Charles Bender | EO Seattle | From a Poor Boy Shining Shoes To Matchmaking and Ending Generational Poverty – Part 1

Charles (Chuck) Bender is the Chief Executive Officer of Attentus Technologies, a leading managed IT services firm serving the Pacific Northwest. He is an experienced executive with a demonstrated history of working in the managed services and internet industries. Chuck is also the President of Skynet Broadband, a company that provides high-speed data, digital phone, and IT services to the Puget Sound region. He has been a member of Entrepreneurs’ Organization (EO) for 22 years and serves as Regional Chair of EO’s West Region.

In this episode of the Smart Business Revolution Podcast, John Corcoran is joined by Chuck Bender, the CEO of Attentus Technologies, to talk about Chuck’s entrepreneurial background and serving leaders through the Entrepreneurs’ Organization (EO). They also talk about the challenges Chuck faced growing up, the business lessons he learned from the Navy, and his experience working in the financial services sector.

Available_Black copy
Available_Black copy
Available_Black copy

Here’s a Glimpse of What You’ll Hear:

  • How Chuck Bender’s childhood influenced his adult life
  • Chuck’s entrepreneurial ventures as a child
  • The challenges Chuck faced as a teenager and why he moved out at 16 years old
  • Chuck talks about joining the Navy, leaving to work in the financial services industry, and his transition to the matchmaking industry
  • Why Chuck joined Entrepreneurs’ Organization (EO) and the lessons he has learned over the years
  • Chuck’s experience as the Chair of EO’s West Region

Resources Mentioned In This Episode

Sponsor: Rise25

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution. 

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

What do you need to start a podcast?

When you use our proven system, all you need is an idea and a voice. We handle the strategy, production, and distribution – you just need to show up and talk.

The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

We make distribution easy

We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPO, EO, Lending Tree, Freshdesk,  and many more.  

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win? 

Contact us now at [email protected] or book a call at

Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

Intro 0:14

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome everyone. John Corcoran here, the host of this show. And if you have not listened to this program before, go check out the archives because we got all kinds of interesting interviews with smart CEOs, founders, and entrepreneurs of all kinds of different companies. And I personally am also the Co-founder of Rise25, where we help connect b2b business owners to their ideal prospects. My guest here today, his name is Chuck Bender, he’s the CEO at Attentus Technologies. He’s a longtime entrepreneur, big fan of ending generational poverty, which we’ll talk about what that means. He, for those who have listened to this program before, you know, I’m an active member, entrepreneurs, organization, EO, very big advocate of that organization. And he is, I’ll call him like the LFA, the president of the western region of the US, he’s technically called the Regional Chair for US West of Entrepreneurs Organization, incredibly well connected within that organization, and totally in his element. You should see the guy at one of these gatherings, he’s just, you can tell, he just lives it and soaks it up. And it’s a joy to watch him thriving in it. So we’ll talk about what he’s gotten out of that organization and why he’s gone so deeply involved in it. This, of course, is brought to you by Rise25, where we help b2b businesses to get clients, referrals, and strategic partnerships with done-for-you podcasts and content marketing. And you can go to, and you can learn all about what we do. All right, Chuck, such a pleasure to have you here today. And in your words, you grew up a poor boy didn’t have a lot of money. And I’m really interested to know how that shaped you as you’re growing up. And some of the ways that you learn these lifelong lessons that obviously shaped the rest of the way that you operated. And the companies you started to tell me about your upbringing?

Charles Bender 2:25

Well, I was I was born in California, Southern California, relocated to Arizona, when I was right at that middle school, from moving from sixth grade into seventh grade, which was a really awkward transition. We always struggled financially, as a family, I think my father’s highest grade completed was maybe ninth or 10th grade. My mom was really intelligent, while hard working but didn’t have a lot of opportunities. She was the oldest of six kids. And they got married, when they learned about me kind of coming along the way and tried to build a life together. So I would say that, for me, the most important things I learned growing up are probably what sticks with me the most in informed my decision making is that money equals freedom. And that’s about it. Right. And, you know, not having it. I just saw my parents struggle. Every every day, you know, everything seemed hard. And I remember my dad always talking about how life is so hard when you get out on your own. And, and that was this thing that that for me. I just watched how tough it was in my childhood. And I thought, man, it can’t be much harder than this. Right. So you know, it basically stripped back a lot of the, I don’t know if fears is the right word, but I didn’t have anything to lose. So you know, I’d go out and take a chance because I really didn’t have anything to lose. You know, I think that really informed me quite a bit in terms of wanting to wanting to change that. As I’ve gotten older. What I’ve noticed is the people from my neighborhood that really escaped and have built really good lives for themselves and their families really had I learned along the way that it’s not really that hard to go out and get yourself into a good middle class opportunity in this country. But what they learned right away was that they had to take control of their own situation instead of making excuses for why they couldn’t do it. And I think for me, that was probably the the most valuable lesson that I’ve learned is that doesn’t matter what the what cards are dealt. You just got to play the hand. You got to play and the best you can and you’ll get more hands if you play the one you got the there’s another deal coming right all the time. So what you have today isn’t what you’re always gonna have.

John Corcoran 4:54

And where are you? Yeah. And were you the kind of kid who was out there hustling, you know, working at a young age Age or starting little micro businesses at eight 910 years old.

