
Cut The Tie | Own Your Success
Define success on your terms, then, "Cut The Tie" to whatever is holding you back from achieving that success.
Inspiring stories from real entrepreneurs sharing their definition of success and how they cut ties to what is holding them back.
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Own your success.
Cut The Tie
Thomas Helfrich
Host & Founder
Cut The Tie | Own Your Success
“Freedom Isn’t 50/50—It’s What You Design It To Be”—Wilson Zehr on Balance, Entrepreneurship, and Reinventing Direct Mail
Cut The Tie Podcast with Wilson Zehr
What does real balance look like for an entrepreneur—and how do you design a business that supports it? In this episode of Cut The Tie, Thomas Helfrich sits down with Wilson Zehr, professor, entrepreneur, and CEO of Zairmail, a company that has been reinventing direct mail for more than 20 years. From navigating massive shifts in the printing industry to building software that gives an old medium new life, Wilson shares how balance, innovation, and persistence fuel his entrepreneurial journey.
About Wilson Zehr
Wilson Zehr is the CEO of Zairmail (a division of Cendix), a B2B SaaS company that automates direct mail programs for organizations across the world. With decades of experience as a technology executive, entrepreneur, and professor, Wilson has built, acquired, and sold companies, while also teaching marketing, entrepreneurship, finance, and business strategy at the university level. A lifelong innovator, he helped pioneer “hybrid mail”—digital files transformed into physical mail delivered to homes and businesses. Passionate about entrepreneurship and balance, Wilson combines his technical expertise with a love of problem-solving, mentoring, and building lasting businesses.
In this episode, Thomas and Wilson discuss:
- Redefining work-life balance
Why balance isn’t a perfect 50/50 split, but something you consciously design as an entrepreneur. - Cutting ties with corporate constraints
Wilson reflects on leaving behind rigid “8-to-7” corporate schedules to build a business on his own terms. - Reinventing direct mail in a digital age
How Zairmail pioneered hybrid mail and gave physical mail new relevance in the era of digital marketing. - The habits that create luck
How consistent daily actions—networking, execution, and showing up—lay the groundwork for “opportunities.” - AI and innovation in print
Wilson’s perspective on how AI serves as a tool, but why creativity and trial-and-error remain uniquely human.
Key Takeaways:
- Balance isn’t about 50/50
True work-life balance means designing a business and lifestyle that actually fit together. - Corporate rules don’t define success
Walking away from rigid schedules opened space for entrepreneurship and freedom. - Old industries can reinvent themselves
With hybrid mail, even “sleepy” products like print can gain new life in a digital-first world. - Luck is built, not found
Opportunities come to those who consistently put themselves in position for them.
Connect with Wilson Zehr:
💼 LinkedIn: https://www.linkedin.com/in/wilsonzehr/
🌐 Website: http://www.zairmail.com
📧 Email: wilson@zairmail.com
Connect with Thomas Helfrich:
📣 Twitter: https://twitter.com/thelfrich
📘 Facebook: https://www.facebook.com/groups/cutthetie/
💼 LinkedIn: https://www
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Welcome to the Cut the Tie Podcast. Hello. I'm your host, Thomas Helfrick, and I'm on a mission to help you cut that tie. Metaphorically to anything cut holding you back from your success. Please define your own success first. Otherwise, you're chasing someone else's dream. Today, Mr. A doctor. Is it doctor? Do I say doctor? Wilson? Zare? Yes. Doctor. Doctor.
SPEAKER_00:And doctor. More of a professor than a medical doctor, but Yeah, you still get the doctor.
SPEAKER_01:It's like a bottle of wine, aging and education. At some point, you get a doctor, though. Why don't you go take a moment, introduce yourself, where you're from, what you do?
