TechPoutine #EP07: The CEO Whisperer with Mark MacLeod

Welcome to Tech Poutine. We're very happy to have a special guest today, Mark McLeod. So Mark, welcome to the podcast.

Thank you for having me, guys.

Mark, really excited to have you today. You've been a brand name in the startup ecosystem for quite some time and I don't know if you remember this, but our relationship basically goes back to 2010. I was living in the Valley and I was coming back to Montreal and someone that is very dear to me, Patrick Lozon, made, made an intro to this guy called Mark. Remember that? And we had a call and right away I knew you meant business because I remember vividly we got on a call was scheduled for 30 minutes, 15 minutes in, it was done.

And you.

Said, I'm going to introduce you to John Stokes. And from there we've talked about the story many, many times about how we eventually launched Founderfield. But that was my first intro to Mark. So welcome to the show.

I love that. Yeah, thanks, Ian. And that's begun a multi year journey and a pretty big impact and founder field. Wouldn't it have happened or been what it was without you? So I'm really glad Pat made that intro.

I was very glad too. And then more recently, you know, we'll talk about your career but more recently we've worked together. You are my coach through the Breathe Life journey. So you know, it's been now 13 years already since we've known each other. So I'm really excited to have you here and I know Gabriel and you have a pretty tight relationship too. So maybe Gabriel, you can talk about your, your relationship with Mark.

Yeah, I don't know if Mark knows. Mark was the probably first and only person that ever interviewed me in, in a job interview. So we had an official job interview and he even gave me a challenge to do like a tear down of a company as part of my interview process for Real Ventures. The behind the scene, behind the scenes story is he gave it to me on like a Thursday. I didn't tell him I had a wedding to go to over the weekend. But I kind of worked on that due dil process over the weekend while my girlfriend at the time was, was at the wedding that we were, we were going to. And that company that I did a tear down on was one of the first investments. I guess I was part of Sweet IQ which ended up being a great investment for real. And I'm happy I still have the notes. I said yes. So I was a fan of that deal. So I think that was like top IRR deal for real at A certain.

Period of time, I completely forgot about that. I guess I was outsourcing due diligence because that was one of my deals. I should have interviewed like so many candidates and just given everyone like my entire pipeline. That would have been great.

Yeah, that would have been a great way to kind of scale your work. But I'm still good friends with Mo and with Mike. I see them pretty often. So definitely was a great, great first experience, kind of stepping into real amazing.

I love that. That's a great story. Thank you.

So Mark, you have a pretty impressive background. You were founder, investor, CFO at one point at FreshBooks, Shopify, et cetera. Now you're a coach. How about you walk us through your journey in your own words?

Yeah, I, I entered the startup world in 1999 completely by luck. I'd helped a client raise a funding round and then joined them. And I had no idea that there was a bubble happening. I just thought I was really good at fundraising. It turns out anyone with a pulse could raise capital at the time. But yeah, I just was hooked. I was hooked with the pace, the intensity, the ambition, the challenges. I loved doing deals and so it was great to be at companies that were continuously needing to do deals. I was just completely hooked. So never left, you know, spent 14 years as CFO for a bunch of companies. A brief but impactful stint at Shopify helping them raise their Series A FreshBooks, as you referenced a bunch of others. I actually did part time CFO work for a bunch of companies long before the technology was in place to scale that like QuickBooks didn't. Cloud didn't even exist. We were literally sending Dropbox files of backup data back and forth. It was horrible, but gave me some great experience. When I left FreshBooks, going back to this theme about loving to do deals, of course I skipped real Ventures. Right. So John and Alan and JS were starting. They had done Montreal startup together that was like an experiment to validate capital, efficient investing into what were called Web 2.0 startups at the time. And that first fund worked. And so they decided to make it real, no pun intended, and recruited me to be the fourth partner. And so I was there for all of the investment period of the first fund. I decided for reasons that we can get into if you like, that I didn't want to be a VC anymore. And so I called Toby at Shopify and Mike at FreshBooks. I'd been involved with both companies before and anyway, I just felt like I couldn't imagine not being a cfo.

Somewhere.

And Shopify already had a cfo, which is the guy that replaced me. And so I went to FreshBooks and had a really great run there. But back to this notion of loving deals. I've always felt constrained just working inside one company. This is the thing I loved about ventures, right. Just like all the variety, right? You have so many companies, so many things, you're looking at just operating one company. I've always ended up being bored by it. And anyway, so I founded and ran a boutique Investment bank called SurePath Capital for five years and had a stupid amount of success with that. We had a office in Toronto, office in San Francisco, clients in Europe. Basically if I was awake, I was working. And that forced some big life changes. But it also prompted some reflection where I realized across all of those roles, the thing I loved most was the one on one coaching and advisory conversations that I had. And that's what led me to shut down the investment bank and go back and get certified and become a coach. And so I'm now in year four of a super specialized practice. I coach some VCs just because I've been one and it's like a unique craft that is hard to figure out. But I mainly coach the CEOs of Venture and private equity funded technology companies that are at scale and absolutely love it. Every day is fantastic.

