The Founder's Journey Podcast

Glad you're back for another Founder's Journey Podcast! In this episode, we explore the high-stakes world of high-growth startups with Mark MacLeod. As a seasoned veteran in the startup ecosystem, Mark shares his invaluable insights on what it takes to drive a startup to success and how founders can evolve with their company.

🕒 Timestamps:

00:01:24 - The Crucial Role of Market Timing in Startup Success
00:04:38 - Founder Evolution: Scaling Up with Your High-Growth Venture
00:07:55 - Rethinking Hustle Culture: Prioritizing Founder Well-being and Sustainable Growth

#StartupGrowth #FounderJourney #HighGrowthStartups #MarketTiming #LeadershipDevelopment #WorkLifeBalance #StartupCulture

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What is The Founder's Journey Podcast?

Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.

Welcome back to The Founder's Journey Podcast. Here, actually flying solo this week by my partner crime here, who's my co-host on these, Peter Dean is off at a golf tournament. So, I'm flying solo, but the proclivity joined Greek yesterday, guy I've been following on LinkedIn for a long time. I've gotten to know a little bit, just an extraordinary background. Mark MacLeod is our guest on the podcast today. Welcome, welcome Mark!

Thanks for having me, Greg. I'm excited to be here.

Yeah, no, glad dad, glad we could, glad we could make it happen. So Mark, Mark's background is really extraordinary in the world of entrepreneurship, being a founder, really being at the kind of the right-hand side of leaders in high-growth companies. A lot of which, you know, he's been as CFO, he's been a VC's investment banker, working with companies like Shopify and FreshBooks. And you know, he's really kind of seen it all as General Partner of Real Ventures, which is Canada's largest seed investment fund, and as founded another venture fund himself, before Culture Path Capital Partners.

And we're actually thinking Best Bank, right?

That's right, it is an investment bank. He's also a CrossFit athlete, electronic music producer, DJ, so definitely a Renaissance man. Big Yogi, I know as well. So, super super thrilled that park on the on the podcast today.

So, start out here, look, I mean, yeah, I don't, you've worked with some really incredible companies. You've, you've not, I think most of us in the startup world, if we can kind of see a run like a Shopify or a FreshBooks, even once in our career, it really is an amazing thing to see it multiple times, it's really extraordinary. What are the, what are the common denominators that you would say, you know, in your view, kind of looking at that now, that really attributed to the success of those companies first to say others that maybe just didn't get to that sort?

But then you saw there, yeah, that's a good question. You know, I'm going to celebrate my 25th year in startup land this May, and if I look back on that, I would say the single biggest factor in any of those, in any outcome, regardless of whether it was good, bad, or indifferent, is market timing. You can have an amazing team, an amazing product, that if you don't get the timing right, it's just not going to work. And so I think, you know, if you look at the case of Shopify, it's funny, when they first started out, it felt like it was a solved problem. You had Yahoo stores, but Yahoo stores was pretty hard to build on, ecommerce was pretty nascent, and, uh, in fact, when Toby went out to raise the Series A, a lot of VCs passed because they thought the TAM was too small. So, kind of funny now when you look back. So I think he just hit a, he built a great product and B, he just nailed market timing in the sense of, uh, broadband adoption, people being on the Internet more, mobile. So much commerce happening on mobile, you know, Internet commerce is still a minority of all commerce, but it's an increasing minority every year. COVID was very good for them, and so that's a factor.

I would say also, great things take time. Toby's been at this for a long time, you know, the FreshBooks founders, they're not active anymore, but, you know, FreshBooks has been around for a very long time as well. So, it has to be your purpose, right? You know, if I go back to Toby from Shopify, is worked and that's because making commerce simpler for everyone. This is life's purpose. And so, I do think because you guys bring up like resilience and you've been a founder, you know the drill, you like, you get punched in the face every day, there has to be something that keeps you coming back, right? And it's because you have a, a burning need to, to solve a problem, right? And so those, those founders that, but do keep going, have that need.

