Inside the Mind of a CEO Coach

Mike Pinkus: Over the last 10 years at ConnectCPA, we've had the privilege of witnessing the incredible journeys of over a thousand businesses. We've been there for the thrilling highs and daunting lows of entrepreneurship. We've celebrated wild successes and monumental exits, and we've also stood by businesses as they've navigated the stormy seas, facing roadblocks and challenges that every entrepreneur encounters in their day-to-day grind. Join us as we dive deep into the stories of these resilient individuals who dared to dream, who persevered, and who were a testament to the power of entrepreneurship. This is their journey, their lessons, and their triumphs. Welcome to GrowthTales. I'm your host, Mike Pinkus, co-founder of ConnectCPA.

Mike Pinkus: I am really excited for today's guest, Mark MacLeod. Mark has built a CEO coaching business where he specializes in working with high-growth startups. Mark has a ton of experience, having served as a CFO for both Shopify and FreshBooks earlier in his career. In addition to his C-suite roles, Mark has also been a long time investment banker. He's been a general partner at Real Ventures, and prior to starting his current business, he had founded his own investment bank, SurePath Capital Partners.

What I believe makes Mark very unique as a CEO coach is not only that he has worked alongside some of the biggest and brightest CEOs and established high-growth companies, but he has also had extensive experience on the financial side of scaling a business, coupled with a deep understanding of deal-making, fundraising, and exits.

I really enjoyed my conversation with Mark, and if you are a CEO of a scaling startup, I believe you have a lot to take away from this episode. Hi, Mark. Thank you so much for joining me today on GrowthTales.

Mark MacLeod: It's a pleasure, Mike. Thanks for having me.

Mike Pinkus: I've been a big fan of what you do. I've been following your podcast. I've been following your writings for a little while now. And, uh, what caught my eye about you, Mark, is that you have a very different, unique background compared to most CEO coaches that I see. Uh, being a CFO of really reputable companies like Shopify and FreshBooks, and being an investment banker—it's just like a very unique, competitive environment that your background is from. And you don't see many CEO coaches in that domain.

So, my first question for you is, what is the origin story between how you came up with the decision to start a CEO coaching business?

Mark MacLeod: Yeah, it's, um, I was intuitively drawn to coaching, to be honest. I bought my first coaching book in 2002—yeah, 2002—but realized that I lacked the gray hair and moral authority to crush it as a coach. I now have a white beard; you can judge the moral authority bit for yourself. But I went through some big life changes in 2019. I got divorced. It was an 18-year relationship, 16-year marriage. And, um, it prompted a bunch of life reflection.

And I've kept a journal for most of my adult life, and I reread a bunch of years, and there was—I often wrote about work, 'cause if I was awake, I was working. By the way, that is not unrelated to getting divorced. But, um, there was this really common pattern right across all of my roles, whether as a CFO acting as a right hand to a CEO, VC trying to help founders become CEOs, an investment banker trying to help CEOs achieve massive outcomes.

The days that I was most excited about were days where I had a one-on-one coaching or advisory conversation. And so I knew at the end of 2019 that if I had a do-over, I'd skip being a banker and I'd just be a coach. And then in March 2020, of course, the world changed. And for a brief moment, companies stopped buying companies. And, you know, it was an initial panic. I had hundreds of millions of dollars of deal flow die in the space of two weeks.

But then I realized this was actually a gift and a golden opportunity. And so I used that window where I wasn't leaving clients hanging to shut down my firm, help my staff get new jobs. And in one case, the guy who led my San Francisco office—I helped him set up a similar firm for himself. And I went back and got certified as a coach. So yeah, I'm now in the fifth year of a really specialized coaching practice. I coach the CEOs of technology companies that have raised institutional capital—so kind of venture capital or private equity.

Mike Pinkus: That's a very interesting story because, uh, it sounds like your path was a very similar, I guess, process that CEOs go through themselves, or founders, where they're in a high-stress environment. The markets are constantly fluctuating. And the fact that you went through that yourself, granted in a different position, uh, you have a lot of overlap with the CEOs that you coach in terms of seeing a lot of the things that they're seeing.

