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Steve Glynn on Building Communities That Drive Innovation
8 Plays6 days ago
In this episode of MustardHub Voices: Behind the Build, Curtis Forbes sits down with Steve Glynn, founder of Experience Milwaukee and self-described Chief Milwaukee Officer, to explore the power of community, connection, and local ecosystems in shaping the future of work.
Drawing from his journey growing up in Milwaukee, building and selling Sprinklr, and dedicating years to connecting entrepreneurs, founders, and business leaders, Steve shares why professional networks can change lives and why cities thrive when people are aligned around a common vision.
The conversation explores what makes strong innovation ecosystems, why talent often goes unrecognized when it doesn't fit traditional career paths, and how communities lose opportunities when entrepreneurs and nontraditional leaders are overlooked. Steve also shares lessons from studying tech hubs across the country, discusses the role of leadership in driving economic growth, and explains why rewarding intelligent failure may be one of the most important shifts organizations can make.
Whether you're a founder, HR leader, business executive, or someone passionate about building stronger workplaces and communities, this episode offers practical insights on leadership, talent, innovation, and the human connections that make lasting impact possible.
Listen now to hear why alignment, community, and a willingness to embrace risk may be the keys to building stronger companies, stronger careers, and stronger cities.
About the Guest
Steve Glynn is the founder of Experience Milwaukee, a media platform focused on the people building Milwaukee’s tech future. Through interviews, articles, and field reporting, he profiles the founders, operators, executives, investors, and community builders shaping where the city is headed, and he helps ambitious people grow their careers, companies, and connections. A founder with an exit, Steve has spent close to two decades cultivating Milwaukee’s tech and creative ecosystem, going back to Spreenkler, the community he built and later sold. More recently, he brought forward Milwaukee’s first Innovation District in Walker’s Point. His work blends storytelling, ecosystem building, and local business insight, and through projects like his City Tech Tour, he studies how other cities grow strong companies and stronger talent so he can bring those lessons home. He also goes by the title Chief Milwaukee Officer, which tells you most of what you need to know about how he feels about his city.
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Transcript
Introduction and Guest Welcome
00:00:05
Speaker
Welcome back to Mustard Hub Voices Behind the Build. In these episodes, I sit down with the people building, backing, and running better workplaces. I'm your host, Curtis Forbes, and my guest today is Steve Glynn.
Steve Glynn's Journey and Contributions
00:00:18
Speaker
Steve is the founder of Experience Milwaukee, a media platform focused on the people building Milwaukee's tech future through... Interviews, articles, and field reporting. He profiles the founders, operators, execs, investors, and community builders, shaping where the city is headed, and he helps ambitious people grow their careers, companies, and connections. a Founder with an exit, Steve has spent Close to two decades cultivating Milwaukee's tech and creative ecosystem, going back to Sprinklr, the community he built and later sold. And more recently, he brought forward Milwaukee's first innovation district in Walker's Point.
00:00:55
Speaker
His work blends storytelling, ecosystem building, and local business insight. And through projects like his City Tech Tour, he studies how other cities grow strong companies and stronger talent so he can bring those lessons home.
Starting Sprinklr: Challenges and Growth
00:01:09
Speaker
He also goes by the title Chief Milwaukee Officer, which tells you most of what you need to know about how he feels about his city. Welcome to Behind the Build, Steve. Thanks for joining me.
00:01:22
Speaker
Curtis, thank you. That was very nice. Yeah. Isn't that fun? Getting your bio read back to you makes you feel like so accomplished. I'm like, yeah, i guess I'll stick around here doing this stuff. I guess I did do those things. I guess it did make a difference. um So a lot of things that I've been looking forward to today, we've gotten to know each other pretty well. And ah I've been pretty excited to have this chat.
00:01:47
Speaker
Before you started, experience Milwaukee, you know, before the innovation district, you you built an eventually sold sprinkler. I want you to take me back to the beginning. Like what, first of all, what pulled you into the work of connecting people yeah and building community in the first place? And the reason why I want to start there, because I know it's so important just to your general ethos. So i want to give everybody, like, I want to set the stage for everybody.
00:02:13
Speaker
Yeah, thank you. And I'm going to back up even further, but I promise it's not going to take all day. Okay, yeah. I grew up in on Milwaukee's South Side in the projects, single parent, low-income household. My dad was in prison my whole childhood. And um when i was when I finally figured out how to get through school, college, for me, um i was the only one in my graduating class without a job offer in a very hot job economy.
00:02:43
Speaker
And so i i reflected on that a few years later. i did it and eventually get a job offer and it was everything turned out great.
Connecting People and Building Community
00:02:53
Speaker
But I was reflecting a few years later and I thought, wow, I was not inheriting a professional network from my parents. I wonder if my classmates were.
00:03:04
Speaker
And so fast forward another maybe decade after that. And i was i was leaving one company to go to another and I thought, boy, I've got like now now I've got a pretty decent network. They're super bright. They're creative, innovative.
00:03:20
Speaker
I love chatting with them. I'm going to a place where I need to maintain a level of creativity. And how could I stay in touch with this with these past coworkers?
