Our guest is Mark McLeod, a seasoned expert in the tech startup world. Mark has an impressive track record having served as CFO for companies such as Shopify and FreshBooks. With over two decades of experience in the venture-backed startup industry, Mark now spends his time coaching and advising CEOs. In this episode, Mark shares his journey of how he transitioned from being a CFO to an executive coach. He highlights how he found his true passion in coaching and advising CEOs, which he feels was the most fulfilling aspect of his previous roles. Mark's mission is to help CEOs of venture or private equity-funded technology companies grow faster than their businesses, a concept he elaborates on during the conversation.

Originally published April 2023

This episode of Actualize is hosted by Rob Pintwala, the founder of First Session.and Kim Foster Yardley, a Clinical Psychologist and mental performance coach and owner of The Mental Game Clinic.

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Mark MacLeod (00:00):

If your family is truly important, it has to get the similar level of intention that you carve out for your business.

Rob Pintwala (00:19):

Welcome to Actualize a podcast focused on the intersection of performance, ambition, and mental health. I'm Rob Pintwala, and I'm joined by my co-host Kim Foster Yardley.

Kim Foster Yardley (00:32):

Rather than fixate on the wins and successes, our mission is to uncover the whole picture of the being behind the performance. Join us as we interview top performers across business, sport, and the arts.

Rob Pintwala (00:47):

Actualize is presented by first session. Have you ever considered trying therapy or simply just wanna level up in your personal or professional life? I started first session back in 2019 to help Canadians find the right mental health professional for them. Since then, we've connected thousands of Canadians with the right therapist, and I'm really passionate about helping each individual find the right fit in the therapist for them. We spend hours and hours interviewing therapists across Canada, and each one of them has a professional video for you to take a look at while you decide who might be the right fit for you. Check us out at firstsession.com.

Kim Foster Yardley (01:24):

Actualize is also presented by the Mantle Game Clinic. TheMantle Game Clinic was founded by myself, Kim Foster Yardley. I combined my 20 years of experience as a clinical psychologist with my passion for sports psychology, and I built a team of therapists who specialize in working with high performers, Olympians and founders. Find us at thementalgame.me.

Rob Pintwala (01:56):

Today's guest is Mark McLeod. Mark brings a depth of experience in the tech startup world. While today Mark Spence's time coaching and advising CEOs in his past, he has served as CFO for companies like Shopify and FreshBooks.


Okay, Mark McLeod is our guest today. Thanks for joining us. Mark, your Twitter profile bio says, I coach the CEOs of high growth companies and help them execute big transactions, former CFO, VC and iBanker.So, welcome, mark. Uh, is there any context you'd like to give to your bio?

Mark MacLeod (02:37):

Uh, yeah. First of all, thanks for having me. Um, yeah, maybe just, uh, fill in a few of the blanks. I've been in the venture backed startup world since 1999. Uh, spent 14 years as CFO for a bunch of companies, including, uh, Shopify and FreshBooks. Uh, three years as a VC, um, five years as an investment banker. The thing I actually loved most across all of those, conversely all of those roles was the one-on-one coaching and advisory conversations that I had with CEOs. And so in 2020, I decided to, uh, just do that. So shut down my investment bank back and get certified as, uh, an exec coach. And, uh, now I exclusively coach the CEOs of either venture or private equity funded technology companies that are at scale. And I see the mission of what I do as helping those CEOs grow faster than their businesses, which is something we can unpack if you'll, if you like.

Kim Foster Yardley (03:37):

It's very interesting. Yeah, I I'd like to ask about how that's a very way interesting way that you phrased that, um, around helping the CEOs to, are you, are you saying, could you speak a bit more to that? I don't want to assume. I'm sure. Curious.

Mark MacLeod (03:55):

Yeah. So again, I'm only in the startup world, so not normal businesses, right? Mm-hmm. <affirmative>. And, um, you know, when you look at the biggest outcomes, they tend to be, uh, founder led, start to finish. So let's call it a hundred percent correlation between that founder's performance and the outcome of the company. Hmm. And if you're going through massive growth, you're doubling every year, in some cases, tripling every year, Your job is totally different 12 months forward than what it was 12 months previously. And so the job's changing all the time. The company is changing all the time, which means the CEO must also transform mm-hmm. <affirmative>.And, uh, and so the, I see that as the purpose of the coaching. Do I always be kinda helping them clear the forest so that they and their leaders can go through kinda as quickly as possible?

