From Layoff to Leadership: Tom Conlon's Journey to a Prosperous Business

Have you ever felt the sting of job loss, the kind that throws you into the deep end, forcing you to swim or sink? That’s exactly where Tom Conlon, founder of North Street, found himself, and it's where our conversation begins. We navigate Tom’s inspiring leap from sudden unemployment to the helm of his own thriving business, dissecting the essence of adaptability and the power of self-agency. Along the way, we share the raw truths of entrepreneurship—things like the need to be a rainmaker and the critical nature of networking and sales—a reality often overshadowed by the passion of the work itself. This candid discussion isn't just about the struggle; it's a treasure trove of insights on how to turn professional lemons into a zesty lemonade stand of your own making.

When was the last time you revisited your business’s communication strategy? If you can't recall, you're in luck, because we're tackling this very subject in depth. Tom pulls back the curtain on my transition from website designer to business owner, while I weigh in with  real estate expertise, underlining the imperative of keeping your outreach fresh and customer-focused.

We're not just talking theory here—we’re offering up actionable strategies to streamline your operations, delegate like a pro, and play to your unique strengths. By the end of this dialogue, you'll have the tools to ensure your communication stands out in a crowded market and connects deeply with your clients' needs. Tune in for a masterclass in shaping a business that not only survives but thrives.

More info @ https://northstreetcreative.com/

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Transcript

Speaker 1: 0:01

Hey everybody, david McElwain, with another episode of Break your Golden Handcuffs. Today I'm excited to have with me the founder of North Street, tom Conlon. He boasts over 20 years of experience in design, web programming, copywriting, operations and people management. Before starting and establishing North Street, tom began his career in the consumer publishing industry, initially as a web designer and developer and later as a writer and editor for esteemed media outlets such as Wired Men's Journal, aol and Popular Science. Tom holds a degree in communications with a minor in history from Fordham University. He proudly participates in the New York City chapter of the Entrepreneurs Organization, where he previously chaired the Accelerator Program for Small Business. Super excited to have Tom on the show today because we're going to dig into small business and how small businesses can face some hurdles and some growth. Tom, welcome to the show.

Speaker 2: 0:53

Awesome. Thanks, david, glad to be here.

Speaker 1: 0:55

So I love reading the bio because I too started my world in advertising many, many years ago, and some of you might not know this, but I worked in the belly of the beast for a while and I love getting together with old East coast advertising people. So tell me, have you ever had that job where you felt like it was a set of golden handcuffs or a set of really bad rusted handcuffs you just couldn't leave?

Speaker 2: 1:23

You know, I think my situation is that I and I'm talking about a magazine job I was younger. I was younger in my career because I think I started North Street when I was in my 30s. But my experience was, I think, like a lot of other folks who maybe go out and start a new business, which is I had a job that I absolutely loved and I worked for a brand that I adored. I worked for a magazine called FHM. It was for him magazine. It was that category of lab magazines that were popular in the early 2000s, late 90s. I was the target market. I mean it was for men, 18 to 34. So I was the target market and so everything about that job was just right for me. I mean I loved.

Speaker 2: 2:09

I started as a web designer, developer, but then I became a writer and editor and I did what I had to do to get you know, you're on a magazine, you're working on a magazine. So you're, there's a literal drop dead deadline and to hit those deadlines I was doing weekend work, I was doing working late at night. I mean really busting, really busting my chops, because I I loved my job, I love my brand, I loved the people I worked with, and one day we were run by a British company. Our British overlords came in, called us into a conference room right around the holidays too. I was young in my career so I didn't really understand what was going on when corporate people call in all hands close to the holidays.

Speaker 1: 2:43

For those of you that don't know, there's going to be a pain. For those of you who don't know what Tom's getting ready to say, it's going to be a bad day.

Speaker 2: 2:50

It's not a good chat. It's not a good chat. They don't have the money gun, you see, or they're just shooting dollar bills at us. They closed our magazine, literally. I was out of a job. I mean, I had to stay on to help close some issues, but I'd been there for five years and overnight I had no job, and what struck me was not the lack of a job, it was that man. I was serious about this brand. I felt like, even though I had zero ownership stake, I really did feel like I had skin in the game, or I felt really invested and it could be taken away from me instantly by decision makers half a world away. And so that was a real. It was a wake up call, but it was also just like man. I don't know if finding another job quote unquote, normal job is my path forward or what's the right next step for me.

