Glenn Harper [00:00:00]:

Hello, everyone. Welcome to another edition, the Empowering Entrepreneurs podcast. I'm Glenn Harper.

Julie Smith [00:00:04]:

Julie Smith.

Glenn Harper [00:00:05]:

What's

Glenn Harper [00:00:05]:

going on, Julie?

Julie Smith [00:00:05]:

You know, it's a good day today.

Glenn Harper [00:00:07]:

Why?

Julie Smith [00:00:07]:

Well, I mean, the weather's kind of okay. I have an extra shot of espresso in my coffee. Oh. Didn't get much sleep, but I'm I'm feeling good.

Glenn Harper [00:00:15]:

Alright. Well, you know, this is a shout out to our sponsors, Caribou Coffee. They're they love us all the time. Well, we've got a amazing guest today. I'd like to introduce Scott Flazer, a CEO in b two b Vertical SaaS. He also dabbles as a senior adviser for SafeSend while being an owner of Mac Real Estate Ventures. His prior 20 years work experience was in many senior leadership positions at Thomson Reuters. We met Scott back in 2018 when he was visiting Ann Arbor on a sabbatical from his post in Switzerland.

Glenn Harper [00:00:43]:

Once you meet this guy, he relays not only he's a good dude, but he also has an incredible gift slash skill set to engage with people and actually listen to them. Even though he's a Michigan fan and alumni, he's one of the good guys. His passion is finding someone with a vision and building, like, the company team, culture, and product around that vision. As a fellow accountant, Scott not only sees the depths and credits, but he has perfected the intangible attributes of psychology, leadership, and execution. These traits are elusive to most people. There are dreamers and doers. Scottie is a doer. Once he's tasted the entrepreneurial nectar, he is unstoppable in his quest to be on the national journey bus.

Glenn Harper [00:01:16]:

Thanks, Scott, for being on our show.

Scott Fleszar [00:01:18]:

It's a pleasure to be here. Wow. What an introduction. I don't know that I'm worthy of all that, but, I'm I'm really excited for this conversation. You know, I'll the first thing I'll say is I'm a fan. You know, I I you know, Glenn and Julie, I think we first met maybe even before 2018 at one of kind of the earlier partner summits, and and I've just been a fan of seeing all the things that you've got involved with, how you've grown your firm, you know, other, entrepreneurial activities that you've, you know, been involved with and just, you know, all of my career has been in, roles where you serve accounting firms with software and technology. And one of the joys for me is just seeing firms grow, people grow, and and get involved with, you know, a variety of things. And and, you know, Glenn and Julie, you both been, you know, you you you've established a high bar for all the things that you've done and all the things you've gotten involved with.

Scott Fleszar [00:02:13]:

And, I also will say that, I didn't know if I'd ever be on this podcast being a University of Michigan degree holder and living in the Ann Arbor area, but I'm really happy to be here. So

Julie Smith [00:02:25]:

We must be at the bottom of the bottom. I'm just No.

Glenn Harper [00:02:27]:

No. We, we changed all the names and dates to protect the innocent. That's how we do it. Well, you know, we love to, when we'd start on this process of bringing on a a guest. And, again, we have the privilege of knowing you prior to, but our fans don't. So we wanted to kinda get a a feel of where you came from, what you do, and,

Julie Smith [00:02:45]:

Fans, wait. I thought we paid people to download.

Glenn Harper [00:02:47]:

Oh, yeah. Absolutely. I got a fund for that. Yeah. But it looks like you grew up in New Boston, Michigan, which is, from what I can tell, it's a massive suburb south of Detroit, just below the Detroit airport. And then I think it's true that McNasty's Saloon is the only place in Michigan you can wear Kabi boots and hat and blend in. Is that true?

Scott Fleszar [00:03:07]:

For for you to even mention New Boston and McNasty's is blowing my mind right now. But, yes. New Boston is my hometown right near Metro Airport, Detroit Metro Airport. And, I'm born and raised in in in Southeast Michigan, and, you know, I'll I'll say humble beginnings. Went to Eastern Michigan University, got an accounting degree, and, and kind of a funny story there which might kick things off, for this conversation is, I don't know, I I go to Eastern Michigan University after, you know, average high school, I'll say academic, standing, and I'm I'm, getting my accounting degree. And the only reason I got my accounting degree is I went to to Eastern Michigan, and I had this idea that I was gonna get business degree. I didn't know which business degree in in accounting 101, which every business major has to take. The instructor said, accounting is a great major to have because the accountants are the ones that make decisions about who gets laid off, and they're not gonna lay themselves off.

Scott Fleszar [00:04:07]:

And I said, that's a good enough reason for me. Why don't I get an accounting degree? And then, you know, forward to my my senior year, I'm like, okay. My grades are good, not great. I don't have any experience. I better do an internship. And that's when went down to career services. This is, you know, the fall semester of my senior year. And they set me up with an interview for an internship with, at the time, one of the big six accounting firms, Deloitte and Touche.

Scott Fleszar [00:04:32]:

And, went to the interview and totally got eaten alive. I was not prepared at all, and I just realized, wow. I'm I'm just not ready to step into the professional arena. And, also, I don't know that I wanna work in an accounting firm and serve clients, and I'm close to getting my degree. Went back to career services, and they said, hey. There's some small I was tail between my legs, but there's, like, there's some small software company down the road called Creative Solutions. They do something with, accounting software. You might wanna check them out.

