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Rob Ruff is the Vice President of Payroll for Strongpoint Partners. Rob has been with HowardSimon the founding partner of Strongpoint for almost 17 years, spending all that time in the payroll division. He talks about his persistence and how it helps him and his team meet the demands of a fast-growing payroll division.

Strongpoint Partners is a network of retirement plan Third Party Administrators (“TPAs”) and payroll services providers based in the Greater Chicagoland area. Strongpoint Partners’ core offerings include 401(k) plan administration, recordkeeping, 3(16) fiduciary services, payroll services and human capital management services for primarily small- and medium-sized businesses. The Company’s goal is to integrate retirement and payroll services on a single platform to best serve employers and their employees.



Rob Ruff: I think it's the thing of focus sometimes too. Just focusing on the little things and really like looking at the details. Like looking at my kids, looking at how they're interacting their facial muscles, how they change and how they adapt, how their hair is falling on their face, how they're reacting to the situation.

Living in those moments and those words and those feelings. It's really soaking those in, searing them into your memory so that you can look back and not have any regrets about those moments. It doesn't mean it's perfect, but it's just about being better than you were before, every day.

Anderson Williams: Welcome to Everyday Heroes, a podcast from Shore Capital Partners that highlights the people who are building our companies from the inside every day, often out of the spotlight.

With this series, we want to pull those heroes out of the shadows. We want to hear their stories. We want to share their stories. We want to understand what drives them, why they do what they do, how they might inspire and support others to become everyday heroes too.

In this episode, I talk with Rob Ruff of HowardSimon, the founding partner of Strongpoint Partners.

Rob Ruff: I am originally from Mount Prospect, Illinois. I grew up there my whole life. I went to Purdue. Currently, though, I live in Wakanda, Illinois, and I have twin daughters, seven-year-old twins. And my kids were born two and a half months premature. They were just over two pounds when they were born. They spent the first two and a half months in the NICU at a hospital, 45 minutes from our house.

So, stress test of marriage like that makes things really easy, right? I have a wife and a house, a dog, Rufus. Rufus Ruff, the alliteration is beautiful there. I'm an Eagle Scout. I have hobbies, a lot of hobbies. I'm a drummer. I like puzzles. I love heavy metal music. I will attend the opera as well, so vastly different musical genres there.

I own a hair salon with my wife. I ran a coaching business. I'm huge into health and fitness, and yep, growth mindset and being a better person every day, and there's plenty of other things. I'm also a sneakerhead. I love collecting Jordans, so.

Where To Start?

Anderson Williams: A dad of twins, a metalhead, a drummer, an opera fan, a sneakerhead, a fitness guru, a coach, an owner of a hair salon with his wife.

With this kind of opening, it's hard to know where the conversation will go. But it's clear there's a lot of depth to Rob Ruff, as you will hear as this interview unfolds. But to start I wanted to make sure I was clear on what he actually does for HowardSimon in Strongpoint.

Tell us where you work and what your role is and a little bit about what Strongpoint does.

Rob Ruff: I work for HowardSimon, Strongpoint. I am the Vice President of the payroll division. And what we do is we offer payroll retirement TPA and record keeping services and payroll services as well. All integrated in house. But to put it simply, you know, we help pay people and ultimately that's what we do and it's important that it's done timely and accurately.

And also we help a lot of people with their retirement, getting the money into their retirement plan and making sure that it's done accurately, again, timely, efficiently, and helping those companies that enable this process and need this process for their employees, making it simple, making it easy.

So we try to provide the best experience possible for them through service and through technology and efficiency.

Anderson Williams: And you've been doing that for 16 years?

Rob Ruff: Yeah, 16 years.

Deep Sense Of Purpose

Anderson Williams: So, say a little bit about that. I mean, I think that's really impressive. I won't guess your age, but that's a good chunk of your life that you've spent doing that.

And as a tenure that a lot of people, myself included, don't achieve in one type of business, much less one company like HowardSimon. Can you just talk a little bit about what's kept you there? What's kept you in this work? How you've stayed connected and engaged over that number of years?

Rob Ruff: 16 years of evolution development.

I say I've grown with HowardSimon. I lived in my parent’s basement when I started working here. I started as a temp. I began an implementation working my way up through the business, but a big part of that have been the founders, Howard, Doug, Brad, and they've fostered and created an environment that's very entrepreneurial.

