Decision Dialogues Episode 11 - Steve Ryder

On Episode 11 of Decision Dialogues, Mark Willoughby of Modera talks to Steve Ryder, the founder of True North Networks, a provider of managed hosting technology, cybersecurity, and IT services. Steve talks about his decision to strike out on his own and found True North, and identifies what his biggest mistake was—which almost prevented True North from ever reaching its full potential.

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Thanks for joining us on Decision Dialogues. We’re thrilled to have you along. My name is Mark Willoughby, and I’m a Principal, Wealth Manager, and Chief Operating Officer of Modera Wealth Management, LLC. Today, I’ll be chatting with Steve Ryder of True North Networks.

And let me give you a quick introduction of who Steve is. Steve is the President and Founder of True North Networks, which is a leading national provider of managed hosting technology and security services within the financial services industry. Back in 2015, True North launched Secure Workplace—a suite of cybersecurity services designed to reduce the likelihood of a successful cyber attack on their clients. And True North recently converted to an employee-owned company, and its mission as a fiduciary is to create a foundation for the success and well being of their clients, employees and the communities in which they serve.

Prior to founding True North, Steve was the CFO of the largest real estate company in New Hampshire, and also worked in the financial services industry serving as Vice President of two banks, and managing relationships with Fannie Mae’s largest New England clients. Steve speaks on various topics throughout the country at various conferences, most notably of which is on cyber security. Welcome, Steve, to the show. 

Thanks, Mark. Thanks for having me.

And as full disclosure to our listeners, I did want to make it clear that our firm has known Steve going back 15 years now.

Probably at least.

It’s about that. They’ve been a really important partner to our firm as we’ve grown on the technology side, so I just wanted to share that with the listeners before we dive into the topics today.

So Steve, I’ve known you for 15 years in your relationship as our technology service provider, but I’m going to bring it back right to the start. Let’s talk about—how did you start out your career? I’m interested in finding out what your path has been to get to where you are now.

Like how far back, like when I was born?

Let’s start when you embarked into the professional marketplace!

You know, it’s kind of funny, I mean, when I was in college, I always thought I wanted to start my own company. I didn’t know what it was at the time, I just always had this entrepreneur thing. And you know, as I started embarking on my career, I initially worked for my father. My father owned some businesses, and at one point there—I have five other siblings—so six of us at one point all worked for my father. Learned a lot from him. Very, very brilliant guy, he just recently passed almost a year ago now. So I certainly miss him. But he was a great, great guy.

And I guess I was the first to defect. I saw, maybe, a different career path for me—although I enjoyed working with my father, I just wanted to do something different. And I embarked in the financial industry. I ended up working for a bank for several years, and then ended up working for Fannie Mae.

So got in the financial industry, and everywhere I went, I liked technology. I always gravitated towards technology. And when I left Fannie Mae, I took some time off—took a summer off—just trying to figure out what I wanted to do when I grew up. I traveled out west with—I have an older daughter from a prior marriage—and spent some time with her, came back and then started searching for a job and then landed a job at a real estate company in New Hampshire. And even though I was a CFO there, I spent a lot of effort in making it more efficient, and really driving better technology to get better reporting, consolidate reporting, and grow that company from seven offices to approximately 18 offices in three years.

And a lot of it was all around technology—how can we better position the company? I was only there three years: ‘97 to 2000. And that’s around the time where I kind of went through a little bit of a midlife crisis, if you will, though I was still kind of young—what I want to do next? And end up deciding I wanted to do IT. I like technology, and then started going down that path.

It sounds like from early on, you had an entrepreneurial mindset. Where did that come from? When did you recognize that you wanted to set up your own business?

You know, I don’t play well with others, you know? I mean, I like, you know, I would say I collaborate well, right? I’m not a dictator, right? I do like to collaborate. I like listening to other people and taking feedback. But ultimately, like—I like making decisions, you know, and I think sometimes, you know, as I’ve told my wife at times, stress comes from the lack of making a decision. People who are indecisive are also are often the most stressed out people in the world because they can’t make a decision.

I suffer from the opposite. I make decisions that may not always work out, but I’ll make a decision, I’ll go down that path, and then I might have to take a left or right. So I like making decisions, I feel I’m a little bit of a risk taker, I feel confident in myself to be able to make mostly good decisions. And being the ultimate say, in my destiny, I guess, and that’s kind of where I felt that way.

