In a recent episode of Cherokee Business Radio, our co-founder and CEO Tommy Ryan joined host Joshua Kornitsky to talk about what it really means to align Microsoft 365 with the purpose of an organization. From building cultures that embrace change, to helping leaders reclaim time and invest it back into what matters most, Tommy shares how mission-driven organizations can turn their vision into momentum — and ultimately, into impact.
You can listen to the full conversation through the iHeart player below, or read the enhanced transcript that follows.
At ThreeWill, we’re passionate about helping mission-driven organizations turn their goals into measurable results. If you’d like to learn more about how your team can get more from Microsoft 365, be sure to follow ThreeWill on LinkedIn or schedule a Discovery Call to speak with Tommy today.
Audio Transcript
Joshua Kornitsky: Broadcasting live from the Business Radio studios in Woodstock, Georgia. It’s time for Cherokee Business Radio. Now, here’s your host.
Welcome back to Cherokee Business Radio. My name is Joshua Kornitsky, professional EOS implementer and host of Cherokee Business Radio. Just a quick note that today’s episode is brought to you in part by our community partner program, the Business Radio Main Street Warriors — defending capitalism, promoting small business, and supporting our local community. For more information, go to MainStreetWarriors.org.
And a special note of thanks to our title sponsor for the Cherokee chapter of Main Street Warriors, Diesel David, Inc. Please go check them out at DieselDavid.com.
Well, we’ve got another great show lined up today. My guest in the studio is Tommy Ryan. Tommy is the co-founder and CEO of ThreeWill, a technology consultancy focused on helping mission-driven organizations gain more value from their Microsoft investment.
Beyond his executive role, Tommy also brings a leadership style rooted in systems thinking, human connection, and curiosity about the natural world.
Good morning, Tommy. How are you?
Tommy Ryan: Good morning, Joshua. I’m doing good.
Joshua Kornitsky: Forgive me — I think I brought the frog in my throat today, and I’m trying to clear him out. It’s great to have you. Thank you so much for taking the time to come in.
Tommy Ryan: Sure.
Joshua Kornitsky: So tell us a little bit about who you are and your background and what led to ThreeWill.
Tommy Ryan: Wow. That’s a big question there, Joshua.
Joshua Kornitsky: Yeah, start large.
Tommy Ryan: Yeah. So this all started — the ThreeWill journey — probably, I’d say, ten years before we started ThreeWill. It was started by me and my brother Danny. And we were curious about this internet stuff.
Joshua Kornitsky: Yeah, I hear it’s going to be big.
Tommy Ryan: Yeah, yeah. And this was back in, let’s say, the early ’90s. He was a Pricewaterhouse consultant. I was a process engineer manufacturing Gore-Tex as a chemical engineer.
And I got very curious about the technology side of process engineering. So I did PLC programming — I don’t know if you’ve ever heard of that before. People in manufacturing would recognize that. It’s kind of the hardened PC technology that operates equipment. And I also worked on the human-machine interfaces for that equipment. And that is something that I would just… the hours would melt by.
Joshua Kornitsky: Sure. You were in the zone with the technology.
Tommy Ryan: Yeah. So I found an early curiosity for technology and how that can systemize things.
Tommy Ryan: So I did that for five years and ended up going to work for and made a transition in my career to support a software product from Siemens that was that HMI, human-machine interface. And during that time, I was talking about starting a company with Danny as it relates to technology. And we said, well, let’s work at the same company to see if we’re compatible.
We did that for, gosh, maybe it was two or three years at a company called Extreme Logic. It was a very solid consultancy in those days, right before the year 2000.
Joshua Kornitsky: Okay.
Tommy Ryan: And they were the Microsoft Partner of the Year. They got acquired by HP. My brother and I were writing technology articles when we were there at Extreme Logic, and a company approached us to write a book. It was actually John Wiley and Sons. And it was a Blueprint series, and it was back when .NET was beta.