So I wanted to ask you—the ICP you went after, which is, um, high-growth companies—is it because you already had fundraising experience, investment banking experience, you knew some of the challenges that they would naturally face, and you've been in that environment? Was that the reason why you went so narrow in terms of who you'd work with? Or was there some other reason?

Mark MacLeod: Yeah, I, like, I deeply believe that competition is overrated. And in everything that I've done, I've aspired to create a category where I have little to no competition.

So when I was a venture capitalist, I went super deep on SaaS, and I was one of the few VCs in Canada who was doing that. I was blogging about it all the time and learning about it and sharing what I was learning. And that attracted entrepreneurs looking to raise capital from us, and it just became this flywheel and self-fulfilling. And when I—um, and all of my investments except for one were, in fact, SMB SaaS companies. And of course, I'd been CFO at Shopify before and FreshBooks after being a VC, and I doubled down on that SMB SaaS specialty with my investment bank.

And there's tons of investment banks. But by the time we were done, San Francisco startups were hiring our Toronto-based investment bank, which is backwards—it makes no sense, right? But it was because we were more specialized than anyone. And so I've applied the same approach to coaching. There's lots of coaches out there, and I'm sure they're all great. But my superpower is that I've personally raised over a billion in capital, I've personally done over a billion of exits, I've been on every side of the table. And so that just gives me very deep context, very deep pattern recognition. I understand what the CEOs are going through.

And, you know, if you're running a high-growth company and you've raised tens or hundreds of millions of dollars, you have giant expectations on your shoulders—huge pressure. And so you need someone to speak to who gets that context, right? And can hang at your level. And so there just aren't a lot of coaches who have that background.

Mike Pinkus: There's no question. And it's definitely something you don't see that often, given your background. And that's why I think it's so valuable.

One of the things I was always curious about, Mark, is you're now meeting with all these different CEOs, and running a startup—or even a scaling business—is incredibly difficult. And so you definitely see those commonalities of the issues that CEOs face. But I wanted to ask you a question: What are some of the things that CEOs come to meet with you about that they think is a significant problem, but you don't see as being that big of a problem?

Like, I'm curious about that—where people are coming to you in a panic and you're like, "Wait a minute, this isn't even that big of an issue." Does that—have you figured out what those things are?

Mark MacLeod: Well, that's a great question, actually. I'd say, listen, we only experience the world through our subjective lens, right? If you think this conversation's boring, you're right. If you think this conversation's exhilarating, you're right. It's the exact same conversation. And so the point of that is, like, I don't want to discredit the reality that the CEO is facing, right? When they show up, it is their reality. And so we have to deal with that.

That being said, I think—and this might actually be true of society at large, but it's certainly true of CEOs—most high-growth CEOs, because of the demands placed on them, just work too much. They have no boundaries, and they end up living in this fight-or-flight place where almost anything can be triggering. So a huge part of my work is actually to get them down from that.

And one of the reasons why I believe so deeply in personal health and advocate that for my clients—sometimes I have my clients, literally, let's do some breath work before we even get into chatting because they've just come from, I dunno, like the sixth hour of back-to-back meetings—which, by the way, is a thing I try and undo in their schedule.

So I think rather than this—you know, your question about like what do they think is a problem that is actually not—the thing that is most prevalent is that a lot of the reasons that bring them to coaching, the problems, if you will, that bring them to seek out a coach, are self-created. And I'm not blaming with that. But like things like:

"I can't keep up with my schedule. I have 10 hours of meetings a day. I have no time to think. I have no time to process email or Slack. I'm doing that at night, and as a result, I have no time for myself or, you know, my family. My health's deteriorating."

All of that is self-created, right? Because we haven't set up boundaries, probably because your leadership team isn't as strong as it can be—because that's your leverage. And maybe you're operating at the wrong altitude, right? Maybe you've inserted yourself into the critical path of too many things.

So I really try and unwind all of that and create a healthy, sustainable pace. You know, I can tell you—again, I've done a lot of exits—and the number one reason why founders choose to sell their company is 'cause they're burnt out. And they're burnt out—again, it's self-created. It doesn't have to be that way.