So, it's a combination of just like that founder magic, being lucky, to be honest, on timing, and you know, 1000 little execution details. You know, what's, what's really interesting when you talk about timing, right, because there's kind of a juxtaposition that you're talking about. One is, this is something we see all the time, right at our own fund, one is timing, but it's also juxtaposed with, they're in it for a long time, right? And you know, it's kind of one of those things where

it's, it's like, if you can hang in the game long enough, you have no idea when that timing is going to catch up to you, and it's, how long can you stay in, to let the timing right, right? And that's the thing, it's a hard thing for people to kind of understand because it's like, you don't have to actually get the timing right on day one, it just has to catch you at some point.

That's right, and like, so here's the deal, right? The reason why companies die is because they run out of money. There are underlying causal reasons that you can keep screwing up as long as you have money, and in both the case of Shopify and FreshBooks, both of them were quite large before they raised venture capital. I raised the first VC round for all, for both companies. But for FreshBooks, there were 130 people, they've been around for a long time, had a lot of customers, had gone in and out of profitability. Shopify was profitable when it raised its Series A, and it had years of cohort data, and when investors looked underneath the hood, they were blown away by what they saw. And so I say this because, maybe not right now because markets are challenged, but like certainly in the previous 18 months, like it was just a VC free for all, this giant spigot in the funding markets, and there's this temptation to just raise capital, but then you just spend it. And if you just blow your brains out spending money ahead of market timing, it's going to fail, or you're just going to have this giant preference stock sitting on top. Like, there's a, there is merit to going slow before you go faster.

Yeah, yeah, and I mean, I think it's, I think it's great advice for any founder, right, where you know, one of the things that I have always struggled with is sort of this mentality that you see in venture a lot where raising venture is the goal, right, and it, it's, it couldn't be further from the truth, where you know, it's, it's a tool, and it's only an effective tool if used at the right time. It's also the tool that will kill your company if used at the wrong time, right, and, you know, finding again that, and that's also a timing issue, right? It's like, where is it when you're raising tons and you see this a lot in your early-stage companies, you're just raising it, raising it, raising it, raising, and the business becomes not about the product, not about the team, talk about the customer, becomes completely about being a fundraising machine.

That's it, right, and she had all the time of Silicon Valley. These are companies that are not famous for any other reason except they've raised so much money.

That's right, yeah, exactly right. So, it just to kind of dig in a little bit deeper on the founders, because you started to hit on this when you said resilience, right, just being one of those factors. There's a concept in the VC world, I'm sure you've heard it before, about you know, we're all investors looking for that generational founder, right, that once-in-a-generation disruptor. At Evergreen Mountain, which is my thought, we call it the find-the-way founder, right? It's that founder who has that combination of resilience and persistence, just the grit to be able to kind of dig through. If you think about those founders that you've worked with, what, what are those characteristics, you know, you mentioned one in resilience, what are those characteristics that really make them that generational, that find-a-way founder?

Yeah, it's another great question. There are definitely traits that are evident after the fact when you do a postmortem, or, you know, you look back. The number one thing that I've always looked for, it's what I looked for as a VC, that's absolutely what I look for now as a CEO coach, is self-awareness, right? You look at the biggest outcomes tend to be founder-led start to finish. So it's a 100% correlation between a founding CEO's performance and the outcome of the company. If the company's doubling every year, then you need to double in your capacity as a leader every year, and that, and therefore, self-awareness is, is the thing that gives you the inputs for that, right? If you think your **** doesn't stink, then you're not looking for feedback, and you just believe your own hype.

Yeah, self-awareness is, is a huge thing, um, attention to detail. You know, someone who can, because you have to context-switch, right, especially as the company gets bigger, you have to be up, looking at deep strategy, and then

down in the weeds, and this pic, I don't like where this pixel is, and back up again. And then you just have to have, I don't like this tortured mind, you're just intolerant of things not being the way you, right? So, so that's definitely a thing.