00:03:32
Speaker
So i um i thought I decided to start a meetup called Sprinklr. And I did my due my diligence as a startup founder, even before people were talking about this. i I checked with my customers on on how what they were doing, how how they valued creative connections. And um i maybe didn't ask the right question when I said, if I started a meetup to bring everyone together every month, would you attend?
00:04:00
Speaker
Because I got 40 yeses out of the 40 people I talked to. Oh, nice. OK. However, the first meetup, four people showed up. and In the second meetup, two people showed up.
00:04:14
Speaker
So I lost half my audience and one of the guys said, Steve, if anyone has a family, a life, a house, they are not coming to your meetup on a Saturday morning summer in Milwaukee.
00:04:29
Speaker
So I switched up the days, ah Wednesday nights at a Mexican restaurant. Suddenly, margaritas and innovation matched up perfectly. And still do. Still do. ah Grew that to the largest meetup in the state on those topics.
00:04:45
Speaker
And Sprinklr, the company, was born from it.
Fostering Milwaukee's Tech Ecosystem
00:04:50
Speaker
And so I talk about my past the way I do, because when you ask a question like, why did it matter to to start a company that was primarily based on connecting young people to the the professional world.
00:05:03
Speaker
I just think that is so such a critical, ah but i mean, it's critical just for your, the advancement of your own career, yeah but also for communities to come together.
00:05:17
Speaker
It's critical for companies to come together. It's critical for people to know. and Yeah. I love that. And think it makes a lot of sense. I think the context is really helpful and kind of important to understand.
00:05:29
Speaker
back in the beginning, right? what what pulled you What pulled you into that? Yeah. I mean. Yeah. And so there was a recent article that came out um by a friend of ours. and and And one of the things that stood out to me was like, and people actually have emailed me now saying, hey, we want to help you make more money. But it was ah it was something like, Steve, in fostering the connective tissue tissue in Milwaukee's tech ecosystem,
00:05:59
Speaker
is doing the work that most people get paid for through grants, having teams, and et cetera. And Steve has done it primarily on sponsorships of his platform or if out of his own pocket, basically.
00:06:14
Speaker
And when I read that, I'm like, damn, that's ah that's that's commitment.
Lessons in Leadership and Company Culture
00:06:21
Speaker
yeah And it's because this isn't something I just like to do. It's deeply wired in me from how I grew up.
00:06:29
Speaker
I mean, your experiences from the beginning really seem to kind of shape the way that you work today, you know, and and you... you know, you you he can you can sense it. You're running, you know, you may not have the grants, but you're certainly running on on coffee and passion. That kind of takes you pretty far. Well, unless it's three in the afternoon, then it's whiskey. Yeah, there you go. Okay. So so you exited Sprinklr. You grew it, right? You were that you were the founder of of that company. You grew it. You were able to exit. What what did building and selling it
00:07:10
Speaker
teach you that you carry into what you do now? Because you you made a really interesting comment, you know, kind of off the cuff that you were listening to your customers. You were trying to do these things early before it was sort of in vogue to do so, right? Yeah.
00:07:25
Speaker
yeah All right. So what did that whole experience as a founder and i guess through that that exit process teach you about what you're doing now?
00:07:37
Speaker
Yeah, so quite a few things. And early on, so we our first year, mostly about how to how to be a ah good leader. and And I say that because in our first year, we lost money.
00:07:53
Speaker
And my rationale was that um every most businesses lose money in their first year. So I managed to that. And at the end of the first year, I told my team,
00:08:05
Speaker
we can't lose money again if we don't have a, there's nowhere here to work. And so ah we changed our goals and we changed our paradigm. And in what that taught me in within that first year was you you do, and i'm Curtis, I'm sure you can say, duh, Steve, like everyone knows this, but you manage to what you set out to do.
00:08:30
Speaker
and And once we changed what we were setting out to do the whole game kind of changed for us. um The other piece I learned, which is ah around culture and and people is um to not be erratic in my behavior. And so I remember one time I walked into the office and ah in in like kind of a desperate need of ah us finding a UX, a user experience designer.
00:09:00
Speaker
And I was just not frantic, but like, we need this, we need it now. and But in a way that could easily have changed everyone's priority, certainly for that in that moment, for that day, maybe the week of focusing off of their work and onto getting a UX designer.
00:09:16
Speaker
And I'm throwing out like, we're I'll pay someone five grand if we find someone. I'm just like doing all the wrong things. And my business partner at the time pulled me aside and said, Hey, you can't do that.
00:09:27
Speaker
We got to talk these things through and before we present them to the organization. yeah So I don't know, to your question, it's more, i was learning a lot about people yeah and how to how to manage and lead people in the right way.
00:09:43
Speaker
um It's really interesting when you talk about expectations because, you know, companies, companies are very are Companies are very much like children in a lot of ways, right? Not necessarily the people within them.
00:09:56
Speaker
Well, actually, sometimes the people within them, but not all the time the people within them. Well, I had a company, of course, I had a company that hired college kids, so I i considered them my kids at the time. There you go. I was like, you are only, and now they, I can't tell you how many marriages and babies have come from the universe of Sprinklr.
00:10:16
Speaker
it's incredible I love knowing that. I love knowing that. That's amazing. um You should be very proud of that, actually. But like, you know, yeah I often I often ah ah or i I believe and I'll often say, you know, that that kids really rise to the expectations that we set for them.