Scott Fleszar [00:05:04]:

Interviewed there, went much better, and started as a product support rep at a small technology company, that was designing software for accounting firms, and that really started my career. And for me, what was unique about it, and I'm sure lots of people have these types of stories, you get a degree and you think you're gonna do something with it and then you do something totally different. So I was able to leverage my accounting degree, but very differently. I'm I wasn't in an accounting firm, wasn't serving clients, but I was at a technology company designing tools for accounting firms. So, that was that was how I got my kind of, I'll say, start in into the profession and and and really been in tech been at technology companies ever since.

Glenn Harper [00:05:47]:

So So when you were in, living in New Boston, you got, what's your mom and dad do? Did they, have real jobs? Were they entrepreneurs? Or they work for the man?

Scott Fleszar [00:05:57]:

Yeah. So so, my mom didn't my mom didn't work. You know, she well, my mom stayed at home and and had a very important job raising the kids and running the household. And my dad, worked actually in computer science, early in computer science, working with data early databases and, we're working for a big organization. So so so not entrepreneurial. But, you know, my grandmother was actually very, very influential in my life. And, she she was the one that really, I I would say, influenced me, regarding just the, you know, work ethic and the important of importance of just showing up, and, you know, the idea that, you you better be, you know, humble and, not try to be the smartest person in the room, and how you treat people is is very important. And, so I actually credit my my grandmother, you know, maybe even more than my parents for the kinds of influence, that that she had on me and and, and kind of how that's guided me throughout my throughout my life, really.

Julie Smith [00:07:04]:

Did your grandma live close to you then growing up?

Scott Fleszar [00:07:07]:

Yeah. Actually, I live with my grandma for most of my child through my teen years, essentially. And, you know, my parents had gotten divorced, so I was actually living with my grandma and and my and my father. And she became just a a huge influence on me and, you know, someone that, you know, I I always I always credit her for, you know, the successes that I've had in life personally and professionally. I really credit to her in the way that she, you know, helped guide me and and and, essentially, steer me away from pitfalls in life. So

Glenn Harper [00:07:44]:

Well, it's funny at at that age and going through all those things, it's it's just somebody to believe in you and then tell you you can. It just takes a little bit, and it makes such an impact for people. And like I said, you can see this is what what for 50, 60 years later from that, I'm kidding. You know, 20, 30 years, it makes such a an impact that you look back and go, wow. Somebody just said I could, and and they guided me and helped me, and and here you

Scott Fleszar [00:08:08]:

are. Right. It it not only said you could and and was supportive, but also tough love too. So so so it was, okay. Now get out there and and do it. And, you know, they're they're you're not gonna sit around the house. You you you're you're not going to, you know, take advantage, of any situation. You know, one of the things I tell my kids I've got I've got 3 kids and they're great kids, but I tell them fundamentally is you are entitled to nothing.

Scott Fleszar [00:08:38]:

And, you know, you you have to remember that, you if if you haven't ever faced adversity, if you haven't ever dealt with adversity, you know, the the idea that smooth sailing is always going to be, you know, how how life rolls for you. It it's just not gonna be the case. So you have to go in a mindset. You're entitled to nothing and no one owes you anything. And if you have that mindset, that's the right mindset to, you know, be thinking about how you develop, especially professionally, as you get out into the workforce.

Glenn Harper [00:09:16]:

Grandma probably had a big wooden spoon too that she swapped people with. You know, that's Absolutely. You don't wanna mess with that.

Julie Smith [00:09:23]:

So so growing up, so you talk about your grandmother. Did you ever, like, you know, paint rocks, do a newspaper route, you know, try to mow lawns. Did you ever have any of that entrepreneur, you know, in you growing up that kind of, you know, maybe drove you a little?

Scott Fleszar [00:09:42]:

Yeah. Actually, one one great experience, that I call upon, you know, my learnings, you know, from from this across my whole life. So I, in New Boston, worked at essentially kind of a combination florist and flower grower. So we we had fields, grew flowers, it grew cut flowers, and and you'd you'd cut these flowers and you'd take them and you'd sell them at the farmer's market. So I'd get to this farm at 2:30 in the morning, We load up the truck, and we get to the Detroit Eastern Farm Detroit Farmers Market is called Eastern Market. We get to Eastern Market, by 4, 4:30. The, wholesale market started at 5 AM, went to 5 to 6, and the retail market started at 6 AM. And that whole experience with in the retail market, you've got, you know, stores, retailers coming up and wanting to buy, you know, flowers in bulk.

Scott Fleszar [00:10:43]:

And it's all about negotiation. And I remember early on, you know, they would buy I'd say, okay. These flowers are $4 a bunch. Well, I wanna, like, you know, I only wanna spend $3 a bunch. And then you'd have to remember quarters, and you have to you you'd have to be really good about understanding how to anchor high so that you can eventually get the price that you want. And and that was that was the wholesale market. Then the retail market would start and, you know, it would be working with individual customers. And, that whole experience was fantastic just dealing with customers, dealing with, you know, you know, all the fickle customers that are out there and understanding how to manage people and, you know, all walks of life.

Scott Fleszar [00:11:24]:

And, so so, yes, working at the farmers market, was a great experience for me and, you know, taught taught me lots of lots of life life lessons and business lessons. I

Glenn Harper [00:11:38]:

feel like, yeah, it's on your resume. She's the commodities broker in the Detroit Exchange. Right.