SPEAKER_00:My name's Wilson Zare. I'm located here in Portland, Oregon. We're on a company called Xare Mail. And it's like airmail with a Z on the front. We automate direct mail programs. So upload a document, upload a list, see a preview of what you're going to be produced, push the button, you're in the mail tomorrow and the next day at a fraction of the cost. And honestly, we're the actual formal Xare Mail is a brand name. So the formal company is called Sendex. We're a software company. We'd have a B2B software as a service software company. We've been in business for 20 plus years now.
SPEAKER_01:Is this one of the offerings then? Basically, is the is the piece, or is that in the offering?
SPEAKER_00:Yeah. So Sendex, software company, and we have we, you know, we do some cult consulting work as well. And we have servers and applications. And the type of application that we have spent the last two decades developing is something called Web2Print. So we automate the ordering of print products. But over that course of time, we actually invented a product called hybrid mail working with the U.S. Postal Service long ago. So hybrid mail is mail that turns starts out digitally, you know, in digital format, and then we turn it into actual physical mail that gets delivered to homes and businesses across America, honestly, anywhere in the world, if you put the right code stamp on it.
SPEAKER_01:Fair enough. In your industry, uh, it there's less competitors, right? I was I did unknowingly, you were going into the next show. I was like, hey, if you invest all your money in print and everything goes digital, don't be pissed it all went digital, right? Uh how have you guys I I gotta ask, how you guys survived, how are you navigating the just a massive change, or is it coming back? People like, I want physical things.
SPEAKER_00:Yeah, no, that's a that's a great question. I mean, uh, the printing industry, not just the mailing industry, but the printing industry has been consolidating for the last 20 years. Uh, you know, if you look at Portland, I I bet there's 30% less printers there was than printing companies than.
SPEAKER_01:Oh, it's even a bit higher, honestly. I thought it would have like a two main ones that you had the capital to survive it.
SPEAKER_00:Yeah, I I don't think it's that small yet, because people are still doing boxes and posters and packaging and lots of different things.
SPEAKER_01:That's good to know. So boxing and let's say posters are uh conference post bigger things, right? Um, that's still considered print. I didn't think boxes is part of that, because definitely boxes is well, yeah.
SPEAKER_00:No, so so that you know, posters is are something they call large format. It's this particular kind of print. Um boxes are interesting. One we did a project once for a company that does um the the they build machines that allow you to create the inner packaging for a box. It turns out a lot of boxes are two layers. There's the cardboard that goes inside, or that thin brown layer, and then there's a a thin layer of paper with the artwork that goes over the top, and those are both adhered together, and and that that's used to create boxes. But I mean, if you what I mean, it doesn't take much to go in the supermarket and look around and see all the printed material everywhere. I mean, that printing is not going away and has not gone away. Now, with that said, a lot of manufacturing has gone other places, and you know, it doesn't always make make sense to print a box here and ship it to China to put a product in it. So we see that industry moving in some form. There's it's um, you know, it's also not immune to lower price labor, and it is capital intensive. Um, so it's a huge, hugely competitive industry. When we got into the business long ago, one of our main competitors was a company called the e-Letter. They were funded by Hummer Winblad. And um, I think they were at the height of the dot-com era, they were burning through about$20 million a quarter. And one of the reasons for burning through that money was that they decided they were going to be a printing company and they bought all the equipment and warehousing and hired all the people. And it just wasn't sustainable. I mean, but at the beginning, we correctly identified, I think, the the idea that there's plenty of capacity out there. Um, we just need to find a way to put it to work so we can use that excess capacity. The same way, you know, Uber harnesses the excess capacity of the car in your driveway for people who want to give rides. Um, so we developed a software company and we handle the front end of the process. When it comes to fulfillment, we'll do print and mail fulfillment through a network of production partners, a nationwide network of production partners. We route the mail electronically to a place where it needs to go and where we print it and mail it. Um it's better for the environment and it also moves a lot faster, it's a lot more efficient. We can track it in to end and and let people know what's going on. So is uh we've taken a sleepy old product and giving it a new life and more new relevance in this digital age.