I saw you post something on LinkedIn about reading a book about coaching maybe a decade ago, 2002. Okay, in 2002. Was that something that was always kind of in the back of your mind that you were kind of, you knew you were interested, attracted to, but you kind of kept pushing, pushing away and it just found its way to, to become your primary thing 100%.

Yeah. You know, one of the biggest influences my, in my career was this guy Harry Nixon, who ran an accounting firm called Smith Nixon and you know, some a CPA by training. And the only way that I could afford to go to university was to do co op where you alternated academic and work terms. And I, I chose Smith Nixon because they were on Bay street and I thought, oh man, it'd be like super cool to be on Bay Street. Anyway, this guy became basically a second father to me and really instilled in me the value of being of service and of being a trusted advisor. And so he wouldn't be, he wouldn't have called himself a coach per se, but you know, like we were not Big four. Like our clients were people who ran their own businesses, right. And so they would turn to Harry in all of their Big moments and decisions. And I just always wanted to be that guy. And that was one of the things I loved most actually about the CFO role is you were like a right hand to a CEO. And being there in those key moments, it's one of the things I loved about a vc. You know, there's an inherent conflict of interest. The CEO can't turn to you for everything. But I really wanted to be that guy. That absolutely was essential to the role of being an investment banker. You know, you think about the decision to sell. It's a really emotional decision. You're basically a highly paid therapist, right? And I had conversations with my CEOs that they didn't even have with their spouses or co founders. Right. It's like a deeply personal relationship. And so I've always found that that one on one human impact to be like the thing I got a bunch of like trophies from getting deals done here. It's not about the size of the dollars. It's that human impact.

I can totally relate to that from, from this side, from being in the, in the CEO role like I was. You talked about certain things that CEOs share with you that they don't share with their co founders or. And that was exactly it. I was at a point where I was continuously bringing stuff back to my wife and at one point it got to a point where it didn't feel fair to her. Right. And I mean, I am an open book, right? Like, there are very few things that I would not share with my co founders or with my investors, especially with the relationship that I had with some of those investors that I've been there for a long, long time. But there are certain things where it's more personal, et cetera, et cetera. And that's. And I'd been looking for someone to help me out and you know, is meeting a lot of different coaches that really have never been in my. In my seat and have never been in tech and they've been in this. And I'm like. And I have this issue with credibility. I was like, I can't. How can this person help me out? Right? And I remember the moment you announced that you were doing this. I reached out right away because I was like, this. This is the person, right? He checks all the boxes of credibility and, and I, and I need this person now because I was going through all kinds of different stuff. So, you know, there are moments where my wife was like, call Mark now.

Like, all of the roles that you mentioned are very important, highly influential, like you said kind of the confidant of the entrepreneur. What's different in this new. Kind of this new role that you're taking as a coach that you couldn't do as a VC or as, you know, as a. As a investment banker or as a cfo? I imagine that there are those opportunities. What gets in the way when you're wearing those hats? That doesn't get in the way when you're a coach.

Great question. First, I'll go back to why I decided not to be a coach in 2002. I concluded at the time that I lacked the gray hair and moral authority to be a credible coach.

You have it now, literally white hair.

Now you can decide on the moral authority, but the hair is white. But to Ian's point around credibility, I feel like you just, like, startups are not normal. It's not normal to take a million bucks and light on a fire every month and have that be strategic. Right? The things that we do, the risks that we take to create outlier outcomes. Like, if you don't come from that world, I don't think you can be a great coach. And so I just intuitively knew I just needed to put the reps in. I needed more scar tissue, more battles won, more companies brought to the finish line. But I guess, you know, so as a vc, you have an inherent conflict of interest, right? Venture is driven by power, laws of returns. Like one or two companies, a small percentage of the portfolio are going to drive the bulk of the returns. And so if you're truly doing your job as a VC, you should actually ignore 80% and just focus on the 20% that are the winners. And so that doesn't feel awesome. Doesn't, you know, kind of sit with my values. So that's a thing. As a cfo, I definitely, like, I brought. I'm a big fan of the Godfather movies. Godfather 3 should never have been made, but Godfathers 1 and 2. Awesome. And, you know, I was the consigliere. I was Tom in Godfather 1. Like, I fucking loved it. But when you're on the inside, it's like, I don't know if you all have kids. Ian's got kids. Ian could say something to his kids. And it goes in one year and out the other. Someone else, Someone else's parent, you know, could say something, and then they're like, oh, my God, did you hear this? Like, such a great idea. Like, so when you're a cfo, you're kind of on the inside. So there's a bit of that Dynamic. Right. Okay.