Scott Fleszar [00:11:44]:

So there was recently it's funny you bring this up because I was talking to someone else about there was recently this Wall Street Journal article that basically said, teens these days do not need fancy internships. They need real jobs where they're working in restaurants, they're working in retail, they're dealing with, you know, unreasonable demands from customers, they're dealing with, you you know, scheduled demands that are gonna be at odd hours. They're they're dealing with the public, and and it's not, you know early on, you you know, these parents think I had to get my, you know, kid into some fancy office with some title for their internship. Well, they need to get out there, roll their sleeves up, and work with the public, work with people, develop people skills, and that's what I did at the farmer's market. And I totally agree with this article, and I was actually just giving a a a talk to, a college classroom when I was referencing this about how important it is to have these jobs and spotlight these jobs once you're starting to get into the professional workspace because, you know, entrepreneurs understand those types of jobs are are where you cut your teeth and you kind of, you know, learn to interact with people and engage with people.

Julie Smith [00:12:52]:

I I've said for a long time that I believe, at least my kids, have to serve or bartend for for an a part of time because they have to learn how to think quick on your feet. That, I think, gives you emotional intelligence because you cannot react. Like, all the things you just said, I couldn't agree more with.

Glenn Harper [00:13:12]:

It's funny. It's, the the mindset now is there's no jobs out there. Not if you wanna work 40 hours a week. You're like Right. Yeah. It's like there's so many the intangibles, there's a skill set, and then there's holistically looking at things. And and how old were you when you were doing getting up at the 2 in the morning, which is awesome, by the way?

Scott Fleszar [00:13:30]:

16.

Glenn Harper [00:13:31]:

16. So game on.

Julie Smith [00:13:33]:

It hasn't stuck with you at all, like, some of that early, like, you know, early morning routine?

Scott Fleszar [00:13:39]:

Yeah. I'm I am an early riser. Not that early, but, yeah, I I still am an early riser, and I I and I like to, I personally like the quiet that you have in the morning to get, you know, heads down work done. Strategic thinking, I think is really I I think I'm sharpest strategically in the morning. Once, you know, you're you're working with people and there's more, you know, distractions, yeah, then you're still you're still working and still, you know, doing good things, but I like the early morning hours to to do heads down, really deep thinking work and strategic work.

Julie Smith [00:14:18]:

Growing up, did you play sports? Were you an athlete, like, in team sports or any

Glenn Harper [00:14:22]:

visual sports? Athlete. You can tell.

Scott Fleszar [00:14:25]:

That's very kind of you, Glenn. Yes. I I was a basketball player. Loved playing basketball. Played high school basketball, even though I was vertically challenged. But, but, yes, the, you know, the team so so I'm a team sports kind of guy and I love I love, you know, the all the stories about great teams and leadership and how, you know, teams gel and and there's, you know, come together and and how they, you know, learn to, you know the the old saying with basketball is that the best team is not the team that has the 5 best players. The team that has the 5 players that play best together. And I totally agree with that.

Scott Fleszar [00:15:03]:

So You know, it's funny, you know, the team sports are good, but I also know you play golf, which

Glenn Harper [00:15:08]:

is definitely not a team sport. But that's just to torture you, right, to get inside your own head. Most of the time, that's how us golfers look at it.

Scott Fleszar [00:15:16]:

Yeah. Totally. I do like to golf, but it's mainly to hang out with my buddies. I'm not very good at it. It is it is a, you know, it's a humbling game. You know, at some point, I hope to get better at it, but, but you're right. That that is very much, you're, you know, you're out there on your own, and you're in your own head. And it's, it's certainly a game that requires mental, sharpness.

Glenn Harper [00:15:42]:

So you're sitting there, and you're, you're you're brokering flowers at 2 AM to the wholesalers, the retailers, and then you're like, yeah. I gotta get to college, and you decided to to go to Eastern Michigan. How'd you pick that school? Just because it was close by?

Scott Fleszar [00:15:57]:

Yeah. You know, I I'm I'm chuckling because for my kids, I got one out of college, I got one that's a senior in in college, and one's a freshman in college. So so my wife and I are empty nesters as of the last 6 weeks, which is which is, new and different, and our house is very quiet. But, but, you know, for our kids, there was, I'll say quite a bit of process around visiting schools, evaluating them. There's obviously information online. I didn't have any any of that back, back in, the eighties, 19 class of 90. So yeah. I I I went to Eastern Michigan because it was close to home, it was affordable, and I could get in.

Scott Fleszar [00:16:45]:

And that was really the extent to which I thought about it. And I knew they had a business school, and I wanted to get a business degree, and and, and there wasn't much, there wasn't much I was thinking about beyond that. So it was pretty simple.

Julie Smith [00:17:00]:

Was your grandmother I don't wanna say forcing you, but a strong force behind saying you've got to go to college, you've got to figure this out, you've got to get something bigger and better?

Scott Fleszar [00:17:12]:

Absolutely. So so my my grandmother, for sure, and also also also my father, and I I was just talking to a classroom I I mentioned and, you know, it seemed back in 1989, 1990, it was if if you wanna make something out of your life, you need to get a college degree and and, you know, that that was the path I took. And I don't wanna I would never talk anyone out of getting a college degree today. But today, I think it's different. I think there's just different paths you can go down. I and I was telling these students, I said, man, I wanna get into the trades and and that's gonna be a different way. And I think the trades, you know, you can you can do very well for yourself there. And and there's other people that are professionals that never got a college degree.