The biggest, here's the thing, there's actually like, I know it's a bit of chicken and egg, right, so the single biggest thing that will grow and develop as CEO is unlocking growth in their business and hanging on for dear life. Right, you look at all the CEOs you admire, Mark Zuckerberg, Mark Benioff, Toby from Shopify, whomever. Toby didn't finish high school, he's stupid smart, like it's scary how smart he is, but he didn't finish high school, he didn't even want to be the CEO, and yet he's the CEO of a 10,000 person company. He's deeply self-aware, I correlate self-awareness quite highly with introversion, he's introverted, so as Mark Zuckerberg, Benioff isn't. They just managed to, like we were talking about surfing before we started, they managed to surf the growth of their company, right? And just stay on top, and so it's this virtuous cycle, right? Like Meta is such a great company because Zuckerberg is such a great leader, Zuckerberg is such a great leader because he gets to lead this company that is great. It's just like this virtuous cycle, right? That just gets better every year.

And you know, as a CEO, especially of a venture-funded company, whether you like it or not, you're going to get a lot of input. You're gonna talk to other CEOs, your VCs are gonna be your ones, gonna tell you to look right, you're just going to tell you to look left, you know, you've got advisors, you've got mentors. And going back to the importance of self-awareness, if you can process all of that, and then make your own decisions, you know, you, you stand a good chance of staying ahead.

And I bring this up, particularly with CEOs, because you often see, you know, you start a company with someone, you've got co-founders and other positions, and they often don't scale as far as the CEO. And my belief is that that is it because they are not getting the same level of input and context, umm, and so they don't keep up, right? So, so that's a big part of it as well, right, it's just being opened it to input.

Like, in the early days, right, you're just super in the weeds, but as you start to scale, as you have a leadership team in place, it's actually important to get out of the building, metaphorically, and get input, get inspiration. Go see he's thinking of hiring a CMO for the first time, go and learn what best in class is, go and speak with some absolute best-in-class CMO, and learn, right?

So, a big part of it, of being a great CEO, is, is learning. The point you made, I think it's, it's such a, it's a great one about, you know, one of the challenges I think of being a CEO, founder CEO, and really high-growth company, is once that curve begins, right, once you start to hit that real scaling curve, you are literally showing up to work at a job every day where you have absolutely no idea what that day is going to be like. You, every day is like running a brand new company, right, because, because it is, you know, and I, I went through this myself, I mean, when you know, and, and some of my earlier businesses, I mean the first time I ever ran a ran a $5,000,000 company was the first time our company had five million, say about 10 million, same at 20, same at 50, right? It's, you just, that, that pace of learning has to stay ahead of the pace of growth of that company.

I just, I think it's such a great point that just gets lost so often where founders start to rest on their own success, right, and look at this thing that I built.

That's right, but that doesn't mean you're the person that necessarily should be leaving it unless you can stay ahead of that growth.

That's it, yeah, you got to be a learning machine. So, you, you had a great tweet recently, around the kind of the bro-hustle culture, right? That, you know, that really is, I mean, I think you were pro hustle culture, is killing us, because of chronic stress, and we need to really focus on trying to help founders become happier and healthier people. Adult better companies

, talk, talk about that a little bit more. I think it's a, it's a really interesting take because you know, especially in tech, and in the financial areas of tech, you know, that bro sort of hustle culture is, coming to your words, it's deadly.

Yeah, more often than not, when CEOs come to me for coaching, they're burnt out, and the burnout is, is largely self-created. A big part of it is they have no boundaries, right? Work will expand to fill all available time. The CEO role is, is super demanding, and so if you actually don't take control and be intentional, actually about every aspect of your life, but certainly be intentional about the slice of the pie that work gets, then it's just going to take you along for the ride. And you lose control, and that creates stress, and that leads to burnout.

But just, you know, we have attention spans in 2024 are shorter than they've ever been, and you know, we're just always on, always reachable, which again goes back to not having boundaries. Yeah, there's just this culture that celebrated like, you know, you catch up with someone you haven't seen them in a while, and you're like, how you doing, like ohh, I'm busy, I'm so busy. I like yeah, me too, I'm so busy. Like, they sell it's like a badge of honor. It's six such ********, hey, and umm, so we celebrate it, and it's just deeply unhealthy.

