Darren Jamieson: On this week’s episode of The Engaging Marketeer, I am speaking with Chris O’Shea, a marketing expert from Halifax, but not Halifax in Yorkshire, Halifax in Canada. I am going to be talking to Chris about marketing, websites, SEO, branding, and how you market yourself as different in a competitive landscape.
He is in Canada. It’s very early in the morning for him, so let’s see quite how lively he is at this stage of the day. I feel like I’m really looking up at you now, because I’ve got a monitor up on the screen up there. Your camera’s really low, so it is properly like I’m looking up at you.
Chris O’Shea:
I’ll look down and we’ll have perfect eye contact. No problem.
Darren Jamieson:
It works. What can I say? It just works.
When we’re editing this together, we really should put your video on top of mine so it properly works like this, not side by side.
Chris O’Shea:
Let’s go with up and down. It’s going to be weird.
Pleasure to connect and meet you in person, virtually. Thank you very much.
Darren Jamieson:
I was just looking you up earlier and it said you were in Halifax. I thought, Yorkshire, that’s about an hour and a half away from me. Not bad. But, no, different Halifax.
Chris O’Shea:
Yeah, absolutely. It’s a bit of a trek across the pond. Just a tad. I have never been to the UK. I would love to come, but I have not had the opportunity to cross the pond. I just got back from Barbados, so that’s as close as I can get, because I was driving on the wrong side of the road, as far as North Americans are concerned.
Darren Jamieson:
I put something on LinkedIn last week about bollards and a security tag outside your car, pressing the code in, being on the wrong side of the road. Somebody from America commented, “Typical British. You drive on the wrong side of the road, and then you blame everybody else for it.”
So I thought I’m going to come back with something smart. I searched why we drive on the left-hand side of the road in the UK.
Chris O’Shea:
Oh, please do tell.
Darren Jamieson:
You’re going to love this. It’s from ancient Roman times. If you go on the left side of the road so that your sword hand is free for anybody oncoming that tries to attack you, you can hit them with your sword.
Chris O’Shea:
Little stabby stabby.
Darren Jamieson:
And a lot of Europe drives on the right side of the road, or as I like to call it, the wrong side. That’s because of Napoleon. He conquered most of Europe. He was left-handed, so he wanted to go on the right side so that he could attack people with his left hand.
Chris O’Shea:
Exactly. Parry and thrust.
Darren Jamieson:
There you go.
Chris O’Shea:
I love it. I think that’s fantastic. I too am a southpaw. So I would be there with Napoleon. I’m all kinds of screwed up when it comes to these things. I’m a very oddball.
In the Canadian way of playing ice hockey, I actually shoot right, which is the opposite of what I should do because I’m left-handed. Same with golf. I’m a righty. I’m an enigma.
Darren Jamieson:
When I play rounders in the UK, or baseball as you guys call it, I can hit it left or right.
Chris O’Shea:
Oh, so you’re in high demand then. Switch hitter.
Darren Jamieson:
I’m equally rubbish at both, but yes.
We seem to have started the podcast, just as we are.
Chris O’Shea:
Amazing. It’s gold.
Darren Jamieson:
I was put in touch with you by one of my former guests, Al Pepper. Al, who is a legend over here in BNI. I’ve seen Al speak live. He’s phenomenal. Massive NFL fan as well.
Chris O’Shea:
Funny story. I had the briefest of American football, Canadian football careers, and that’s where Al and I met. We were at the same university.
I wasn’t a football player in high school, but I always loved the game and wanted to try it. I had chosen my university and I literally harassed the head football coach to give me a chance. He was like, “Fine, stop bothering me. Come try out.”
So I spent two solid weeks trying to play football with large men who were trying to hurt me very badly. I wound up hurting my hamstring very badly, and I kind of hung it up. But that’s where Al and I connected. He was on that same squad.
I bailed early because I knew that was a bad idea. Then I had the smart idea of playing rugby. So that was phase two for me.
Darren Jamieson:
A smart idea, you think, playing rugby after football?
Chris O’Shea:
Not at all. I have the wounds to account for it.
That rugby lasted longer, but equally tragic. Our university had a rugby programme. My rugby coach was a Scottish guy, Ed Carty. He’s still coaching rugby well into his 80s. He was my philosophy professor. Fantastic human.
I picked up the oval ball, knew nothing of the game other than what I had seen somewhere, and we wound up having a hell of a career. I never lost a match in my university career. To be fair, I’m Division Two at best.