Scott Fleszar [00:17:55]:

I still think a college degree is very good, and I think there's can be great return on investment. But, back when I made the decision, it was that is, you know, there there isn't that's your that is the path you need to take. Otherwise, you're cut you're you're selling yourself short, which I think is a little bit different today. But, yeah, that was my mindset back then.

Glenn Harper [00:18:13]:

Yeah. They didn't have the, dockworker salaries like they have now back when we went to college. Like, that's where

Scott Fleszar [00:18:18]:

you can

Glenn Harper [00:18:18]:

go work, make your 300,000 a year working on the dock, but that's a whole different story. But, you know, it's funny, you know, when you you pick the school you go to, I you know, a funny story. I picked Ohio State because, it was close. It was cheap, and and they actually accepted me. And I was like, well, that's cool. And then I realized later that they had to accept me. It's, like, dang it. I thought I was special, but I I was not.

Glenn Harper [00:18:38]:

So here

Scott Fleszar [00:18:38]:

you are.

Glenn Harper [00:18:39]:

You go to you go to school. You're on the Eastern Michigan, and you're doing your thing. And then you said, you know, I'm I'm good here. I'm you're gonna go to work. And then you have this epiphany that lets you go back to school at the Pee wee Football School, University of Michigan to earn your MBA in strategy and leadership. Like, how did this come along and say, you know what? Accounting was cool, but I need this MBA in strategy and leadership. What was it the company said, hey. We would like you to do this, or you were just like, I could have some more letters after my name?

Scott Fleszar [00:19:06]:

Yeah. Great great question. So so, professionally, I had a a really strong mentor, that that helped me in my career, especially early in my career at Creative Solutions, which became Thomson Reuters. They started at the small software company called Creative Solutions, then Thomson Reuters acquired Creative Solutions. And, she was, a big advocate for me and someone that mentored me. And, and at the time, I had held roles in at this organization called user services. So support, customer service, and training. And, she had tried to recruit me into a completely different role, and it wasn't something I wanted at the time.

Scott Fleszar [00:19:48]:

And then she said, have you ever thought about getting your MBA? And that can probably allow you to better pivot your career. And also, again, at the time, it was, certainly a stepping stone in corporate America to bigger and better things. So very fortunate that, this was funded by, Thompson Reuters, and they were looking to develop me as a leader. So I had a I had great support from the organization. I had great support from this mentor, and and my MBA was invaluable for me to really pivot my career because, I was basically in one function at Thomson Reuters for my first 12 years, got my MBA, and then I went and really started doing a lot of different things that led to leading marketing for 5 years, then I got in the product management, then I began running some smaller businesses for Thomson Reuters. So it was a big, springboard for me. And, certainly, I had people, you know, executives in the organization that, were encouraging me to go down this path, and and they saw potential in me, which is, you know, I'm grateful for. And and, and then I was able to, you know, do a a variety of other things, because it really broke me out of the mold of where I was at.

Scott Fleszar [00:21:06]:

I was very specialized, and then I became more of a, you know, kind of a strategic executive leader at that point. So

Glenn Harper [00:21:13]:

This is one of those cool things where, you know, we, Juliana, we always are talking, like, Mega Corp, small business, Mega Corp, entrepreneurs, Mega Corp. You know, it seems like the people that end up going to Mega Corp, and they go there. And if they believe in them and they feel like not I wouldn't say safe, but feel like that the company believes them, the company will invest in you. And you have way more opportunities available to you than you would have at small company. It just doesn't work that way. And it's just a cool thing that you were they were able to recognize it, you accepted it, and you're already doing you had a fabulous career there from what I understand it. At some point, I think you were in Switzerland, and, I didn't even know. It says on your bio that you learned how to you're fluent in English and Switzerland, which I think means German, French, and Italian.

Glenn Harper [00:22:03]:

Did you have to learn all three of those languages to live there?

Scott Fleszar [00:22:07]:

Yeah. It's Switzerland, first of all, I I did do you know, we we did an overseas assignment in Switzerland. Thompson Reuters has offices there. Switzerland is a beautiful country. So so, you know, feel very blessed and fortunate to have had that opportunity. It was great personally, professionally for our family. And, yes, in Central Switzerland, literally, there's signage there that has English, Swiss German, Italian, and French on it because, there's influence of all those countries there. And, we learned enough Swiss German, to get by, like ordering a beer, gross a beer, and, saying hello, and, but but didn't certainly didn't need to be fluent in any of those, and I'm not fluent in any of those, in those languages.

Glenn Harper [00:22:55]:

So It's funny because you think they have their own currency. You think they have their own language, But, no, it's a blend, which is kinda funny.

Scott Fleszar [00:23:01]:

Yes. Yeah.

Julie Smith [00:23:03]:

So you you took your family then to Switzerland from what I'm understanding. And so you immersed your kids into that culture, and they did school over there and everything?

Scott Fleszar [00:23:14]:

Yeah. So, my my boss at the time, at Thompson Reuters you know, I'm I'm here in the Ann Arbor office. He comes in my office and says, hey. I've got a potentially really unique opportunity for you. And I knew I knew we had offices there, and I knew people that had had, done these assignments over there, and he and he laid it out to me. And at the time, you know, I I freshman in high school, a 6th grader, and a 3rd grader, and came home, and spoke to my wife. She wasn't immediately thrilled about this idea of, you know, going over there for 2 to 3 years. But we both said, okay.