Kim Foster Yardley (04:49):

Hmm. Because the landscape is changing all the time,

Mark MacLeod (04:54):

Oh it's the nature of technology, right? Especially the biggest outcomes tend to be disruptive and that disruption, well, first of all, it happens to a market, but then it also just creates a significant change within the company. Right?

Rob Pintwala (05:11):

Love that. Love that Mark. Um, yeah, I've worked at two venture backed, or I guess three venture backed companies and have not been the ceo, but holy smokes, has it been a lot for, for the CEOs that I've worked with, um,

Mark MacLeod (05:23):

It's a tough role.

Rob Pintwala (05:24):

I've heard you say before that most CEOs come to you as a coach, completely burnt out when they start working with you. Yep. Yep. What does that look like? Like how, what, what, what, how are they describing, or how are you helping them identify that burnout?

Mark MacLeod (05:40):

At the most basic level, they just can't keep up, right? And, um, you know, over time, you, when you start out, um, you do everything.You do the most strategic things, and you do the most mundane, and you're in the critical path of everything. But over time, you go from working in the business, you know, building products, trying to get customers to working on the business. Do I have the right people? Are they focused in the right direction?Do they get the vision? So it's a change in altitude. More often than not, the burnout comes from not adequately changing altitude. You've hired leaders, but you continue to be in the critical path. You, you can't let things go. This happens a lot with product and technically oriented founders, if I stereotype.So very often, um, the burnout that they're experiencing when they show up is self-created.


Okay? It shows up in a bunch of different ways. You know, they're maybe, first of all, their mood is worse, they're more cynical, they're more critical. Maybe they have a hard time getting up in the morning, um, irritable at home, uh, lots of stress, um, difficulty concentrating, um, I guess all the classic symptoms of burnout. But when you dig underneath the hood, it tends to be, uh, self-created, which is not a criticism, it's a difficult role. Like every other role. I was a CFO for a long time, and you apprentice for that role by being an accountant and then a controller, and then a director of finance's, like a path. And of course, there's a body of work, uh, you know, I'm a CPA by training, right? So there's a, a path to become a finance leader the same way there's a path to become a CMO or a CTO. CEO, you just give yourself the title and then hang on for dear life. Like, it's a really difficult job, you know?Mm-hmm. <affirmative>. So it's, it's, I'm not surprised this happens, but yeah, it happens a lot.

Rob Pintwala (07:51):

I had another question, uh, about, about that the CEO role. You've worked with CEOs for a long time now, uh, directly and also indirectly supporting them. I've heard you talk about trying to compliment their skillsets when you were a CFO, uh, and take things off their plate. From a motivational perspective, uh, is there any sort of pattern matching that you've been able to do? Or is it very, a lot as far as why, specifically founder CEOs? Like what drives them? Why did they take the venture backed startup route and try to blow it up big? Like, is there a lot of different, um, basis for the, for their motivation, or is it, can you, can you sum it up simply?

Mark MacLeod (08:40):

I think there's lots of different, um, motivations at the start. I remember when I was CFO at FreshBooks, you know, that was, um, a 10year old company with 130 employees before it raised its first penny of venture capital. And Mike, the ceo, just talked about, well, I'm just putting one foot in front of the other, you know, and we'll see where I get to, you know, at a certain point, he just had enough conviction, but yeah, okay. It's time to really go for it. I think some folks start companies for the wrong reasons.They see a big market, uh, like if you're in love with the market, uh, because it's a big market, well, that's not an enduring source of motivation because money is not an enduring source of motivation for people. Like, you give someone a pay raise and they feel great for like a day, and then they get on with the rest of their lives. So money's not the thing. If you have built a product and you're in love with your product, then that's also not great, because then you have a closed mindset. All you're trying to do is convince people and evangelism, look at this amazing widget that I've built. Like, and then you're not listening to the market. So actually the only enduring source of motivation is that you're in love with the problem.

Kim Foster Yardley (09:58):

Oh, that's amazing.

Mark MacLeod (09:58):

It's your purpose. It's why you get up in the morning.You're just so endlessly fascinated by the problem. And, you know, when I think of, you know, I spent a lot of my time, uh, with software companies that serve the, uh, smb, so the small and business market, you know, my coaching practice is broader then that now. But when I was operating and, uh, when I was a VC and a banker, SMB was my focus. And, uh, one of the characteristics of that market is it's large and evergreen. It's kinda been around forever, and it's gonna be around forever. And I bring that up because that means you could operate well kind of forever, right? And you look at Toby at Shopify, he's been endlessly fascinated with making commerce simpler for a long time now, and he's still nowhere near or done, right. Uh, whereas contrast that with an enterprise software company serving the Fortune 500, well, guess what? You got 500 prospects. And so it's kind of like a land grab. Whoever gets there first wins the market. So it's completely different game, if that makes sense.