And you know, I deeply believe that happy healthy humans build bigger, better companies. Like I was an investment banker for a while, and I've done billions in exits, and I can tell you, the number one reason why founders want to sell is because they're burnt out. And yes, they could theoretically replace themselves and someone else could keep growing, but there are three issues with that. One is, they're for better or worse, their identity is completely wrapped up in that company, two, all they're net worth is tied up in that company, and three, they're unemployable. And so they're just like, screwed, I'm going to sell.

So, who knows, you know, if, if they actually have been more balanced, can't even be test this ship, but maybe they wouldn't have sold, you know? And so I, I, and then by the way, creating a startup out of nothing is, well, obviously a creative exercise, it's hard to be creative when you're stressed. It's much easier to be creative when you're free and relaxed. And so this is easy for me to, to say from the cheap seats now as a coach, running a one-person business. But I did practice this, even when I was a banker. I was running six deals at a time, office in Toronto, office San Francisco, clients in Europe, but I still did CrossFit 5 mornings a week. And I had no meetings in the morning, that was when I was freshest. That was like my deep strategic thinking time, that's when I think about deal strategy, review documents before they went out to the buyers or the investors. That was my deep thinking time, the afternoons and evenings, complete shitshow. I didn't care because I crushed the day. My most strategic things were done before lunch, um, and so I created boundaries there, you know, and so that's what we need, right?

Like, we are not just a CEO, we're, uh, you know, a spouse, or a parent, we're a child, we're a friend. We actually have to create space for all of these other roles, we have to feed all of these other roles, right? So if I stereotype, like in the startup world, a lot of my CEO clients are male, they give everything to their work out of the 0% that's left, they find some drugs for their children, they have literally nothing left for their spouse, their wife, and, and they're miserable, you know. So yeah, I just, I, I think it's deeply unhealthy.

You, you've written about focusing, one way to kind of help with this is to focus on the big rocks, right? Is that, when you say that, is that kind of what you were just talking about in the example you gave of yourself, of kind, it's carving out that time so you can focus on the most strategic things in the time that you're, that you're freshest?

That's a huge part of it, right? It's about being intentional, right? You driving the bus versus you being driven. Right, most people, their day is organized around what's in their inbox and in their slack, right? They are reacting, your inbox is other people's produce. And so if that's how

you run your role, you're a passenger, right? You're reacting, so and then you're out of control, you don't, you don't control that.

So, so a big part of it is just being intentional. Like, the day before, here are the three things that need to happen tomorrow, or tomorrow to be a success. Now, by the way, if you don't have that, if you don't have that definition of success, but you just keep working because the work never stops coming in. But if you've defined success in advance, yeah, I thought that, I went to the spa at lunch once my work was done, right? My deep work was done. But it sure is easier to shut down when I know OK, everything I said I had to do today, I did. Then it's easier to actually say, Yep, you know what, I'm going to shut down. I'm going to go catch my kid's hockey game, whatever, right? So, it's super important.

And then a big part of it, I was, I used talking to a CEO recently, here's VC-backed business. He bought investors back and therefore was postponing exit indefinitely. And so sat down with his wife and was like, well, what life changes do we need to make, because I'm not exiting anytime soon? She's like, we need to do more real vacations. And so he started doing two-week vacations. And what he found was, when he came back each time, there were less and less demands on him because the team figured out actually how to operate autonomously without him. So, a big part of it is also just creating space and giving people, you know, room for your people to step up.

You know, I, I always find that interesting, right? And it is an easy trap to fall into when you see, you see founders sort of create this world where this kind of isolation becomes overwhelming because they've taken the entire company and they've put it on their shoulders, right? And I've worked with founders through that process, take another companies to market where that's been the case, and to try to, to try to explain the founders that look, set aside the fact that this is just awful for you as a person, right? Nobody should need to live that way, you're ruining the value of your company. That the more you take on as a founder, you all you're doing is two things, right? You're limiting the potential growth of that company because now it can only grow as fast as you can move, and two, who in the right mind wants to buy a company that is 100% dependent on this one person, right? So it's, you know, it's a, it's a hard dynamic to break, to say you, you have to start to like, forget about the fact that you're sort of resigning yourself to live a pretty difficult existence, do it for the fact that you're not going to be draining value of your company on a daily basis, you know?

