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Investment Banking, Entrepreneurship, And The Future Of Work, With Greg Martin

Are we heading back into office work, or will businesses continue the road of hybrid and remote work? These are what companies are thinking after COVID. In this episode, J.R. Lowry is joined by the Managing Director at Origin Merchant Partners, Greg Martin. Greg takes us into his entrepreneurial endeavor. Entering the world of work, he provides insights about the future of work after the pandemic. Greg also shares his take on kids entering university. Greg brings a bucket of golden nuggets, so jump into today’s conversation!

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit A full written transcript of this episode is also available at

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Investment Banking, Entrepreneurship, And The Future Of Work, With Greg Martin

Managing Director With Origin Merchant Partners

This show is brought to you by PathWise is dedicated to helping you be the best professional you can be, providing a mix of career and leadership coaching, courses, content, and community. Basic membership is free, so what are you waiting for? Visit PathWise and join. My guest is Greg Martin. Greg is an investment banker, angel investor, entrepreneur, and regular host of a career podcast about the world of work and business. His day job involves advising corporate clients and business owners as a Managing Director with Origin Merchant Partners, which is focused on providing advice around mergers and acquisitions, strategy, and capital raising for some of Canada’s best companies.

Greg’s particular focus is on the food consumer technology and insurance sectors. Greg was also a Cofounder of Farm’r Prepared Meals, a restaurant and office catering business that transformed into an eCommerce meal delivery company post-pandemic. His earlier career was also in investment banking, with stints at several firms along the way. He earned his Bachelor’s degree in Business Administration from the Lazaridis School of Business and Economics at Wilfrid Laurier University. He lives in the Toronto area.


Greg, welcome. Thanks for joining me.

Thanks for having me.

Let’s start with your day job. I know you’ve got a podcast that you do on the side. We’ll get to that a little bit later. Tell us a little bit about what your primary job is.

I am what we call an investment banker, but I’m focused on the advisory side. My typical day job is helping companies. Typically, that’s owners and founders when they want to exit their business. First and foremost, I am helping them with that, conducting a sale process, and ultimately doing all the steps and consulting them on selling their business. That’s what I do as my day job. I started a little bit more broad, and as I’ve gotten through my career, I have become that much more niche. That’s what we do primarily. I work at a company called Origin Merchant Partners. We’re about 50 people across Chicago, Toronto, and Montreal. That’s my day job.

What industries do you tend to focus on?

Personally, food, consumer, and tech a little bit. That’s where I focus. As a firm, we are quite broad and do a lot of things, but that’s my niche.

How did you get into those?

Through a lot of experience and stuff that I’ve done as well. I had an entrepreneurial stint in a food business. That was a lot of what gave me the background as an operator and into that world. It’s only a small part of it. The food world is super complex out there. I saw a part of it. Over the years of working with companies in the various roles that I’ve had, I’ve gotten more intimate and familiar with what goes on there. I’ve learned more. I bring a lot more expertise in those areas. At the same time, my background has been in M&A. I typically understand well what it takes, what companies are looking for the good and bad of making an acquisition or the right time to sell, and all those things. That’s what we advise our clients to do all the time.

How big are these companies typically when they’re coming to you and looking to execute a sale?

It’s called the enterprise value of the business. Anywhere from $25 million to $200 million is our sweet spot. We go bigger and smaller depending on the situation, but that’s most commonly where we provide the most advice and call it our area of the market at Origin.

Are they typically selling to a strategic buyer of somebody else in their industry to a private equity or some other structure?

Both. It’s going to depend on the situation. You’ll have a company where it makes a lot of sense to go to a strategic. There are others where maybe there aren’t a lot of strategies where a financial buyer, a private equity firm, or someone with an investment horizon is looking at the ultimate better buyer. In a lot of processes that we’re running when we go out and do these sorts of things, we’re going to both try to see who out there is willing to pay the most and come up with the best offer, structure, etc., to people that are looking to sell.

How much do you get into advising them on the right timing, the right sale approach, and all of those kinds of things?