SPEAKER_01:Yeah, I well, let me ask you this. So I think that's interesting because that solves a problem for for like someone like me. Let's say like I think I made the thing of like, hey, I want to build a power washing business. Also I can go to you and say, let's go see if anybody cares. Do a test run. You could put it in mailboxes in a certain zip code, and you find the local, all the things that fulfill that capacity gap. Hey, do you you you broker it effectively? Correct?
SPEAKER_00:Yeah, yeah, and you could do a mail for a test like that. You could you could do a test online or something, depending on on what kind of audience you were getting at. The thing about all of these advertising meetings is that they're tools. And as a marketer, as a professional marketer, um that's the way I kind of look at them. I started out my career as a mechanic, an auto mechanic years ago. And at that time, they had something called the flat rate manual. So they'd assign you a car, they'd say RR repair and replace transmission, and they give you 2.5 hours for it. And if you could do it in one hour, then you did really well. And if you took you four hours, then you, you know, it was a bad day. And so it turned out that having the right tools was really important. And the same is true for marketing. I mean, direct mail does some things or the mail does some things that other tools don't do, and you need to know where it's appropriate to use and where you should use something else. If we think about how we're marketing our own business, I mean, we use AdWords and we use email just like everybody else. I mean, we in and we use it in the places that make sense, but we also use mail, direct mail, and we do it for for our clients. And I can give you lots of examples of uh how that works.
SPEAKER_01:Well, let me start with how do you just personally define success right now?
SPEAKER_00:How do I define success? That's a great question. Um, then I'm not sure. I think it may depend on the day. Um for me, I mean, success is not all about work or professional endeavors. I mean, I do having a healthy, happy family that loves and supports each other is is probably top of the list. Um, I am a lifelong entrepreneur and and technology executive. So I like and an engineer by training. So I I love building things, software things, and solving problems and working with customers. I mean, unlike uh a lot of the other folks in our in our segment. I mean, if you look at our website, that toll-free number is right there. It's big and bold, right in the middle of the site. We want to talk to people, you know, we want to hear about your problems. We want to talk to you about how we can solve them. And uh have we run out of we never run out of time. If we thought we were running out of time, we just hire more people to answer the phone.
SPEAKER_01:So having having that kind of like success for family around those pieces, one of the questions I always ask is is just follow. Just, you know, you talk about your journey a little bit, but what's been one of the biggest like you know metaphoric ties you've had to cut to achieve that success?
SPEAKER_00:Hmm. I don't know. I mean, once again, great question, but it it it's interesting to me because forever people have talking about talked about a work-life balance, which I which I think is very important. I mean, uh I'm I have uh I've been a competitive swimmer my whole life, and I swim a lot. And I we live in uh we're fortunate enough to live in a very beautiful part of the country. I have a another place in the Columbia River Gorge, which is National Snake Area, beautiful spot, lots of places to hike and swim and do stuff. So we'd like to be able to get on and do that. Um, but somehow in the in his work-life balance model, it's it's implied that you spend 50% of your day doing fun stuff and 50% of well, I mean, if you're doing what you like, I guess it's all fun stuff, but 50% of your day doing professional stuff, 50% of your day doing other lifestyle things. And it seems like it doesn't really work that way. You know, you'll have two weeks where you're just crunching it out, working on professional stuff, trying to hit deadlines, trying to get stuff delivered, and then maybe spend uh you know, you know, uh another large piece of time just you know trying to decompress and work, you know, spend time with family and friends and things of that nature. So being able to to balance that and balance it in a way that makes sense, um, so that you're not just completely owned by the business. Um that can still be successful. Uh it seems to be important.
SPEAKER_01:Yeah. I mean, that is that the so from the metaphoric sense of the show, right? Cut the tie. Uh, is it's it was you learning what balance actually was. Like, I don't think it's ever 50-50. A third of it's sleeping if you're you're lucky. Um, I didn't count that. Like, can you make do on the days it can you decompress long enough when you know you could to take advantage of the space that you've created for yourself? Like that is a hard thing to get used to doing is allowing yourself to take your foot off the gas for a couple of days or for a day or something like that, and enjoy and be present in the moment around you.