So early on, you recognize that in yourself, and then you spent how many years in the corporate world before you set up True North?

Hmm. So I left college, I graduated in 82. So almost 20 years.

So you spent 20 years between most of the time in the financial services industry, and then some time in the real estate industry.

Yeah. Interestingly enough, I never worked anywhere for more than four years until I started my own company. I worked, I got bored, I kind of figured things out. I got bored, I moved on.

You moved on to the next challenge.

It was just a pattern I had.

Okay, now, you’ve ended up after 20 years in the corporate world, founding a firm in the technology space. You didn’t set out to set up an IT company, I assume?

No. I didn’t.

You started out wanting to be an entrepreneur.


Was that part of the grand plan, wanting to spend some time in the corporate world to cut your teeth?

Uh, you know, it’s interesting you say that. I didn’t really know exactly what I wanted to do: “Here’s my path of entrepreneurship of where I wanted to possibly go.” You know, I thought of just because of all the different backgrounds I have, I thought of becoming a plumber, I thought of becoming an electrician, I thought of opening a mortgage company—thought of starting a mortgage company. And I started naturally gravitating towards technology, so anywhere I started going, you know, as technology started becoming more and more mainstay and necessary. You know, as I was working for the real estate company, I gravitated toward technology. Even when I was working for Fannie Mae, I gravitated towards technology. You know, at one point, and it was at Fannie Mae, I was the customer account manager, and they had a position open for—I can’t remember the name of the title—but basically was a technology marketing person. And I thought of going for that. 

All along, you’re almost getting more and more comfortable in teaching yourself the whole technology space.

And I started a company without even having an IT background!

Well, let’s let’s let’s talk about that. So now you’re almost 20 years into your career, you’ve worked, you’re worked at a number of different types of firms. Technology has been calling you—let’s put it that way. You’ve gotten a certain level of understanding. After the real estate company, is that when you started thinking about setting up your own firm, back in the early 2000s?

Yes. I wasn’t sure what I wanted to do, but I knew I didn’t want to work for the real estate firm anymore. So I left—I resigned without a job in mind. I resigned thinking I want to take some time off and get some technology certifications, to change paths at that time. At that time, I was 40 years old. I wasn’t sure at that time whether I was going to start my own company, but I wanted to change paths.

Tell me about the financial part of the decision. You know, we’re financial planners. So what fascinates us is when I look at it, a business owner like you: you’re 40 years old—I’m sure you’ve got bills to pay at that point. You’ve resigned without another job to go to. Talk to me about the financial preparations to taking a step out of the workforce to do the next thing. Can you remember that?

Oh, God, yeah. Most people can remember this because it was painful at the time. I mean, and here’s a funny story: My wife was also working, so we went from dual income, no kids as such. I mean, I had an older daughter from a prior marriage, but she was out of the house at the time. So technically, at that point, we were dual income, no kids. And when I decided, when I up and quit my job and said, “I don’t want to do this anymore,” my wife had just given birth. So we were, we went from dual income, no kids to no income with kid.

Why not jump in with both feet?

Rip the band-aid off!

So talk to us about—I mean, like, I’m assuming you had saved some money.

Yeah, the funny thing is, so my 2000 tax return literally had zero for income. So my 2000—I’m sorry, my 2001 tax return had zero for income when I filed my tax return, I literally had no income.

I don’t know. At the time, I look back, and I must have been out of my mind, you know, thinking, why would I do this? We had a bunch of money in the bank at the time, we had saved some money over the years. We were pretty frugal, my wife and I, and I felt comfortable enough that I think I had enough money in the bank that it’s like “You know, now’s the time to take the risk. I think I can do this. I think I could do this.”

If the 40-year-old Steve Ryder was in front of you right now, what would you say to him?

Yeah… Here’s the biggest mistake I made at the time. I figured I was still young enough, and I had enough talent, that if I couldn’t survive starting my own company, I could go get a job. So I think the biggest mistake and I’ve told other entrepreneurs the same thing—if you are going to start a business, you have to go all in. And for the first couple years. I was not all in, you know? I was kind of half in, half out.

I find that interesting. Knowing you as I know you I find that interesting. You didn’t go 100% necessarily.