And has allowed a lot of creativity in a seemingly uncreative industry. It's a sandbox in a way and how we can do things the best way possible. And I think it relates back to people. So, we're directly impacting a lot of lives. A lot of people depend on a paycheck to get paid, and a lot of people are living paycheck to paycheck.

Not everybody has that comfort of savings and we're also dealing with businesses and the economy, economic numbers. It's all intertwined and related. So, the way I look at it is we're making lives better. We're improving not only companies operations and the people that they employ that work there, but also ensuring that their employees are being treated well and have a system that they can get into and retrieve their information and understand it and digest it and file taxes with it, right?

All the life events. All those things get impact, getting married, death, birth, all the things. It's the full spectrum of life in dollars, really.

Anderson Williams: It's clear that Rob has a deep sense of purpose in what he does, and why it matters. And it's honestly quite inspiring how it has evolved and deepened over 16 years.

But as we heard in the opening, Rob has a lot of interests and extracurriculars, so I wanted to come back to see if there were any connections to be made there.

I'm curious what your experience as an entrepreneur with your wife, but also in your coaching business, you know, does that provide you a little bit of a different perspective or empathy for those people on the other side of your business for your clients?

How do you connect those two?

Rob Ruff: Yeah, absolutely. It's presented a lot of empathy, I would call it perspective, not only for those clients, but for our founders as well, the business as a whole to understand the risks that it takes, the stress that it imposes. And so, it's not just about you as a owner of a business.

There's other people involved. And I think people, the common mindset is like, ownership doesn't care about us. You know, we're just a number and maybe there's some outliers where that is the case, but I think holistically and really across the board, that it's not the case that you're hiring people, and you care about them and what happens to them.

And that's part of a symbiotic relationship really, where you need each other.

Anderson Williams: And that's been HowardSimon's approach, which then makes it easier to mirror to your customers and clients, I imagine, right?

Rob Ruff: Absolutely.


Anderson Williams: So, you mentioned when we started that you are also an Eagle Scout. So, I can't help but go back and see if I can draw a parallel there because that takes a long-term commitment to achieve as well.

That's not a one-year, two-year kind of thing. So, there's something in you that's willing and able to stick with things over time. And I'm just curious how you draw those things together in terms of those long-term commitments, those evolution, those growth kinds of things that you went through.

Rob Ruff: Yep. I have a persistence, I would say.

I put my mind to doing something and I commit to it. And I say, I'm going to do it. It doesn't mean I don't feel like quitting. I have in multiple facets. It doesn't mean that it isn't hard, that it is easy. It's something that if you do it multiple times, you start to understand that it's worth sticking it through and seeing it out.

And sometimes it pays off and sometimes it doesn't. And so, especially like with HowardSimon, you know, maybe for instance, I felt there was a glass ceiling over my head and there was nowhere else to go. And Shore Capital comes along and bam the glass ceiling shattered. And so, Shore came in and fused us with some capital and all of a sudden, the doors blew open of opportunity.

And for someone like me, that's extremely motivating. It's also really bakes into the why for me, being part of something bigger. So ultimately, that all of a sudden has blown the doors off of my why. And now there's all this opportunity to create something bigger than myself that will outlast me and other people.

And to be part of that and do things a little differently than other companies. And to not forget what made us successful to this point. And it was having that faith in a way that, you know, one of my favorite authors, Ryan Holiday, he has this phrase, chop wood, carry water. And just the way I look at it is put your head down, keep doing the work, keep doing the work, and eventually it'll pay off.

I've stuck with it and cultivated and become an expert. I've never really considered myself the smartest person in the room, but I'll work hard. I'll outwork other people for sure. And so, I've carried that mindset a long way. And I think naturally too, as you could probably tell, I'm probably prone to doing more work than is probably good for my health.

And I've learned over the years how to adapt and take care of myself. And it doesn't mean it's perfect. And I still run into issues with that, but it's about maintaining energy. And there's a symbiotic relationship, a yin and yang with work and rest and family and making sure that you're being taken care of and you're taking care of others.

Constant Improvement

Anderson Williams: This sense of symbiosis and the idea of understanding how work and life and family feed each other, rather than take from each other, is a wisdom I can tell that has been hard earned for Rob. And it's been his own willingness to grow that has helped him come to this degree of clarity. So, I wanted to ask Michael Heflin, the VP of growth at Strongpoint Partners, about what this looks like from his perspective and through the work he sees Rob doing every day.