SPEAKER_00:It is. It's hard. But then again, as an entrepreneur, assuming that we get it right, I mean, we can we design a business around our lifestyle or uh around what we want to do. Right. I mean, if I'm working at uh a Fortune 500 company, I have to be there at whatever time, eight eight o'clock in the morning.
SPEAKER_01:And arbitrary uh industrial time like eight to five, like why like in noon and seven as well.
SPEAKER_00:Well, I think I've worked at those kind of companies. I mean, I I remember working at uh a very successful computer company where it was responsible for a very large revenue generating product. And I mean, you were expected to be there every day between it, wasn't eight to five, it was more like eight to seven, and most of the day was meetings, which means once you got finished with your day, you had to figure out how to actually do work, you know. So you just get went from meeting to meeting, gathering a list of the stuff that you had to do, and then you had to spend, you know, after hours time trying to get it done. Um and that doesn't lend itself very well to work life balance, that's for sure.
SPEAKER_01:No balance on that for sure, because you're just like by the time you get home, we're like, I don't want to do anything. Um if you go back in time though, in any part of your timeline, go back, what would you do differently?
SPEAKER_00:And that's a great question, too. And I mean uh you got lots of great questions. We're getting deeper. We're gonna keep um Yeah, I I'm not sure really. I mean, I I I'm not sure that I would I would change anything exactly. I mean, I mean, there have been, you know, I career-wise, there have been ups and downs. You know, I've built lots, you know, successful companies and I've had some that were less successful. I've acquired companies and I've sold companies. I've taken advantage of opportunities and I've missed opportunities. Um, but I would say from every one of those circumstances, whether it's up or down, I've learned stuff that allowed me to move forward and and do something else I wanted to do. I have this model I worked on. I I well, you mentioned I have a PhD. I also teach at the university environment, you know, when I'm not doing startups. Uh, and I've done that for a lot of years. I usually teach marketing, entrepreneurship, finance, and business strategy, not computer science, interestingly enough. But one of the models that we work on is around strategic planning. And so you say, you know, what what's our strategic plan for the coming year? And that's a function of, you know, there's one side of it is what is the environment you're working in? So what kind of opportunities you're presenting. Another piece of it is, what are my um core capabilities, right? What resources do I have to work with? What what could I do? Being able to match those two. But you know, the you know, forecasting future is not an you know, uh I would say not an exact science, right? Things challenge. And so we have to be fuzzy. I mean, how far out do you plan? Five years? Maybe that's too far for most people. Two weeks, I'm that's gonna be almost exact, but does that help? I I don't know. But I do know that anywhere along that timeline, the what I can do today is a function of what I've done in the past, what I've planned for, what I've done, what I know, what I have the resources for. So the stuff I want to do today, I've really had to start putting in place, you know, long ago, you know, maybe a month ago, maybe six months ago. And the same goes with life experiences, right? I mean, the the the place I am today and the choices I make today are a function of everything I've learned in the past. And so, yeah, so I could have taken away some of these experiences and maybe avoided some pain or maybe you know, some angst. But in doing that, I would you know decrease my options for the future. I would have less options and less insight and to um guide me forward.
SPEAKER_01:Yeah, I mean that that's a great answer because it's like it, you know, that stuff's happening for you and not to you, and if you take it that way. But I do like I wouldn't call that something out. You said the things you're doing today, the habits you form, the things you do, will determine what's gonna happen or likely could happen tomorrow. So did you go to that networking event? Did you send the email? Did you get your work done? Like all those little things stack up to present the next thing. And if you don't take any action or do anything that's positive or do things that are less, then then the next step coming is gonna be triggered around your own action. And I always find that interesting when people are like, oh, I never I'm not lucky. I'm like, oh did you create luck? I'm like, did you get it out there and look for what you needed to go do? So I I I like that you have to execute daily to figure out a year or two weeks, whatever, to go in the direction where else right.