No, I thought, “You know, if this doesn’t work out, I can go get a job.” I think for probably a couple years—the defining moment for me was when I had very, very little money in my business bank account—I remember my bank account after I did payroll was like 38 cents left. And after I did payroll, I’ll never forget that number. I remembered being down in the basement with my wife and pissing through most of my money. I said, “If I ever touch my wife’s retirement or her money, I will have failed.” You know, got my house in a line, went through all my retirement account, all my savings. And just, that moment in time was that defining moment was like, “You know what, I don’t want to go work for somebody else. I am going to get through this.” I got my back up and said, “I’m going to make this work.” And at that moment in time, I don’t remember the exact day, but I remember that moment and just saying, “You know what, I’m not going back. I’m not going to go work for somebody else.”

So that’s interesting to me. So you started out knowing early on that you’re entrepreneurial, yet for the first two years of your real entrepreneurial career, you kind of kept a foot in both camps.

Yeah. And you know why? Because I had money. You know, I wasn’t rolling in it, okay? But I had enough money—and this is kind of the, you know, it’s kind of funny, I was watching Shark Tank the other night. And I can’t remember if it was Robert, or one of the guys on Shark Tank said, “Sometimes the point in time where you have enough money that you make mistakes, because you like—”

You’re not hungry enough.

You’re not hungry enough. Great point. I wasn’t hungry enough.

Or desperate enough.

Good point. Or desperate.

Fear is a great motivator, right?

Yes, fear is a great motivator, and once I started—once I drained all my accounts and got to that point where I needed to make smarter decisions, and I don’t have enough money to go through anymore, and I got to make smarter decisions, I got to be thinking about—

The real light bulb moment, it went off at that point.

Correct. Yeah. And then it went back to my college days and saying, “Yes, you want to be an entrepreneur, you’re here. But how bad do you want it?” You know. And then I decided that I really do want this.

So lesson number one from Steve’s older brother. When you go entrepreneurial, go all-in.

You got to go all-in, and you got to have perseverance. You can’t give up. I mean, I had people ask me that, as you know, I’m sure you’ve talked seeing people come and go start businesses, leave businesses that can’t make it and close up shop. But just this constant perseverance, you know, never giving up. 

You know, again, as I said, for the first two years, I never really was in it to give up. But yeah, one point, once I decided I was in, I was like, “I’m never giving this up. I’ll lose my house before I—”

So that’s interesting. So that sounds like it happened around 2002, 2003, give or take that time. And knowing the business that you’re in, Steve, it’s such a challenging business—things are changing so much so often. So, you know, you hear stories about the US government being hacked by the Russian whoever, right? But talk to me about—were there any other existential moments during the course of True North, that you had to retool, kind of look at the way you were doing business and change things up significantly?

Yeah, several times. I think early on I had a partner, I bought him out early on. And at one point, January 28th of 2003, I’ll never forget the date, he was working on a server and did a routine thing, and Microsoft suggested what to do and he end up deleting all their data. It was not a good day. And I remember walking into the owner of the company, and basically said, “I don’t know how I’m gonna do this, but we’re gonna figure this out.” And long story short, we had to ship the disk to data recovery. It cost me about ten thousand bucks that I didn’t really have, but you know, kind of did the right thing out of my pocket to make it right. And the client actually referred us to other clients. So that, again, was another defining moment.

The hardest decisions, I think, for a business owner is, as they say—it’s just business, right? And there’s times you hire people that will get you to one point, that may might get you to the next point. And so I’ve had to make some really, really difficult decisions of parting ways with people during my path that aren’t fun. But they just can’t foresee or get you to the next level that you need to be. So those were some tough moments over the years where, you know, I remember making some decisions that were not fun decisions, but I had to make the right decision.

And as they say, you have a responsibility for both you and that person, you know, to make the right decision for everybody concerned. And every time I’ve made those decisions, I’ve treated those people, when they’ve had to part ways, probably better than most small businesses would do. In fact, I remember having these conversations with my wife, as I’ve made those decisions over the years, and she said, “What are you doing paying them for that many months or that much?” And I’m like, “You know, I want to sleep at night, you know, these people have gotten me from here to there.” And she’s like—she used to work at Liberty Mutual, Fortune, what, 100 company? “You’re not Liberty Mutual!” I’m like, “I know, but these people helped me, you know, and—”

It’s one of the hardest things when running any sort of business, the people aspect of it.