00:10:32
Speaker
Right. um Companies will often do the same thing. Right. You know, when it comes to your goals, when it comes to your mission and your vision and your values and all of these things, you know, provided that you actually live them and you believe in them and you're actually focused on them, the organizations will generally rise to the expectations that you set for them.
00:10:51
Speaker
Right. And, uh, or it's, it's a core belief of mine. Certainly that doesn't account for externalities, you know, beyond your control, right. When it comes to, you know, sales targets, you know, or, or know what different sort of macroeconomic things that obviously can affect your, your company, but notwithstanding those things, um,
00:11:12
Speaker
You know, that it's really important, I think, from a leadership standpoint, right? You talk about learning how to manage people, right? Patience, steadiness, right? It all starts from the top down, right? And if you exhibit those things and then also, I think, make it clear that there's an expectation that that same behavior, you know, gets exhibited by others, you're going to find that.
00:11:35
Speaker
yeah Yeah, I did actually read something during that time, ah exactly to your point, ah because i I would often send emails at three in the morning. And i and then I read something that said what you do ah communicates to your team, what it can communicate to your team, what behaviors are expected.
00:11:57
Speaker
Right. right And so I was i just started to become really ah hyper aware of what I said, what I did, when I did and all that stuff. Yeah. Yeah. And it's true, i think, personally. I mean, not not
Experience Milwaukee: Vision and Impact
00:12:09
Speaker
just what is okay, but what is expected, you know? Right. And, um you know, again, that's setting culture from from the top down. So um I do want to talk about experience Milwaukee.
00:12:22
Speaker
Yeah. So for for maybe for somebody who's never heard of it, you know give me give me the details. What is it? What are you trying to do with it? We'll start it there and then we'll we'll dive in deep. Yeah, so this is why I love that we start started where we started because um after selling Sprinkler and taking a few years and doing a bit of consulting, ah tried ah a job that wasn't a fit for me, that's when I really realized corporate, it was going to be super hard for me to ever fit back in corporate again. Yeah, the 3 p.m. whiskey also might have something. Yeah, that can get in the way. Actually, at this place, it it didn't. You were encouraged to have whiskey at your desk. Oh, good, okay.
00:13:02
Speaker
um But ah ah where we started in this conversation, how I grew up and where I grew up after having sold a company then, this kid that came from nothing, it was like, how do I give back to a city that embraced me?
00:13:18
Speaker
And also, how do i do something that can earn me free beer and whiskey? And so I started Experience Milwaukee as a way to shine a light on the entrepreneurs, the people who are building, starting businesses that are the fabric of how you experience a city.
00:13:36
Speaker
So bars and restaurants and festivals and all of those things, artists, musicians. um But I always, because work culture and and business and technology has such a meaning to me,
00:13:49
Speaker
even in the scope of that kind of a podcast, which Experience Milwaukee started as, I always found a way to inject a monthly show on those topics, work culture, business, or tech.
00:14:02
Speaker
And so finally, at the end of last year, 2025, I said, dude, stop flirting around with that idea. Stop. You know where your heart is. Let's make you got we have now enough people talking about cheese curds and beer and all this stuff here. um Let's get deeper into business and and again, go back to your roots, not just write about the stuff, but in a way that helps people connect to the people you're writing about. Literally, that they're able to find them on LinkedIn, set up a coffee meeting and help this you know like the connectedness of the city expand.
00:14:41
Speaker
I love that. So that that you're, a lot of your pitch is basically helping people see who is doing what and how to plug in really. Right. And, and so i guess I would, I would ask like, why does that, how to plug in piece, why does it matter so much? What happens like to people in cities when it's missing, I guess, is it maybe a better question?
00:15:07
Speaker
Yeah, I, I think, um, As much as we have a term here in Milwaukee, it's called small walkie. And it's it's not in reference to the size of the city or the capabilities of the city or the cultural robustness of the city. It's in relation to how closely connected everybody is.
00:15:32
Speaker
And what I hear time and time again from people who visit from Chicago or New York or San Francisco is they come into a space, a common space in Milwaukee.
00:15:45
Speaker
They start to meet people. They get seven connection referral kind of recommendations from everybody they meet based on what they want to do.
00:15:56
Speaker
And they look at ah me and they say, wow, this would never happen where I'm from. People just don't share like this or people just don't know. And so I think I would guess, because I'm born and raised in Milwaukee, I would guess, Curtis, that if a city doesn't have that, you can feel lost.
00:16:17
Speaker
Yeah. Yeah, I think you can. I think you can. um And that's really interesting. Small walkie. I'm curious where that got coined. but um I think what you're describing, first of all, I mean, what you're describing, I think is every, is is something everybody would like to experience, right? It's like the, it's like the song from Cheers, right? Yeah. Everyone knows your name. Everyone knows your name. Like you want to be in this place where, you know, you can, it feels thick that, you know what, it's that community feeling, right? It's the community feeling that you talk about that you're trying to build. yeah It's hard to do in a lot of other places that are, um you know,
00:17:01
Speaker
where things are more disparate or distributed, right? Where there's ah a lack of that connective tissue, I think. And it sounds like it's in Milwaukee in spades. So you took over a cafe, you turned it into a coworking space and and gathering space, right?