So it's.

There's. Your words will be taken more seriously when you're on the outside. Also, there's a. There's a cycle to life. I think there's, like. I actually think you need to be in the second half of your life to be a great coach. Not saying I'm going to die anytime soon, but in that first half of your life, especially as a guy, you're out trying to stake your claim in the world and grab your piece of it. And it's my ambition. I'm trying to achieve this. And in the second half of your life, you're focused on things that matter far more than that. And I think that enables you to. It's not about you and enables you to be of service. And that's, I think, the right frame to be a coach. You know, I don't think a coach. But, yes, I put myself out there. You mentioned, you know, I have a brand, but that's only strategic. I do that for impact. I do that so people will learn. Right. I'm not trying to be a celebrity because then it's about me, and then my ego is getting in the way. And I think that it's difficult to. I wouldn't have had that approach 20 years ago because it's. It still would have been about me. So I think it's not a coincidence that most of the coaches that crush it are like, you know, my vintage.

There's a lot of coaches. It feels like everyone's becoming a coach. Are there too many coaches?

No, no. It's funny. So back in 2002, when I bought that first book, which I still have, if somebody said, hey, you need a coach to be like, what's wrong with me? It was like, remedial. So now that's absolutely not the case. And again, I only coach CEOs of companies that have raised institutional capital. And those CEOs have huge expectations on their shoulders. And so I liken them to professional athletes. Like LeBron James has, like, a team around him to make him peak. LeBron, he's got someone cooking, like, the perfect macro meals. I'm sure he's got a sports psychologist, he's got therapists, you name it. Whatever he needs, he's got it. And, you know, my biggest client, their company's doing 220 million in revenue. That. That person's got huge expectations on their shoulders. And so I think they need a coach. You know, at one point, Toby from Shopify had two coaches, you know, so, yeah, I don't Know that there are too many. I think the good and the bad thing is anyone can call themselves a coach. So they come in all shapes and sizes. And so yeah, there are probably some not so great coaches out there.

I feel like Mark, there's been much more acceptance considering how many high profile CEOs, like from Steve Jobs all the way to, you know, like Larry Page and Down have had coaches. You're like, you're not Steve Jobs. So if he had a coach, maybe you should as well. So there's much more acceptance, particularly in tech. So I think, which is a good thing, like you said, because it's very lonely. It's a job that has immense pressure. And maybe a more tactile question, how much of your job is to do like the like the business side like strategy, growth tactics versus the more therapy side of like friction with the team, just you know, imposter syndrome, anxiety, all the like the emotional side and human elements. Right. There's one that's more business, the other one more human. And maybe it's the wrong kind of like framework to approach it, but I'd love to get your perspective.

No, it's a great question. All of my relationships involve a mix of coaching and advice. Coaching is where I ask questions, I probe, I take the conversation in a direction where you generate your own insights. Advice is where I share. Here, here's what worked with me. Let's see if it works for your context. Also, all of my relationships involve to your question, a mix of working on the business and working on the person. Now, like I'll give you one like a call. A literal call I had last year was three agenda items. One, I'm no longer in love with my wife. Two, I have massive imposter syndrome. Three, can you review my cohort attribution model and pick holes in it? So the point is we can go literally anywhere and everywhere. I only work with growth stage CEOs because before that you're really working in the business. You're building product, you're selling product, you're taking out the trash. And in that context, speaking with a coach twice a month is a distraction because your day to day reality is actually putting out fires. And so I'm just slowing you down from putting out today's fire. But over time, with scale, you work on the business. Do I have the right people? Are they pointed in the right direction? Do they have the resources they need to succeed? That's where I can have the most impact as a coach, is giving that person the leverage. Right. Because if you look at the biggest outcomes, they're founder led, start to finish, 100% correlation between the CEO's performance and the impact the results of the company. And so the challenge and opportunity for venture backed CEOs is to always grow faster than their business. If your business is doubling every year, you need to double as a leader leader every year. So that's really where I play. Right. Once you take that money, there's no turning backs like taking the red pill and matrix or whatever color it was like you are on your way to deliver an outcome. And I've been on every side of that one way journey for 24 years now, so I can help folks navigate it. So if we're really at putting out tactical fires, then we're at the wrong altitude for our coaching. But more importantly, the CEO is probably operating at the wrong altitude. And that is actually often a big catalyst for people to seek out coaching because they're burning out. They're Both at the 30,000 foot Super Strategic level and they're in the weeds now. You have to context switch. There's no avoiding that. But it's like what is your normal base altitude? If it's not high enough, you'll never keep up, you know. So that's definitely a flag and a thing that I look for.