Kim Foster Yardley (11:00):

I mean, mark, to me, what you're saying resonates so much with, um, with theories around motivation and how, um, motivation really, when it's extrinsic, it's isn't sustainable, like you said, around right. Money, and, but I, what I, what I really value around what you're saying when you kind of bring in your specialist knowledge around the startup world is how that, that it's not just enough. Like you said, when you have a, a product that you're orientated towards, you invested in a particular outcome, you're close to others. Whereas if you are problem focused and you have that intrinsic motivation to, to solve that problem, you actually have a much more open mind.

Mark MacLeod (11:39):

Right? Exactly. And that's so key to disrupting a market, right? Because by definition, at the start, the market doesn't exist, or, you know, like that, you know, there's like an ancient, like, again, Shopify's a great example, right? There was Yahoo Commerce before Shopify showed up, orGoogle, like, search was a solved problem. There was geo cities and ask Jeeves and, and Yahoo, and then Google came on along with a solution. It was just completely disruptive. And none of those companies are around anymore, right?So disruption requires, actually, in some ways it's a mix at the start, you have to kind of be single-minded. And perhaps Steve Jobs was, you know, nobody knew they needed an iPhone until they invented the iPhone, but after that, you're listening to your customers and you're iterating. Um, and when your pre-product market fit kind of in the early stages, it's crucial that you have that feedback loop where you listen to what the early users are saying and iterate until you find some segment of the market that is actually pulling you, you know? So, and if you're closed minded and you're not listening to feedback, you just know, you just don't get that. I've built this amazing thing, you're not using it correctly. You're just gonna run outta money and die. And that happens.

Rob Pintwala (12:58):

And, and Mark, I've heard you'd say that you've been offered the CEO role maybe more than once. Uh, I know you've been the CEO of your own company. Um, but as far as taking on the CEO role out of, at a super, you know, rocket ship, um, you've declined those roles in the past, and why, why have you declined? And did you, after you declined, and it sounds like you might have declined multiple times, but how did you keep that conviction? Like how did you pass that up?

Mark MacLeod (13:34):

Yeah, so, you know, I've been at the right hand of CEOs, uh, my entire career. And so have a deep appreciation for how difficult the role is. And the bigger you get, there's just, you have more targets on your back. Everybody wants a piece of you. And I've been the knit number two leader and, and these companies many times and just noticed a huge difference between the pressures that were on me versus the pressures that were on, on the other person. So that was, that was a huge part of it. It's not laziness. It was just like self-preservation, you know, coupled with them, you know, I, uh, I'm not technical. Like I think, you know, there's, if you think about, uh, software business, like I'm mostly in software, right? There's two cores. There's building product and selling product. Everything else, while it's important is in service of those two things. And I am not technical, uh, and I am not a goto market person. And so I could add some value, but I think, I think the best founders have some depth in one or two of those areas, right? Mm. And so I, just, I didn't feel that I could really crush it as a ceo, but the main reason was self-preservation.

Rob Pintwala (14:55):

Yeah. Thanks for that. Yeah. Um, regarding that pressure that the CEO takes on, and, and Kim, I'm sure you have, um, some perspective on this too, like how do you coach the CEO to be able to withstand all these targets on their back and all these hits that they're constantly taking it as their company gets bigger? Like, I think about Toby, uh, you know, at Shopify, and I'm just so impressed by how, like, how he's been able to stay at the helm.Uh, it's, it's incredible to watch. Oh yeah. How would you, you know, is that just part of the game?

Mark MacLeod (15:30):

It is, and it isn't. Um, I think that, uh, startups existing one of two extremes. They're either struggling to find growth or struggling to keep up with growth. And, um, it's, it's very rarely a steady state in between. Uh, and, and so growth forgives all sins, right? All else being equal.The rate of year and year revenue growth is a single largest driver of valuation when investors are thinking of investing in your company. And that absolute amount of revenue and kind of the momentum that you have is a magnet.It attracts talent that wants to work for you. It attracts companies that wanna partner with you and buy you, it attracts investors. So a huge part of what I, um, working on with clients is unlocking revenue growth and then hanging on for dear life. And so a lot of the criticism, a lot of the pressure that CEOs face is cuz they haven't yet found that unlocked.