Mark MacLeod: Right? You know, when I interviewed Tobi for my podcast, The Startup CEO Show, literally that week was the 20th anniversary of Tobi incorporating Shopify. And I asked him why he hasn’t burnt out. And, you know, it’s pretty fascinating. But he has boundaries. For the longest time, if you look at his Twitter bio, it says, "CEO by day, father in the evening, hacker by night," something like that. The point is, he’s created these distinct boundaries for himself. It’s not just CEO—there’s a whole bunch more to it.

But boundaries—honoring all of the different parts of ourselves. Like yourself, you're presumably a husband, you’re a father, you’re a son, you’re a friend. All of these roles need real estate. They need to be a part of your life. If you’re going to live a fulfilled and meaningful life, all of them feed you. Right?

But with so many CEOs, work takes up everything. And, you know, let’s generalize, right? The startup CEO—most startup CEOs are male. Not all, obviously—I have female clients—but generally speaking, male-dominated space. Those males give everything to work. Out of the 0% that’s remaining, they find something in the dregs for their children. They have nothing left for their wives or partners and nothing left for themselves. And it just leads to, well, ultimately burnout and a lot of unhappiness.

And if you think about the CEO role, it’s really about making decisions, right? At scale. And you make decisions every day—some small, some large—and the thing that you need to make great decisions is mental clarity. And it’s hard to have that when you’re in fight-or-flight and you create no space, no time to think.

And so yeah, I’m on a personal crusade to create that time, right? And to create sustainable balance for my CEOs and their companies. I deeply believe that happy, healthy humans build bigger, better companies.

Mike Pinkus: Yeah. That perspective of it being self-inflicted is—it's very interesting. Like I see Warren Buffett at, like, 90 years old, choosing to work. Obviously has no reason to have to work.

Mark MacLeod: He does not. He does not have to work.

Mike Pinkus: I would put Tobi into that same category. Absolutely. I mean, I'm assuming he's a billionaire, and there's no reason he has to—

Mark MacLeod: Time over.

Mike Pinkus: Yeah. And that’s—he could—

Mark MacLeod: Buy an island beside Richard Branson’s and just kite surf, but he works harder than ever.

Mike Pinkus: Exactly. But I’m sure not all your CEOs fall into that camp. And so what I’m curious about a little bit is: how much of that self-inflicted pressure—not just from, obviously, there's expectations from your team, from your VC, from everyone around you who's got high expectations—but the financial side... I'm sure some of your CEOs have taken secondaries at some point in their journey, some of them haven’t. Some of them are growing multi-million dollar businesses where there's a stack of pressures hanging over their head.

And so how much does the financial pressure of not yet being personally wealthy influence that stress level for some of the CEOs? Because I’m sure you have a mixed camp, Mark, of some that are first-or-second time founders, some are very wealthy, some are not wealthy yet but they’re building great businesses. How much does their personal financial situation play into their overall mental state of running a high-growth startup?

Mark MacLeod: Yeah, that’s a great question. I’ve found that there are three sources of motivation. I can be in love with the market—it’s a big market, I think there’s an opportunity to make money. I could be in love with the product—I’ve got this amazing widget and now I want to sell my widget. Or I can be in love with the problem.

I’ve found the market or money to actually not be an enduring source of motivation. Like, you—back when you were employed by someone else’s company, you got a pay raise and you felt good for a minute, and then you get on with the rest of your life. Like, money is not an enduring source of motivation.

And so, to your question, I think VCs certainly have a concern that, hey, if someone does a meaningful secondary, they’re not going to be as hungry. They're going to be distracted. They’re going to be doing angel investments, doing all this other stuff. And that does happen. But in my experience, it doesn’t happen to the A-players—the people who are really going to build the outlier companies, the Shopifys, right? The Airbnbs. Money doesn’t change them, you know? And it hasn’t, in the case of Tobi, as an example. Mark Zuckerberg, right? I just listened to Mark Zuckerberg’s interview with Acquired. Like, this guy’s settling in for the long haul, right? And again, he’s—

Mike Pinkus: Still—

Mark MacLeod: Doing it, doing it many, many times over. Right? And that’s actually because, you know, those really, really great entrepreneurs—they're in love with the problem. It is their mission. It’s the reason why they wake up in the morning. Let’s go to Tobi, because it’s a closer example, right? Tobi’s mission is to make commerce simpler for everyone, to reduce the friction so anyone who wants to start a product-based business can do so easily. He’s not done, right? And so he works hard.