Scott Fleszar [00:24:01]:

If the kids are in for this, then, then we'll do it. But we sat the kids down and said, hey. This is a great opportunity. However, we're not gonna force you to go. So this is something you need to think about. And the one piece of advice I'll give you is you might not ever have this opportunity again. So just remember that. And and my daughter was an immediate no and she was completely against it.

Scott Fleszar [00:24:25]:

She just, you know, she was on a ice hockey team here that was doing really well, and she, you know, she had friends and and she just you know, for her, it was it was an absolute no. My 2 boys were a little bit more open to it. But then behind the scenes, she did her own research. She connected to the international school on LinkedIn, I'm sorry, on on Instagram. She chatted with friends of ours who had done this before, with with their, one of their daughters. And and she had basically not without without telling us, I did some research. She she came to me, like, a week and a half later, and she goes, is this still a possibility? I said, well, I kinda already told my boss no. So but she said, I'm in.

Scott Fleszar [00:25:06]:

And and I was really proud of our kids because this wasn't easy for them, and it was going to be adversity for them, you know. New culture, new school, new friends, new currency, you know, new language even though international school that it's it's it's English based, but, it was a fantastic experience for them. They loved it. They still have friends that are my son was just in Finland for a few days hanging out with his buddies there. Oh, really? Yeah. So so so it was it was a great experience for us, you know, as a whole family and for for the for our kids and because they had to deal with some adversity. I mean, going to Switzerland doesn't sound like adversity, but for high school students, middle school students, you know, this is a whole all kinds of change for them. I just feel they're so much better off, not only for the, you know, international experience for itself, but just getting out of their comfort zone.

Scott Fleszar [00:26:05]:

They got way out of their comfort zone and, and so did my myself and my wife, and and, we very much enjoyed. You know? Enjoyed it.

Glenn Harper [00:26:14]:

The this is, you said something that resonates. Like, you asked your kids, like, back when I was growing up, your parents didn't ask their kids nothing. You just did what they said. Right. For you to do it in a different way to get their buy in, already, you know, you had those skill sets. But, you know, to put your family first on that, to recognize, you know, professionally and personally, it was a big, big deal, but you're like, let them make the decision. Like, who lets a 3rd grader make a decision?

Julie Smith [00:26:40]:

But I but I can't get over is, like, how is your daughter the oldest one?

Scott Fleszar [00:26:44]:

No. She's the middle. Oh, man. I know. She was in middle school.

Julie Smith [00:26:50]:

She's gonna do great things.

Glenn Harper [00:26:51]:

Oh, boy.

Julie Smith [00:26:51]:

The fact that she had enough emotional intelligence to be like, maybe I, you know, got react, like, you know, like, reacted just right off the thing, and then to go research to figure it out herself and not use her parents at all? I mean She'll

Glenn Harper [00:27:08]:

be on the podcast in a few years.

Julie Smith [00:27:10]:

Yeah. I mean, what's she she what's she gonna do?

Scott Fleszar [00:27:12]:

Yeah. Very proud of her. So she's a senior at the University of Michigan. She plays ice hockey there, and she already has a job, in investment banking in New York City for after graduation. So in July, of 2025, she'll be in New York City working in investment banking. I hope she knows what she's getting into, but I'm really proud of her. And, yeah, she's, all all 3 of my kids are are are really on great paths, and and I think I think at least in part, it was because of the international experience and just, again, getting out of their comfort zone.

Glenn Harper [00:27:45]:

Well done, well done, dad. Yeah. So, you know, I'm curious. You know, the University of Michigan is really easy to get into, so it's not like an exclusive school or anything. But I think you picked their because they they have picture books, which is important because that's easy to get in. Right. I'm totally messing with you know, University of Michigan is a fabulous institution for for education. But I feel like once you got in there as well, that's a great alumni network.

Glenn Harper [00:28:08]:

You get plugged in everywhere with that. And now that you're back, you know, I guess you left for a little social, and you're you're back living, now you're living in Picney, Michigan, another thriving metropolis of 24100 15 residents, and, of course, the hometown of Chris Sabin of WWE, eFAME. Did you know this? This is I

Scott Fleszar [00:28:28]:

didn't know that. Yeah. I did not know that.

Glenn Harper [00:28:30]:

Big deal on the WWE. But, again, you settled back, but you guys decided not to live in the major city. You're living in, like, a small town and doing your thing. And how'd that work out for you? How'd you make that decision? Did you feel like you you could live there? You didn't have to be in the big city? Or how'd you settle back in Michigan just because it's home?

Scott Fleszar [00:28:47]:

Yeah. Just because it's home. Southeast Michigan Southeast Michigan is is kinda home for us. We've got family here, and and so when we came back from Switzerland, you know, certainly, we could've we probably could've decided to live anywhere, but but this is home to us. Mhmm. You know, call us crazy. We like the change of season, and, Yeah. We we like the lakes, and, and yeah.

Scott Fleszar [00:29:13]:

Yeah. For for us, it it it just felt it it just feels like home. So

Julie Smith [00:29:18]:

So you come back from Switzerland. You're back in Michigan. You're still working with Thomson Reuters, but at some point, that changes.