00:17:16
Speaker
And yeah it was it was a preexisting kind of coworking and gathering, but ah it wasn't achieving what it could. Right. what but so And now you, you carry the title chief Milwaukee officer, which I love by the way. Thank you.
00:17:31
Speaker
Give me the bigger vision. Like what are you building towards? Yeah. So, um, uh, love this question. And, and by the way, ah it was like probably, i don't know, a few years ago, four or five years ago, my, my wife who's in communications was writing a press release for experience Milwaukee and she coined the title. So I, like I have to give her credit for that one.
00:17:51
Speaker
And I'm like, this is brilliant. Why has no one thought about this? And, uh, and so, uh, so I've been using it ever since, but, uh, I've spent a lot of I spent the first part of the career kind of learning.
00:18:06
Speaker
um i spent my whole 20s actually studying business, not just in school, ah but reading everything I get my hands on every weekend ah where a lot of people are out. and I did my fair share of, you know, going out with the guys for beers, but where people are mostly doing that, I spent the whole decade studying. And then in my thirties, I spent that, that decade practicing and starting sprinkler.
00:18:29
Speaker
And, uh, and so I've seen a lot in, in, in over the last decade, I've, uh, I've been telling stories about the city.
00:18:41
Speaker
So learning, doing, and then storytelling. and And when you ask what the bit what the vision is or where where do i want to go it's that ah I think I feel a sense of responsibility that my stories have to become less rainbows and butterflies and more the realities of where we are as a city in a region, particularly in tech and innovation.
00:19:05
Speaker
And so I actually have a 20 page. I was putting it away when you were we were logging on, but I've got this nice 20 page report. Like a manifesto. ah and Exactly. on um On how Milwaukee is falling behind and what is our plan for action. And we have this saying here when the Bucks won the championship.
00:19:31
Speaker
It was coined ah Bucks in six and to win in six games. And so I have, a in in being inspired by that, I have labeled this manifesto MKE for Milwaukee, MKE in six. In six. there six A six pillar plan in six years.
00:19:53
Speaker
What do we need to do to get to where we where we think we are today? and so i you know The more fun answer to your question is from Sprinklr to Experience Milwaukee and everything in between, it's been ah it's been a friendly poke, a friendly poke to the community to say, look what's possible.
00:20:17
Speaker
Look what we could do. Look what
MKE in Six and City Leadership Challenges
00:20:19
Speaker
we can achieve. We were a band of misfits at Sprinklr, yet we were one of five agencies from around the world that were invited to Zappos at the height of Zappos success to pitch to be their agency of record.
00:20:32
Speaker
So we don't, we poke in a fun way, but we don't mess around. We take this shit seriously. And, but we want to get people to think about our city in a different way. Yeah. Through, through your, through your tech tour, your city tech tour, you, you know, you, you, you study how other cities build strong tech ecosystems. What is something that you've seen elsewhere that you wish,
00:21:00
Speaker
you know, more places like Milwaukee included, obviously, understood. like Yeah. you know A thousand percent, my number one answer, and it's ah it's a number two would be a distant second, it's alignment.
00:21:14
Speaker
It is alignment on where the city or the state or the region is intending to go and getting everyone rallied around Where do you find most of the disconnect? Like at what level? Is it at the is it at the state or municipal? Is it yeah like... the business leaders in a particular community? Like where is that disconnect that you see most often?
00:21:36
Speaker
Do you mean and in in general? Well, when you talk about alignment, right, to get everybody pulling in the same direction, who is it, where do you see the folks pulling in the opposite direction? Yeah, so I'll say, um ah when i meant when I said in general, i meant like in general i'll across the cities I kind of talk to or like, but i'll be I can be specific to Milwaukee and I'll tell you this, our elected officials And our our leaders, whether that's business or even some of the organizations like the like the citywide chamber, um none of them that I'm aware of have communicated a vision for technology and innovation and how we participate, not just nationally, but globally in that ah and those economies, a vision for what this state stands for.
00:22:28
Speaker
No one. And so our startup founders have, they don't all know this because they just do their thing. And some of them are young and and a little bit you know new and naive to this.
00:22:42
Speaker
They don't have direction. They don't know what the, they don't know clearly what the core strengths we as a state want to dig into so that they can build around some of those things. Interesting. Okay. And so from startups to the top, everyone just kind of does stuff that they think it will be beneficial because they're not malicious, right? Their intention is to make the environment, the community better, but there's no alignment to a North star.
00:23:12
Speaker
When, um, When you look at the at the cities or the companies that grow maybe strong talent versus the ones that don't, what do you think like separates them? Is it money, leadership, culture? you know Alignment, obviously, number one, you know and from the state and the cities, the municipal level, i think, yeah, having that sort of clear North Star about what you want to be and you know maybe then how to how to get there.
00:23:41
Speaker
yeah What do you think is a big separator between those successful cities and companies that are growing talent and the ones that aren't? at I got ah two kind of quick takes on that. One, it I want to debunk the the money issue.