It depends on the client. We’d always love to be doing that and doing it early. Honestly, some people think about it right when they’re starting a business. In their early days of, “I’m going to start this business,” they start thinking about, “How am I going to exit? Where’s it going to go? Who am I going to sell to?” That may change over the evolution of a business, but you can start to get involved in thinking early.

However, a lot of clients tend to call us or seek us out when they are pretty close to wanting to do it. It’s sometimes not too late in that sense, but where they’re saying, “A bunch of things have happened. I’m in a situation,” whatever it might be. They’re like, “I need someone to help me now because I want to sell now.” That’s probably the more common situation, frankly.

What percent of the time do they stay involved after the sale?

It’s pretty common unless you’re selling to your direct competitor, in which case they want you as a founder out of there quickly. If that’s not the case, then it’s quite common to stay for at least six months. In some cases, it’s longer, especially if you’re selling to a financial buyer. It’s common. More often than not, whoever the founder is is sticking around at least a little bit. The question is more so around how long.

I imagine in some of these cases, there’s an earnout of an incentive for them to help make sure it’s successful and they get extra funding if they’re able to do that.

For sure. That’s a common common structure, depending on who the buyer is. There’s a bit of a disconnect potentially where the buyer thinks, “There’s going to be a bunch of risks.” If it’s an industry you know well and it’s your biggest competitor, and you understand what’s going on, then potentially saying a non-compete like, “You can’t go start a competing business tomorrow or within the next couple years. Otherwise, I’m going to be pretty covered,” is fine. That’s very common. If you’ve got a situation where a financial buyer or someone who’s less familiar isn’t operating in that exact same industry, then they’ll probably think towards an earnout to keep you involved as an owner or founder trying to sell their business.

You’ve been doing this for most of your career. I know you had an entrepreneurial stint in there, which we’ll get to in a second, but how and why did you get into doing M&A?

It was my first job. I liked it. I was good at it and I kept going. That was part of the story. I knew I liked finance. I started in university thinking I would go along the accounting path and become an accountant of some sort maybe, and then decide however. I discovered finance all of a sudden and realized, “This makes more sense. I like this better. It uses accounting, but isn’t that all day long.”

I got into finance and found M&A because that was where I started working. The challenge in investment banking, where I started my career as an analyst, is that you’re working very easily, sometimes 100 hours or sometimes more than 100-hour weeks. For me, I had to mentally prepare myself for that and effectively tell myself, “I’m going to do it for 2 or 3 years.” I hit the 10-year mark and looked at myself saying, “What am I doing here?” It’s not 100-hour weeks for all those 10 years by any means. It gets better and it changes, but it is a stark change. It was this big thing that I had to do. That’s what led me to think about something different, which turned out to be an entrepreneurial endeavor.

Tell us a bit about that.

It was before I hit the ten-year mark, but I started thinking about it anyway. I left the job probably around the eleven-year mark. I have been thinking about this entrepreneurial thing for a long time. I was struggling with it. I didn’t have a business I was passionate about, that I wanted to do, or that I even felt was going to save the world or make me a billionaire, or however you get into these things, but I knew I liked the food world. I had done a bunch in that space, so I said, “Even if this business isn’t super successful,” because I was already thinking about the downside going into it, “At least I’ll learn a lot about the food world.”

We started a business. I partnered with a couple of people. One was an operator who was going to effectively run this business and did. It was a catering and restaurant business. We were a restaurant for lunch, and we did a ton of office catering. We started the business. I spent a bunch of time there, but I was still doing my day job. I was half-time there for a while, helping them out.

I reached a certain point where I felt like I wasn’t doing it justice. I needed to take the plunge. I quit and spent a bunch of time more acutely in that business. It was a good experience. I felt like I had an impact on the business. We were improving things. We were getting somewhere, but then the pandemic hit. We were offices. We were office lunches and office catering, so as soon as that happened, within a week or two, I knew we were done for. Even if people came back to work, it was still going to be challenging for our business to be what it was. We started to pivot and do home delivery and these other things, but it was challenging. I found myself, as the pandemic developed, going back into investment banking because I knew it and I had an expertise there.