And so you got all these armchair pilots like the VCs at the board meeting, like, you should do this, you should do that. Um, but once the thing has found that unlocked, then suddenly that CEO who was kind of in the penalty box before is now like the smartest person in the room. So that's a huge portion of what I'm trying to do is, is, um, is help them find that unlock. And a lot of that is focus, right? We get, uh, so much satisfaction from banging things out, and we may have a hundred emails in our inbox and blast through them and all of these slack messages and anyway, we can do a hundred things in a day and go home, which I realize at the moment is not a geographical thing. It's just a <laugh> shut down your laptop thing for the most part.


But like, you could feel good about the day, but how many of those things were truly on the critical path of unlocking revenue growth? So a big part of of this is actually focus and then, um, the CEO job is all encompassing, right? It's a 360 degree context, but within that, there are gonna be aspects that you love and, and that you don't. And so, from the very first session, actually in my onboarding questionnaire, I am curious about what a CEO's superpower is, and conversely, what is their kryptonite? So what do the things that they love to do where in complete flow time just stops? And conversely, what are the things that they absolutely hate? And try and design their role and their or chart around maximizing those superpowers. And, and by the way, doing that tends to actually result in higher revenue growth because they're, they're crushing it.


And like, you know, living their best lives. Now in a utopian world, every person in the company would be, their role would be designed around their superpower. Now, of course, we don't live in that world.And so I'm stuck just, I'm trying to deal with that at the very top and making sure that the leadership team surrounding that c e o, you know, truly compliments the ceo, enabling them to do what they do best. And, and if we do that, that tends to result in higher performance. And, uh, tends to put some of those kind of criticisms and pressures to bed. And there's a lot of time spent dealing with, um, just helping them understand that not every criticism or ask or request is actually worthy of spending time on, you know, so like, again, II just again, comes back to focus.

Kim Foster Yardley (19:22):

I think this connects with something I read in on your blog actually, mark around, um, how, um, CEOs are always at war. I think that was the Yes. The one that I was reading, right? And, and just that idea of that the, that this, that there's almost a, a false feeling of winning when you're in the high revenue phase, which is actually mm-hmm. <affirmative> false, you're still mm-hmm. <affirmative> in a fight state. And you know, as a psychologist and, and someone who works in kind of all the performance side of things, I'm, I'm thinking of regulation, right? And like that the environment is always going to be stressful. Like a state of war is a state of stress. Um, you can't get around that really. And it sounds like you have, you help CEOs within that to find the strategies where they can actually leverage that in the best way possible for them.


So it's not about mm-hmm. <affirmative>. Cause I think, I actually think this idea that this work-life balance is not true. I don't think it exists. <laugh>, um, no <laugh>, I, I dunno if you can concur. Um, and, and so that, that's what I'm very interested and curious about around how do you help them. So you've spoken a bit about, you know, very much around focus, what to mm-hmm. <affirmative>, what to focus on, how to leverage the superpowers. Um, how do you advise them around managing that high level of stress and actually just really it's the way things are. How, how do you engage them around that, if at all?

Mark MacLeod (20:48):

Well, I think these CEOs are, um, not unlike professional athletes. And so it's interesting given that you work with athletes, uh, a professional athlete, first of all is completely elite. They're the best of the best and they invest a lot of time in, um, being the best of the best. They practice, right? I heard a story back in the day that Michael Jordan took a hun a thousand, uh, practice free throws a day cuz he knew he was gonna be fouled all the time and be taking free throws. And so he just wanted to be amazing at them. Um, and then they come in and they perform really, really hard and then they rest and they place a significant emphasis on rest. And so now let's look at a CEO also has huge expectations. The more capital you raise, um, you know, the, there are huge return requirements on that. Um, you have to be elite at what you do in order to actually generate the return on that capital. Cause it's, it's super hard. Um, and the best leaders tend to attract the best people to work directly for them. And that is absolutely on the critical path to succeeding. I think where most folks struggle today is on the rest part, I think there's this, um, bro culture. Uh, cause the startup world is pretty male of, you know, I'll sleep when I die and, um,

Kim Foster Yardley (22:27):

Like in the army <laugh>, but even if the monetary race

Mark MacLeod (22:31):

<laugh> kinda crazy and, uh, you know, that doesn't work. You know, um, we're not machines and even just like, just on this not machine bit, so many CEOs just go from thing to thing meeting to meeting to meeting call to call, to call, no downtime, complete context switching. Like, sorry, your brain wasn't designed for that. Like, that's not a thing. So, you know, I'm really pushing folks to recognize that the human beings and not machines, um, you know, work will expand to fill all available time. So I'm just trying to help them create boundaries. And my thesis, which has been burnout, uh, by kind of actual evidence is the work will still get done in the, the reduced time. But meanwhile you've created space for physical health, uh, for sleep, et cetera. Uh, for me, and that's easy to say now cuz I'm a coach and I don't, I'm not grinding anywhere near what I used to.