Michael Heflin: There are people who get energy from facing a Herculean task and there are people for whom facing a Herculean task zaps their energy. Rob is 1000 percent the kind of person who gets energy from seeing a mountain in front of him, right? I think if anything, Rob would tell you, it's those days when he's just sort of walking down easy street that zap him a little bit.

It's the days when he gets to wake up and get excited, cause today is day for monumental change that he gets really excited about. And I think you can see that in all of these things. I think the other side of it is, there is, with all attributes in life, good and bad, I think that Rob has a bit of a perfectionist tendency in him.

I love that, as someone who wishes they were more of a perfectionist. And you can see that over time, right? He loves that he gets to make constant improvement. That if yesterday he was 98 percent good at this, today he's going be 98.1 percent good at this. And he likes watching that. And I think that that's really awesome also to watch from the outside.

Anderson Williams: Rob's mindset and this drive for constant improvement are having a significant impact on the company. He mentioned earlier that the Shore investment had shattered any sense of a ceiling he might have felt at work. And Rob has undeniably seized this opportunity.

Now you're actually leading the larger platform's fastest growing product area, right?

Rob Ruff: Yeah. There's nothing that excites me more than this.

Anderson Williams: That's pretty exciting.

Rob Ruff: And especially because the investment thesis really wasn't based on payroll. So, I love being the underdog.

Anderson Williams: Being motivated as the underdog and being driven individually is one thing. But Rob's nomination as an everyday hero specifically spoke to his high standards and ability to provide great customer service.

So, I asked Rob to draw the lines between his personal drive, the rapid growth of payroll, and this passion for customer service.

Rob Ruff: Well, it's a little deep question. It's an evolution over many decades. I was a caddy for 15, 16 years. Again, longevity. A lot of summers hoofing bags around a golf course, working for a lot of different personalities and types of people at a high-income level.

And it helped me really hone and develop a to improve a process, process improvement to develop customer service skills. So, you know, you mess up, here's what I did, apologize. Here's how it won't happen again and move forward. How to work with different personalities. And so, bringing that experience and poofing that into payroll and client service itself.

We have a direct dial system where it's not just a call center. You can call a general hotline to get anyone if you wish, but you have a person on our team. That's your person. And there's a relationship that we build with our clients. Each person on the team builds a relationship. And so, we know our people and there's all the life events.

And that's just a reflection of the service we provide is that we care about each other and our clients care about us. So that's vital to our differentiation strategy.


Anderson Williams: So, 16 years a caddy, 16 years at HowardSimon, how many years did it take to become an Eagle Scout? I think it's fascinating because I think your persistence perspective is nuanced.

And I want to just ask you to think about. You are persistent and stick with something, but you're also staying hungry somehow or finding the next learning edge somehow. It's not persistence in the face of I'm going to stick with this because it's comfortable. I'm going to stick with this because it's a good job.

You're doing something more. You have an ability to look at something or maybe it's be patient to let things unfold. Help me characterize the nuance to your persistence because there's something there that's different and I think unique.

Rob Ruff: I guess I've never had anyone try to, not question it, but put it that way to me.

And it's interesting as I hear it reflected back. And look at Michael Jordan. Best basketball player of all time. The GOAT. He was never satisfied. There was no amount of improvement you could do where he would stop. And I feel the same way, in a way. I'm not saying I'm the GOAT by any means. But I am saying that that drive, the continual evolution, it just never stops.

And there'll never be a time where I say that this is enough. But I just, I like to use that as a, as a reference, I am not comparing myself to Michael Jordan, but I like that, I like that example, right?

Anderson Williams: So, to extend the fact that you think you're Michael Jordan of payroll.

Rob Ruff: Call me Scottie Pippen, I'll feel better now.

Anderson Williams: All jokes aside, Rob's drive is there, whether referencing Michael Jordan or Scottie Pippen. Here again is Michael Heflin.

Michael Heflin: He's one of those like zero or 100 and sort of no in between, right? If he's doing something, he's doing it. So, we're talking about CrossFit and he's like, oh my gosh, I tried it. And I was like, wait a minute, I can tell you right now why you can't do CrossFit.

He's like, why can't I do CrossFit? And I was like, because you're one of those people who's going to wake up tomorrow and the heaviest barbell in there is going to get lifted. And whatever the most complicated movement is going to be the movement that gets tried because you have no chill in this process.