Speaker 1: 3:49

I tell you what I can really resonate with that. I have been in places where I was committed to the organization and I lost my job without it having nothing to do with my performance. And if you listen to this podcast, a lot you'll hear me say it's not if you lose your job, it's when and how will you lose your job? And a big part of this concept of breaking your golden handcuffs for me is having people get agency around some crucial elements of their life Economic agency, professional agency and personal agency and what I mean by that is really taking ownership for all elements of your life and not being subjected to the whims of other people's decision-making. So for me that meant I went, I started some businesses right and you did the same thing. So tell me, what was a Genesis for birth in North street?

Speaker 2: 4:47

Yeah, so, and, and something that you just made me think of, uh, we can come back to. It is something that I always get back to is someone said to me once nothing is forever Um, so kind of related to that like it's not when you're going to lose your job. If another is like nothing's forever, and so that goes for like how my business is today, how it was when I started, and what it'll be like in five years. I mean, the people, what we're doing, like everything is up, is up for change. The genesis for starting North Street was really, I mean, I came out of magazines as a freelance. I came out as a freelance writer. That's what I was doing while I was looking for jobs, uh, cause I'd been writing for for FHM. So you know, naturally, I just reached out to my network of other people.

Speaker 1: 5:29

I knew and I started.

Speaker 2: 5:30

I started as a freelance writer Now, at the same time, I'm trying to make a living right and so I had friends who remembered that I used to do websites and I designed logos. Friends and, like you know, business associates started asking me for this type of work and so I was doing both. For a bit. I was kind of just and again, this is all by myself I was writing articles for Wired, for Maxim, for Popular Science regularly, and there's some of those gigs were regular gigs, but on the other hand, I was doing things like creating logos or websites for friends. What I realized really quickly was and, david, you might have experience with this, but making a living, at least in the early 2000s. I think it's actually gotten worse, but in the early 2000s, as a freelance writer, making a living doing that was grueling. I could spend three days of my week just thinking about pitch ideas to then pitch to the various magazines that I knew. If I heard back which was, you know, that was a long shot. Anyway, if I heard back, they wanted to pay me nothing. I mean, I remember doing articles for a magazine I won't name them, but it was like it was a two-page article article. They wanted me to call in a bunch of products, organize a photo shoot, research and write something about all of the pieces and then handle the returns of all the pieces. And I think they wanted to pay me $500. And so it was like, just if I looked at the hourly rate, it was like I can't make a living doing it. And so I started to think more about well, wow, these logos and websites that I'm doing for people, they're paying me for them. And so I started to think more about, well, wow, these logos and websites that I'm doing for people, they're paying me for them and I can do them. And I can do a number of them, or at least bill enough per week that I can make a living here way less painfully and more effectively than I could as a freelance writer.

Speaker 2: 7:20

So after my magazine job I kind of straddled the line a bit between writing and doing this sort of creative design and development. But about two years in I was like, oh, wow, I'll just forget writing. If something comes up I'll say yes, but I'm going to go full on into this website design and development. And, honestly, people talk about the business plan that they wrote when they went to go sit down and start their business. I didn't do that. I don't have a business degree or a business background. I never created a business plan.

Speaker 2: 7:57

I just started working and at a certain point I got busy. I got good busy, I got people, I got more work than I could handle, but then I also got projects that were above my pay grade. I was a fairly decent designer and developer, but I wasn't an amazing designer and I wasn't an amazing developer, and so I started to kind of think at that point like, well, okay, maybe if I'm going to stay a freelancer and there's nothing wrong with that, this is before the gig economy. So it was. It wasn't as popular as it is now I'm like, okay, I'll be a freelancer, but there are going to be opportunities that I have to say no to and I'm going to hit a ceiling pretty quickly. Or maybe I can start bringing people in to do certain pieces, like build the website. Or maybe, if I have multiple logo projects, I can bring in a designer and oversee that designer.

Speaker 2: 8:48

And that was really the beginning of what became North Street. It started as me realizing that like, oh, I don't have to do every single thing. I can start calling in some help. And then, as soon as I called in some help, it just organically grew. Suddenly these contractors became part-time employees. And then I'd say 2014,. 2015 is when we had full-time employees. We had an office lease. I mean a couple of years in it transitioned from being a freelancer with some sort of partners to being a business with employees.

Speaker 1: 9:28

You know. I think this is really interesting because what I'm hearing you say is the same thing I've heard time and time again from every business owner I've talked to in almost every field, and I'm going to summarize it this way the business was born out of solving a problem. The problem that was born if I heard this correctly and please tell me where I'm wrong in this the problem is that you weren't making a living doing what you were doing. The marketplace was evolving and there were new skills that were needed that you had, so the problem was a solution of those things. And then from there it became successful, out of connections and work and performance, and from there it started to grow. And that's the same with real estate, it's the same with precious metals, or it's the same with anything that I've talked to.