But even when I was running an investment bank, uh, investment banking is not a lifestyle business in any way, shape or form. I have an office in Toronto, office in San Francisco, clients in Europe. If I was awake, I was on running six deals concurrently. It was high stress. So for me, like, first of all, I began my day by doing CrossFit and I would, would workout five days a week. So I created that space. The days where I missed it, I had less energy, I was less sharp. But the days where I did it, I was like on, and by the way, CrossFit's kinda crazy and you do some weird stuff and you routinely go through a limit that you either legitimately had or only thought you had. And if you just ended up doing 24 handstand pushups or like you crushed your deadlift record and then you show up at work, you're like, I'm invincible.


I'm gonna like crush today. So there's a mindset thing.And then if you're serious about it, well it forces you to eat well and sleep well, you know? And, um, CrossFit is not just a cult. It actually works. Uh, it's like the opposite of fight club. You're supposed to talk about it. SoI've, I've checked the box there and I've converted more than one client to, uh, go to CrossFit. So it doesn't have to be that. But anyway, physical fitness is a thing, right? You know, we identify with our brains like, this is, we think this is it, this is me right here. But like we, our body is so much bigger and we actually do have to use them in proportion. Uh, so I'm, I really push folks to exercise, um, push them to sleep, and, um, haven't really gone on to the nutrition yet.


Um, but this ties into what I was saying earlier about, um, operating at the right altitude because if you're at the wrong altitude, you can't create that space mm-hmm. <affirmative>. So it's actually by elevating and removing yourself from things that you don't have to be in, um, by having the right leaders, you know, I spend a huge amount of time on the leadership team, um, because that is the CEO's leverage and often through no fault of their own, they have people reporting to them that are good, where, whereas everyone should be great. And maybe that person used to be great, but just didn't keep up and grow at the same pace as the business, or they were never great, but it was in a functional area where the CEO wasn't competent and just didn't know what great it was. And so, um, yeah, there's been, that's been a huge area and has resulted in lots of changes to the org charts of my client's companies that has been transformative, you know, and, and CEOs just didn't even realize, like, there's like, oh my God, I can breathe. Cause now I have someone in the chair who actually is crushing it, you know? And it's not that you abdicate, you still have to run the function, but like, it's a completely different ballgame when you have an a player in there versus, uh, aC player, you know? So I dunno if any of that makes sense, but just some random thoughts.

Rob Pintwala (26:55):

Oh, it resonates with me, for sure. You, you said, when you were talking about running the investment bank earlier, you said sometimes you had six deals going on at once. I come from a bit of a sales background, uh, probably weren't close, I wasn't closing deals probably that size. But, you know, you get this rush of like excitement when you, you know, are closing deals or you are shipping products or whatever. Like I'm sure there's some dopamine going on there, something like that, you know? Um, and then when, imagine when you change altitudes as a CEO or if you're exiting a business or, you know, even if you're an Olympian who's just retired, like, like my question comes to like, what's the similarity between kind of the addictiveness of that activity and trying to put a pause on it or transition out of it? Like do you, do you find that maybe a CEO is not able to rise up because they're just, they get so much kind of, you know, so much of a rush out of a certain area of the business? Like how do you help them transition that?

Mark MacLeod (28:02):

That's a great question. Um, as a CFO and, uh, as definitely as a banker, I went through explicit retraining to not experience those rushes. If you're se you're a founder selling those, the business, it's inevitable emotional rollercoaster. You're picturing the Ferrari that you're gonna buy, you're thinking about all the years of effort that you put in and, um, you can't be objective. And, and then it's, there's always drama. And so I needed to be the rock. I couldn't ride those highs and lows with the CEOs. Um, always kind of needed to be pretty. And so the, the lows were never particularly low and the highs were never particularly high. Uh, and so for me it was actually about, uh, I think it was what I was saying earlier about falling in love with the problem. For me, I was just endlessly fascinated by the work.