So we used that as a launching point to say, well, maybe this is the time to start a business. We did that in 2001. Our first sales call was September 11, 2001 — a very interesting day.
Joshua Kornitsky: Wow.
Tommy Ryan: And they say that’s when to start a business, when times are tough, because it makes you run lean, makes you get focused very quickly.
Joshua Kornitsky: So obviously you learned you could work well with your brother.
Tommy Ryan: We did. We worked for 20 years together, and it was a great journey as brothers. And now we’re putting a full-time effort towards being brothers versus business partners.
Joshua Kornitsky: That’s fantastic. I support that completely. So I mentioned in your introduction that you really help the organizations you work with get much more value out of their Microsoft investment. Right? Tell us what that means.
Tommy Ryan: Well, typically what we find in organizations that are using Microsoft technologies — Microsoft 365 in particular — they’re very comfortable with email. They use that communication mechanism to also collaborate with each other and to share content. And it’s a very dated, very reliable technology. Going business to business, if you’re not in the same collaboration environment, sending emails is a good way to get information.
Joshua Kornitsky: Sure. Communicating, accepted norm.
Tommy Ryan: Yes. And people are comfortable with that. But we help organizations start embracing the other parts of the toolset that help with better communication, collaboration, and automation of the standard things that they do — to bring more predictability to their business.
Joshua Kornitsky: In the case of [Microsoft] 365, in many cases, don’t they already have the license to utilize that technology?
Tommy Ryan: Yeah, they do.
Joshua Kornitsky:And they probably paying for it and they’re not using it.
Tommy Ryan: That’s right. They’re probably using 10, 20%. That’s common for us to see when we look across what they own and what they actually use. We believe that it takes a custom tailoring of looking at their business, understanding what are the core processes that drive that organization, and looking at where they are in the maturity spectrum of using technology — meeting them where they are and taking them on the next step in that journey.
Joshua Kornitsky: So you’ve got to kind of do a deep dive with them to understand where they’re at before you can figure out where you can go.
Tommy Ryan: Yes, yes. That early on kind of analysis, discovery of understanding what makes that company tick, and what type of people do they have working there. You know, is it people that are in their 50s or people in their 20s? You approach technology differently depending on what the demographic looks like in the company.
Joshua Kornitsky: I imagine that your background in systems thinking and human design must give you a great deal of insight into understanding where they’re at.
Tommy Ryan: Yeah. When we look at productivity, we like to look at ourselves as a fractional productivity department for our customer. Where they’ve got the guide or the expertise to help them take what they do in their work day to day and humanize that work by taking the mundane and repeatable things and letting technology take care of that.
So when we think about that journey with a customer, the first step in that journey is making sure they have the right culture. Are they willing to change? Because we can show them a new way, but if they’re not hungry to improve what they’re doing, if they don’t have the leadership support to say, we are going in a direction where we’re going to adopt more technology to enable the mission, then, you know, we’re fighting an uphill battle that we’ll never win.
Joshua Kornitsky: In my other life as an implementer, we say if you have to drag them in, you’re going to have to drag them around. If they don’t want to do it…
Tommy Ryan: Yeah.
Joshua Kornitsky: …then you’re just pushing it uphill. And so I fully agree with you on that analysis. So let’s talk about the kind of clients you work with. Is there a specific vertical — because you have a background in manufacturing — or who do you help?
Tommy Ryan: Yeah. So the first 20 years of ThreeWill was in the space of really enterprise, just general enterprise. So, you know, some of the clients we still have today, but also big companies like Ernst & Young, AT&T, Warner Media, CVS Health. And we were helping those organizations with custom SharePoint development.
They had SharePoint on premises. They wanted it to work in a way that they thought it should work, versus just embracing what’s there.
Joshua Kornitsky: Bend it to their will.
Tommy Ryan: Yeah, yeah. And spending a lot of money to do that. And there’s a lot of history to what made us pivot the business, but one of the key things we wanted to do as a business was have longer term clients where we’re taking a journey with them.