Amongst all of that learning about myself, the world of work, what I was looking for with a job, and all those things, I ended up starting a podcast amongst all that as well because I was going through this. I was talking to a lot of people who were in their mid-30s, as well as my peers, who were having the same challenges about their careers, what they wanted to do, what they were doing, and where they were going with everything. That’s what led me to the podcast and ultimately led me back to the world of investment banking.

Did the company end up shutting down or is it still going in some form?

I sold parts of it and then shut down the rest of it. We kept going for a while, even after I returned to investment banking, but it was too hard. It was a new business in an ever-changing climate, which was challenging to do. It kept me up at night. I couldn’t spend the time that I needed to make it the right thing. It almost felt like I had gotten all I wanted to or could at the time.

It was stressful to go through this pandemic not knowing what was going on, how much it was going to cost you, what was going to happen to your business, and whether people were going to buy your product and all that. For me and my almost mental health, I had to ultimately leave and stop. It wasn’t easy, though. Once you have a business, it is not as easy as a job of quitting and moving to a different city or something. There is a lot more to it than that. It took a lot of steps to ultimately exit, but it’s done.

Apart from all of that, what do you feel like you got out of your entrepreneurial journey?

It was my MBA. Effectively, it was a lesson in all things business. I’m a consultant. I was a consultant. I am a consultant. It felt silly telling people what to do when you’ve never done it yourself, so I, at some point, wanted to go do it for myself, which is what I did. Wearing so many hats, doing so many different things, seeing that whole cycle of starting from scratch, going up into a real business, falling apart, and all that stuff of dealing with people and customer suppliers was this incredible experience of stuff.

It’s even hard to tangibly say what I learned other than how to run a business and how to be an entrepreneur. That’s what I learned, but there are so many things within that that I did learn. You take those away. I do feel like coming back to the same world that I was in before as a different person because I’ve learned so much doing that. It’s hard to tangibly tell you what those things are, but it feels different. It feels like I’ve got a different perspective, which is probably the biggest thing.

You go from an environment where you’ve got an office, an assistant, all the support staff to help you, and analysts. Then, you and your co-founders, especially in the beginning, I would imagine, probably had to set up everything yourselves and do a lot of different things yourselves. You become a Jack of All Trades very quickly.

Exactly. There’s good and bad. There are some benefits to that, especially when you’re trying to learn, especially if you’re in a certain stage of life, and especially if you really want that. I see it as a pros and cons. For me, looking back, it was something I had to do. It was something that I couldn’t get out of my head. I would’ve been kicking myself if I had never done it. It did work out in a different way, but the business itself didn’t work out. It wasn’t this huge successful thing. I don’t know if that would’ve changed if the pandemic didn’t happen. I honestly don’t know, but it was a great experience to go through.

I do encourage people still, if they want to be entrepreneurs, to think about it hard, especially if they are like me. At the same time though, it isn’t the be-all-end-all. We tend to romanticize entrepreneurship in many ways because we hear a lot in the business world, the newspapers, and the media about all the great stories, the accolades, and all the good things people do. It’s a lot of work. There’s a lot of stuff going on there. There are a lot of failures. We don’t always hear about that part.

There’s a reason they call unicorns unicorns.

Incredibly. They don’t seem that rare when you listen to the media, but they are.

I don’t know what the stats are in Canada and the US. There are something like 10, 12, or 14 million small businesses out there in the United States. Maybe 100 of them ultimately would grow to become billion-dollar-plus valuation companies. It is pretty rare, but those are the ones you always hear about. It’s the PayPals, the Googles, the Facebooks, etc. You mentioned you started a podcast during the pandemic as well. Was it stemming from comparing notes with people of your age about where they were in their careers and whether they were thinking about doing something different or was there something more to it than that?

Part of the rationale at the time was, in the pandemic, I hadn’t been talking to people the same way. All of a sudden, I was doing these calls like a podcast. You’re effectively like, “We should catch up. We haven’t talked in a while.” I realized, “I should record these.” The topic of conversations I was having was a lot about this. It was about my career and what I did, and then whoever I was talking to and what they were doing. It’s incredible.