You know, the thing with deals, and you know, I'm mainly a coach now, but in 2021 I still advised on 580 million of sell side deals justas a side hustle. Um, I'm endlessly fascinated by deals because they're all encompassing. In order to get someone to invest in your company or buy a company, you have to completely articulate everything, the market opportunity, the product, why it's disruptive, the positioning, who's gonna buy at the revenue model, uh, operations, you know, what's a competitive landscape, how will you go to market, which channels you have to reflect all of that in a model that people understand, like you end up learning so much about, uh, businesses and entire industries. And, um, and so I find that work just endlessly fascinating, right? And I learned so much from that. And, um, I think part of what's been enabled me to coach, uh, so many CEOs in so many different industries has just been that broad exposure and, and investing in companies, selling companies over and over again where you have to understand everything about that company and can digest it, you know? So for me it was wasn't the rush. I actually find, you know, in path, I did 110 million deal, um, want just a single deal. I get more excitement out of a coaching conversation where like a CEO has a big unlock, then I, you know, that I have a tombstone gathering dust behind me for that hundred 10 million deal. You know, kinda who cares? But, you know, completely impacting a human being is, is way cooler. So if, ifI get a rush at all, it, it's there.

Kim Foster Yardley (31:05):

I was just curious about how you trained yourself not to get on the emotional rollercoaster. Was that a learning? Was just that from experience, from that exposure of all those, those up highs and lows? What was it that that helped you?

Mark MacLeod (31:17):

Well, first of all, in the early days I was riding the stress with the ceo. And, um, I was drinking a lot. And I realized that both of those things and realized that as the CEO's right hand, I needed to be solid. I couldn't be freaking out at the same time as the CEO was freaking out. So it was forced at the start, you know, fake it till you make it, I guess. But I just realized that I, and so I ate the stress, which is obviously a doesn't work. You can't bury stuff down. It's still gonna, it's, it's gonna manifest, it's gonna show up in your body. Um, but I ate it to start and then just worked on, on different techniques. You know, I, I became really, really serious about yoga. I've been practicing Kundalini yoga for 15 years and it's a huge part of my life.


And actually in the process of becoming a, a yoga teacher now, uh, not that I'm gonna stop coaching, but just, just cuz I love it so much just to further my practice. And, um, that has been, uh, tremendously helpful. Um, I took, uh, Buddhist vows in 2019, it's helpful to realize where all of this fits. Like you're inside a startup and you think it's life or death, but then if you actually zoom out, you realize it's actually totally irrelevant. And, um, so having a a broader perspective, uh, helps. Um, and yeah, like I say, really creating those boundaries, right? Uh, and a lot of these lessons are hard earned. Uh, I got divorced, uh, while I was running the investment bank into small part because other than those boundaries around kind of working out in sleep, if I was awake, I was working. And even if I was physically present at home, I don't think I was mentally present.


I was either completely exhausted or preparing for the next day's the marathon of meetings, uh, or unpacking today's marathon on meetings so I could digest the learnings and the action items. Like it was a lot. And so I think a lot of CEOs go through that as well. Like, it's, it's tough to keep up with the role and the role, not that people are in offices now, but it doesn't end right. You know, especially with laptops and mobiles and notifications and all that stuff. So it's, it's difficult. So for me, yeah, that perspective was, um, over many years and it was hard earned, that's for sure. But the CEOs appreciate that I'm super transparent, uh, and I share these stories with them and, uh, and, and it resonates, you know,

Rob Pintwala (34:20):

How often have you seen it not be hard earned? You know, like if someone is running a company that's growing several times over a per year and they're in the trenches and they're trying to elevate themselves and maybe they even have a couple kids, um, you know how I'm sure you being open or vulnerable with your CEOs is very helpful for them, but they're still just stuck in it. Are they not? Like, how do you really, do you need to feel the pain to change? Or how can you, how can you help them get that perspective when they, their whole world is wrapped up into this business?

Mark MacLeod (35:01):

Well, it is and it isn't, right? So this is the broader perspective, you know, um, I think of companies I was part of where at the time it was my entire world, but now it's not. I'm still around, but I'm not in that thing. So what I tell CEOs regularly is like, this company will be a chapter or two or three chapters in your book. There's not all of your book. This comes up often in the context of marriage. Um, now marriages have about a 50% success rate and um, a lot of the CEOs that I work with, uh, are putting all of themselves into their business and as a result, their partner gets the drags of what's left. Um, and then they have this conflict. They struggle because they're like, I love my, I'm gonna say wife cuz most of my CEOs are male.