When you coach founders, how do you, is there a magic bowl to get them to understand that, like how, how do you try to work on that? Because it is something that's super common, I think not out of any not for any other reason that they don't know any other way, right? It's this Superman syndrome, the Superman complex that comes in and says everybody else is an idiot. I can figure this out. These people don't know what the **** they're doing, I'm doing this.

Right, yeah, I mean, after I do my initial onboarding, the first place I go to with CEOs is their leadership team, because that's their leverage, and often through no fault of their own, they're tolerating good people. People who used to be great and no longer are. And so a big part of the role of a coach is just to shine a mirror back to the CEO, right? CEOs don't get a lot of feedback, don't get a lot of input. They can't necessarily share everything that's going on because few people get their context. And so that's the role of a great coach. And you know, so often, they'll realize like, yeah, you're absolutely right, I've been tolerating, you know, subpar here.

The big game changer, the big aha, is when they hire that really amazing leader, and then it becomes like cracks, like, Oh my God, I need more of this. And then I deeply believe that the CEO role should be organized around the CEO superpowers, and that they should build a leadership team based on that, right? So we'll go back to that, to the Shopify example, Toby's very technical, very introverted. He's not the guy who's going to go and charm Wall Street. So what did he do? He hired his polar opposite, Harley

Finkelstein, uh, to be his right hand and now the president. And so all those things that would have been stereotypically part of the CEO role that actually drained him, are not his superpower, or actually his kryptonite, somebody else does. And then meanwhile, he's directly driving product and technology vision, obviously overall company vision, he's doing the things that are right down the center of the plate for it. And so that's, that's, that's huge work, doesn't feel like work, right? You're, you're not doing things that drain you. I'm sure he's doing some things that drain them, but he's designed a role based around giving him energy.

Yeah, I think, you know, the thing for me, I think, to at that point, the thing I always found just enormously beneficial, if, if you can get somebody to do it, it's just going to community frontrunners, right? I was a member of EO for more than a decade, and remember YPO for years, and you know, that if you can get that group of founders who actually do understand the world that you're living in, but can still call you to the carpet, it's a really, really powerful thing. Because you're right, you're just, you're not getting that kind of feedback, right? Unless you're working with a coach like yourself, or you're, you know, you're in some community of people who really understand it. They could say, hey, look, it's, it's kind of ********, what's going on, right? I mean, you got six people on your on your leadership team, and all you do is talk trash about them, right? Like, but you've been doing it for a year now, like, you know, at what point are you actually going to make a move here?

That's right. Every one of my CEOs is part of a peer group, either a formal one like YPO or just informal. Super value.

Yeah, it really is. So, you know, you, you've obviously, you've got huge, you know, a real wide variation of interest rate yourself. You don't think you'll get to CrossFit, we talked about this stuff in the intro. I mean, how were you, and you started to mention this a little there, were these sort of passions of yours as you were building these businesses, I mean, how did that, how did that help to manage, keep your stress in check, right? Because you've got, you know, obviously, I mean, you were, you're taking companies public, you know, a couple of these.

How did you, how, how did you manage it yourself?

Yeah, I started doing yoga, I mean off on and off since my 20s, but got serious about it 15 years ago, is because I was a stress case. And so it was hugely beneficial, learning to breathe intentionally, learning to release tension in my body, slowing down, becoming present, not thinking about 5 million things. So that, you know, has taken on a, a bigger and bigger role in my life to the point where I, I just completed an advanced teacher training, and in Kundalini Yoga, which is the kind that I've been practicing for, for most of this time. And she's my first retreat to India last year, which was amazing. So that's put it, ongoing part of my, my journey for a long time. And it worked out, you know, on and off casually like everyone else but still had like a dad bod. And I don't know, in 2018, I was just like, this is ********, I watched the CrossFit games, and I was watching these guys do like superhuman things, and I was like, I'm going to give CrossFit to try. So I joined in next week, and my body's been sore ever since.