So yeah, secondaries—in this case, his personal wealth is orders of magnitude above any kind of secondary we might see in the venture market, and it hasn’t affected his motivation. And so I think the people—yeah, to wrap this up—I think the people whose motivation comes down as a result of a secondary were probably not the people that were going to create the outlier outcome anyway.

Mike Pinkus: Yeah, that makes sense. And yeah, you have to be motivated by solving that problem, because the money comes in the long tail to a lot of these really high-growth... It’s a high-risk endeavor, meaning you’re going all in. And especially if you pick that path, that makes a lot of sense—that money can’t be the motivator or you’re going to give up at some point, right?

Mark MacLeod: There are way easier ways to make money than being a founder.

Mike Pinkus: Yeah. So, speaking of which—of the founders—you’re meeting with all these different types of founders and you see some really successful ones. You see some that are brilliant, but they can't break through. What are some of the attributes—one or two of the attributes—that you see, Mark, in CEOs who are really effective?

I know there are obviously external circumstances that are out of their control—there’s a lot out of a founder’s control—but of the ones that you’ve seen that are really successful or figure out those difficult challenges, what are some of the attributes that they have?

Mark MacLeod: First of all, I want to be clear that at least 50% of any outcome is luck and timing, which is independent of the founder.

That being said, the attributes that stand out for me—first of all, resilience. Right? You're going to get punched in the face every day, and yet you show up with a smile on your face the next day.

Self-awareness—that is the number one thing that I looked for as an investor and the number one thing that I look for as a coach. And Tobi puts it really well, right? He said for years, "I need to requalify for my job every year." It’s not the same job. And the thing that enables him to do that is self-awareness. That ability to, as objectively as possible, review himself and find opportunities for growth.

In the case of Tobi, he literally replays his day—it’s almost like a movie in his mind: “Oh, I don’t like how I behaved in this meeting.” “We used the wrong inputs to reach this decision.” He goes through a learning loop every single day, which brings up another of his mantras, which is: "Get 1% better every day." Which sounds like a cheesy poster in the hallway—but he lives it.

And 1% improvement every day is a 37x improvement in a year. It’s completely transformational. So self-awareness is a huge thing.

I can tell you—and this really ties into luck and timing—the number one thing that grows CEOs is to unlock revenue growth in the business and just hang on for dear life. Just figure out how to keep up. That is the thing.

You could be the smartest person in the world, read all the books, all the blog posts, have all the coaches, mentors—none of that will matter unless you actually unlock revenue growth.

Mike Pinkus: And that makes a lot of sense. Because if revenue is—if you figure out that product-market fit—it’s all... whatever you thought you were going to have to figure out, when you start scaling like crazy and you're generating revenue, whatever you thought you had to fix, or the next feature, you’re probably wrong. I’m assuming you’re going to have to pivot 80 times anyway.

So if you’re going to get one thing right, you’re saying revenue’s the thing you need to get right.

Mark MacLeod: Yeah. Listen, ultimately product matters. If you look at the most disruptive companies, they have disruptive product. But if I had a pie chart for all the elements of value creation over the life cycle of a company, by far, the biggest single slice of the pie is go-to-market.

That’s why Microsoft—with, I would argue, pretty shitty products—is, you know, a giant company, right? Way back in the day, when you bought Microsoft Office with either floppy disks or CDs, they owned the shelf. You would walk into Staples (in Canada, of course), and all you would see is, like, the main shelf at eye level—just Microsoft. They owned the shelf. So that’s distribution. That’s go-to-market.

Deep channels, formidable go-to-market expertise—you know, that’s the key lever.