00:23:56
Speaker
Everyone complains about money in their ecosystems. We don't have enough investors. We don't have enough money. That to me is could not be more BS. i have and i know I know there are cities that are struggling economically. I know there there are, right? But i've never I have not seen money be an issue because the money will find the problems. Even if they are grants to make to turn a desolate economy unoccupied neighborhood and refresh it back into tech and innovation. I'm speaking in the tech and innovation. yeah
00:24:29
Speaker
Right. So debunk the money thing. The number one thing that gets in the way, in my opinion, is ego. Oh, hundred percent, man. I'm, I'm ego i'm with but um' behind you a hundred percent.
00:24:44
Speaker
So it's the people who sit in the in the in the seats that could make the change, that could bring their fellow leaders together who go, well, I got another four or five years.
00:24:57
Speaker
I just keep quiet, cash my checks. we're gonna be I'm going to be good. That's my opinion. I think there's a complacent, there's not ah there's not urgency, there's a complacent kind of approach to, hey, we're doing our thing as an organization.
00:25:14
Speaker
As long as we're fulfilling our mission and I get my paycheck, I got another five years, we're good. That's how I see it. You know, well, I feel like we could hold ah we could have a whole other podcast on this particular issue because a lot of things come to mind, you know, especially when I think about a lot of those leaders, I think probably the ones that that you're referring to. And I've seen it. I mean, I saw it i saw it growing up myself. I grew up in in West Texas. change...
00:25:43
Speaker
change was a really hard thing for folks to accept, even positive change and progress, right? When it comes to a whether it's city beautification, right? Or whether it comes in, in like in the form of investing in, um you know, projects, infrastructure, companies, and things like that.
00:26:06
Speaker
um it means that change will come. And that's a hard thing for a lot of people to digest, especially those people who are really comfortable, right? And so ah you tend to get the naysayers, right? And you tend to get a lot of pushback from folks who are comfortable in what, you know,
00:26:24
Speaker
that space looks like today for them. and You know, a lot of when you also get a lot of folks in the room, especially politicians, you know, politicians have egos. That's, that's, you know, I think, I think in order to be a politician, right, there has to be, you know, even a small sense of elitism to think that, you know what, I'm capable and qualified enough to lead an entire state worth of my constituents, possibly be a leader of a free world. I don't know.
00:26:49
Speaker
Under my name, right? Under my name. I worked at an agency once and and Subaru was a client. And one of the executives at Subaru said to me, hey, do you know how to tell which car dealership ah the owner has an ego and or who doesn't? And I'm like, oh, no, I'm i'm a young kid. i don't I'm 20 something. i'm like, I don't know. what How do you know?
00:27:13
Speaker
Look at the car dealerships you have, they're the person's name on it. Versus the car dealerships that don't. And I thought that was super interesting, whether accurate or not.
00:27:23
Speaker
And I want to clarify one thing on ego. I don't necessarily mean in every case that the ego problem is someone set thinks they're great and everyone else sucks.
00:27:35
Speaker
I think it's never been... as A couple of things are happening right now in the world of work and in and specifically what I do. Tech has never been changing more quickly.
00:27:48
Speaker
And there's never been more uncertainty on what's going to happen. And so when you are in a position of leadership or power or influence and those two things are going on,
00:28:03
Speaker
The ego can tell you, don't disrupt. Don't change. Don't just stay in the lane. yeah So, um you know, i I just wanted to clarify that kind of thing. And I think that's ah irresponsible of people who have that ability and that and that responsibility.
Skill Recognition and Non-Traditional Careers
00:28:21
Speaker
Well, I want to... let's use that as sort of a jumping off point because I i want to spend some time talking about, you know, talent and skills.
00:28:33
Speaker
Um, something I think that you care a lot about, you know, you've you've pointed to a pattern, I think where founder, somebody with some non-traditional background, you know, tries to kind of step back into the workforce and,
00:28:50
Speaker
companies sometimes just don't know how to read them. and And I think that- I'll update your answer. And and for my ah my opinion, only they never know how to, they don't, they just simply across the board don't know do it. Talk to me about that. where Where does the breakdown actually look like up close?
00:29:09
Speaker
Yeah, i so I've, a couple of things I've been studying lately. um ah One, I was digging into the um people who make- a Decisions that are made on purely on logic versus on ah decisions that are made purely on the person.
00:29:30
Speaker
and And I don't mean emotion, but more like knowing who the knowing person more than like logical factors. And then how do you get in the middle where you're like taking the person into account and logic?
00:29:42
Speaker
um And so decision making on those things, on those two variables. And then um I've been looking at, I've been studying job descriptions. h across the country, across marketing, sales, product management, community, ah though mainly those areas.
00:30:04
Speaker
And from companies that you might think are kind of stuffy and conservative to companies leading in tech like Anthropic and every job description, even if they have a small disclaimer about, hey, these are just these are, you know, the requirements we kind of go by, but we really want to get to know you.
00:30:25
Speaker
Right. They don't. it The outline of what is required is built for people who have been doing those things. In my case now, as I'm looking at the late 40s, early 50s kind of population, they expect you have been doing these things in a corporate setting with escalating responsibility for 10 or 15 years or more.
00:30:48
Speaker
That doesn't fit an entrepreneur. Right. Further in my studies, I sit in small business communities, groups of people who have gone off to do their own thing. One, mostly one person company, sometimes two or three across the board.