Scott Fleszar [00:29:26]:

Yeah. So, yeah, the the, when I when I while I was in Switzerland, quite a bit of change going on with the business back in the US, the business that serves, you know, accounting firms of software and technology. When I got back, there was new leadership, and and I and I was, part of that organization for about 8 months after getting back. And then they decided to move in a new direction, and they, essentially combined some teams. And my role was eliminated, and that certainly was a little unexpected, kinda, you know, kind of a kick in the pants, but, really, an opportunity for me to reset and just decide, okay, what what do I wanna do at this point? I've, you know, I've had this, you know, great career at Thompson Reuters, and I have absolutely nothing but gratitude for all my years at Thompson Reuters. Just just tremendous. I I was able to hold various leadership roles. They funded my, you know, MBA.

Scott Fleszar [00:30:22]:

They had me, you know, do an international assignment. Just just a tremendous career, Thompson Reuters, but, that's when, I realized how important networking is and how important your network is. So I started a network. This was the summer of of 2019, and I had met the 2 cofounders of a business called SafeSend, a year earlier at the conference and reached out to, one of the cofounders and and or was just networking saying, hey. I'm I'm looking for my next opportunity, you know, if if you know of anything or, you know, can we just catch up and talk, you know, about how your business is doing? One thing led to another, and, I met with the the the cofounders and realized they have a great business and a great product, but it's small and they don't have expertise with growing and scaling a business. And I realized, wow, I can really help with that because that's what I did for years at Thomson Reuters. And so, joined, in in q 4 of 2019. And, at the time, the the, the one cofounder that, was CEO, he indicated, I love working on the product, and I like, figuring out ways that technology can solve real world problems for accounting firms.

Scott Fleszar [00:31:49]:

I don't necessarily enjoy running a company and, you know, leading a company on a day to day basis. So if this works out, potentially, there's an opportunity for you to lead the lead the business, overall. I came on as a chief operating strategy officer, really embraced the team there and and began to, you know, help with growing and scaling that business. And then a year later, I was was appointed CEO and, was, you know, really kind of the the pinnacle of my career was growing this business and and being part of, you know, a business that when I joined was roughly 40 employees and grew to almost 200, you know, revenues over the four and a half years. Our I was there grew 8 x, and, you know, great net promoter scores for the product, great, employee engagements and low turnover, great culture. So, you know, I was able to build out that leadership team, grow and scale the business, really put, you know, the different functions in place and and and lead a high growth business. So it was just a fantastic opportunity for me, and, and I really, you know, grateful to the cofounders for giving me that opportunity and then, you know, having the trust in me to lead the organization and and then, you know, drove it to, to to a high growth business that got outside private equity investment. And, so that was really a big career pivot for me.

Scott Fleszar [00:33:26]:

I went from, you know, big global multinational corporation to really a small organization, relatively speaking, high growth, business, and, you know, a vertical b to b SaaS business and and, that was just, fantastic. I just had a blast doing it. So

Glenn Harper [00:33:45]:

It's it's funny how that career path just bounces around and, you you end up where you're supposed to be. And as you continue on this, I assume you're still at SafeSend. Right?

Scott Fleszar [00:33:55]:

Yeah. Right now, I'm in a a senior adviser role with them. So I work with the board on kind of strategic activities and, you know, just, looking out at the marketplace and understanding what's going on at the marketplace. But, yeah. I'm still there. But I'm also, at this point, kind of looking for what my next opportunity might be in terms of, you know, I'd love to get back into leading a business, you know, potentially leading another technology business. So so so at this point, I'm I'm, still working with SafeSend, but also, you know, looking from an ex opportunity, which, I'm really fortunate to have flexibility to do that. And, and I've been doing a lot of networking and and, you know, doing things like these podcasts are great for me to, to meet new people and and to get exposure.

Julie Smith [00:34:43]:

So I'm gonna make a couple statements here.

Glenn Harper [00:34:45]:

And Please do.

Julie Smith [00:34:46]:

You know, this is me being quiet, not being loud. SafeSend, though, like to I was waiting for you to full circle that. SafeSend works with Thompson Reuters clients. And so I think you were able to take, you know, what TR gave you as a corp corporate conglomerate and use that at SafeSend, but I think the closing of that circle is the fact that you somehow found yourself back in that circle. Right? Like Yeah.

Glenn Harper [00:35:16]:

Yeah. It's like the mafia. You get sucked right back in.

Scott Fleszar [00:35:19]:

Right. Right. You know, Glenn, earlier, you made the comment about, you know, how at at big organizations, you can really take advantage of lots of opportunities. And and, I think sometimes big organizations get a bad rap. But one of the downsides of a large organization is, you know, you don't get to know everyone in the business, and, there's just, you know, more layers, more bureaucracy. What I loved about SafeSend, what I still love about SafeSend, is you get to know everyone in the business. It's a flat organization. You know, I was be able to be involved in everything that we were doing as a business.