And he was like, that is exactly right. He's like, it's all go. I need to be getting better at everything I do, and I need to do it every day. He's like, and I can't handle it. I know I'll hurt myself. And I was like, yep, you and I are going to get along swimmingly. He's just, his energy is incredible.

You Are Capable

Anderson Williams: Michael hits on something that Rob also wanted to be clear about.

He works hard to manage the potential downside of this energy and this growth and this drive for perfection and understanding where it all comes from. He shares his journey with his own mental health.

Rob Ruff: I got picked on as a kid, hazed. All those things. And I carried that with me for a long time. Self-hatred in a way.

It came in through drinking and other things and talking to myself poorly. And then I would say that it's an ongoing process. It's a process. Well, for one, it took me to stop drinking. That was one. It took me to do a lot of self-reflection, meditation, talking to therapists. I mean, honestly, I talked to a therapist.

I didn't think I even need to. I didn't have a reason to. Everything was good for the most part. You know, I didn't have any trauma to unpack or anything like that, but I started talking and I realized maybe there's some things I need to develop. And even just through coaching and learning about health and fitness and the stress system and hormones, the endocrine system.

It's all interrelated, and how you talk to yourself and how you treat yourself is all important. Dealing with anxiety in an appropriate manner and way. Poking it in, in the dark, in the dark details, the things that you're trying to avoid. Why am I avoiding that? Why do I not want to talk about that? Why did I act like that?

Why do I feel like that? Why do I feel overwhelmed? What's stressing me? Like, just really poking and digging into the painful parts. And part of that is with health and fitness, like taking cold showers, jumping into cold lake, lifting heavy things, you know, doing hard things, things that you don't think you're capable of is the most amazing superhero power of all time is doing something you don't think you can do continually over and over again and proving yourself wrong.

That you are capable and repeating that over and over again, the iteration right there is something very powerful that I think a lot of people shy away from the difficult things. Those are the things you got to head to. And part of that is that self-evaluation and reflection and having the difficult conversations with yourself.

The most important part of my life was when I decided to quit drinking. And it was one of those conversations with myself. It was hard to do because I wasn't out of control in the sense that I had to drink every day. I was the weekend warrior. I picked it up from college. It was like work hard, play hard, work hard, play hard.

I got my stuff done and then I let loose. And when I let loose, boy, I let loose. And it was a problem cause it continued into my 30s. And my daughters were coming, and I just reached a breaking point of that was enough. This is not what I'm going to subject my children to. And I'm going to take ownership of this. And when you remove that, I never realized what a prisoner I was to that.

All of a sudden, doors start opening, light bulbs start going off. And the fact of the matter is, for a year or two, I thought everything was resolved because I had stopped, personally. And then I found out that, oh no, there's work. There's a lot of work to be done here.

Anderson Williams: If you look back at those days and from where you're sitting now, what advice do you give that earlier version of you that was maybe initially coming to grips with those realities, things you needed to work on earlier in your career?

What advice do you give that younger version of you?

Rob Ruff: You're good enough. You're good enough. You know, you're good enough. And it doesn't matter what anyone else thinks about what you think. Can you live with yourself? And yeah, you're worth it.

Anderson Williams: And when you think about how your journey informs your daughter's, what advice do you have for seven-year-old twins as they embark on the world?

Based on where your journey has led to date, what's the key point of wisdom you want to make sure for where you are today that they know?

Rob Ruff: Stay curious. Keep looking at the world with that childlike awe. Love yourself, be grateful, take inventory on that, understand yourself and your values and what matters to you and know that in the end, all that really matters is the person that you are.

Anderson Williams: Rob Ruff is an everyday hero whose superpower is his growth mindset. Rob has seized every moment and opportunity for growth as he's looked outward to the world in his work and payroll. But more importantly, he has turned that growth mindset inward. To invest in himself at his core. To know himself better, knowing that if he can grow there, he will also grow as a husband, a dad and a leader at Strongpoint.

This podcast was produced by Shore Capital Partners with story and narration by Anderson Williams. Recording and editing by Andrew Malone. Editing by Reel Audiobooks. Sound design, mixing and mastering by Mark Galup of Reel Audiobooks.

Special thanks to Rob Ruff and Michael Heflin.

This podcast is the property of Shore Capital Partners, LLC. None of the content herein is investment advice and offer of investment advisory services, nor a recommendation or offer relating to any security. See the terms of use page on the Shore Capital website for other important information.

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