00:31:05
Speaker
What I hear the most from them is, hey, I started my own company. So now I know I've got to make it work because I know that having started my company, I'm now unemployable. It's just a sentiment, right? Yeah. Yeah. I think about that all. I think about that all the time. I mean, I have, um i i I think about on the one hand, I feel like I've been fortunate enough, right? Since my 20s and the first organization I started 25 years ago, right?
00:31:35
Speaker
Scaled that one, built a roll up, started another startup. You know, i've I've sort of always, you know, a serial entrepreneur, I think, so to speak, and have never, I've never really set foot in corporate America and often wonder, am i totally unemployable. And i that it's it's it's the sentiment, right? So I think on the one hand, I'm fortunate, but also on the other hand, I'm i'm not so sure that that's that that's being fortunate. I don't really know. Why do you think companies are so bad at mapping somebody's real skills to like an open role that like the moment that the resume stops fitting this clean template?
00:32:17
Speaker
um I think it's it goes back to my exploration around logic decision, logic as ah as a filter or lens to make a decision versus person as a filter or lens to make a decision.
00:32:31
Speaker
And oftentimes, logic is used as a defense mechanism so that if something goes awry and they say, well, how the hell did this happen?
00:32:42
Speaker
You can say, well, I don't know because I logically went through all the criteria that we filter to. So it's not my fault that it didn't work.
00:32:54
Speaker
that's that That's a hypothesis I'm toying with right now to understand in in this community of late 40s, early 50s, kind of what's going on and why they, if they leave, can they get back in Or what's, kind what if they started a business a decade before that, yeah where do they see themselves now if it's not working the way they thought it would?
00:33:15
Speaker
how How does that change the way that you've got to prove your value when you don't show up with the expected credentials? Yeah. Like as the as the individual on the other side of that that interview, right? Like what what changes in the way that you have to prove that?
00:33:32
Speaker
i'm I'm really struggling with that one right now. And i have talked to some people in the space of HR of like, why why is there not –
00:33:45
Speaker
How come you don't ask, have you taken an idea from zero to a functioning something? Have you taken revenue from zero to some significant or any number, right? Have you rallied a team of misfits around the vision and gotten them all to to get momentum on an idea or or a company? Like those are the kinds of things I think you have to start answering.
00:34:07
Speaker
If in addition or in replacement to some, you know, some of the more corporate ones, the one i did come across a company who's doing this in a really interesting way. They're called shift group.
00:34:19
Speaker
Okay. They're on the East coast and, uh, they focus, uh, we're talking about entrepreneurs. They focus on veterans and elite athletes.
00:34:32
Speaker
Hmm. How do they take what they've learned and and rewire them, reconfigure them into what you're asking, right? The skills that then become more um clearly communicated to a ah corporate setting.
00:34:50
Speaker
You know, that's really interesting, by the way, and I can i can totally see why there's a ah need for that. and it's it it And it maps kind of cleanly even to those – those founders, those business owners, right? um Because your resume doesn't fit that that template, so to speak. But I like to sometimes approach the the question from sort of ah ah the opposite direction. what's What's the cost to you know a company, to a community or or to a city, right?
00:35:23
Speaker
when a lot of these capable people can't get those skills recognized. Like
Entrepreneurial Resources and Talent Retention
00:35:29
Speaker
what gets left on the table when they can't, you know, get those gigs?
00:35:36
Speaker
Yeah, ah I mean, besides besides the the the money factor, I mean, the people leave. Yeah, they leave. And and and they you wind up getting a a community starved of some some pretty you know significant talent or potentially.
00:35:53
Speaker
Talent leaves, tax base erodes. yeah ah Cities become less attractive. it's It's a cascading issue, I think.
00:36:05
Speaker
And um ah i what i what I wonder, though, about your question and this topic is, are there cities who...
00:36:17
Speaker
um cities where ah if you have more of a non-traditional last five or 10 years of experience, is it easier to get in through a conversation than in other places?
00:36:32
Speaker
You know, and like we can pick on San Fran, right? Like our San Fran is San Fran going to understand entrepreneurs better than yeah a Milwaukee or. that's That's where my mind went instantly is is is that is a very non-traditional path community like that.
00:36:53
Speaker
going to be able to to do it more more easily or will they do it more quickly you know than ah than a Milwaukee, I guess. Yeah. And to your question of what's left on the table, it's interesting that um that I've talked to five of the eight.
00:37:09
Speaker
Yeah, there, yes, yes, there are eight candidates for governor for Wisconsin this year. And I've talked to five of them and they all say we need more resources for entrepreneurs because they recognize entrepreneurs can, and I think it's been said in in in studies that startups create, they're there that's the job creation engine, right? Net new jobs come from startups.
00:37:37
Speaker
And so if people are afraid to start companies because they don't, can't find the funding, that's one, right? So states have gotten better at addressing that.
00:37:50
Speaker
If people, um the other factors I think that are more important though, that leaves money on the table, not just for someone getting a salary or the city losing tax dollars because someone moves out, but for a state economically is if you have a,
00:38:06
Speaker
ah a large number of people not starting companies because they're afraid that failure is going to be a mark on their career forever. Or if they're afraid if they leave a place to go start something and if they leave, they can never get back in that they don't leave.