Then I played senior men’s rugby here in Nova Scotia with a team called Cole Harbour. Cole Harbour produced some pretty stellar Canadian talent. One of my scrum-halves was Morgan Williams, whose father’s from Wales, but he grew up with the game. Morgan played four Rugby World Cup tournaments for Canada.
I made the tragic error of calling it a beer sport. I would practise, play, then drink beer. Morgan would practise, play, get physio, then go to the gym. Two different paths.
I injured my knee pretty heavily and I wasn’t getting paid, so I thought, you know what, I’m good. I hung my boots up around 97 or 98, with a couple of concussions, a couple of shoulder separations, a few fractures. It is what it is.
Darren Jamieson:
I was distracted then. An alert sound popped up and I don’t know whether it was you or me. It shouldn’t have been me, because I deactivate everything.
Chris O’Shea:
If I’m pinging, let me close all of this. Microsoft has a habit of undoing deactivation sounds.
Darren Jamieson:
Why would you possibly want to not have pinging throughout your day? This very important random email is somebody giving you a thumbs up on a WhatsApp message you sent five weeks ago.
Chris O’Shea:
Story of our lives.
Darren Jamieson:
While you were at university trying to start an NFL career that didn’t last very long, and a rugby career that did, what were you actually at university for?
Chris O’Shea:
There was no rugby scholarship in my future. I took a winding road but wound up in the business programme at St. Francis Xavier University in Antigonish, Nova Scotia. Beautiful spot, great campus. Best four years of my life, enjoying life, learning some things.
My graduating year was probably one of the worst years of the 20th century to graduate and try to find a job. It was a struggle. I started with sales jobs. I tried a few different things. Nothing stuck.
A good friend of mine, one of my roommates, went back to school and went into tech. There was a nine month immersive tech programme that could get you into programming. I was like, “Hell yeah.” I wasn’t going anywhere with what I had.
I went into tech. I graduated from that programme and it was Y2K. If you were in a tech role of any kind, there was a job for you somewhere.
My fiancée at the time, who is now my wife, and I decided to go across the border. I could have gotten a job in San Diego, Houston, Boston. I wound up working with a small SAP web development company in Boca Raton, Florida. We packed up from the cold Arctic of Canada and moved to sunny South Florida. Quite a difference.
We spent six years down there. It was a unique time in tech. We went through the dot com bust, the whole nine yards. I learned half a dozen programming languages that nobody wants me to program in anymore, which is a very good idea.
It set me up for future success. I came back, worked in tech consulting in Nova Scotia, then transitioned into marketing. I was at a marketing agency for a couple of years, and now I’m with the Business Development Bank of Canada.
It’s a stellar organisation. We support entrepreneurs across Canada. There’s a functional financial institution side, and then there’s advisory services, which is where I live. I support clients with whatever they need to do. I work in growth. Someone says they want to grow their small business, I’m in. Let’s go. Sales, marketing, digital technology, all of it. That backstory feeds where I’m at today.
We touch every type of industry you can think of. Everyone who works here is in for the mandate, which is to help small business succeed. Not too dissimilar to what you’re doing with BNI. We have a chapter in Halifax. I’m familiar with what it does.
It’s a forward-thinking organisation, trying to get companies living in the world we live in right now, not 10 years ago. Many still want to live in the 10 year world, and we try to help them do that.
Darren Jamieson:
There are a lot of businesses that keep trying to market like it was the 1990s or early 2000s and think that stuff works. Older style businesses like golf clubs keep trying the same thing and wonder why membership is dwindling.
When you were working in web design in the early 2000s in Boca Raton, could you have foreseen how the digital world would have changed in the 20 odd years since then?
Chris O’Shea:
Oh my god, no. Not even.
We were coding HTML 4 straight up. Then we would use ASP if you were doing something on the Microsoft side. Java as middleware, depending on what we were building. We did a lot of tax integrations, SAP and tax integrations, ABAP programming. Nobody wants me to do that anymore.
WordPress and Shopify type tools were a revelation. I don’t have to code from line one, this is fantastic. To see it mature into enterprise level tooling is huge. Back then everything was hands-on and manual.
I’m a C++ programmer at best. When you’re in an ecosystem with A+ talent and they just know what to do, it’s eye-opening. I’ve seen the same thing in finance with people who algorithmically think that way. I’m not even that guy.
Marketing is more my speed. Being out of my element but learning, drinking through a fire hose, it’s wondrous to see how those things get built.