Tommy Ryan: So we went in a direction of a managed service that’s affordable. You know, just like you hire a fractional HR person or a fractional bookkeeper to fill a need without needing it full time — without having to staff that department. You’re too small to do that, or maybe it’s just not in your DNA to have a technology group.
So we went in that direction, and we’ve been doing that for the past almost three years. And we’ve found that’s where it’s more meaningful work for us, because we get to know them better over time, and we get to make sure that the technology that’s put in place actually thrives and gets return on investment for them.
And what we’ve seen emerge is three different verticals, and we’re focusing on one very strongly this year to get it off the ground in a more formal way — around home and community-based services. So think of senior living, home health care, community clinics — a lot of the care that the community gets that doesn’t come through traditional institutions like a hospital.
Joshua Kornitsky: Right.
Tommy Ryan: Sometimes, in many cases, underserved or in challenging situations where you might have an adult child that’s 25, still living at their home, can’t live on their own. But if they’re in the right kind of community that has the right kind of support, that child can move on into an adult life. So that’s something that kind of breaks our heart. And we were like, hey, if we’re going to help people be more productive, let’s do it where it’s going to be a better world after we’ve done the work.
Joshua Kornitsky: That’s very much aligned with who you are. I think that’s fantastic. When you engage in those, well — you said there were two other verticals. What are the other two?
Tommy Ryan: The other vertical is real estate development, which is interesting. That industry has definitely been through some turmoil with COVID and hybrid work and how people are getting work done. And just, you know, spaces are actually becoming more popular for this work-live-play type of environment we’re seeing pop up everywhere.
And we help those organizations with the workflow that goes between departments. There can be a breakdown in communication, a breakdown in the flow of information. So it’s things like multifamily homes that people are managing — they want the quickest turnaround from the time a tenant leaves to when a new tenant comes. They really appreciate having process to expedite that and have high visibility of where it is in the whole scheme of things.
Joshua Kornitsky: And you work with those types of property management companies?
Tommy Ryan: Yes, we do.
Joshua Kornitsky: Wonderful.
Tommy Ryan: And the other vertical that’s taking shape is family offices and credit unions. It’s kind of a niche in small financial services — not big banks. But there’s a theme of community. We enjoy creating a better member experience for when people come into a local community bank — making information flow well from the time they walk in the door to the time they leave. So those are the three verticals.
And at the end of the day, Joshua, if I could have just one vertical, I think it would be best for our company and our customers because it allows us to focus all of our energy into that domain, and come to a customer with a strong point of view, assets to bear, and an understanding of the challenges they face.
Joshua Kornitsky: Sure. The more sharpened the point on the pencil, the more you can probably help them. But it’s good to know that you’re able to service across multiple sectors. And obviously that comes from time. You had said that all of your endeavors are tailored to meet what the client’s needs are. How do you broadly define success, or is that something you collaborate on to determine at the beginning?
Tommy Ryan: That’s interesting. So, you’re familiar with EOS?
Joshua Kornitsky: Definitely.
Tommy Ryan: We are a company that runs on EOS. And part of that is you define what your three uniques are. For us, our three uniques are: we have “Depth of Knowledge” — and that doesn’t mean just Microsoft technologies, but the domain knowledge of the client.
“Journey with you”. That influenced us going in a managed services route, because we feel like we best serve a client over time versus a big bang project where we do some technology and hand it off and say goodbye.
And our last unique is “Measuring Your Success”. When you look at productivity, a lot of times that’s thought of as a very squishy thing. We want to put more science around that. And so every customer we work with, we measure the time that we reclaim by putting technology in place.
Joshua Kornitsky: That is an incredibly valuable service. Because often when I work with my clients, they have a goal of a 10% increase in metric X, Y, or Z over a period of time. But my very first question is — that’s a great goal, but what’s the metric today? And usually they don’t know. So my immediate response is always: how do you know you’ll be 10% better?