Mike Pinkus: And I’m going to pivot a little bit here, Mark. We were talking about Tobi, we were talking about Zuckerberg, and something that I’ve thought about a lot—I don’t know if you’ve noticed this or not—but a lot of these high-achieving CEOs, for some reason or another, are really fit.

Like, I look at Zuckerberg, who does jiu-jitsu—they’re just like, they’re crazy fit. Most of them talk about their meditation practices and all these things. So I wanted to ask you, in your subset of all the CEOs that you work with, how important is mental health and physical health to being effective as a CEO?

Mark MacLeod: For me, it's the foundation, right? If you're building a tall building, you have a big, strong foundation. And that is the foundation—physical health, mental health.

It’s a thing that I advocate for all of my CEOs. Not all of them follow it. And it’s a thing I practiced. When I was running my investment bank, it was stupid—the pace that we had, right? We were doing six deals at a time. I had an office in San Francisco. I had clients in Europe. If I was awake, I was working.

But back to boundaries—I created boundaries. I did CrossFit five days a week. And the beautiful thing about CrossFit is no matter what city I was in, I could find—they call them boxes—I could go to a box and get a CrossFit workout, and I was good to go.

And that completely set me up for the day. The days where I would skip it, I found I had less energy, less confidence, less mental clarity. And so if you get serious about physical fitness, it then forces you to get serious about nutrition—to fuel you—and it forces you to get serious about sleep.

And the number one “get healthy quick” thing—the number one fad for health—is to sleep enough. Eight hours ideally, of good quality sleep every night. And so it’s this just compounding virtuous cycle.

And then, yeah, meditation—super important, right? Again, going back, what does a CEO do? They make decisions. Mental clarity.

And you and I were talking about Kundalini yoga before we went on air. And here’s the thing: our rational brain is 10% of our capacity. And our subconscious mind—our intuition—is far more powerful.

Mark MacLeod: And when you're living in this fight-or-flight place—just going from meeting to meeting, Zoom to Zoom, pounding emails, pounding Slack messages—you leave no space for your intuition or subconscious to go to work.

And that’s why you have these aha moments if you go on a hike or you're in the shower or something, right? I went back—my last operating role was at FreshBooks—and I used to have what I called “Fresh-mares,” which are like FreshBooks nightmares. And I would solve business challenges while I was asleep. I'd wake up and have to write them down or I’d forget, or I wouldn’t be able to get back to sleep. So, not the most refreshing sleep.

But the point is, I wasn’t working, and so my subconscious went to work. And so this is one of the reasons why I’ve been drawn to Kundalini yoga—because I am deliberately building my subconscious and intuition and turning on parts of my brain that are dormant.

And, you know, meditation in general helps do that. Meditation in combination with conscious breathing—that could be a whole podcast unto itself.

Mike Pinkus: Well, the fact that you have a background in understanding just the mental health, the physical health, yoga, meditation—I think is very powerful. Because I would imagine CEOs probably come to you and they’re like, “This is the problem. I have a VP that’s not performing. I have a co-founder conflict.” And that’s why I started with that question of: they think it’s the thing.

But like you said—what you’ve been reiterating—is resilience, and the altitude you’re at as a CEO. To think clearly from 30,000 feet of all these issues that are going on is sometimes the thing that helps you through.

So I’m kind of curious—when someone comes to you, and startups aren’t always fun, there’s always the problem or the burning thing that someone is looking for help with—and Mark, you have that tactical ability to give advice on things like fundraising and unit economics, being an ex-CFO…

Mike Pinkus: Do you ever cause the CEOs to go, “Let’s zoom out for this session. We’re not going to tackle that thing you think is burning”? Or like, how do you approach it when someone is in fight-or-flight, but you are looking at all these things that the CEO needs?

How do you address that? What I’m getting at is—you’re dealing with someone who’s under high stress, high pressure, and there are all these tools, and they approach you because you have tactical ability and strategic insight. How do you know what to deploy in any given one-hour increment or an hour-and-a-half meeting?