It definitely feels like the perspective or acceptance of founders CEOs getting coaches has changed in the last 10 years. Are you seeing that it's something that VCs are recommending to their executive team?

Yeah, yeah. I get a lot of interest from VCs.

From VCs.

Okay. Yeah, yeah. And Calistus Ventures actually has allocated a chunk of their management fees to help pay for this for their portfolio CEOs I find. So again I play really a kind of growth stage and also private equity. And both the true growth stage venture funds and the private equity funds all have what they call impact teams. And so they're trying to figure out ways beyond capital to add value to their companies. And so like I had a private equity fund, you know, literally interview me and reference my CEOs. So that could be in a small list of, you know, coaches for them to refer. So yeah, they're definitely looking for that.

And having the CEOs specifically or to the full management team. Mark, I know you do see.

I only do see. Yeah, I only do.

But are you seeing it for management teams too or I mean not, not a year.

I don't know if the VCs are involved in that, but I'm definitely seeing. I'm definitely seeing CEOs want coaches for their leaders. I have a client who's hired a coach for every single one of his leaders.

So the, the permanent capital fund behind Zinnia, which is a company that acquired my company, they, they actually like we have an executive coach now. That is, that came from a recommendation from, from Eldridge. Right. And this person's been working with, with the CEO, with, with the executive team. And we started that about six months ago and it's been really good.

Yeah, that's cool. It's great to, to see the startup world, venture world start to accept the importance of coaches. In my previous life when I was working at hedge funds, coaches were very normal. I think it was recognize if you're going to entrust someone with so much money in terms of making a decision, they better be in like peak state of mind. And so it was something that we saw very often and I had a personal coach when, when I was working at a hedge fund and it was very helpful.

Yeah, it's like, right. If you guys have seen billions like the. Yeah.

Yes.

Telling us a coach inside. And it's funny you mentioned Mark, like I'm in the process of raising a fund. It's our first fund and the impact team is something we definitely want to invest our management fees into. And you know, like there's the classic value creation frameworks and go to market and growing. But it's like a lot of the conversations I've been having with founders far. It's like a lot of it's just like founder success. A lot of it's like mental health executive coaching. So anyways, yeah, I'll ask you for your physical business card, but it's like it's called google.com. yeah.

Now I will say like there's been far more acceptance of an awareness of not just coaching, but actually the importance of founder health. Post Covid, you know, Covid was like a pretty crazy time. We were forced to be alone, you know, at home. Every single one of my clients has downsized. So you're dealing with that. You kill yourself to get a company to a certain level, only to cut it back. And then you're like, why? Why am I killing myself? You know, you really start to think about what matters. So yeah, I think that context of those two years or whatever it was has really. Yeah, I guess a lot of people are thinking about coaching therapy, you know, boundaries between personal life, work life, you know, all the things like all of our default assumptions I think have been thrown, you know, up in the air.

Yeah. 100. Yeah. It's like during. During COVID it was, you know, founder of a small consulting company, and, you know, she hit the fan. Things were going well. We had a bunch of customers that were like, you know, like retail and entertainment space. Like, we had to fire half the team. It was just horrible. And for the remaining team, it's like we ended up getting them, like, online therapy sessions that we paid for. And, you know, typically, maybe a little macho, I wouldn't have gone for this for myself. And I said, well, technically, I'm paying for this. Maybe I'll do a therapy session. And I remember it's like, what am I gonna say? You know, like, there's 60 minutes. And I remember it was like, minute 59, and I hadn't shut up for an hour.

There you go.

But I think, yeah, the taboo of it, I think, is really, you know, thankfully starting to move. Move away.

Yeah.

So is that the tipping point, Mark? Because I feel like, I mean, I've certainly been thinking about this for. For longer than. Than Covid. Like, when we started Breed Life in. In 2000, late 2017, one of the things that I really wanted to do is try to create, you know, an environment that is, you know, sensible and creating that. Yes, working hard. Like, my friends who work at Bell Canada always thought we were crazy, but, you know, we were not pushing for that. 80 hours a week. Like, the whole stigma, which I had done previously in. In the Valley where I was working, like, I mean, it was only work, like you said earlier, like, every. Every moment I was up, I was working. And I feel like that's changed a lot. And you've written a lot about that. But to you, the tipping point is. Is Covid, where people started saying, hold on a second, what am I doing here?