There was a friend that I have that’s a cardiologist. I had him on the podcast. What you have to go through to be a cardiologist out there is crazy. There’s a lot of training, validly so. I had a good friend that I’ve known for 25 years. I never talked to him about it, though, so to sit there for 45 minutes or 1 hour and ask questions was helpful not only for me but for people out there trying to figure out what they wanted to do.

It doesn’t mean you want to be a cardiologist that you’re going to listen to them. It’s anything. What is he trying to do and get out of his job? How was he approaching it? How are the steps in his job as he develops and thinks about his career and those things? Through doing all these interviews, you start to develop opinions. I don’t want to call it a career expert, but it is something along the way where I’m headed there.

As you get more senior in the world, you get asked more often for advice. I figured out, “Let’s record some of this advice and help young people and people who may be struggling at any time given time.” When you’re 40 or 50, you can be struggling with your career. I never claimed to have it all figured out, even myself. Having those conversations is the idea. It’s called Lifetime at Work. It’s an interview every time with a different guest about their job, their career journey, and what they get out of the working world.

My starting point was very similar in that I have always been curious about how people have made the career decisions that they have and what they’ve learned. I described it to people that I work with one day as we all talk to people that we don’t work with. I’m doing it in a structured way, recording it, and releasing it for other people to tune into. There are a lot of people that I’ve had whom I’ve known for a long time, some of whom I’ve gone a long time without talking to. It’s fun to catch up, but you also get a much deeper sense of what their past has been like since they finished school or whatever.

It’s what we focus on. It’s what we do. That’s why I call it Lifetime at Work. It becomes our lives. We have all these other things in our lives. We have families, hobbies, and all these things, but you can’t dismiss a lot of our achievements from being tied to work.

What’s your mix of guests look like?

As I’ve evolved, I’ve tried to tone it in a little bit. I was more scattered, probably at the beginning of talking to anyone. I had a cardiologist. I had an Olympic figure skater on. I had various types of guests. Where I am headed to is a lot more into the business world. I am niching into having a lawyer, a marketing person, or an HR person. In a lot of ways, where I’m headed is more toward business leaders and the moves that they’ve made and how they’ve gotten there.

It’s interesting and hard, I find it, in some ways, to break through. You can break through what got them there. You mentioned unicorns earlier. You listen to these interviews because they’re everywhere of a founder or a unicorn and they’re very nonchalant about it. There were some clear things they were good at or had to do to get to this point of being an incredible company. As you do have to do if you’re trying to become a CEO of a large corporation, like the breaks you have, there are niches you do, but to get that from people is hard. Some of the secrets, advice, or whatever is what I’m trying to get to, and you don’t always get at them. Sometimes, people have their guard up and you can’t penetrate. You don’t know.

Ultimately, what I hope to try to take away from each episode is advice from that guest about what they’ve done, what they suggest that you do if you are in that zone, or if you want something like what that person has or a lifestyle that that person has. Getting an insight into it is interesting because there are so many different types of jobs and so many different avenues out there. Exploring them is helpful because it’s hard to know what’s out there for us all.

Exactly. How many episodes in are you?

I recorded about 50.

I’m creeping up on 100. I’ve got a rhythm at this point. I would never describe myself as a professional interviewer, though.

Do you listen to them again after?

Yeah, pretty much.

It’s helpful to listen to yourself. You work on your speaking skills. You notice things. I’m probably my biggest critic, ultimately. My wife, as well. She’ll always let me know things, or tips or whatever to get it through to people. It’s an interesting skill that you never thought you would need or have. You are not quite sure who makes a good interviewer or not. Part of it though also comes with a guest and them being open and clicking and connecting with them, which isn’t always easy as well.

It's helpful to listen to yourself. Click To Tweet

It takes work. I typically put probably an hour into prepping questions and thinking about what I want to cover with this person and how it’s going to build on what I’ve previously covered with other people. It is so that there is something different about each episode or sometimes than others. I know one topic that you talk about is the future of work. You were certainly affected personally by the pandemic. We’re coming up on four years since it started. I feel like we’re still finding our way into this world of remote work, hybrid work, and all of that. There’s a lot of debate about whether we’re going to go back to a full in-office norm or whether remote and hybrid will stay. What’s your sense of things?