Mark MacLeod: Yeah. Yeah. That’s a fantastic question. That becomes easy the more you spend time together—because you deeply know the person. These relationships are trusted and intimate. Like, I don’t even tell people who I coach. There are conversations my clients have with me that they don’t have with their spouses or co-founders. It’s a deep relationship.

And so over time, as I get to know them, you know, I think a key job for a coach is to hold up a mirror and be like, “This is what I’m seeing.” And sometimes that means we’ve got to go to the uncomfortable places.

You know, I had a conversation with a client recently—we were talking about these things you mentioned, like, “Hey, I’ve got a VP that’s not working out.” These are actually symptoms, not the cause. And he showed up with a list of symptoms, but we diverted the conversation to the cause. No need to get into what that is in this case, but yeah—that’s my job: to go where we need to go, whether it’s comfortable for the person or not.

And so that’s a little harder right at the beginning, because I don’t necessarily have the context and I don’t deeply know the person yet. But once we’re up and running, then it becomes pretty evident.

And back to Kundalini yoga and subconscious intuition—I practice every day. I have a deep meditation practice, a deep spiritual practice. I don’t grind anywhere near to the extent that my CEOs do, so I have time to reflect. And very often, my intuition will tell me very clearly where we need to go in a conversation.

Mike Pinkus: That’s amazing. And the fact that you’re seeing it clearly now, but you’ve sat in those high-pressure seats. And so there’s a lot of trust and authority, I think, because you have sat in that seat.

Which is what’s very unique about you as a coach, Mark. It’s the fact that you’re not speaking just off of gut feel alone. You’ve been in the high-growth startup. You’ve been closing deals in investment banking. And so I think it gives a very unique perspective to the problems that your CEOs are bringing to you.

I want to ask you one more thing, because I know we’re running low on time here, and I want to be respectful of your time. 2023 and 2024 have been more challenging. Some founders have only seen bull markets. They’ve seen everything being perfect...

Mike Pinkus: These last few years in particular, in tech, have definitely been—they’ve been unique. They’ve been challenging. I’ve seen that some of the people you’ve interviewed on your podcast are customers of ours, or clients of ours that we’ve known for years. And I don’t see that intimate side that you do—into the deep, deep-rooted issues.

I wanted to ask you: what advice have you been giving CEOs about the things that are out of their control, like over these last two years? How are you getting CEOs to cope with the fact that things just might be shit for a little while? Like, you're going to have to deal with the fact the macro environment sucks. How have you been able to deal with that with your CEOs?

Mark MacLeod: Yeah, you know, to your point about things being out of their control, that’s the first point, right? Here’s an issue—is it something I can do something about or not?

If it’s something I can do something about—great, let’s do it. And if it isn’t, then we just have to accept it. Now, the surest way to be disappointed is to have inflated expectations. And so part of this is working on expectations, right?

If you’ve never seen anything but good times and you raised money in 2021, then your expectations are going to be inflated. And, you know, I’ve been able to kind of just share—like, I went through the dot-com crash. I went through the 2008 mortgage crisis. In 2008–2009, there was such a downturn in the public stock markets that VCs literally were not writing checks. Their LPs wouldn’t give them capital. There was just a complete shutdown of the market.

And just reminding my clients as well, right? Like the vast majority—let’s call it 99.5% of companies in the world—need to make more in revenue than they spend in costs. And, you know, it’s good to remember that and like—

Mike Pinkus: There were times where that wasn’t a thing, but yes.

Mark MacLeod: Right. Rationalize. Rationalize your spending.

I deeply believe everything in life happens for you, not to you. And this downturn has made every single one of my CEOs a better operator. Every single one of them has had to go through a downsizing. And that’s been tough, right? They’ve had to look at people who agreed to join their company—signed up for their mission—look them in the eye and say, “I have to let you go,” and live with that.

And deal with: “I put so much blood, sweat, and tears to build up to, let’s say, 100 people. And now I’m at 70 people. Why was I killing myself?”

To recognize that maybe, hey—I need to just dial it back a little bit and be a bit more sustainable. Because this thing is so tenuous, right? You know, it could fail.