Charles Bender 5:04

I was always hustling. So my, I remember, probably my first gig beyond, beyond a paper route was back in the late 70s. During the gas line crunches, like a you know, it’s kind of funny, we were dealing with gas again today. But in the late mid 70s, you had, you could only get gas every other day. And it basically was based on whether you had an odd or even number on your license plate and the lines would be miles long in the summertime. And I take my little brother and sister and my wagon wheel and I’d go by water and I was literally having my sister and brother go up and down the car line. You know this and I’m I’m eight my sister’s five cute as hell, right? Just little girl. And we’re selling water and this gas line just trying to try to figure out how we could make a buck. Yeah. But I would say my first real business that I that I did was after we moved to Arizona, my dad was in the shoe repair business. So he was a shoe repair tradesman and minority partner in the shoe repair store. And, and he fired me because I was a terrible shoe repair kid. When I was 12. Apparently I was ruining more shoes than I was fixing. But he he basically i He wanted me to come and work and learn a work ethic, right? So he suggested I build a shoe shine box and go shine shoes. And I’m like, Well, why not? I’ll try that out. Well, it wasn’t long before Kashia. That was a 1979 8081 82. During the summers, I was making more money than both of my parents combined shining shoes. So I’m literally in Prescott, Arizona, there’s this place called Whiskey Row that surrounds the courthouse in the downtown center. It’s like a traditional old town, right. And I would I knew all the owners of the bars. And I would literally go in the front door, go through the bar shining shoes, go out the back door and just we’d do this whole zigzag pattern up and down Whiskey Row. Then I’d hit all of the courthouse offices, all the judges, the police station was right there, the sheriff’s office right there. So all the attorneys, all the lawyers, all the judges, all the police officers, and most of the Cowboys knew me from the time I was a little like 12 13 14 year old. So when I started getting into trouble when I was 16. It really served me well. But there were many times where you know that we’d have some financial struggle, because the economy inflation was 9%. You know, it was nuts. We’re kind of feeling that again, really interesting time.

John Corcoran 7:37

Did you end up having to help the family in some way, because you’re making money?

Charles Bender 7:41

Many times. We had a single wide trailer, it was I think 60 feet long. And the mortgage was $123 a month on this thing. And there were several times where my shoeshine money got it out of foreclosure. Because we were about to lose the lose the trailer. That’s how how rough it was for a time,

John Corcoran 8:02

Were you resentful of that?

Charles Bender 8:04

Um, I think I was embarrassed by it. Resentful is probably the wrong word. I think I was just embarrassed. I think there was this. You know, we, when we lived in California, we at least had a house, it was a really small house. And I remember when we first moved to Arizona, and we moved into this trailer, I just remember thinking to myself that I’ve just never going to have any friends come to my house. Right? It was just embarrassing. And, and ironically, I’m a little ashamed to say that today because I know my parents are just doing the best they could. Yeah, I’m with the tools that they had available and what they had been taught, which honestly, I don’t think, you know, when we talk about generational poverty, I think that what what we’re often taught by our parents is how to think about opportunity. And if we’re taught by our parents, that opportunity doesn’t exist, because pick reason XYZ. It doesn’t really matter what the reason is, but if we believe that if we come to believe that, that there is no opportunity, we really limit ourselves in so many ways. And I think the difference between families that are a little bit more fluent, that have more opportunities that we’re always teaching about opportunity. Right, you know, your oyster, you can crack it open, every door is wide open.

John Corcoran 9:22

Yeah. It’s funny, I just put this poster on both my couple of my kids walls with growth mindset versus, you know, limited mindset and kind of like trying to teach him some of these principles. Yeah,

Charles Bender 9:35

it’s I mean, it’s great. Like both of my kids when they started high school, I remember sitting them down and just saying, Hey, listen, today. Every single door is wide open for the rest of your life. You’re starting your freshman year, and every door is wide open. And what you do over the next four years is going to close some of those doors. Right now it’s up to you to close those doors and now it’s up to me, my job as your parent is to try and help If you keep as many of those doors open as possible, so you understand my motivation is to help you with that, you know, you know what you decide to do with your time and how you focus your energy and, and the results and outcomes that you generate over this period of time, is really going to create a fork in the road for you in about four years.

John Corcoran 10:19

And I want to ask you about your kids. But before before we get to that, there’s one thing you mentioned, I’ve noticed that I asked a lot of these interviewees about this when they’re a kid, and a lot of people start entrepreneurial businesses, but there’s a real distinction between the ones that start some kind of hustle, that is just them, and those that bring in others, like siblings and friends and start employing them. And they had definitely have a leg up when they get to adulthood, and they start real businesses, because they’ve already realized the power of bringing in others and having it not just be them doing the work. And it sounds like for you, you said you brought in your sister on those gas lines, you already can kind of you’d already realized the value of that and the how to make it bigger than just you.

Charles Bender 11:03

Yeah, I would say that. There’s a principle that I don’t remember where I learned it. But it’s the Ope, O P T, OPM, other people’s time, other people’s energy and other people’s money is the key to massive opportunity and success. Right. So and, and I would add today, then I’ll make a joke, Opp, other people’s passion, right? So.

John Corcoran 11:32

But you’ve been tapping into other people’s passion, what they’re passionate about as a way to make money if their passion

Charles Bender 11:38

for their lives and their opportunities. I have a soft spot for the underdog, that kid that grew up like I did, right. And I used to joke that, you know, I use these acronyms, a PSD degree was always the people who I found that I connected with the most. And I felt like, work the hardest. And what I call a PSD degree is basically someone who was poor, someone who was smart, and someone who was deeply determined to change that. Right? By that person, and you put a little fuel on the fire, give them a little guidance, and they can they can set the world on fire.

John Corcoran 12:13

I do want to get into that. Because, you know, you obviously aren’t poor now. And you’ve had you’ve raised kids that weren’t poor, or they were in a family that wasn’t poor. And I and I want to talk about some of the things you did in order to adapt to that, you know, raising kids in affluence. Before we do, though, you mentioned you started to get in trouble when you’re 16. Tell me a little bit about that.