Tommy Ryan: That’s right.
Joshua Kornitsky: If you don’t know where you are today, you don’t have a benchmark. There’s no way to determine if you’ve improved. “Better than yesterday” is a wonderful goal, but in order to really grow, they’ve got to know where they are.
Tommy Ryan: That’s right.
Joshua Kornitsky: So that’s great, so you’re able to help them understand where they are and then build towards their long-term goals on the journey with them.
Because that’s what you do.
Tommy Ryan: Yeah, yeah.
And we have a pretty lofty goal. As EOS teaches, you set a 10-year target. For us, it’s reclaiming 10 million hours over the next ten years with our clients.
Joshua Kornitsky: That’s an amazing and really thought-provoking goal. I love that. I hope that you achieve it. Are you well on your way?
Tommy Ryan: We’re in year two, and we’ve got 367,000 hours we’ve reclaimed so far.
Joshua Kornitsky: That’s fantastic. I wish you well on that journey. Now, earlier you shared with me that you’ve got some interesting interests outside of work. Let’s talk a little bit about that — maybe how that influences the way you run the organization and how you see the world. What do you do when you’re not helping others?
Tommy Ryan: Well, I’ve got this nice little side hustle of growing vegetables. That’s kind of my history — I’m a two-time cancer survivor. So I got into organic growing to know where my food comes from and to essentially try to infuse more good stuff into my diet.
I love donuts. I love French fries. I eat all those things. But I look at: can I put a little bit more healthy food into my diet? And I’m so curious about how nature works. As I was in the garden, just doing the day-to-day things, I would see something or experience something and say, “You know what, that is a natural law that applies to my business.” And I can tell a story about it so people can grasp that concept.
Those things started piling up in my head, and I said, one day I have to start writing these down. So about 25 weeks ago, I started the Sowing Success newsletter on LinkedIn. And basically every week I’m finding — I haven’t exhausted them yet — but I’m finding these concepts where something happens in nature and I can apply it to my business.
Joshua Kornitsky: Sure. There’s a long history of the natural world being the inspiration for almost everything, right? Can you give us one or two of the takeaways briefly that you’ve learned?
Tommy Ryan: Yeah. Gosh, if I reflect back on some of them — one is abundance. If you nurture something, it can grow in abundance. Pouring into something, believing in it, and caring for it creates fruit at the end of the day. You can see that with your employees — the more you pour into them, with trust and space, you’ll see things flourish because you’re investing in that relationship.
Also, there are concepts like pruning. That might seem negative — oh, I’m cutting back. When you prune, like a bush in your yard, it can look ugly after you prune it. But how it grows back — stronger and healthier — those are some of the hard things you need to do in business but are the right things to do to help your business flourish.
Joshua Kornitsky: That’s a really great observation. I appreciate you sharing that, because the reality is sometimes we have to make hard decisions both in the garden and in the business in order for the business to grow. They’re not always fun, and cutting away the flowers may make the bush look ugly for a little while, but come the spring, it’s going to be beautiful.
Well, you mentioned earlier, Tommy, that ThreeWill is over two decades old. In those two decades, what are some of the biggest lessons you’ve learned along that journey? Flipping it now onto the business side of your perspective, a little bit out of the garden.
Tommy Ryan: On the topic of pruning, I think some of the hardest things I’ve had to do in the business is letting people go. And I think for most business owners, that’s the hardest part of the business. What I’ve learned is, letting people go when I have the data and the know-how — when the business is moving in this direction. “Do I have a seat for this person on the bus?” It’s not personal. It’s: “Okay. I need these seats in the bus, do I have the people for that?”
And for the people who don’t have a seat, it doesn’t do them any service to hold onto them and let them struggle. Making that decision faster …
Joshua Kornitsky: Sure. It’s a kindness. As much as it may not seem it — it’s a kindness.
Tommy Ryan: Yeah.