Progress to where we are with gen AI tools now, I had no crystal ball for that. I’m trying to stay on the front foot and keep up with what’s going on around me. That background serves me well. Do I comprehend it all? No. Can I talk the talk enough to understand what’s going on? Absolutely.
Now here I am 20 years later trying to help small businesses wrap their minds around it, and they are not in that space at all.
Darren Jamieson:
As you specialise in helping small businesses, one problem I’ve found is that as technology got easier, WordPress and Wix came out, and anybody with no experience can say, “I’m a web designer.” They can charge people to build a Wix website that the business could do themselves, but other people charge them for it.
Do you think that’s damaging small businesses, that the barrier to entry is non-existent now?
Chris O’Shea:
I posted last week how many times I have seen entrepreneurs sold a bill of goods. Maybe it was good, maybe it wasn’t, but they have no yardstick to measure. Is this good? Is this not good? Someone says it’s $10,000 or £10,000. What does that mean?
My broad statement was, if you own a business you need to know how this stuff works. Do you need to code a website? Absolutely not. But you need to understand the mechanisms. Otherwise someone can hang their shingle out, say they’re a web designer, use a templatized Wix site, copy paste, and that’s a problem.
Has the industry done itself a disservice by allowing that? A little bit. Some of it is not nefarious. Some people see an opportunity and try to learn as they go. Some of that works, some doesn’t. My job is to come behind it and point out the elephants in the room. That’s not good, why did you do that, and so on.
I am the worst designer in the history of designers, so I have no commentary.
Darren Jamieson:
I bet you’re not.
Chris O’Shea:
I would challenge your statement, but I’ll take it.
For me, the goal is this. If you are going to build a website, what do you want it to do? What is the outcome? And when it doesn’t do what you want, why?
Is it the designer or developer’s fault? Or do you not know what to do with it? Do you know what SEO and meta tags are? Do you know what an alt tag is?
If they don’t understand and they expect an outcome, I’m like, time out. Not how this works. You cannot expect an outcome from something you do not understand.
For most companies, they don’t have the expertise. They expect a third party to bring expertise. Maybe they do, maybe they don’t. It’s a mixed bag.
At the end of the day, if it’s your website and it’s not doing what you want, that is a learning opportunity. Best case scenario, if it isn’t working, ask ChatGPT what’s going on. Maybe it is right, maybe it isn’t, but it’s at least something you can get your teeth into.
This is the responsibility I want business owners to take advantage of. Ownership. And they don’t even own the domain half the time.
Darren Jamieson:
We had that today. Their web designer owned the domain, not them.
Chris O’Shea:
Exactly. You don’t know what you don’t know. I’m not expecting entrepreneurs to become web developers after talking to me, but be aware you need access to these things.
If I’m a chiropractor, I’m good at chiropractic. I have no idea what SEO is. Totally fair. But if you want to scale and grow, this becomes part of your job, as challenging as that might be.
Darren Jamieson:
The most frustrating thing is people already have websites, or want SEO audits, but if the website is rubbish, there is no amount of SEO or traffic you can send to it that makes it work.
Loads of people have a website built by hobby, son-in-law, or Wix, and it’s a crap website, but they pay for Facebook ads, Google ads, or SEO. They ask why they are not getting traffic. Traffic is not the problem. Nobody is going to trust you. Sometimes it’s high value services like financial advisers, estate planners. They expect to look after people’s money, but the site looks like it was built by a four-year-old. That really winds me up.
Chris O’Shea:
I completely agree. They carry on thinking more ads will fix it. None of that is true.
Even worse, there is so much data available and they never look at it. Google Analytics, never looked. Heat mapping, don’t know what that is. Stuff that would tell them, move your form up the page.
You land on a site and there’s a massive photograph. You have to scroll three times to find what you are looking at.
I had a client with a responsive, well-built website as far as he was concerned. I asked them to do this: you are the customer, find the Contact Us button. Thumb, thumb, thumb, thumb. Oh, there it is. Does that seem like a good idea?
That is the value we bring. We have been punched in the face enough times to know how it is supposed to work. You thought you got something amazing, you got something that doesn’t convert.
You have to look at it through the lens of the customer. The lightbulbs come on quickly when you do.
SEO is such a long play. Competitors, keywords, meta tags, now AEO and GEO on top. I always say, take it back to the customer and work forward. If customers ask for something all the time, create a page for it.