SPEAKER_00:I mean, I mean, it's I mean, opportunities do per present themselves. You know, there's a case for being opportunistic. You have to recognize the opportunities, but you also have to put yourself in the right place to have those opportunities available.
unknown:Right.
SPEAKER_00:Exactly. Not everybody can do that. You know, that's but in and it often, you know, what people see say is see as good luck is a lot of hard work.
SPEAKER_01:Now, if there's a question today I should have asked you, I didn't. What would that question have been?
SPEAKER_00:You know, to be honest, I'm not sure what your listeners would want to hear most about. I mean, if uh we can talk about, you know, it seems like everything's AI today. We can talk about how important that is and what that really looks like. I can opinion around that. Sure.
SPEAKER_01:Actually, when it comes to printing, how much how much is AI impacting your world?
SPEAKER_00:AI has impact. I mean, everything, everybody wants to have an AI story these days. So there's some impact. I'm not sure if I'm putting ink on paper, um then um I'm not sure how much it impacts that. It may impact knowledge, you know. If I want to, if I want to produce a certain kind of product, I may be able to learn how to do that quicker. I may be able to find additional resources or additional shortcuts and things. I it's it's interesting. I I I will, you know, step into this argument a little bit because I I've been doing computer science a very long time. And even back when I was in school, people talked about AI, you know, and and what that meant. You know, it was more like a sentient creating a sentient being rather than, you know, uh an executive assistant. Um and you know, we talk about at that time, they talk about how the space odyssey, right? How how the computer or more recently irobot, you know, with Will Smith, you know, creating these thinking, reasoning beings. The AI we we have today seems to be, it seems to revolve around more efficient ways of finding data and or using data, and that um, which is not a bad thing. It's a good thing. I completed a couple of years ago, I I went through, I completed a data analytics program at Harvard University right at the beginning of this, you know, of this uh current AI push. And it was um looking at large language models and you know, letting the data bubble out, uh bubble up and how do we use it. And it's incredibly powerful, but once again, it is it's mostly just a tool. It's powerful in the hands of a of a person or a set of people, you know, a team, and it's powerful for doing a certain set of tasks. But if you think about a pet rant here, I mean, if you think about innovation and creativity, which is the area where I got my PhD. And it relates back to the conversation we had earlier, too. Um with something like AI, we would tend to go back and look at all the good ideas that people had and try to see if there's a common theme and ways that we can use that to create new good ideas. But if I think about good ideas and innovation, a lot of them are the product of bad ideas, not good ideas, you know, and they're accidentally right. As the story goes, you know, when you uh ask Edison, you know, it took him something like a thousand tries to figure out how to make an incandescent light bulb. And people asked him, so why do you keep doing this? You keep failing. I mean, it looks impossible. Why do you do this? And he says, Because every time I learn another way how not to do it. Right. And so, I mean, we we we try things, we have a premise, we try things, we make mistakes, it doesn't work. We try something different, see if that works. And through that process, we come up with ideas that gain traction and and work. But the problem with some of the models we have today, first of all, they don't know the model doesn't know whether it's right or wrong. So a human has to look at it and say, Oh, that makes sense, or that doesn't make sense, or I can't use that, or something. Um and they don't have that trial and error process without the human involved and uh, you know, so um so that that process of innovation and creativity at that level is something kind of uniquely human. Um, if we were to to somehow reorient it so that we create an algorithm that could could you know could mimic the human experience and do that kind of thing, maybe, but but we're a long way from that, based on what the technology I see today.
SPEAKER_01:I think the idea to create a neuro like neurolink and the idea of quantum computing, what you're describing is the human brain to some effectiveness, like probably fully utilized. It's probably somewhere in interconnectivity of human brains working together would be the quantum. That's how you'll solve it is through biological centered.
SPEAKER_00:Well, I I saw I saw a quote one time. Right, the uh yeah, I saw a quote one time that's saying he's saying that you know that we still don't understand. We think we do, but we still don't understand how the human brain works. And if even if we if we did, we might conclude that if it's that simple, we may not, you know, may not be a problem we're solving. You know.