Speaker 1: 10:19

In any industry, they always have this what's the problem I'm solving? How do I improve it? How do I help the marketplace perform? And that's I love hearing these stories time and again, because you never quite know the twist it's going to take, and they're all individual and unique, but they're so patternistic is the wrong way to say it. There's so much a pattern, right, and so, as a listener. We talk often about alternative investing strategies, but really this conversation is a strategic thought process conversation around either your agency of your life agency, of your business agency, of your investing. It's the same challenge each and every time. So I'm just curious, having been in business now for a while and slept a couple nights and learned some things, if you're at the beginning of this journey and you're looking back, what advice would you give yourself about starting a new business now that you didn't know then?

Speaker 2: 11:29

Yeah, there's a lot when you're starting out, it's all about making ends meet. You're a solo, so you are just doing everything yourself. That I've realized over the years. One is a lot of folks start their new. A lot of folks start a business because they are working a corporate job and they sort of like they get they, they, they take, they leave to become a consultant and their former employer is like their first client, right? Or they leave because they've got a couple of freelance projects that are going really well and they're like oh yeah, this is great, I'm going to make the jump.

Speaker 2: 12:07

One thing I wish I had thought of and I would tell anybody to think about this, is realize that when you start a business, it's not just about the work you do. In fact, that's a fraction of what you're going to be spending your time on. So for me, I was a website designer and developer. I thought, okay, great, well. And for me I was a website designer and developer, I thought, okay, great, well, I'll start this business and I'll just be designing websites and logos all day. What I didn't consider was well, first of all, where is my next project coming from? And I think that's the big thing, right. It's like if you start a consultancy and your former employer is your big client well, back to my point before before, nothing is forever, that that relationship is going to end or adapt or evolve somehow, either beneficially or not for you. So you have to be prepared Like what is? You can't just I couldn't just spend eight hours a day building websites and creating logos. I needed to go out and get new business.

Speaker 2: 13:01

So I'd say the first thing is realize that if you are going to go start your own business that is part of your job. You are the rainmaker. Even if it's a team of one you're going to have to go out and get the new business. So ask yourself where that's going to come from and what you're going to do to get there. Because I remember sitting in my office one day we had, I think, three proposals out.

Speaker 2: 13:26

This is years ago. We had three proposals out and I was like I felt really good about all of them and then none of them came in and I just remember thinking like my God, I don't even know where my next, I'm not even having conversations that are like early conversations I want a deposit on a project next week and like I'm not even having those initial conversations. So I need to start. I need to start doing that, and then that was that led me down a whole path of like figuring out how to network and what all that was. But that's the first one I'd say is you know, just identify that you're going to need to to be a salesperson as much as you are the technician or the producer, right?

Speaker 1: 14:07

Man, I can't agree with you more. If I can pile in on this yeah, when I left corporate.

Speaker 1: 14:13

America and I started my residential real estate business.

Speaker 1: 14:17

I went through the real estate training and I thought I'm just going to handle the transactions and be a dealmaker, which is what I had done in the past, and the reality was that, as a real estate professional, what I had to do was build a marketing engine, and that marketing engine I didn't want to do. I love doing direct, face-to-face sales. I hate doing one-to-many marketing, face-to-face sales. I hate doing one-to-many marketing and I didn't understand what part of the job was going to be, and so that took a long time for me to get my real estate business really growing to where I wanted it to be, because I was avoided of the number one most important thing and people remember I ran sales forces across the country. I know that the pipeline is the most important thing you have, and what Tom's saying is if you don't have a pipeline of growth and new business and you don't understand that sales is everybody's role, it will be challenging. I just think that's so accurate and it's something that people ignore left and right.

Speaker 2: 15:21

Yeah, and that's a big piece of it, but there's also a hundred percent. But then there's other things. Right, it's like for me, I'm at my core, I'm a creative person and so running a business requires payroll taxes, reconciling your books, making sure that, I mean. I remember I used to get envelopes in the mail from the IRS, new York state, and I'm like I don't even know what this is. You know, is this, is this a bill? Is this a summons? Like am I in trouble or is this a good thing?