It’s hard to say. It’s so tied to the business and the organization. Over time, though, what’s going to happen for the work-from-home location is that there will be people who want to work from home. They will go down a path and think about a career where that can be true. There will be people who hate that who want to be a part of a company and be there in person. Maybe it’s not five days a week, but it’s often. They will head down a path for them.

Even if you are an accountant, there will be accounting firms that are tailored well towards people who want to work anywhere, and there will be some who want to work in an office. That would be how we think. It’s hard to think that way because we are not sure. Companies are still trying to figure it out. My company has 50 people and we’ve got a few different offices, but we don’t know. We’re still trying to figure it out.

What has happened is people within our organization have very different perspectives. Some really like and have enjoyed the work anywhere or work from home and others hate it. You have these organizations that haven’t been constructed with that in mind. We built the company mostly before that. You have this big change and everyone’s a little bit different and trying to align.

It’s even how we work within our organization. The office setup is changing. It will continue to evolve over time. It’s interesting, though. It’s one of these topics that I can’t get enough of because it doesn’t have an answer. It’s going to be one that we’re iterating and trying. It’s going to be different depending on the company. It’s the remnants that the pandemic left us.

Certainly, there are companies out there that have committed to being and staying remote. They’re probably more the exception than the rule. I heard a Microsoft statistic probably from a few years ago that at the time, 13% of jobs that were posted on LinkedIn were fully remote jobs and 50% of the applications that were put in against all jobs were for those 13%. There certainly was a lot of interest in people and being in those remote places and there weren’t nearly as many jobs. We’ll see how things play out as we all continue to find our way back into it, the norms around it, and how you handle hybrid meetings and all of those kinds of things.

We’re still trying to figure out, honestly, what the right balance is. It’s different for every organization, but it’s interesting. If that’s the case, that’s a cool stat. That could be an effective tactic. As long as you can still operate, can still make money, and have a business plan that works on that basis, then why not try to offer that work-from-home as being a perk to an organization and retain people that way? Although, it’s not always so simple.

For some industries, it doesn’t work. For other industries, maybe the company culture doesn’t support it. Everybody’s got a different opinion on this one, so we’ll see how things shake out. There has been a lot of talk also about the idea of the balance of power between workers and companies. From living in London and looking back at the US, I’ve certainly seen the unionization efforts at places like Amazon and Starbucks. I’ve seen strikes in the automotive industry. It seems like unions are having a little bit of a rebirth. Do you feel like in your conversations with the business leaders and others that you talk to, the balance of power is tipping more in favor of workers?

Maybe. Part of the reason is going back to some of these work-from-home situations where you’ll have a leader who says, “We need to get back in the office,” and then the people don’t do it. They’re perfectly happy to wait it out and not go into the office and see what the punishment might be, if any. It does show a little bit of that shift.

When push comes to shove, maybe the economy is not bad enough. If you’ve got enough confidence that you’ll get another job, then fine. You’ve got power and you’re not worried about it. You then reach a certain point where that shifts. It can be actual. It can be the media. It can be based on job postings or whatever it is that’s industry-specific.  All of a sudden, you feel like, “I don’t have as much power as I once had.”

I agree with you. It does feel like, in a lot of ways, people and employees are dictating more within an organization. It is in the best interest of a company’s leadership to think, “How can we get these people on our side? They’re very important to the success of our organization. How can we be a team that can be together?” It gets to the culture of the firm and what you’re trying to achieve. It is easier said than done in many ways.

Think through how to get people on our side because they're important to the organization's success. Click To Tweet

There’s a social contract that comes with work, but there’s also a financial contract that comes with it. Probably, both sides need to give in a little bit in terms of how this is all playing out after the return to office. There’s always an economic factor in it as well. If the economy’s good, then it’s going to be easier to find a job elsewhere. You probably won’t put up with things in the way that you might if the economy’s lousy and you’re happy to have your job.

There is something going on in terms of different expectations. That’s a generational thing. It’s Gen Z. It was Millennials before that and then Gen X before that. Every generation brings a little bit of a different social expectation and the world of work evolves with it. If it doesn’t, then there’s a little bit of rebellion. If it does, then everybody marches on toward the next generation. We had a dislocation in the global financial crisis and a dislocation here with the pandemic. Those things tend to create some sort of change in the way that things work.