Oh, my God. Yeah.

One of the other things I wanted to touch on too: I’ve known you for 15 years now. I’ve seen you grow your firm. You have clients all over the country at this point. The decision to bring True North to be an employee-owned company, I have to say fascinates me.

Yeah I mean, to me, you know, money is not a motivator for me, as you know, I pissed it all away back in the early 2000s! Obviously you have to make a living, right? I got to make money, I got to make a living. But to me, it’s always been, you know, I’ve never really considered success on my own. Really, I’m a team player, and as I said, while I may like to make the decisions, I also realize I haven’t gotten successful on my own. I might have taken all the risk and gotten where we are  But, you know, it’s kind of funny. I mean, I don’t know, if you may or may not remember, but I remember talking with Tom Orecchio, your partner. I’ve talked with a few other business owners, you know, “What have they done? What are they doing, succession planning, trying to think about the future.” Talked with many, many people including some other people who started employee-owned companies, and I just felt like that seemed to be the way to go for me, you know, to, you know, try to have other people benefit from employee ownership. So at some point, you know, selling it or selling shares, or at some point when I ever have an event that other people will benefit from that event, because they will be shareholders as well, and be able to benefit from it as well. That it’s not all coming my way. But other people will benefit as well.

Have you—I know if you’re not comfortable answering this question, but have you noticed a change in your team since you put that in place?

Yeah, I think so. I mean, we have an ESOP Committee that has gotten together and started to talk about things. And yeah, I think people are excited, you know, and we certainly care about our team, but I think people have gotten a little bit more excited about being an employee-owned company, and you know, feeling stronger about the commitment, that ultimately I do care and, you know, I want to put my money where my mouth is and say, it’s one thing to thank people, but it’s another thing to, you know, show them with value..

Yeah, yeah. So in the last few minutes, what I wanted to do is just change tactics a little bit, considering the expertise you have Steve, and the fact that you travel they country talking about cybersecurity. You know, for those listeners, maybe we can have a lightning round of one or two minutes of, you know, what are your biggest concerns around cybersecurity? For those people, you know, any listener, I’m sure, is going to be computing—let’s put it that way—and are going to be on the internet. What are the top two or three things you would say to them?

Apathy. People don’t really take it seriously—as seriously as they should. You know, it scares me at times when you know, for example, I’m not obviously gonna say any names, but we’re trying to force people, right, just simple, simple things like, you know, multi-factor authentication, right? Just even on your email. Forget everything else, just do it on your email.

For the uninitiated, just explain to them in English, what multi-factor authentication is.

Alright, so when you log into your email, you log into any other software, you have a username and password. And then you might have a token on your phone, or something recognizing your computer—that, you know, second factor. So it makes it difficult to compromise an account if you give up your password, because you still have to have the token to do it.

So we have literally been pleading with companies to do it. We have had a client actually get breached, because they didn’t have multi factor authentication, and the client still doesn’t have multi factor authentication after they experienced the data breach.


So and I’m like, I just, you know, we’ve taken a tack to saying, “You know what, if clients don’t do some of the basic simple security things, you know, are as you know, Mark, our contracts are kind of this “all-inclusive, all-you-can-eat, we’re your IT department,” whatever. But we’re now saying, “Look, if you’re not going to do some of the basic levels of security—”

There’s not a whole lot you can do for them.

Yeah! Look, you got a data breach, not using multi-factor authentication. I mean, I know we’re not liable for it, but you’re if whatever dollars or effort we got to spend from our labor side, you’re paying for it. You know, because it’s extra effort on our side.

And that multi-factor, Steve, is opening up to stuff like bank accounts, logging into bank accounts. And would it be fair to say you’d recommend everybody to do that?

Everything you can possibly… like, I mean, I pull up my phone here, I have it on, we’re gonna think of—QuickBooks for Intuit, GoDaddy for my domains, all my different, you know, obviously, all our business technologies we use to support our clients, my GMail account, my Office365 account. I mean, almost anything. My Amazon account—you know, even my Amazon account, I have two factor authentication. I mean, I have it on everything I can possibly imagine.

And yes, it is a pain in the butt.


But that’s the price you pay. It’s the lowest hanging fruit currently, right, multi-factor?

It’s the lowest hanging fruit. And the reality is that the bad guys aren’t stupid. They’re gonna go after the people who don’t have it.