Mark MacLeod: You know, I tell my CEOs all the time—an average startup lasts seven to ten years. And when you're in it, it feels like everything. But when you zoom out to the context of your life, it’s just a chapter. Your life is actually more important.

If you’re in a relationship—if you’re married, as an example—well, you’ve made a promise to be with your partner until you die. That’s more important than this startup that’s going to last seven to ten years. If you’re a parent, well, that’s your most important startup. And, you know, hopefully you create more time for that.

So a big thing that I’ve seen come out of COVID is people’s priorities have rebalanced, and they’ve actually realized, “Hey, you know what? These things matter a little bit more—actually a lot more.”

Mike Pinkus: Mark, do you mind me asking what the average age of a typical CEO that you work with is? Like, on average? I know it’s obviously a wide spectrum.

Mark MacLeod: Yeah, it’s all over, honestly. My youngest is still in his twenties—he was on the Forbes 30 Under 30 list. Deeply impressive human. My eldest is probably in his early fifties.

Mike Pinkus: Yeah.

Mark MacLeod: So maybe in the thirties is the average. But yeah, it’s a wide cross-section.

Mike Pinkus: Yeah. And the reason why I asked that is—hindsight being 20/20—and you started this conversation by saying you had to wait until you had the experience level. You said a gray beard—I have a gray beard too, although I shave it down.

But I understand what you're saying now: what comes with the years is wisdom, right? And experience. And you need a lot of energy as a founder in a high-growth environment, and there are stages in life. But I love how you said a lot of CEOs—it's a part of their identity. Their business is their identity. And I appreciate your transparency in talking about your past and your relationships, because that perspective—to share with someone and go, “You view these next seven to ten years as everything...”

Mike Pinkus: But you won’t look at it like that down the road. But you have to have been through that yourself in order to give that type of advice and wisdom to someone. It’s, like I said, similar to how you sat in the seat of CFO and investment banking and all these things.

I think it’s super valuable, Mark, that you’re doing something where you just have a very unique perspective on these things. And I want to conclude by thanking you for coming on—because this has been really insightful for me as well. Running a business—not to the altitude I’d say that most of your CEOs are at—but really insightful, the things you’ve shared, Mark, on just the challenges and the things that CEOs go through.

Mark MacLeod: Thank you. This is one of my favorite topics in the world. This is my purpose. It’s why I get up in the morning. So I’m happy to talk about this all day, every day.

Mike Pinkus: Awesome. Well, thanks again, Mark. Appreciate you taking the time for this. And to any of our clients—if, like you see Mark—I mean, we’ve already had overlap, and I’ve been loving what you’ve been doing over this last little while.

Mark, how can people find you? What’s the best way to get in contact with you?

Mark MacLeod: Uh, yeah. I write online on LinkedIn every day. markmacleod.me  is my website. You can find blog posts and links to the podcast there.

And then, you know, right now I run the world’s least scalable business, right? Which is one-on-one coaching. And so I’ve only been doing that for growth-stage CEOs. But I hear from early-stage CEOs all the time. And so, to date, all I’ve been able to say is no—which is not particularly helpful.

And so late in Q4, I’ll be launching a mastermind group coaching program for early-stage CEOs. So there’ll be details of that on my website as well.

Mike Pinkus: Amazing. I thought you were going to say you were going to clone yourself with AI—that would’ve been just as effective and scalable.

Mark MacLeod: Yeah. Yeah. Yeah, that’d be handy.

Mike Pinkus: Thanks again, Mark. Really appreciate it.

Mark MacLeod: Thank you, Mike.

Mike Pinkus: That was Mark MacLeod, CEO coach to some of the fastest-growing startups in North America. Mark shared many lessons for CEOs, but two stood out above the rest.

Number one: Mark is in the process of becoming a yoga instructor, and he teaches all of his CEOs to prioritize their health, as it is the foundation to being able to function as a high-performing CEO.

Number two: When I asked Mark the most important character traits of high-performing CEOs, he noted that while luck and timing play a huge factor in success, he has always believed that individuals with high levels of resilience and self-awareness have the highest odds of success.

That's it for today. As always, keep scaling up and breaking barriers.