Yeah, so across it's amazing, and you know, functional fitness like real movements, a mix of, you know, resistance training, which is super important, especially when you're over 40, and 40 is a very very long time ago for me at this point, and you lose 1% of your, your, your body mass every year after 40 unless you work to maintain it, and it's got a cardio aspect to it as well, you know, umm, so I found it to be, yeah, really great.

Here's the thing, you do some like batshit crazy stuff in cross it, and I found during my banker days, when you break through a, a limit that you either just thought you had or legitimately had, you hit a one Rep Max deadlift, or you do a bunch of handstand push-ups, or finally figure out double unders, which is where you jump once and the rope goes around twice,

you come into work, and you're like, I'm gonna ******* crush today. I am invincible, you know? And that was the mindset I had, uh, so often. So, it was a great start to my day, and then I would found the few days where I skipped it, I wasn't as sharp, I wasn't as focused, and there's just a confidence that comes from having that energy, you know? So, and then it forces good habits, if you start to get serious about it, you're like, ohh, I should really sleep more, I should eat real food, you know, like Whole Foods that exist in nature. So, it just, it starts you down a very helpful path.

Yeah, so these have just been things, yoga's been a long time, and you know, CrossFit is more recent.

Yeah, it's, it's funny. I know when I started my last, my last business, right? Peter Dean, who's our co-host on this, who's obviously not here today, and I started, we started our businesses at the same time, we both started training for, to, to start to do Ironman triathlons together. But that's, you know, that was the thing, and I used to, people used to say all the time, even investors, you know, would say like, I don't understand how you could do these two things, like, you just, you can't, you can't possibly, if you're going to commit yourself to Iron Man, you're, you need to, you know, you can't commit yourself to the company. And I'd say, it's, it's the exact opposite of that, right? It's, I mean, you, you couldn't, you could not make it more inaccurate statement.

And that whether it's CrossFit or it's yoga, or triathlon, or whatever it is, right, it's that, it's that mental outlet that can give you that sort of complete focus on something. You can't do CrossFit why you're thinking about closing a deal. I mean, if you can, we're going to get hurt, if done CrossFit enough to know like, you know, you can't be on your bike in a triathlon, where you're sitting there just thinking about, you know, stressing over work, you, it's virtually impossible to do those two things, right? But it's the other habits like you said, I think that come with that, because it wasn't, it wasn't Iron Man itself, or wasn't triathlon itself that I mean that obviously created big benefits, but it was the fact that I was going to bet it 8:30 at night, I was eating great, I wasn't drinking during the week, I was, you know, I mean, all of these, all of these things start to converge, and suddenly you're leading just a much healthier life, which gives you sort of that mental fortitude, right? In the confidence, like you said. And I think that's, that's a part of this that gets missed, is you know, in, in the fund, I mean, we hear founders talk like this all the time, and, and I try to talk to him about it. It's like, don't be the founder who walks in telling me you're working 20 hours a day. Not only is that not impressive to me, I'm not investing. And you're going to fail, I mean, it's, it's, there's no other way, there's nothing impressive about that, but it goes back to that hustle culture, right? It's like this indoctrination that I need to be working 20 hours a day. You do not, you know, yes, I know Elon talks about sleeping on the factory floor. That tip, he's, he's only wanted a generation, right? He's, it's once a month, and I would never want to be him, that's for sure.

No, no, you probably wouldn't want to hang out with them for very long, right? It's, it's, you know, you don't, you don't have to, that's not what this takes, right? What it takes is some, some balance. If you're, you know, family, or an outside interest, or, or, you have to have that outlet, because I know you and I talked, you know, previous to this on a zoom call, Mark, and I said to you, one of the one of the things that is so, that was so difficult for me is, I, I know more than one founder who has committed suicide. And it's, but it's because they don't catch it, and you're just live this life where you, it just stacks and stacks and stacks and stacks. And I think it goes

away in two different areas, right? It either goes, it either eats you alive while you're running the company, or where I've actually seen it even more the case is, the day you leave the company, umm, you got nothing. You lose your purpose, that's right, your entire identity is gone. And I think that's the, that's the really hard part to try to get somebody who's in their 20s in the 30s who's trying to build this thing. You don't understand, this is a 10/15 year journey you're on. And when you get to the end of this, you're not going to be in your 20s or 30s anymore. And at that point, you need to have something else, you need to actually have a human inside this CEO founder body.