00:38:23
Speaker
Those are big issues. Yeah. Yeah. Those are big issues. Um, You know, ah across the the founders and the operators you talk to, i guess even not necessarily those, but but I guess all of the prac HR practitioners, any of the large organizations that you're affiliated with, I mean, what's the most common people problem that you hear about? The things that kind of keep surfacing no matter the the industry or the location or the size?
00:38:55
Speaker
Um, uncertainty certainly is a big issue right now. Um, but, uh, I think that's kind of a macro issue.
00:39:07
Speaker
And when I get down to some of the micro issues within certain organizations, I think, um, quite honestly, it's, uh, people are, they don't,
00:39:21
Speaker
They don't, as much as there is ah anxiety around, is AI going to replace my job? Do I need to learn new skills? I think the companies I'm talking to are actually on a path that um of upskilling that seems encouraging.
00:39:37
Speaker
But
00:39:41
Speaker
to answer your question, it's, I think companies are one are looking around going who's going to leave? Yeah. Yeah. Who's going to leave? I don't know. Where should I invest if they're just going to leave?
00:39:54
Speaker
And I think that's ah at least for the companies I talk to there, if they have any kind of unless they have a super stellar, which I only know one I've talked to, a super stellar retention rate um because of how they intake.
00:40:07
Speaker
um They're worried about who's going to leave. And I think what I'm feeling is people are going people who are getting want jobs or have jobs are like, where do I invest my next three years so I don't get left behind by by technology?
00:40:22
Speaker
And companies are are are thinking in the same way. How do we invest when people are kind of maybe thinking about bolting? You know, that this one's kind of near and dear to us.
00:40:33
Speaker
Yeah. At Mustard Hub, right? I mean, we're focused on surfacing a lot of those early signals about people before they show up as turnover or disengagement or or whatever. So, um you know, in in these conversations that you're having and your experience, like by the time a leader actually notices a problem,
00:40:54
Speaker
how late are they usually catching it? Is it, is it, are, is it, are they usually, you know, is this more coroner style diagnostics or are they able to catch things, you know, while there's still time to do something about it?
00:41:11
Speaker
I don't know anyone who's able to, to spot, anything early. What I see more is people say, Oh yeah, I told my employer, I, you know, I'm leaving cause I got a new or I got whatever the reason is. Right. And, uh, and they're like, Whoa, Whoa, Whoa, wait, wait, let's ah talk about this. And by then it's too late. Cause it's awkward.
00:41:32
Speaker
Yeah. It's too late. It's awkward at best. And, and, and cause everyone knows where their feelings are at that point. Cause if someone was going to leave, you know, so ah Yeah. I don't, I don't know. Companies tell me, Oh, we, we have a good read on when people are getting a little off track. we yeah and You know, we do, we take some, we're proactive instead of reactive.
00:41:54
Speaker
No one is telling me that. Well, and I'm sure that probably a lot of them wish that they were. So let's, let's, let's look ahead. Let's talk about the future of, of work of cities. I don't know of Milwaukee. Maybe when you think of the next five years and how careers are actually getting built, um,
00:42:12
Speaker
what what shift do you think most people are underestimating i don't know that a lot of people are underestimating ai but um you know i there's always something that doesn't make headlines that winds up being you know a big factor i so i got a couple of thoughts on this and one i got i i talked to a lot of people in the um ah like the communication space, PR kind of stuff. and um and and And someone said to me, it's always interesting to see when ah when there's an emerging tech where things actually end up versus the headlines you're reading in the early stages. Yeah.
00:42:58
Speaker
he And he even went on to say it's never congruent, right? It's never what you're you're reading, right? So that is something that's interesting. The other thing is, and this is a generational loss, miss.
00:43:14
Speaker
oh You can go back as far as you want, I think. Don't underestimate the kids.
Encouraging Innovation Through Embracing Failure
00:43:24
Speaker
The young people that I'm talking to,
00:43:27
Speaker
And everyone's saying, oh, they i know i know there are issues with them getting jobs. I know there's there are issues with entry-level jobs and AI and all that stuff.
00:43:38
Speaker
But the kids are adapting quickly. And the young people I'm talking to, even one the other day who has shifted her approach to... um Oh, I wish I could remember. She's like a pilot architecture or something.
00:43:54
Speaker
She creates proofs of concepts, proofs proofs of concept. So she can take she's built like 20 or 30 different ideas. Interesting. And she thinks that that type of architecture person is going to be needed. Someone who can rapidly produce ideas into something visual and you can visit physically look and see and touch and feel.
00:44:16
Speaker
And so they're starting to use AI to take what they're learning in school and take four steps forward into where they think it's going to go And I don't know if mid-level management's even thinking about that kind of stuff.
00:44:31
Speaker
cause they're all worried about being replaced by AI and trying to figure out how to use the prompts properly. Right. And these kids are building. That's really interesting. Now, I mean, you've bet hard on a city.
00:44:44
Speaker
A lot of people overlook, you know, Milwaukee isn't usually, I I'm, I'm being diplomatic. I, I, I like it there. You know, it's generally not when, when people think about,
00:44:56
Speaker
um you know tech and in the future, it's it's not always you know in the in the the top of the list. so i mean what Not always. I have research that says never.