I think it was a tipping point. Yeah, for sure. Because you never questioned a commute before COVID You didn't question. You know, you look at a lot of the Valley, big companies, right? They were doing everything to keep you in the office. I'm going to do your laundry for you. I'm going to, like, do, you know, you're going to have all your meals. Like, all of that got thrown out of the window. Now I'm home, right? Right now I realize, like, oh, walking outside is nice. Having a dog is nice. You just never had an opportunity to do those things before. Right. What do you say? You live in San Francisco. You'd get on, like, the shuttle bus to go down the Google campus in the Valley and They'd have Internet so you could plug away and work like feed you, bring your laundry, we'll do it. You know what I mean? Like you just, you just were a passenger. Right. And then that all stopped.

Do you find? I'm following your post on LinkedIn and you talk about growth often that that's the number one objective for, for a company that's raised VC kind of growth solves all problems. It feels like when I'm talking to entrepreneurs these days, I'd say probably post 2022, there seems to be a change in perspective around going down this venture path. Growth at all costs, focusing on economics, reducing burn, making sure that you have enough Runway. How do those two worlds kind of jive for you? Because it feels like founders have changed their perspective as well.

Yeah, as have investors. Right. Like it's harder to raise money. There's always been a tension and I've always recognized that there's tension and trade offs here. Like most companies should not raise venture. Venture capital consumes like a disproportionate amount of our mind share because VCs are blogging and tweeting and speaking at conferences. And of course there are those outlier companies that we aspire to be part of. Right. Or create. You know, we aspire to turn our own company into. And so there are role models. But you know, venture is built for outlier outcomes. And so if you don't want to go for one of those, if you don't want to take the risks, then your venture is probably not great for you. Now. As a guy who's sold a lot of startups, you know, I can tell you that most exits are modest. They're too small to be reported by the buyers for the most part. What that actually means is most exits are sub $50 million. And so I sold lots of companies where we sold them for a strong revenue multiple, but the founder shares were worthless and so all they got was a carve out. And so that's tragic. Obviously you work for seven years and all you get is the Carta. So there's definitely a trade off here.

Yeah.

Is there something that exists or can be created? Maybe it exists already between bootstrapping and venture, it feels like there's a lot of companies that get on the venture train because they need capital to build their product or to, to scale the, to figure out product market fit, but end up kind of staying on this venture train. I know there's companies like Clearco and others, revenue based financing. Do you feel like the industry needs a Shakeup or something needs to change in terms of how VCs even think about investing or deploying capital into these companies that maybe shouldn't be venture backed.

Yeah, I think.

So.

Smaller funds like real ventures can handle early exits. Like a $50 million exit. That first fund was a $50 million fund. You know, a company selling for 50 million is actually relevant if you're NEA or Andreessen Horowitz. And if you've got billions under management, it's like a total distraction. So I think you have to choose investors, you know, based on your ambitions. I think, you know, optionality is a thing. You know, When I joined FreshBooks, I'd been an advisor to that company for years and they were 130 person company before they raised their first penny of venture capital. They had raised angel rounds before and Mike the CEO always talked about taking the company through dolphin dives. I'm going to raise some money, I'm going to go burn. I come back up to profitability and I do it again. But each time I come back up, it's at a level, a size and scale of a business that I wouldn't have achieved without the capital. But every time I decide to fundraise, it's from a position of strength. Because I'm profitable, I don't need to raise. So that's actually quite powerful. Optionality is everything. When I was a banker, I would have long term relationships with the clients and the world I was trying to create is one where the company had first of all could get to cash flow, break even in Runway if it wasn't there, already had the run rate and unit economics to be able to raise anytime it wants to and was known to its most natural acquirers and so could enter into a qualified exit process anytime it wanted to. That company has options and options equal valuation leverage. So yeah, that's the thing, it's just not the default. Don't just keep raising, don't keep digging a hole. Build optionality every step of the way and they're going to raise the big round. Take some off the table.

Yeah, I think you alluded to it. Unfortunately, the media is so strong for kind of this like go big or go home mentality of venture that there's a lot of. I find especially new entrepreneurs that think they should be all in. But when I talk to more seasoned entrepreneurs, they always express to me they have multiple plans and one of those plans is always a path to break even and even. I remember specifically some entrepreneurs who I had coffee with after I Left real ventures and they were telling me like, yeah, I had all of these other paths, you know, I was focused on and communicating to you guys the venture path. But I always had this exit path and I always had this break even path. And so I don't know if that story or that gets told enough that people that have these, you know, have these alternate paths and are thinking about optionality at all times.