Speaker 2: 15:54

And like, not only is my brain not wired to like just work that way, but like I had other stuff to do, Like I had to do the marketing and sales and I had to do the work. And so one of the things I did early on, which I'm very grateful for and I would recommend anybody do, is, like you know, make a list of those kind of like administrative tasks, um, or administrative jobs. Some of them aren't tasks, some of them are functions, um and like there's this, there's this really fun matrix that, um, there's this, there's this business, um, there's this really fun matrix that there's this business operations platform called the Entrepreneurial Operating System, and one of their tools is called Delegate and Elevate, and it's this really interesting matrix where you say, you, as an individual list, what are the things I like and I'm good at, what are the things I love and I'm good at, what are the things that I'm good at but I don't like and what are the things that I'm not good?

Speaker 2: 16:44

at and I hate. And it's like list all of the things that you do on a daily basis. Put those in that matrix and the idea is, those two bottom ones, the things that I'm good at but I don't like to do, and the things that I don't like to do and I'm also bad at, those should be the things that are just you. Just get rid of those, delegate those. Find somebody else to do those, even if you are an individual business, because it'll save you time and it'll save you energy and headache and stress in the long run. And you got to remember that that's costly you, you, you're, you know you're that's costly, even though you know you don't feel it, maybe on like the, the in your bank account, like that's time that you could be spent being more proactive or just more effective in other parts of your business. So I think the big, the big point is like figure out, like the tasks that you really shouldn't be doing in your business and find someone or some people to help you do them.

Speaker 1: 18:06

Yeah, I think that's such a big part of it and there's a lot in the real estate world that a lot of our listeners have done looking at how do you create VAs, how do you create offshore support staff and it's such a good point of it. And it's the same with everything in our lives. If we can distill down where our value lies and we can delegate the rest of it, our life gets better and we get more agency. I'll never forget I was mowing my yard and it took me two hours one day and the grass had grown really long and it was a pretty big yard and I figured out that at the time I was making about $500 an hour working and I just spent $1,000 to mow my own yard.

Speaker 1: 18:50

Yes, I had a company employed the next week and it was a real simple question Is my free time worth to me, what it's worth to my employer and what I came away with was it's worth more? And it's that same kind of question of what can you get rid of in your life that improves it? And my guess is that that's part of the problem. You solve at North Street is creating that. What can I get rid of? That's not my skillset, because I am not a creative. I'm a unique problem solver, but I am not a designer, and so that makes me wonder for the listeners on here. You guys do all this implementation and creation. What kind of clients do you have? Who do you work with? What kind of people should be thinking about? Oh, they might solve a problem for me sure.

Speaker 2: 19:50

So so what we do, the what of what we do, is you know it's, it's branding, so that can be visual branding. You know the look and feel of something. It can be the verbal branding, like the way a brand talks about itself or positions itself, even what it's named. And then we do that strategy and then we do the execution piece, which is okay. Now that we've got the visual identity and the tone of voice and the messaging, let's put that on a website, let's put that in an investor deck, let's put that in social media templates, et cetera. An investor deck, let's put that on in social media templates, et cetera.

Speaker 2: 20:26

So we do the strategy and the execution of who we do it for is fairly focused, I mean, and it's gotten a lot more focused over the years. So we really like our sweet spot is institutional financial services, so investment banks, hedge funds, private equity professional services, like you know, equity Professional services, like you know large law firms, large accounting firms. We also work in healthcare, kind of like large hospital systems or healthcare tech startups, and real estate. Actually, what we don't do is, you know, we don't do e-commerce websites that are selling sneakers. We don't do media buying like I'm not going to buy you a billboard on the side of the highway. So that's what we do for our clients and that's who our clients are.

Speaker 1: 21:22

Yeah, so you mentioned the real estate in there and obviously we got a lot of real estate listeners. What kind of problems have you solved for real estate companies in the past that might be worth listening about?

Speaker 2: 21:33

Yeah, I think the big, honestly the biggest thing that we if I zoomed out and I looked at the problems or issues that all of my clients have are issues that all of my clients have One of the biggest issues I always see is that a firm's internal story and processes and maturity and people and ways of doing business have changed and evolved and innovated, right Like there's been innovation at the company. Problem is it's all. It's all locked internally. No one, they're not. That's not how they're talking about themselves.

Speaker 2: 22:14

So you see their website and it's like it's from four years ago and it does not describe.

Speaker 2: 22:21

It doesn't describe this current version of this business. It describes a version of the business that's five years old and, um, the danger there is that like not only is it like out of date and out of touch, but it's potentially like detrimental, right, it's a. There are certain times there that we've run into certain clients and certain projects where it almost be better if they had no website than the website that they currently have because it's so old. So the big problem we solve for really is that the external facing, messaging and brand need to keep pace with the innovation and evolution that is happening within the business, and then it should also set a marker ahead, more of an aspirational one that's like okay, well, this is where we were, this is where we are and this is where we're going. This is where we're going. I think that's probably universally the biggest challenge that we solve for. Another one, of course, is startups, but it's just a that's a different version, right, Like you are literally starting from.