00:45:06
Speaker
you Does the future of work make places like Milwaukee more relevant or less? you know i think that there I personally think that there is a little hotbed of of talent when it comes to HR tech there in the upper Midwest. so Tell me what you think about the future of work and in places like Milwaukee.
00:45:26
Speaker
So that I do ah i do ah agree on. um What I tell people is, ah so I've been talking for a number of years on on um just to kind of level set with people like, hey we're not a we're not a tech startup town.
00:45:40
Speaker
Do we have tech startups? Sure we do, but we are not a tech startup town. We're not teaching our kids to be founders. We are not. The stop, stop. We're not doing it. We can if we want to. We're better than we ever have been, but we are not teaching kids to be founders. We are teaching kids to get enterprise tech jobs.
00:46:01
Speaker
Right. OK. So it's because we have a ah good, really good density of large enterprise fortune companies that um need to hire these young people.
00:46:16
Speaker
And so what I have have said to your point and what you're asking about aye h r and in that kind of talent and workforce is um few if any other cities can scale technology in 100-year-old companies like Milwaukee can.
00:46:38
Speaker
In 100-year-old, yeah. Right? Because that's a very special talent. ah To get a 100-year-old company to 125 to 150 to 180, right? That's a really special talent because most companies die way before that.
00:46:54
Speaker
Yeah. We know how to do it. And I think i what I think is, to your point, it's because of workforce innovation. Right. It's because we are doing, and I don't, I haven't dug in, I haven't uncovered, I haven't researched, but I believe that that is, it has to be why we can do this.
00:47:16
Speaker
And it's not sexy, it's not glamorous, but we, we're doing something in that area that I think has just, at least for me, recently been kind of poked at.
00:47:28
Speaker
I think so too. um You know, i'm curious. So, I always really like to kind of wrap up this way, you know, and, and, think about if ah if a business leader, if an entrepreneur, a founder, you know, if if one of your next three governor conversations,
00:47:51
Speaker
it if somebody comes to you and and and wants to know, they you know, and and or asks, you know, that they want to they want to find, they want to grow, they want to keep great people, you know, even if, even those folks who don't fit that usual mold, right? That template that like we talked about, what's the single most important piece of advice you can give that organization?
00:48:14
Speaker
um We have to, ah we have to be real about ah how we reward failure. i love that answer. Keep going. so there was one,
00:48:31
Speaker
in the What got me thinking about that is there was one of the gubernatorial candidates I talked to, Kelda Royce, who said, i want to change the culture around failure in our state.
00:48:45
Speaker
And even though ah everyone literally says, Embrace failure. It's great. You'll learn. As long as you learn, your no, it sucks. Everyone hates the process of failure. It hurts.
00:49:02
Speaker
It's often awful. And um do you learn and get those things? Yes. But hey, guess what? the last time I checked, most of the people who are failing in corporate don't have jobs anymore.
00:49:12
Speaker
They're fired. And so if we can find a way to reward failure, right? In in with guardrails, right? Good leadership.
00:49:24
Speaker
I think we're going to keep more people here We're going to have more people starting interesting things. That's really interesting. And i I love that. I think
Conclusion: Learning from Failure and Innovation
00:49:33
Speaker
that um and there's a lot to even really unpack with that, too, you know, the because the reality is and I tell my kids this every morning when they're off to school that.
00:49:44
Speaker
you know it's it's not about failure you you you either win or you learn right um you know if you can take those experiences and really make something of it you know then that turns it into a really positive experience and um you know changing that that mindset about what failure means right and and this idea of falling forward right um I think could be incredibly impactful for a community right that wants innovation. Because you see organizations, companies, large enterprises that have these values that that want to encourage people to take risks, but then
00:50:28
Speaker
when something happens and those folks fail, they get kicked out, right? they're not really They're not really rewarding folks for taking those risks that they're being encouraged to do in the first place, yeah right? It's just a word on a wall. It's not really their value. As much as they want talk about wanting people to take risks, right, there's still the stigma that goes along with it and somebody's got to take the fall when the reality is is you're either winning or you're learning. And learning sometimes is just as valuable.
00:50:57
Speaker
Right. And and let's go let's circle it, full circle it back to our earlier part of our conversation. I took a huge risk in starting my own company.
00:51:09
Speaker
And guess what? the the the What's not getting paid on that risk, even though I've had degrees of success and sold one company,
00:51:20
Speaker
is the companies aren't willing to take a chance. Few are willing to take a chance on where what I know. Yeah, that's right, right? And those folks who do take the risks, who have done the learning, aren't always getting a fair shake at the opportunity. I like that. That's a really great... um That's a great point and a good one to end on. Steve, thank you so much. Appreciate you taking the time to join me today.
00:51:45
Speaker
Same here. Thanks, bud. That was fun. And ah thank you to all you watching and listening to Mustard Hub Voices Behind the Build. Be sure to subscribe so you don't miss the next episode. Feel free to visit mustardhub.com to learn more about Mustard Hub and discover how we help companies become destinations for workplace happiness and turn culture into a competitive edge. Until next time.