Not entirely, but most, uh, I love my wife anyway. I love my partner, but, and I love my kids if I have kids, but I just ha I'm giving everything to my business. So this is where I'm asking them to think really about the vision for their lives, the end game for their lives. Uh, because if you truly love your partner, this is poignant for me cause I'm getting married in six days. So this is a highly relevant topic. Congratulations. But, uh, well thank you. Um, then that should reflect in like the pie chart of how you prioritize your life. If your family is truly important, it has to get the similar level of intention that you carve out for your business. Now, there are 24 hours in a day you need to sleep for a third of them ideally. So this is again about raising altitude.


It only works if you raise altitude. Now let's talk aboutElon Musk for a second. I don't think he's the poster child of balance. Mm-hmm.Uh, I also don't think he's human. I think he's from Mars, but that's a separate topic. But, um, the reason why he is able to run multiple companies simultaneously is because, well, a's I balance, but let's set that aside. It's because he operates at the right altitude. He is not in the minutiae of any of those companies. Uh, Jack Dorsey, you know, ran Square and Twitter simultaneously for a while. And same thing, he knew his superpower, it was product. He was heavily involved in product direction, product, vision, everything else was trust. You know, had he had trusted Lieutenants stealing with. So there are, there are absolute lessons to be learned

Rob Pintwala (38:01):

There. You mentioned most of your CEO clients are male, but maybe not all. Um, Kim and I have had separate discussions about, um, female leaders in, in, in the workplace. And I guess in this context in tech startup world, um, what perspective do you have on maybe the unique challenges of a female leaders in CEO positions or high level executive positions in this high stress venture tech world?

Mark MacLeod (38:32):

Yeah, many. Uh, so this is the outside looking in cuz as you said, I am a male. Um, but the stats are pretty clear. It's much harder for women's CEOs to raise capital. And so that's difficult when you're trying to create big outcomes. Uh, cuz it's easier than ever to start a company easier and cheaper than ever to start. But it is as hard and as expensive as ever togo all the way and build a market leader. So that's a difficult thing. Um, and then there's still like guys can't give birth, thank God for that. But, um, so women still have to give birth and you know, I don't know if there's an expectation that they're their primary caregiver, but there's things that another can do that a father cannot. Um, so I do think there's some societal expectations or just, or pressures on themselves, uh, around that.


You know, as an aside, one of my red flag words is should when clients tell me, oh, I should be doing this, I should be doing that I'd be like, says who? That word just implies expectations of someone else. Like tell me objectively where that rule is that you feel that you're currently violating. I bring that up because I think women are, uh, if I'm stereotyping hard on themselves, uh, and do feel they should be doing everything and feel as a result, they're not doing anything well, for what it's worth. Mm-hmm.<affirmative>, uh, cause I've looked into this gender disparity thing in the startup world, uh, for a long time. Um, and uh, I'm an advisor to and and limited partner in, uh, standup ventures, uh, fund that's focused on, uh, female founded companies. And the stats are also clear here as well. Actually female run companies outperform male run companies in terms of success rate.


At the end of the day, they do struggle to raise capital, but the success rate is, is clearer. Uh, as an aside, if you look at the countries that have been run by women, they tended to be run better. You know, Angela Merkel in Germany for a long time, look who crushed Covid, it was New Zealand. I forget their prime minister's name, but like, I think women are great leaders. They possess an intelligence and, uh, intuition that I think, uh, males struggle to tap into. And they are, um, more collaborative. You know, they seek discussion, uh, and get a lot of input before making decisions. So I,I think, uh, I'm completely stereotyping across everything I've just discussed here. Cause there's exceptions to everything, but I think on, on a balance ceo, uh, women can make fantastic CEOs.

Kim Foster Yardley (41:19):

I mean just, I think maybe because, I don't know if it's because I'm a woman, but I do end up having a lot of female elite athletes and female, um, founders that I work with. And it's, what you're saying resonates really around, particularly around raising funds, feeling like you're the only female in the room and you're not being taken seriously. Cuz often you're quite young. No. And so a lot of what you're, what you say is dismissed and yeah, you can't push it either cuz then you come across as forceful and then it's like this bit of a double bind, we know, but then you're being aggressive. And how do you advise women in those situations?

Mark MacLeod (41:58):

It's tough. I mean, I've literally seen VCs ignore a CEO and ask the male co-founder a question, which is total bullshit. Um, hopefullyI'm allowed to say bullshit anyway, whatever. Um, absolutely

Kim Foster Yardley (42:13):

Also go for it.