Speaker 1: 23:21

Nothing.

Speaker 2: 23:22

You're starting from nothing, you're starting from nothing.

Speaker 1: 23:26

So what I'm hearing is it goes back to that earlier mantra that nothing stays the same forever, and what you're running into is stale communication to the end user, to the customer and as a business. If your communication gets stale, the customers atrophy and they don't return, and that's a death spiral.

Speaker 2: 23:48

So if you're a business owner, right, it's a total death spiral.

Speaker 1: 23:53

And if you're a business owner and you're thinking about this, you're like, huh, I haven't touched this in five years. What questions should you ask yourself to see if your communication message is stale or you're starting to hit that death spiral from your chair? What are some questions that say, oh, that guy needs to pay attention to what he's doing, or that woman's missing the boat here. Are there some questions people ask themselves that are real good indicators of this.

Speaker 2: 24:19

Yeah, I mean. The first is just look at your communications materials now. So for most people that's a website. It's like is this even accurate? That's number one. Does this even describe what you do? Is it missing big pieces of your business that you do now since the website was updated? So that's one it's like. Is it even up to date?

Speaker 2: 24:41

The second is I mean it's really like look at yourself in the context of your competitors, and I mean like your direct competitors, right, like who are the people when your customer has a variety of choices in front of them and you're one of them. Do you stand out? Do you look special? Like it's not even looking special. It's like does your messaging, um, does your messaging connect with me, the buyer? Um, because what you don't want to be is you don't want to be.

Speaker 2: 25:15

You know, one company just drowned out in a sea of sameness, right, um, and I think related to that and another big piece is I don't know if it was ever in vogue, but it was definitely a trend where or maybe it's just where people get this wrong, is that a lot of communication? I see marketing communication or brand communication misses the mark because it's talking about it's. It's if, if a company or agency is leading with who they are, what they do, why they're so great, what they're missing is actually connecting to the end user, buyer, and like their motivations for buying right. Like I don't, I don't, I don't need you know when. So, for example, like North Street, like we, we, we.

Speaker 2: 26:07

Basically what we do is we help companies bridge that gap between, like where their, where their marketing and messaging was, or where it is externally, and where the company is internally in terms of its, in terms of its evolution. So I can speak to that pain point right, like I can speak very specifically to that pain point before I talk about here's how many employees we have, here's how many offices we have, here's how long we've been in business, here's some examples of our work, because, like, that's stuff that any agency like mine would have. And so I think a lot of folks, regardless of the industry, are just missing a really big opportunity, which is, before you talk about yourself and how wonderful you are, talk about what keeps your client or your prospective buyer up at night and speak to those issues and how your experience and services may be a fit for that.

Speaker 1: 27:07

I love that. So we're kind of running down to the end of the program and so I'd love to ask a couple of other questions. I ask a lot, which is, you know we talked about pieces of advice you wish you had or the wish you'd learned, and if you're going to distill the best piece of advice you could give to yourself from 10 years ago, what would it be?

Speaker 2: 27:31

I think it would be, I think it really would be. I'd sit myself down and say Tom, you need to delegate, you cannot do the 100 things on your list. So, and I think it's, is it Dan Sullivan, the strategic coach, who has that like? One unique ability, your one unique ability.

Speaker 2: 27:49

It's like identify what you're really good at. You know, and imagine you're the highest paid person in this company. Like what do I want you doing and what do I not want you doing? I don't want you doing mailing checks and checking the mailbox for things, so, so delegate would be. Delegate to people who want to do the things you don't want to do and are going to be better at them for you, because it will be to your point about mowing the lawn. It will be a money saver in the end.

Speaker 1: 28:15

Yes, every time. I've really enjoyed talking with this, Tom. If people want to learn more, how do they contact you?

Speaker 2: 28:22

Yeah, thanks, david. This has been great. Our website is northstreetcreativecom. I'm on LinkedIn as Thomas-Conlon. We're on Instagram as North Street, so find us. I'd love to talk Awesome.

Speaker 1: 28:39

Well, thanks so much for joining us, tom. It's been a pleasure. You've been listening to another episode of Break your Golden Handcuffs and, if you like us, hit the subscribe button and you'll get notified every time we publish an episode. We publish them two times a week. Look forward to hearing from you as listeners and please reach out with questions, thoughts or comments. All of us love to hear it. Thanks for listening and have a wonderful day.