I don't think it gets told enough. I think it's changed a little bit now. Post Covid but before, if you spoke to any founder and asked them how their company's doing, they're crushing it.

Right.

You talk to nadc, how's your portfolio? Yeah. Crushing is not accurate. Most startups fail. I'll be crushing it.

It's interesting too, right. If you look at the last few years like we went from growth at all costs, revenue later to a period where no, no, you need to make revenue. And now it's like no, no, you got to have a path to profitability. You know, I mean like they're, they're big phases. Right. And right now it's like if you don't have a path to profitability soon, man, you better figure it out because. Yeah, yeah, you're going to be in trouble.

Yeah.

Yep.

Do you think there's something specific about Canadian startups that we've seen this pattern where a lot of the larger, more successful ones started off bootstrapped. Like I'm thinking about, you know, Shopify and Lights.

Yeah, that's right.

Even one password I don't believe raised a lot of capital up for a.

Lot of those examples is that.

Yeah.

Yeah, they were profitable very, very.

Quickly for lro even when they raised, they did so like Mark said, from a position of fingers, kind of like a series D, didn't need it. I think it speaks to, I think Mark's excellent point of like you know, having leverage in negotiation.

Yep. Yeah, for sure. Like I said, FreshBooks 130 person company, Shopify was profitable and it raised the a hootsuite used to be an agency. FreshBooks was an agency before it was a startup. Yeah. I think we raise venture too early and therefore we're on the back foot from day one. Yeah, yeah.

I think it depends. A company like GSoft now called Work Leap is, you know they recently just raised 100 million from and they're extremely profitable and similar story also started as an agency and transformed it to a SaaS business. It's one of those things that depends what you want to do. Right. Like, if you want to build, you know, the first quantum computer that's ever been created, well, chances are it's going to take years. So it is context.

Yeah.

There's definitely businesses that you have to raise up front. I'll say. So for mission, we grew the business off of revenue for the first two years. And I must say that building off of revenue forces a lot of good habits. Those habits are easier to scale than going from the opposite, where you're kind of burning and not really on top of how efficient. And then trying to get definitely a different perspective. Like, very different.

I make a joke out of all the time. Eighteen months ago, I've learned a new word. Do you guys have any guess what that new word is? Simply profitability. Profitability. I never thought about that in my life or something. Yeah, exactly. For having been like, in. In the tech.

What language are you speaking for almost.

20 years and raising a lot of money through that. I've never thought about that for a second until, like, the last couple. Couple of years.

Yeah.

Yeah, I definitely was guilty of it. Like, at real, we spent a lot of time focusing on fundraise. Right. We built this series a readiness program. We had the checklist, Mark, that you created the MVP for. And it was just really about getting to that next fundraising milestone. It wasn't about getting to break even. And so it's interesting.

It's all your fault, Gabriel.

That perspective has maybe shifted.

I think you're going to say something.

Yep.

It's all my fault.

That's right.

Yeah. No, it's fine. I was. I wanted to, like, change something. Go back to founder health and use this a little bit as a therapy or slash, free coaching session on my own. I don't think. I don't feel like a word for this. And, like, I follow you on Twitter, Mark, and I see that there's, you know, one of the Twitter fights always is, should you work 80 hours or should you have a more of a balanced life? And I always found the workaholism creeping in a lot into my life. And a lot of it's around this guilt of, like, it's Saturday night and I'm not working on my company, and, like, I feel I should be doing some reading something. And how do you address this with your, you know, the founders you work with? Right. It's always like this. This mix. Right. Sometimes you need to sprint, Sometimes you need to, you know, like, take a step back. But, yeah, curious if you have anything, you know, guidance you provide or framework for people to be able to navigate. Like obviously when you're working, it's, especially in a startup, it's very intense. There's a lot of demands on your time.