Scott Fleszar [00:36:03]:

And then because it's a platform, again, for accounting firms and it really, you know, helps accounting firms collect information they need from their clients to prepare tax returns and then deliver completed tax returns to their clients, that meant working with Thomson Reuters again very closely as well as the other vendors out there. So, you're right. It was, quite a bit of overlap in terms of this new culture I was in, and then also working very much with the large large organizations that I that I had all my experience with prior. And and it did almost come full circle in that. I was able to you know, one of the things about working in large organizations, it's important. Your structure's important and cross company communication and collaboration's important. And those are some of the kinds of things I was able to, you know, put in place at, SafeSend, which is build out a leadership team, build out an organization structure that's gonna support growth, you know, make sure we have great cross company communication and collaboration, and, you know, make sure that we celebrate wins and recognize people and individuals, build a great culture where no one feels isolated, that they always have resources, and they can get help if they run into challenges. So so, yes, in what what I like to think, Julie, is that I I was able to apply a lot of the, you know, domain knowledge I picked up over, you know, a couple decades at Thompson Reuters and apply that in all the great you know, in all the best ways possible to help a small business grow in scale and and then also, you know, work in in partnership with, an organization like Thomson Reuters.

Glenn Harper [00:37:56]:

They you know, when you have that the small company knowing the, quote, the trade secrets and the speed you can implement because you don't have a committee, you don't have to go market it to somebody else for the big company. So you had the ability to to move a speed over here and save some, but at the same time, you know how TR worked. You know how to get things done, which is very unique and very probably great for both companies.

Julie Smith [00:38:19]:

Yeah. No. So, Scott, so a lot of a lot of our listeners are, like, growing their business. They're probably, you know, resonating with you in regards to that small business and growing and scaling. And I think entrepreneurs have a hard time finding people like yourself that are going to run their business as if it's their own, but it's not. And I think that skill set, that quality is really hard to find, and I think you might be one of the, you know, you you're great at that. What advice could you give our listeners out there that are trying to grow and scale a business, and I think we hear this all the time, of just no one does it like I would do it. And, you know, to grow and scale, you can't be the master of everything.

Julie Smith [00:39:12]:

You know, like, you you just can't. So for our listeners, what advice could you give them as they're going through this from your standpoint?

Scott Fleszar [00:39:23]:

Yeah. Great great question. I'll just I'll just give you some of the some of the ways I I tried, some some of the ways I tried to do this at SafeSend because, certainly, it was very small when I got there, but then we grew where I had to also rely upon people. You know, I I wasn't able to, you know, make all the decision, do all the work. So, first of all, if you have someone that you're working with today, that's in your business today that shows potential, I think there's really good value in investing in them, you know, and getting to a point where if this person has potential and they're showing, you know, the drive and passion that you would expect someone to have, that you would, you know, trust to to help run your business, You're gonna need to invest in this person, and and that's going to be, you know, mentoring and developing them. And and potentially, that's certainly your own time, but then maybe outside resources. And and and then you wanna put guardrails in place. So, you're not go they're not gonna make every decision, you know, exactly the way you would, and they're probably going to make some mistakes.

Scott Fleszar [00:40:44]:

But if you have guardrails in place, you give them the opportunity to grow and develop, and, you can free yourself then to be doing other things, you know, this classic yeah. You're not working in your business. Yeah. You know, you're you're working on your business. You you wanna be in a position where you're working on your business and you're gonna have to have people that you can trust, but you have to put guardrails in place. So so I I think of I think maybe the first thing is just guardrails is is invest in them, develop them, but then give them guardrails and just know that they're probably going to make some mistakes. And then secondly, you want to have a culture of psychological safety. I think this is a huge, you know, there was a there was a leader I worked with at one point that said, you know, when I when I lead, my people kind of fear me.

Scott Fleszar [00:41:34]:

And I think that's exactly the wrong approach that you want because in that kind of environment, if mistakes happen, they're gonna get buried, and you're not gonna understand what's going on. In an environment where there's psychological safety, that means your people are not afraid to raise their hand and say, hey. We got a problem. Raise their hand and say, hey. I made a mistake. And and this is going to invite your people to, be able to take calculated risks. You're gonna need them to take calculated risks, and it and it's gonna invite your people to feel comfortable that, you know, my leader is has has placed trust in me, doesn't expect me to be perfect, but expects me to get better. And I think that's maybe the third one is, a mantra of continuous improvement.

Scott Fleszar [00:42:22]:

If you instill a mantra of continuous improvement, the trend line to me was always important. I just wanna make sure our trend line is that we're always improving. You know, month to month, quarter to quarter, year to year, we wanna be always improving. So, you know, I I I don't know if that exactly answers your question, but, you know, if I if I think about, you know, those things, you wanna invest in people, people that you you feel, have potential, put guardrails in place, support an environment of psychological safety so that people can be genuine and authentic, and they can raise their hand when things aren't going well and they're not gonna bury problems. And then, can't even remember what I said last, but, you know, the the, Safe.

Glenn Harper [00:43:09]:

Safe.

Scott Fleszar [00:43:10]:

Yeah. Safe. Yeah. Yeah. Yeah. And and and there these you you're right. Finding these people is hard and and and I always think when you're building out a team, as your organization grows, You're best off having a combination of people you've promoted from within and you've developed from within and and then some outside outside hires that bring in outside perspective and, you know, can help you with, you know, blind spots that you might have as an organization because everyone's, you know, working on the same things. So

Glenn Harper [00:43:42]:

It's so hard to as an entrepreneur to to trust that somebody can do it, you know, not necessarily as good as you, but it's more of, like, can they take it and handle it and not screw it up? It's so hard for entrepreneurs to do that. But, ultimately, you will never get to the next level if you don't. Right? And

Scott Fleszar [00:43:58]:

Absolutely. Your

Glenn Harper [00:43:59]:

your guardrail comment is probably the most resonant point. Like, they might screw up, but it's not gonna sink the ship. It just might be a little dent.