It becomes very big in your life and mixes everything up and makes you try to figure out where you are.

It’s expensive to go to school. It used to be that it was common wisdom that if you wanted to get ahead in the world, you needed to go to get a university degree. There was going to be a massive difference in terms of your lifetime earning potential if you did go to school or didn’t go to school. School has gotten more expensive. In the US, you’ve got kids leaving school with six-figure loans to pay back.

Over here in the UK, there seems to be more of a move to create apprentice-type programs that are aimed at kids who don’t want to go to college or university. They get them in and teach them the ropes while their peers are off at university. The idea is that by the time they hit 3 or 4 years when they’re 21 or 22 years old, they can start on an even footing. They got their training on the job. What’s your take again? Does this come up in any of the conversations that you have in your podcast or with some of these business owners or your friends who may be having kids approaching university age?

It’s interesting. There is one friend that I’m thinking of in my head. I went to high school with him. He went to university. He wanted to leave university and his parents wouldn’t let him. They said, “We’re paying for it. Don’t worry. You finished what you need as a university degree.” My advice to him at the time, which I still think was good advice, was he was great with his hands. He loves building anything, like home renovation or construction, in any way. There was this stigma of the group that he was in or from his parents and from whatever that he shouldn’t do it, so he didn’t. He kept going to university. Out of university, he got a completely different job and never went back and pursued any of that. He does a lot of stuff around the house.

For some reason, to me, there has been this disconnect around we, as parents and elders maybe, feel like the job of someone who is doing something manual labor-ish or you could be owning the company that does whatever it is that there’s something wrong with that. There’s something that’s like, “This shouldn’t be my offspring,” for whatever reason. I don’t know. It’s a hard thing. We have to get over it a little bit because we do need those types of people. We do need those jobs. We do need a lot of people to build what the things are in the world. It does feel like, in a lot of ways, over time, they’re getting lesser.

We do need many people to build the things in the world. Click To Tweet

To your point on the cost of all these things, it’s a pretty fascinating one that is a whole separate episode topic in and of itself, which is on education and the cost of it. To me, a lot of education and higher university college education seems to be the credential or the badge. It’s so much less about what you learned there. It’s more like, “You went to Oxford,” or whatever it is. That has its own badge. It’s like working at Facebook, Google, or whatever. They’re like, “It doesn’t matter. You have this badge. Someone validated you. Since it’s hard to interview someone and tell who they are and what they’re about, I’m going to rely on that university that they worked at or that establishment.” We do it out of convenience as hiring managers.

You would think that shouldn’t last or that it shouldn’t be ultimately in a world economy job market that that should be the case, but it is. It is expensive. It does make it challenging for people without the means who don’t come from a background of that to compete with the same people. I do see it as a problem and a little bit of an onus on us, those who are in the hiring decisions, to be able to think through how you offer jobs and opportunities for everyone.

We’ve pretty much banned putting educational requirements into a job description when you’re posting something online unless it’s for a new grad. If somebody’s 5 or 7 years out of school, does it matter where they went to school? What matters is how they’ve adapted to the work world and what they’re able to achieve. Back to your badge point, it’s like, “You went to XYZ school. You worked at XYZ company,” or whatever the case may be. It’s street credibility, even if it’s a bad indicator in the scheme of things.

I have one last future of work topic, which is artificial intelligence. It’s hard to escape that one this 2024. It’s been out there longer than 2024, but with ChatGPT getting into all the news right around Christmas time 2023, it’s been a huge explosion since then. What’s your take? I hear people talk about how AI is going to take all our jobs. I hear people say it’s going to going to revolutionize everything about the world in a positive way. Where are you on that continuum?

It’s hard for me to know whether I am an optimist or whether I’ve done the diligence required to properly assess this. I’m not sure. I’m generally positive because what we can hopefully allow AI to do in an office job is to do the stuff that we don’t want to do ourselves. It’s the tedious stuff or the stuff that we ultimately want to train AI to do instead of us. There are limits to that.