SPEAKER_01:Well, we're very good, you know, we create our own problems, right, to solve. So positive and negative, you know, a creation and like from a human mind. Um it's a part of the environment, but it's also to me sometimes similar to like creation of life, right? It's it's not fully understood how it happens, there's like the physics of it, but why, right? And and and it just kind of something that's born or happens based on lots of things, genetics, things, code, you know, chemicals. And so until you can create and understand what that spark is and truly understand why it happens, then there's no way you're replicating that. And if you could, there's a random factor that's somewhere coded in us that there's that's still not accounted for.
SPEAKER_00:So no, exactly. I went to this lecture long ago, just as I was starting my career, it was that something, it was like the cognizance of a digital computer. And one of the things they were talking about was this idea that if you look back through time, people have tried to, you know, to they want a mental model for kind of how things work because it helps people and think they feel like they understand, right? What's going on? It's more comfortable for people. And so through time, they've often explained the the working of the human mind as whatever the most advanced technology of the time may be. I mean, there was a a time where they thought the human mind worked like uh a windmill, you know, or or something like the electric generator. And at that period of time of this lecture, they were trying to say it was like a digital computer. And of course, the computers have have become way more advanced since then. Now we're we're talking about, you know, different kinds of AI chips and stuff. But it's still we're still trying to use the model we have, the most advanced technology model we have to describe the brain. But but if if the pattern I'm describing continues 10 years from now, 20 years from now, we'll be using some new technology to describe the way the brain works. We still won't get it.
SPEAKER_01:Yeah, everything we have today has always been on Earth, right? Like there's a bunch of stuff we haven't discovered yet. All right, uh we'll see iPy could do a whole show on that. Uh but who do you want to get a hold of you and how do they do that? Um, what was that? It's shameless plug time for you. Um who do you want to get a hold of you? And uh, how do they do that?
SPEAKER_00:Um, yeah, the easiest way to get a hold of me is is through our company XareMail. So www.zare mail.com. Zare mail spelled like airmail with a Z on the front. We've got a toll free number run on the webpage, or you can reach me, Wilson at ZareMail.com. That it works. I'm on LinkedIn, you can connect, and I, you know, I'm top five percent elected LinkedIn, so I connect to a lot of people and I'm happy to do it. Um we're doing we're automating mail programs these days for for a lot of organizations that do not only marketing but do collections and and things of that nature. So if you have mailing or you have jobs you think might be well suited for mailing that we could help with, we're happy to work on that. And we'd love to hear more about that. Um and uh, you know, I'm uh as you can tell, I'm a professor and I'm uh you know, lifelong entrepreneur. So I'd be happy to talk about other business ideas and ways that we can help. I'm I'm always happy happy to have a discussion and share what I know. Um thank you by the way for coming on the let me add one other thing, if I could. I mean we have a we have a new product offering we're just rolling out called Speedy. It's www.zirmil.com slash speedy. It's a free download. It puts an icon on your desktop. If you want it, if you take a word dog or a PDF, you know, a letter of some kind, you drop it on the icon, it says, where do you want it to go? Even one letter, you type in an address, it turns into a letter and goes into mail and gets delivered to people. And the first two letters are free. So uh it's the only product in the world like that. It's free to use. I would encourage everybody to give it a try. You know, whether you're talking to your landlord or you want to send something to your grandma or you got a bill to pay. It's a great tool, and it's not gonna cost you anything to try.
SPEAKER_01:Thank you. That's that's that actually sounds like a fun little uh tool to try and play with and see what you can do with it. Thank you again for coming on, Wilson. Appreciate it.
SPEAKER_00:Well, thank you for the opportunity. Really appreciate it.
SPEAKER_01:It was everyone who made it this far in the show. Thank you for uh for being here. If you're the first time, I hope it's the first of many. Get out there, go cut a tie to whatever's holding you back from your success.