Yeah. I mean there's no avoiding those moments, that's for sure. The thing I bring my CEOs back to is intentional. What are your intentions for your life and what matters most to you? Right. You know, the average startup lasts seven to 10 years and it feels all encompassing when you're in it. But when you look back over the context of your life, it's a chapter. It's not your book. It's a chapter in your book. Right. Like there are times where I was CFO of a company and it felt like completely all encompassing. When I was at FreshBooks, I joked about having fresh bench, excuse me, fresh mares like which are FreshBooks nightmares. And they were so common that I kept a little notebook by my bed because I would process business issues and solve them in my sleep and so I'd have to write them down. So that's a thing. And it's harder for, I'm going to stereotype a 20 something year old to have that kind of perspective. I think as you get a little bit older, right. I see you're a father, you have like other hats, right. You're a husband or a boyfriend or girlfriend, you're a parent, you're a sibling, you're a friend. And so you have to be intentional. Like what is the proportion of importance that I give to each of those roles? Right. I was a father of young kids in my super hard charging days. And I can tell you with the benefit of hindsight that very often I might have been physically present but I was not mentally present. I was replaying the day, I was preparing for tomorrow. I was like stressed out, like I was not there. And so I've made a decision to live my life in a much more intentional and balanced way. And, and so I'm trying to share that with, with people. Not because I'm trying to purge my errors, it's more because I realized like first of all, work expands to fill all available time. And so if you don't put it in a, in some kind of boundary, it'll, it'll just consume everything. Second, I deeply believe that happy healthy humans build better, bigger companies. And think about the act of creating a startup going from zero to something. You can't actually be optimally creative when you're stressed. Cortisol, like these stress hormones, they actually prevent you from being creative. You're most creative when you're in free flow.

Right.

This is why we have these aha moments when we're like out on a hike in nature or in the shower, because we've actually created space for our intuitive brain to kind of do the work. And our intuitive brain is far more powerful than our rational brain. And so this notion, like the CEOs that go from thing to thing to thing and they're double booked and the meetings over lunch and are pounding on emails at night, they are not tapping into their intuition. Right. And our brains are just not designed for that. Like, we're not robots. Right. Or at least not yet. And so I actually think we can create things that are far more powerful by creating space and have a lot more fun along the way. Very often when I start off coaching calls, I'm like, how happy have you been in the last two weeks?

I can't, I can't agree more. Like, you know, so our fifth value of real life. We're not fun.

Yeah.

Because if we're gonna bust our ass towards this, this vision of ours, like, we better have fun along the way. Right? And fun doesn't mean like ping pong tables and things like that. It's like actually like laughing during meetings and just enjoying the ride.

Right.

Like, we gotta have fun.

Yeah.

Yeah, yeah, yeah. I mean, I'm a big basketball fan and when I go to the Raptors games.

Yeah.

High stakes, right? You're playing like a really tough team on the other side. There's thousands of people watching, but you look, they're smiling, they're having a blast. They're doing what they love. Like they're having fun.

Yeah.

I definitely can say that I've struggled with the balance aspect. I think part of it is because I enjoy what I do. And so I like the grind. I like, you know, putting a lot of hours in. I don't golf or play hockey. I, you know, work on. I work on startup stuff. I just enjoy it. I think the being present part has been more challenging. Right. It's just like you're saying, recognizing when you're not doing that to not be just kind of there, thinking about the other stuff, I think is, is the part that's been a little bit more of a struggle. It almost feels for me that in the early stages of a startup, it's hard to be balanced.

Okay.

It's just if you're trying to get something off of the ground, you have to be all in, but it's not sustainable to stay that way. And I don't know for You.

Or just before you answer that, the other angle, I was talking to Daniel.

Around that depending on what Mark and.

Gabriel Noel, I think, I don't know if. Yeah. And I was telling him that we were going to have you on the show today and how I wanted to talk about this very subject about like balance and stuff like that. And he said that. So similar to your comment in the early days of a startup, but he was talking more about most people who have been around the block, had success, have this, this as a belief. Right. That equilibrium or something that that is important in building a business. Do you think it has to do with the stage of the business or the maturity of the entrepreneur? Or maybe it's both. Right. Like it was a question I was hoping to ask today. So is it early days of the startup or maturity of the entrepreneur or both?

It's hard to separate them, you know. Right. You brought up SuiteIQ. Mo's now the founder of SuiteIQ or one of them is now working on his second startup. He's a completely different person. Right. So the early stage of SuiteIQ is likely very different than the early stage of his new company work. So it's hard to separate them. I think if there is an urgency, like if you have a brand new startup with very little cash and you're burning, then you're dying. Right. Every day you're getting a little bit closer to death and so there is some kind of urgency and so you need to iterate to product market fit as rapidly as possible. Whereas if you're more established and especially if you're profitable, then you don't have any of that existential free. Right, that's, that's for sure. So you know, I think it's hard to separate those two, that's for sure. And I agree.

It's also life stage. Definitely earlier in our careers it feels much easier to be imbalanced because you don't have a lot of the other responsibilities that you typically have when you start to get older. Some people have them when they're younger, of course, but definitely it feels like life becomes more demanding as, as you start to move further along.