People are going to get replaced, for sure. Ultimately, if a computer can do something better, then there’s more reason to do that. There’s going to be a cost advantage, but at the same time, it will keep us on our toes, for sure, in terms of having to find the next thing. I’m generally an optimist because of that. It will make us more efficient.

We’ll still need people to do a lot of these things. That’s been proven over the years as technology has advanced. I think about what people would’ve said in my career in investment banking where you make models in Excel. Before Excel, these were done on pen and paper and little tables. Has that made it so that there are fewer people writing on pens and paper? I guess so, but it’s also allowed us to do so much more. It’s because of that that I’m probably an optimist and I see it as being more of an opportunity.

For people out there, the advice I’m giving them is to start learning. I spent probably fifteen minutes earlier trying to figure out how an AI program out there could help me with something. I learned a little bit. We’re not quite there where it could, right away, do whatever you want and it’s super easy. You do have to figure out, “How do I use it to my advantage the best so it’s setting myself into a routine where it’s helpful?” We have to explore and understand it. Those people who do understand it at least will be better ahead because they’ll be able to take advantage of it earlier and recognize when it is either taking their job or helping them do their job better.

We’ve all been benefiting from artificial intelligence in different forms for longer than a year. It’s crept into a lot of different products that we use. Siri or Alexa would be two easy examples. It’s going to be a dislocation for some people. It’s the same way that manufacturing and moving overseas was a dislocation and the same way that workplace automation was a dislocation. It forces you to adapt.

We’re going to have another one of those cases where people are going to adapt. Some people will adapt well, and some people will struggle. That’s going to have social consequences that come with it, but we are going to have to work through it. It’s hard not to see the many benefits that it could also have in terms of being able to make things easier, identify problems more quickly, and all the things that it’s already being used for.

To your point on the future of work, and that was the last question, the future of work is being that much more nimble. We’ve had so many different types of jobs. That idea that you can go to school, learn one set of skills, and then do that job for the rest of your life, I don’t know if that’s going to be the case anymore. It doesn’t necessarily mean that you have to go to school every ten years to learn something brand new. It means you have to pivot a little bit. You’re going to have to get into a different field. You have to learn some new skills. That is the way work is going to be. You have to be on your toes and aware of it. You can’t sit there and hope that you’re going to retire before you need to learn something new.

We talked a little bit about the future of work. Let’s spend a few minutes on the today of work. I know you talked to your podcast guests about how to navigate the workplace. What do you hear from them about the particular challenges in the work world?

There’s a stat, which I don’t have very exact. Something like 67% of people are unhappy in their jobs of some sort. You do these surveys out there. That’s the reason why I do the podcast. It is to try to flip that number, maybe potentially upside down and see if we can get more people to like their job. Through that experience that I mentioned to you about myself, I did go through a bunch of, “I hate this. I love this.” I was learning about myself and what about work was key for me.

One of the big takeaways I had was people. I had no appreciation for how much the people around me every day mattered in making my day, my job, and what I was doing important. It was almost to the point where I think it is more important. In our heads, we think, “I want promotions. I want more money. I want prestige,” and all these other things. You think that way. Maybe it should be a lot more about like, “I want to be around these people because they’re fun and they challenge me,” and those things. I realized that.

We all are out there trying to figure out our jobs and how to get through whatever we’re doing to be fulfilled by work. Listening to people and hearing how they’re doing it, their perspectives, and all that are super important. Trying different things is helpful as well because with each new thing that you do, each new position, or whatever it might be, you learn more about yourself. You learn more about the world of work. A little bit, too, with the podcast is as I’m interviewing people, I’m trying to get that as well from them. I’m like, “What did you do? Why did you do it? What did that teach you?” Maybe that is a mistake or an experience I need to do and make.

Listening to people and hearing how they're doing it and their perspectives are super important. Click To Tweet

That statistic that you quoted probably is Gallup. They have been running employee surveys forever and ever. The statistic that you hear is that only 30% of people, which are Americans, are engaged at work. It is the opposite way of saying what you are saying. What’s crazy is it has been like that for decades. It has been roughly flat at 30% for decades.