Scott Fleszar [00:44:06]:

Right. Exactly.

Julie Smith [00:44:08]:

I think it's a great segue to one of my favorite questions, which is what is your superpower?

Scott Fleszar [00:44:16]:

Yeah. I I I mean, you know, I I I always try to, you know, stay humble and and, you know, make sure that I'm, always coming from a position of gratitude. But what I've had what I've had people tell me, people that I've been able to coach and mentor and lead is is that really is kind of my superpower, which is understanding organization dynamics, team dynamics, and, you know, building teams that are cohesive, that, have people that not only do a great job in what they're asked to do or what their domain is or their function is, but then also make others around them better. So I love building teams. I love building cultures. I think I feel that's my superpower, and that's a combination of coaching and mentoring individual people and then also thinking about team dynamics, how people work together. You know, I I will start, you know, important strategic meetings oftentimes with statements like, I wanna make sure everyone's checked their ego at the door. We we we, you know, egos are gonna kill anything that we're trying to accomplish in this next meeting.

Scott Fleszar [00:45:37]:

And and it's always trying to make sure that people are all working together and not competing against each other and and making the team better. So for for me, it's building teams, it's building cultures, and and building, and when you have a great team and a great culture, those are high performing teams. And and and that's always what I'm looking for is high performance teams. And for me, certainly, you know, the metrics that I can point to for how some of the businesses I've led have done are are are impressive, and and I'm certainly proud of that. But but what I'm most proud of and what, you know, the juices for me and what what, brings a smile to my, you know, face and brings me joy is seeing people grow and develop and, accomplish new things and take on new responsibilities. I love that. And those those are the kinds of things I think about most about, you know, the joy I've had over my career.

Julie Smith [00:46:38]:

So then I have one last question. This is a little different because, you know, just a little different. But what is your end game? So you're an empty nester. You're sitting on the board of a of a company that you grew way bigger than probably you thought even at the beginning could be. You're looking for your next you know, beyond all of that, what's your end game?

Scott Fleszar [00:47:00]:

Yeah. Great question. I've been asking myself that. Yeah.

Julie Smith [00:47:04]:

Don't we all?

Scott Fleszar [00:47:05]:

Yeah. As much as I love technology and I love the accounting profession, which is where I've spent all of my years, I really would love to do something with a little more purpose. You know, at the end of the day, helping accountants be more productive, hey. That's great. But if I could do something that was a little bit more, you know, purpose driven that had, you know, maybe more of a, you know, a a charter to to help people or help, you know, society, I I'd love to be able to do that. I've had an opportunity, over the last few months to work with a charitable charitable organization, that provides meals, for for those that don't have means, and that's been, you know, very, rewarding and and and feels good. So I'd love to have some type of opportunity to do things that more clearly are helping humanity and are more purpose driven, and that's in part because I've got, you know, I'm I'm blessed and fortunate to have kind of the opportunity to do that if I'd like. So, you know, the Canvas is is kinda blank for me right now, but but I guess my ultimate end game is retirement doesn't sound fun at all.

Scott Fleszar [00:48:23]:

You know, sitting around doing nothing actually doesn't sound fun. I want to be I wanna have a reason to get up every day, and if that reason is around helping people or helping humanity or, you know, doing good, so to speak, that would be ideal. So so that that's probably my end game, Julie. And, and I'm just starting down that path.

Julie Smith [00:48:43]:

So I love that answer, especially coming from kind of a non entrepreneur, but there is no end game for you. And I think, you know, driven successful individuals, whether you're an entrepreneur or you take ownership of an entrepreneur's company, there is no end game because your mind can't sit still. You can't sit still. Like you said, you had to get up with some purpose and passion every day. And so I think, you know, for our listeners out there, what a great full circle. Right?

Glenn Harper [00:49:09]:

You know too much. Why would you stop? Now you know the shortcuts. You your amount of effort to get results is exponentially less than it was 20 years ago because you know the shortcut. So why would you stop?

Julie Smith [00:49:21]:

I think also he's coming from a point of gratitude at this point where I don't wanna say our younger selves don't understand that. But, like, when you get up in the morning and you're 26 years old going to your corporate job, that gratitude and, you know, doesn't always come first. And I think you're at a point in your career where you start with gratitude and end with gratitude.

Glenn Harper [00:49:44]:

He put his time in. Now it's time to enjoy the benefits of it. Well, I tell you, Scott, it was great having you on the show. I think our listeners will get a lot of cool nuggets out of this. And, you know, if there's a do you have a plug where people can get ahold of you just in case they might, need what you may have to offer?

Scott Fleszar [00:50:02]:

Yeah. I I mean, yeah. Probably easiest to find me on LinkedIn, you know, Scott Flazar Flazar is hard to spell. But if you if if you if you look up safesend, all one word, safesend, you you'll see me there, as as one of the, people with that organization. So

Julie Smith [00:50:20]:

We'll link your buyer or we'll link that in our show notes for everyone to be able to get to you.

Scott Fleszar [00:50:25]:

That'd be great. Yeah. My my LinkedIn, is the best way to connect with me. So

Glenn Harper [00:50:29]:

Awesome. Well, Scott, appreciate you being on the show. This is, Glenn Harper.

Julie Smith [00:50:33]:

Julie Smith.