Mark MacLeod (42:14):

<laugh> <laugh>. I think you just have to be yourself. Uh, I say this to, to people all the time. Like the startup game is long. You know, we read, if you read TechCrunch all the time, you think that companies are, you know, start to finish inside three years and you sell for 300 million bucks. And it happens. But it's absolutely the exception, not the rule. And it's the only way you will thrive over a long startup life cycle is actually by being yourself. And so not trying to be who you think your investors want to you to be. Um, so that's easy. It sounds like a great Hallmark card saying, I know it's harder to do, but, um, I think you just end up having to network that much harder to get in front of more VCs to find the ones who actually love you for who you are.

Kim Foster Yardley (43:13):

Yeah, I think it's, for me, exactly, it's about finding those spaces where you're not having to fight a fight where the other person isn't aligned with your values or what you're seeing. Uh, it's a waste of energy. I think a lot of the time when I'm working with females, um, founders, it's around really not being reactive to that environment, right? Like choose, um, finding those spaces that will support you and also being very clear around your values and where you are coming from.

Mark MacLeod (43:41):

Yeah, exactly. Yeah.

Rob Pintwala (43:42):

Maybe to wrap things up, I, I wanted to bring it back to values and, um, I know that's about being yourself too, but like, where do values can, can, can someone's values change over time? Like a CEO for example, or they just need to dig deeper and kind of find that, and like, why are, why do you advise folks to focus on values from however early they can?

Mark MacLeod (44:10):

All right, so there's multiple questions there. Maybe I'll start with the last one around why, I guess the importance of values and why II, yeah. Place emphasis on them. This is again about, uh, changing altitude.The CEO cannot be in the critical path of every micro decision that is made, or he or she will blow up. And so without creating a bunch of clones, you need to create enough context that, and enough institutional knowledge and alignment such that the individual contributor or the small team or the manager or the director or the VP can make a decision that is consistent with what the CEO would make if he or she was in the decision making meeting. Um, and that comes through values in part, right? And understanding kind of what matters to us, why we're here, what is important, what is not, how we behave towards one another.


You know, I think most companies do a bad job at values.Um, for many, they're just like cheesy posters on a wall. But I actually believe that every disagreement or lack of alignment in the company can be traced back to either, uh, conflicting or unarticulated value. Um, cause it's just, these are just instincts that we operate from. Uh, so I find them to be supremely important. Um, I have been encouraging my CEOs to bake values into the performance reviews. Like literally half of the review should be based on whether you're living the values or not. Um, I think in any meeting when there is this kind of conflict that's going on, okay, let's bring it back. What value is not being lived here or, you know, let's bring it back to that. And that tends to, you know, create a lot of focus. Um, I do think, you know, the core of who you are, uh, I think is reasonably stable.


Um, but, but not locked in stone. They do think values change. Uh, or maybe the relative emphasis of values change. Again, let's takeToby from Shopify. Like I'm certain he's not in no, in, no, like he's, his role, his day-to-day reality is completely different than what it was 10 years ago. And I'm sure what he, what was most important to him then is not what's most important to him now. Uh, so things change, that's for sure. But the core of who he is in terms of like a deep technologist and his complete fascination with making commerce simpler for everyone, I think that's unchanging. You know, so there's some things that are just absolutely kinda locked and key to who you are and other things that are more fluid. There's no point having white hair if you can't dispel a, you know, a, a pearl of wisdom every now and again. Right?So this, uh, this is actually my secret weapon when I stroke it, the insights come out. So yeah. <laugh>, um,

Rob Pintwala (47:27):

I hope that stays for the wedding, Mark.

Mark MacLeod (47:29):

<laugh>. Oh yeah. Thanks for the wedding.Absolutely. Staying with the wedding.

Rob Pintwala (47:32):

Love it. Alright, well that's a great time to end it, Mark. Thank you very much. I know folks can find you on Twitter at Mark McLeod underscore, I think.

Mark MacLeod (47:41):

Right? Yeah, yeah. I'm pretty passive on Twitter these days. Uh, but yeah, I'm on on LinkedIn and, um, blog pretty regularly at Mark.

Rob Pintwala (47:52):

Yeah. Amazing blog. So thank you so much, mark, and we'll chat

Mark MacLeod (47:56):

Again. Thank you.

Rob Pintwala (48:09):

Thank you for listening to this episode of The ActualizedPodcast. You can find the show notes for this episode as well as all other episodes at first session.com/podcast. If you like this podcast, please leave us a review on your favorite podcast platform. Thank you again, and we'll see you next time.

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