For a generation, 70% of people go to work not engaged, which feels pretty awful. You wonder, “How do you change that dynamic?” It’s all the things that have happened in the work world, good and bad. It’s been roughly flat at that level. I can’t imagine spending my whole career going to work and not being engaged and excited about what I’m doing. It would make life tedious. That’s part of the reason I got into doing some of this stuff as well. It is to try and help people figure out what’s going to work for them.

I talk to people all the time with my job and the podcast. One of my pet peeves is when it’s a Monday and people are upset about it or it’s a Friday and people are happy. I’m trying to instill in people that you can have them all be good. There are going to be days that you don’t like and days that are better than others, but it’s not a default like, “The work week is over.” There’s a lot you can get out of your job.

The big thing that I’ve come away with from listening to, talking to, and interviewing all these people through my podcast is that you can achieve a lot of these things that you want to and that you’re trying to get out of life. You can learn a lot about yourself. You can achieve a lot. You can do all these things through your job, and that provides a ton of satisfaction as long as you align it right.

Maybe the unfortunate part is a lot of it is in our heads. That almost makes it harder. It’s not so easy as getting a new job and this job will all of a sudden be the holy grail of whatever. Unfortunately, a lot of it is in your own head. You have to be able to look at yourself and say, “Why am I so unhappy today?” or, “What is wrong with this? How do I change my frame of mind?” That’s hard to do.

You need to have great awareness. You have to know yourself. You have to talk to people. There are all these things that you need to do, and even then, you may still be in that situation. It’s not easy, but it’s out there. What we should strive for, though, is liking what we do and getting out of it. You’re not going to love every day, but to enjoy the journey, the battle, and the day-to-day is important for life.

Changing my frame of mind is hard to do. You should have a great awareness. Click To Tweet

Where does all this leave you in terms of any final advice that you would want to give our audience?

A pretty good point to leave on is this idea of finding what you like. A piece of advice I would ask people to do, especially when you are unsure, is to talk to the people that are around you. It might be your good friends, your neighbors, your family members, or whoever might be around you. Have a genuine conversation with them about your career. I know that sounds pretty easy.

Spend 10 minutes, 30 minutes, or whatever, laying out to them, “Here’s what I want to achieve. Here’s where I’m at to date. Here’s what I’m thinking,” as honestly as you can. You’ll be shocked if you do that with five people and they’re all going to tell you the same thing. It’s going to be the first time you’re going to say, “I don’t know.” Eventually, you’ll realize that it’s super obvious.

I found over time that people know you and we overthink ourselves. If you can lay it out for others, and even saying it out loud five times or whatever, it will help you in understanding, “Should I leave my job? Should I get a new one? How do I like this job better? How do I deal with this problem that I’m having?” Use the people that are around you. In some cases, even the connection that you make with that person, that neighbor, or that family member through having that conversation is what you’re looking for. Doing that is what we’re striving for because it’s this learning experience for all of us.

Good advice to close on. Thanks for doing this with me.

Thanks for having me on the show. Your show has a lot of similarities to mine, so hopefully, your guests found this helpful. Thank you.


I want to thank Greg for joining me to cover his work in investment banking, his entrepreneurial journey, his career podcast, his thoughts on the future of work, and a little bit of his thoughts on navigating the world of work. If you’d like to make the most of your career, visit and become a member. Basic membership is free. You can also sign up on our website for our newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram, and TikTok. Thanks. Have a great day.

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About Greg Martin

Career Sessions, Career Lessons | Greg Martin | Future Of WorkGreg Martin is an investment banker, angel investor, entrepreneur and regular host of a career podcast himself about the world of work and business. His day job involves advising corporate clients and business owners as a Managing Director with Origin Merchant Partners, which is focused on providing advice around mergers and acquisitions, strategy and capital raising for some of Canada’s best companies. Greg’s particular focus is on the food/consumer, technology and insurance sectors.

Greg was also a co-founder of Farm’r Prepared Foods, a restaurant and office catering business that transformed into an e-commerce meal delivery company post pandemic. His earlier career was also in investment banking, with stints at several firms along the way. He earned his Bachelors’ degree in Business Administration from the Lazaridis School of Business & Economics at Wilfrid Laurier University. He and his family live in Toronto.

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