I will say no. But like I think about mastery a lot. Mastery is a core value for me and nobody who is truly a master in their domain has been balanced every step of the way. I think it's Malcolm Gladwell who talks about 10,000 hours. Well, 10,000 hours takes 10,000 hours. It's just like a lot of time you have to put the reps in and you know Lots of businesses like you have to figure out or lots of roles you have to figure out as you go. I coach some VCs and Venturer is an apprentice driven craft and with a very long feedback cycle. You don't even know if you're a good investor until like probably a decade actually. So that's a tough one. I was CFO for a bunch of companies. I gotta tell you, I was like a far better CFO for the last one than for the first one. And so there is mastery. That just happens over time, you know. So yeah, there's no avoiding putting the reps in. So now I bring this back to intention. If I intend to achieve a certain outcome, if I want to be great, but I also am a spouse, father, etc. Then the thing to do is to be intentional. Like, hey, I'm about to fundraise for this period of time, honey, I just have to be all in. As opposed to just doing it and ignoring your spouse and then feeling guilty. The thing to do is to call a spade a spade up front. And you both agree for this period of time, I'm all in. Like you. You are. You're telling that person.

I would, I would say that's even.

In the early days of thinking of launching business.

Right.

Telling your significant other, like, I want to do this. Are you okay? Like it's, it's actually a decision that should be had together.

Right.

Because there's impact and it's going to change your relationship.

Right?

Yeah.

Yeah, you're definitely bringing everybody into that decision.

That's right.

To be respectful of your time. Mark, just maybe a few more minutes. I'd be curious. You spoke about mastery, which I find fascinating subject. Is there anything. What have you learned the most? You know, maybe a two part question. What have you learned the most in the past few years as a coach? And is there anything that one of your clients has taught you?

Hmm. Well, yeah. So this is the thing. What you asked is actually the thing that I love the most about coaching. I do this for impact and so I learn from my every session. Right. There's a virtuous cycle. The more people I coach especially, and the bigger their companies, the better I become as a coach, which helps me have more impact on them and helps me attract the next bigger client. So it's a virtuous cycle, you know. Yeah. I'm in year four now.

That's good to say.

I actually cringe when I think about what my year one coaching calls were like. Sorry, Ian. Oh, yeah. So I don't know if I've answered both parts of your questions, but this is the thing that I love the most. Like, I've learned so much and it's. It's why I do it. Like, finance is like objective discipline. There's a certain way to do things. It can be changed periodically. But, like, there's a finite body of knowledge. Humans are infinitely complex. There's endless layers to the onion. And so it's just super fascinating.

Can I selfishly, and maybe for some others that are listening, ask if people are considering a coach, what are some of the questions they should ask? What is the framework that someone should evaluate whether working with one coach is the right coach versus another?

Yeah, that's a good question. I mean, it's subjective. It has to be somebody that you feel really comfortable with. And so you can be open. You're going to tell that person everything. I personally think there's a major credibility thing here. You know, I think people need to have walked the walk and come from this world specifically. I am personally skeptical of coaches that have not been in the startup world. I do think that person should be committed to coaching in some way. Meaning, like, I'm not coaching because I'm between gigs, and as soon as I do my next thing, I'm done. And like, I've educated myself. Like, there's a skill set to remaining curious and keeping asking questions versus just prescribing getting an answer.

I think I saw on LinkedIn you actually went through a training program, right? Or you got certified as a coach?

It was the first thing I did, yeah. Right.

Do you feel like that that frame or that training was helpful and you would recommend people to work with coaches that have had formal training?

Yeah, yeah. I mean, I'm part of the International Coaching Federation, which is the most widely recognized body for that. Yeah. I don't think I could have been a good coach without it.

I have one, one, one closing question, if you don't mind. Anything new we should expect from you in 2024.

Yeah. Continue to bombard People's inboxes and LinkedIn profiles with daily content. When I look back, all of my most important relationships have come through people reading what I had to say. And also writing. I learned through the process of writing, so it'll be more of that. But also, ironically, that I'm on a podcast. Today I recorded the first episode of my own podcast, which is called the Startup CEO Show. I can't believe that name was available. I even have the domain. And anyway, so that's going to be launching very early next year, so I'm pretty excited for that. Awesome.

Well, thanks for putting out all the great content. I don't like every single one of them, but I will say that my CEO and I, I've shared a lot.

Of your content with the exact team here at Zinnia as well. So you're, you're getting traction in New York City area as well. Thanks, mark.

Thank you so much.

Thanks so much, Mark.

Thank you.