Yep, no, 100%. Well said. And the challenge, like I deeply believe everything you're saying, and I preach this, the challenge is that, you know, like I only coach CEOs of, of venture or private equity-backed companies, and for them, speed matters, right? There's certain markets, so Shopify, FreshBooks sell to SMB, it's sort of mathematically impossible to run out of Tam, and so you can go at, you can either go slower, you can go fast, it's sort of up to you, yeah.

Did you sell the Fortune 500? Well, guess what, you have a TAM of 500 customers, and whoever gets there first wins on the market. And so, speed is a thing. I think the mistake is that people equate speed with just more. I just have to work more, but meanwhile, they're like being super inefficient, hey, because they're frying their brain. They're pretending they're robots and trying to work all the time, and, and therefore, there's diminishing marginal returns on each incremental unit of productivity. But B, again, creating a startup is a creative exercise, and it's hard to create when you're stressed. And when you look back, there's a few key, big moments that were game changers. And what you actually want is maximum clarity in those moments to seize that opportunity and make the best decisions. And I think most, many CEOs **** the bed in those moments because they're just frazzled and can't think straight.

Yeah, yeah, it, I've, I've had that conversation with founders in our portfolio, outside of the portfolio, where coach advisor companies stuff like that, and that's it, you know, one of the things that talked about a lot with them is look, there's probably four or five decisions you're going to make in the life of this company that are going to be responsible for 95% of the value that you ever generate. The rest is not going to matter, like it's just not. But if you're not there, if you're not present, if you're not ready to make, to capitalize on those four or five opportunities when they come, that's it, right? And, you know, that's, and that, and it's hard, right, because you don't always know. It's clear after the fact, but you don't always know what those four or five things are as they're occurring, right? But, but it is the case, right? And if you're not able to start to discern, hey, where is the real opportunity from, where am I just saying yes to everything? And I'm running 300 different directions, it's, you're, you're never going to be, you're never going to have that presence of mind that you're going to need when those opportunities actually, to actually do develop.

Your experience in this stuff, and I think you're sort of presence in and seeing and being a part of, you know, just some extraordinary companies getting built is really, is really amazing. But it just to kind of wrap it up, talk a little bit about what you're doing today. I know you've got a new podcast, you know, I know you're, you're really big on, on LinkedIn, you and I are engaging almost daily on that. Like, talk about the kind of stuff that you're doing, how somebody can, can find, yeah.

So, I'm, yeah, I'm on LinkedIn every day. When I look back over my career, all of my most important relationships will come through writing, and had Toby at Shopify reached out, many other folks. And so I, I write every day, clarifies my thinking. I learned through writing, so I love to do it, lots of content on my website, markmacleod.me, on LinkedIn, and yeah, I just started a podcast called the Startup CEO Show. I can't believe that name was available. I even have a domain, I don't know if I'll do anything with it, but I have

it. And yeah, I'm like six episodes in, and it's going really really well, and, uh, as you might guess from the title, I interviewed startup CEOs and really try and unpack that role, and, and get folks to share the real hard truths, the real lessons learned. And again, you know, I learned through this as well. Like, I learn in every coaching conversation, I learn in every podcast. And so yeah, I'm having a real blast doing that.

That's awesome. And best way for somebody to connect? It through LinkedIn, or?

Sure, LinkedIn, or yeah, LinkedIn is probably the best, yeah.

I've enjoyed getting to know you so far, and in our interactions, and really, you know, love following your, your daily writing and everything. So, really encourage people, if you're not following Mark on LinkedIn today, go, go and do it, uh, go and do it immediately. And start listening to his podcast, and, and following the, the advice that he's giving you. So Mark, it's great to, great to have you on The Founder's Journey Podcast.

Amazing. I'm really glad we connected, Greg, and thanks for having me.