Joshua Kornitsky: That’s a hard but true lesson. But I also know from the time we’ve spent talking, and a little before the show, that you work to grow — specifically in your community. What are some of the things you’re doing to help local leaders?
Tommy Ryan: At ThreeWill we have this abundance mentality. We’re about pouring into other people — our clients, our employees, our community. After COVID, we found that we weren’t having those person-to-person interactions, and we needed more of that. How could we be a part of that? So we started a luncheon for that.
We first started with CEOs, to give them a forum to talk to other CEOs about employee productivity and thriving employees, and to bring topics to the table. More recently, in the past two years, we’ve focused in on partners — what we call our Alliance Luncheon.
There’s no requirement, no boxes you have to check. It’s more: are you in this local community, trying to drive services for organizations? Then come join us. I’ll pay for lunch, and you can learn from others and create a tangible network. Of course, we’ve got LinkedIn, and that works. I’ve met a lot of people through that. But to have a physical network — that’s where the magic occurs. Face to face, getting to know people. That’s what we focus on. It’s about getting to know your neighboring business owners and leaders who are trying to make things work in their business.
Joshua Kornitsky: Sure. People always do business with those they know and have a connection with. When is the lunch, and is it open to anyone that wants to attend?
Tommy Ryan: Yes. Just reach out to me on LinkedIn — that’s the best way. You’ll see posts I put out occasionally: “Hey, if you’re interested, come join us.” I do those once a quarter. I think our next one is in October. I’ll post something on LinkedIn in the next couple days after this broadcast so people know.
Joshua Kornitsky: When we go live, we’ll post all your social links, your website, your LinkedIn, and your phone number. But if people want to get in touch with ThreeWill, how do they do that?
Tommy Ryan: Of course you can go to ThreeWill.com — it’s spelled out, T-H-R-E-E-W-I-L-L.com. You can reach out to me on LinkedIn. There’s a Contact Us page on our website. You can learn about our verticals, learn about who we are as an organization, and what we care about. And I’m going to be releasing the ThreeWill Productivity Manifesto at the end of this week or beginning of next week. That’s a great way to understand who we are as a company. It’s the “why” for us — why we care about productivity — and it gives a framework for people to think about productivity.
Joshua Kornitsky: We’ll have to have you back on so you can share some of the highlights of that, and also some of the feedback you get after it’s been out for a little while.
Tommy Ryan: I’d love to do that.
Joshua Kornitsky: Because ultimately it’s about serving our community, which is what we’re about here. Is there anything I missed, Tommy? Anything else you wanted to share that I didn’t think to ask about?
Tommy Ryan: I think this is a journey, Joshua. This is part one. And we can continue to unpeel the layers.
Joshua Kornitsky: Well, I can’t tell you how much I appreciate your transparency and your willingness to share, and to even go “into the danger,” to talk about some of the hard subjects. Because understanding — and I should say, getting advice and direction on when it may be appropriate to do some pruning, which is not your primary focus in the universe, but it is a focus you help folks understand, along with process and along with getting greater value out of their current investments — you’re doing hard work. And as someone who works with a lot of similar businesses, I can tell you it’s needed and appreciated.
Thank you again. My guest today has been Tommy Ryan, the co-founder and CEO of ThreeWill. They’re a technology consulting firm focused on helping mission-driven organizations get more value from their Microsoft investment — and also, from what I understand, even farming.
Tommy Ryan: I appreciate the opportunity, Joshua. Thank you.
Joshua Kornitsky: Again, today’s episode is brought to you in part by the Community Partner Program, the Business Radio Main Street Warriors — defending capitalism, promoting small business, and supporting our local community. For more information, go to MainStreetWarriors.org. And a special note of thanks to our title sponsor for the Cherokee chapter of Main Street Warriors, Diesel David, Inc. Please go check them out at DieselDavid.com.
If you’re interested in learning more about the Community Partner Program, please just reach out to me, Joshua Kornitsky, your host. Thank you again for joining us for Cherokee Business Radio, and we’ll see you next time.