Business owners need ownership. If the website is the conversion path, you have to own it. It is not the web developer’s conversion path.
Darren Jamieson:
That’s why we stopped doing ranking reports years ago. Where you rank is irrelevant. What matters is how many people enquire, whether they are the right kind of enquiries, who buys, whether they buy again. That’s what matters. How much money are you making?
Chris O’Shea:
Business results and customers. That’s it.
Now with AI, I’m watching what people are seeing from AI search versus traditional Google. Google is still much bigger, but it will change.
We are throwing all this on top of what entrepreneurs already deal with. It’s a hard ask. When they have someone they can trust who can translate, here’s what the web company said, here’s what it means, here’s the action plan, off you go, that helps.
When they do not have that and still expect an outcome, that is tough.
Darren Jamieson:
You wrote down in correspondence before this interview about boring marketing for B2B businesses.
Some clients are exciting, content is easy. Others are a stretch. What is your view on boring marketing for B2B clients?
Chris O’Shea:
I have a lot of opinions.
Marketing in 2025 is very difficult for many reasons. One reason is that most brands are boring. They are not saying anything their core customer would recognise as interesting, educational, helpful, funny, cute, whatever.
I do not expect a funeral home to be funny. That’s not the goal, although I have seen some that are.
They need to understand what will get someone interested in what they do. If I need a funeral home, who do I choose? How do I decide?
In B2B, there are commercial and industrial companies that still have to get a human being to interact with them, even if that person is not a customer today.
It is reverse engineering the customer.
Who is the director of procurement making the decision? Word of mouth is great, but short of that, what else have you got?
How do we make sure we are relevant and interesting to that buyer so they understand who we are, what we do, why we are different?
Companies are good at the whats and the hows. They are terrible at the whys. What we do, they can talk all day. How we do it, all day. Why we do it, they cannot.
Standing apart is everything. Do not say the same thing everyone else says and expect a different outcome. Vanilla. Vanilla. Vanilla. How about we be chocolate?
If you are in an oversubscribed business and the phone rings, I still want you to build the flywheel. If the phone ever stops ringing, you do not want to start from zero.
Darren Jamieson:
There are brands in the UK you would consider boring brands, but they inject personality. Aldi is one. In the UK they start wars with other supermarkets.
How far should a company go if they want to stand out, but not go too far so people think they cannot be trusted as serious in business?
Chris O’Shea:
That is a risk. In B2B, risk aversion is everywhere. We have to be serious, professional, structured.
A good example is Ryan Reynolds and Maximum Effort. There was a commercial for a 3PL company moving goods, very boring business. The thesis of the ad was “What’s a ton? We move a ton of stuff. What’s a ton?” They were talking about tons and buttloads. Awesome. They have personality on top of serious delivery.
That is what I want B2B companies thinking about. Do they have to do that? No. Do they have to make a mark, take a stand, be bolder? Yes.
Darren Jamieson:
I hear objections all the time: “I don’t need networking or SEO, I get all my business from word of mouth.” Who knows what happens when that stops?
Chris O’Shea:
Exactly. Two problems.
There is a tsunami of entrepreneurs in Canada hitting a point where they want to sell. They go to the market and the market says, how do you get business? Word of mouth. What do you do for marketing? Nothing. What money do you spend on sales? Nothing. You want $26 million? No.
They are getting hit square between the eyes because they have not built the fundamentals. I love the conversation where someone says they do not need marketing because word of mouth is strong. What happens if someone has a bad experience, you get poor reviews, someone says you are a jerk, AI makes up lies about you, and word of mouth goes? Now what?
The fundamentals do not change. Build the machine.
The hardest thing for entrepreneurs is saying no. I want to say no all the time because I am so busy. I want the phone ringing off the hook. See you in six months. Demand creation.
When the phone stops ringing and you have not built a demand engine, you have nothing. Build the flywheel.
Darren Jamieson:
We have bought businesses and seen this. They have word of mouth, but it is that person. When they sell, there is no pipeline, no sales team, no process.
On the other side, they want all the money.
Chris O’Shea:
Everybody thinks their business is worth a million dollars. There is retirement funding built into that model. Technology is a poster child. Website built by the nephew 17 years ago. They still want all the money.
In Canada it will be a buyer market for businesses for the foreseeable future.
Darren Jamieson:
If I’m a boring business owner, say a stationery seller or an accountant, and I want to stand out, how do I do that?