So that’s our good deed done for the day. We’ve kind of hammered that multi-factor into our listeners. And a couple of quick—just, what’s next for True North? What big decision are you grappling with right now?

Okay, so the biggest decision we’re grappling with, you know, it’s kind of funny—back in 2016, we moved into a new building. And I remember walking into the building, telling the landlord, “Can I sub-lease this? Because there’s no way I’m ever going to fill this space.” So now, it’s four years later, or a little over four years later—

And you foresaw the pandemic four years ago?

Of course, of course, I was ready to go! No, but seriously, four years later, and we’re—we need more space! You’d think for the pandemic, you’d think you’re thinking the opposite, “I don’t need the space.” I need more space,

Even with some of your folks working virtually or from home?

Yeah, we have some working from home, most are still in the office here. We’re still, I mean, despite the pandemic, we are blowing out at the seams here in the office. And we have, I think we have five new people starting in the next three weeks? So we continue to grow, you know, so those are the challenges, integrating, you know, more people into the team.

And then again, one of the challenges, integrating people for training remotely, that we’re still grappling with, you know. We had a couple people we tried hiring and tried integrating and training them remotely, and that didn’t work out. Just didn’t have a good experience, or they didn’t have a good experience. And we got to figure our way through that, too.

Yeah, it’s challenging. We’ve had to do that with two new employees ourselves. It’s possible to do it. 

Of course.

But it needs a whole lot more consideration than when you’re actually in the office and in person. 

Absolutely. And even to some extent to the collaboration, which, you know—trying to figure out a way, and obviously we have Teams, and just trying to figure out, “How do you have a virtual water cooler conversation,” right? I mean, those are the things that I think—I see a lot of collaboration in it, you know, or something. When it’s like, trying to troubleshoot something, and somebody hears it over the, you know, when there’s collaboration, that I think, which is kind of good to have most of the people back in the office right now.

But it’s definitely a struggle. You know, for people who have, as you know, you have, you know, you have a risky situation with your family situation. There’s people I have that have risky situations that, you know, would prefer to work from home—which is absolutely fine. But how do you really provide that collaborative experience? Like it’s being in the office. 

Like it’s over the water cooler, right? 


Just, it’s almost like, it’s in the air, and it’s not directed at you, but you pick it up. I know that I’ve given a bad analogy there, but we struggle with the same thing ourselves.

As we wrap this up, we like to wrap this up with one last question, we pose this question to all of our guests. And it seems to be the question that stumps most of our guests, actually. So the question is, what’s the last non-financial decision you’ve had to make today?

I would say my last decision I had to do—so every, I guess technically, for me, it’s not a financial, well, I guess, indirectly, maybe a financial decision. But the decision I had to make today was, we have Salad Mondays here. We provide salads for people. And so my decision was what salad do I want today? So there’s a local, again, we try to support the local economy here, so we have a local restaurant here that we support, and I got the chicken caesar quinoa bowl. So it’s a chicken caesar with quinoa and it’s really, really good.

That sounds too healthy for me!

Okay, thanks very much, Steve Ryder of True North for letting us listen in today. We appreciate his time and his perspectives. And thank you for tuning in. We hope you’ll join us next time on Decision Dialogues for more stories from successful business owners like Steve. So long for now.


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About Steve

Portrait of Steve Ryder

Steven Ryder founded True North Networks in 2002, a now employee-owned company providing professional IT Support for clients across the United States. True North serves as a fully outsourced IT department and covering servers, network infrastructure, computers, workstations, and mobile devices, with end-to-end solutions.

Prior to founding True North, Steve served as CFO for Better Homes and Gardens Real Estate, and worked as an Account Manager with Fannie Mae. But his self-described “entrepreneurial spirit” led him to found True North Networks.

Steve earned his Associate’s Degree in Business Administration from Middlesex Community College in 1980 and his Bachelor’s in Accounting from the Massachusetts College of Liberal Arts in 1982.


Modera is an SEC registered investment adviser which does not imply any level of skill or training. For additional information see our Form ADV available at which contains a full description of our business, operations and service offerings including fees. Statements made in the podcast are not to be construed as personalized investment or financial planning advice, may not be suitable for everyone and should not be considered a solicitation to engage in any particular investment or planning strategy. Statements made are subject to change without notice.