, we have a
whole normal suite of things we do. In fact, in the tech space, we actually give
tech tests and stuff like that. So we're pretty rigorous in what we do. But there's
a final thing to that whole process. And that is, as I'm interviewing someone and
I'm looking at them, I'm picturing tomorrow morning at 7 o 'clock or 730 in the
morning, I'm standing with them at the coffee maker looking at them getting our cup
of coffee. And we're both kind of bleary eyed and tired and I'm thinking, is this
someone that I and actually enjoy standing there, making small talk, getting a cup
of coffee together tomorrow morning. - Yeah, I've never heard that test. - And if
they're not, I'm like, okay, I need to think about this, like why is that? 'Cause
I've made some bad decisions in my career where I've hired people that were really
good in a lot of ways. - Technical experts, but-- - But just not a lot of fun to
be around. And I guess that's what it comes down to. There's a fun factor, you
know, and I wanna be around people that I enjoy. - Yeah, chemistry matters. I mean
it's just it really does and there's a lot of fun people out there. So let's hire
those people. They're also good. They're also good. Of course you have to be good
at what you do but there's a lot of people and they're fun. You know so that's
been a big thing for me. I'm like I'm not gonna hire folks I don't really want to
be around basically you know. The coffee maker test I love I love that. That's it.
Okay Chicago you're in all different places in Chicago. What's something you'd love
about the city? - That's a great question. Of course, I mean, I am a Chicago, kind
of a bigot. I'd even go that far to say, I mean, I love Chicago. And even people
who came from Chicago go to do other big things, like I teased Dave Blanchard from
Praxis 'cause Dave's from Chicago originally. - Is he really? - 100%. So officially
I'm going on the air saying, and Dave and I teased about this. - You're welcome
back. - Yeah, exactly. I call Praxis, it's actually a Chicago -based thing, you know,
that he would say, "No, it's not." But anyway... We'll add that to their LinkedIn
comments. Exactly. But Chicago is just... It's really a remarkable city in so many
ways. I won't go into all that, but it's just... It's beautiful. We have so many
things, especially this time of year, right? It's just spectacular city. And what's
so exciting about it is all the positive things that are happening in the city, you
know? I really... Again, part of my excitement about Chicago is just I know a lot
about what's going on. It's just super encouraging. I mean, yeah, there's bad news.
Of course, I could give you a thousand things that are bad news, but there's a lot
of good news too. That's just really energizing to me. The churches that are
investing in their communities, the nonprofits that are making a big difference, the
pastors who are just day in, day out caring for people. There's a lot of that.
It's beautiful what's happening. So I think it, for me, I guess it always comes
back to people, doesn't it? It's the people of Chicago that are doing the work that
I love and admire. Well, so your last question is not a people question. It's a,
this is new, I'm adding this just because it seems like it's everywhere as an AI
question. So we mentioned earlier ways that AI could help with translation work and
all sorts of things. But from your seat, what are you paying attention to when it
comes to artificial intelligence, what do listeners need to just be making sure
they're aware of? Is AI going to replace humans? I don't know if you have the
right question to ask, but the final short answer in this beat round is talk to us
about AI. Oh, sure. In 10 seconds, right? Yeah, define AI, right. Well,
I'd just say this, the productivity gains that AI gives in industry after industry
are real and groundbreaking and world -changing. In the software engineering world,
we use it all the time. And the productivity gains that we're getting in code
generation is remarkable. Now, you still need super talented engineers to assemble it
and put it all together and all kinds of things. So, will it replace some people?
Yes, it will replace some people, but it'll also create new jobs as well, which
almost every tech transformation does. Mark Sears is a leading thinker in the AI
space. He's a strong Christian guy, got to know him through Praxis actually, and he
has an AI company called Sprout AI,
and it's really interesting. He wrote an article called "The Builders," and in this
article I really recommend it. It's on his website, but It's this idea that the
traditional way that companies got built was through acquiring venture capital and you
had hire all these engineers. Short story, now with the AI capabilities, one person
who understands a business problem really well can actually assemble a lot of
technology very quickly. In short circuit, a lot of the steps that it used to take,
the millions of dollars of funding, it still takes funding but a different kind of
funding and so I think the truth is each of us are becoming and can become much
more productive in whatever thing we're trying to do. I find in myself I use this
engine called a Claude it's from Anthropic and I use it all the time and I'm doing
less and less with traditional web searching I still do that a little bit but I
get better answers when I'm trying to do something, I get better answers from Claude
than I do on other things. - Yeah, one of the things I just read on, I don't
remember if it was Claude specifically, but with search engine optimization, SEO is
out and AIO is in, and that's really like, how do you actually, what's Claude gonna
say? Is he gonna spit out Dylan Kane as one of the options? - Precisely. - How do
you now rewrite all your information so that you land in that answer? And it seems
you know, oh my goodness, just when we thought we had Google search engine stuff
optimized. Exactly. It's gone. Exactly. And that's how the world keeps changing,
right? And yeah, there's downsides, there's already downsides, but there's also upsides
too. And I'm sort of this eternal optimist. That's great. Yeah. So I just feel like
there's a lot of productivity, translating scripture, right? I mean, translating or
taking Tim Keller sermons into other languages. I mean, not just the transcription of
the language. But what would have been the work of a team of people for years and
years and years? I mean, what can happen in that field?
Confidentially, we already have Tim Keller preaching in Spanish where you hear him
speak in the Spanish language very persuasively. So, I mean, that's incredible,
right? I mean, we want to do that many times over. So, I mean, AI is a very
exciting thing and a scary thing. Like any technology, we have to be, it's sort of
the whole point of faith in work, right? Is like the character of the people
matters who are the ones implementing this. - Absolutely. - And so we need Christians
in all different phases of working in the AI space. - Right, asking the right
questions to guide what's coming our way. So, well, we went through a ton of things
and thanks for staying with me this long, and in the speed round with a few
additional questions here. David, it's been great. There will be lots of show notes
that I'm at it. I wrote down lots of things, so we'll come back and fill in the
different things. There's Nehemiah manufacturing, or spread AI, and some of that
stuff. So anyone who's listening, you can find the things that David was mentioning
in the show notes. And really great to have you today. Thanks for being with us.
Thanks, Ben. Been good to be here.
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