Chris O’Shea:
Brand strategy has to live with who you are. I do not want someone trying to be funny if they are not funny.
If you are a serious professional who knows what you do to the nth degree, present that. Not an expert, the expert. Decide what personality the brand has, then make everything reflective of that.
You cannot be cute one day and serious the next. It confuses the customer.
Standing apart matters. You cannot say the same thing and expect a different outcome.
If it is a serious professional, I want them on every podcast about that profession. Build the brand in a way that is true to who you are.
Darren Jamieson:
You also mentioned creating demand.
We have The Apprentice. They do market research after they’ve built the product, and it is the wrong way round for good TV.
How do you create demand for your product when you are already in business, instead of doing it the wrong way round?
Chris O’Shea:
Very few companies invest enough in product market fit, market research, understanding.
The customer is everything. Not just demographics, but what makes them tick. If you do not know that, you cannot influence behaviour.
You can create demand. You cannot manufacture it. If it does not exist, it does not exist.
A lot of companies talk about total addressable market. That matters to IBM and Microsoft. For a small company it means nothing.
Understand why the market is interested in what you offer, if it is at all. Then what will you put in front of them that gets them thinking about it?
Darren Jamieson:
That reminds me of The Simpsons when Marge went to a franchise fair and Disco Stu was picking selective stats about disco going up 600%.
Chris O’Shea:
Yes, there is a lot of disco out there.
Darren Jamieson:
If someone wants to find you, speak to you, hear you speak, what is the best way?
Chris O’Shea:
I put content on LinkedIn with some regularity. LinkedIn is probably a great place to start. Not because I’m trying to get views, but because it is my thesis. I have to get it out of my head.
I have been in the small business space, including marketing, for around 15 years. You see patterns. You stay current on trends. The way we have done things is not the way we are going to do things in the future. That shift could be next week or 2028, but it is coming.
My ideal client is a small business in Canada. I do not do side consulting. I work with Canadian entrepreneurs based on my current role.
It is a tough time for Canadian companies dealing with the American market. Every day is a different day. Some are good days, some are really not.
Darren Jamieson:
That was a long-winded answer and a really upbeat message to end on.
Chris O’Shea:
All the positivity. We will bring in some music. Benny Hill theme or something.
Darren Jamieson:
I will put links to your LinkedIn and YouTube in the show notes so people can scroll down, click, follow Chris, and watch his videos. Watch him walk his dog. Think of his poor dog.
Chris O’Shea:
The dog is either an expert in marketing by now or looking for a new home.
Darren Jamieson:
Chris, thank you very much for being a guest on the podcast.
Chris O’Shea:
My absolute pleasure. This was amazing.
Most businesses don’t struggle because they’re bad at what they do. They struggle because nobody finds them interesting enough to care!
Today’s episode of The Engaging Marketeer is all about what actually makes a business stand out when everyone sounds the same, looks the same and says the same safe things.
From why so much marketing feels painfully boring, to how trust is really built and why relying on word of mouth alone is a dangerous game, this one pulls apart a lot of assumptions people have come to rely on.
The full episode with Canadian marketing expert Chris O’Shea is now available to stream on all platforms.
More about Chris:
Chris O’Shea is a marketing and business advisor based in Canada, working closely with small and growing businesses to help them stand out, build demand, and grow sustainably.
With a background spanning tech, marketing, and advisory work, Chris focuses on cutting through noise, challenging safe thinking, and helping business owners understand what actually drives attention, trust, and long-term value. His work sits at the intersection of strategy, marketing, and real-world business fundamentals, with a strong emphasis on clarity, relevance, and human connection.
Chris regularly shares his thinking through LinkedIn content and public speaking, offering practical insight for business owners navigating change in an increasingly competitive and fast-moving landscape.
You can connect with Chris here:
LinkedIn: https://www.linkedin.com/in/chrisoshea11/
YouTube: https://www.youtube.com/@ChrisOShea
About your host:
Darren has worked within digital marketing since the last century, and was the first in-house web designer for video games retailer GAME in the UK, known as Electronics Boutique in the States. After co-founding his own agency, Engage Web, in 2009, Darren has worked with clients around the world, including Australia, Canada and the USA.
iTunes: https://podcasts.apple.com/gb/podcast/engaging-marketeer/id1612454837
LinkedIn: https://www.linkedin.com/in/darrenjamieson/
Engaging Marketeer: https://engagingmarketeer.com
Engage Web: https://www.engageweb.co.uk
