Wondering how much your VC-backed startup's tax return will cost?   Check out our startup tax cost calculator to get an estimate now!


With Scott Orn

A Startup Podcast by Kruze Consulting

Subscribe on:

Scott Orn

Scott Orn, CFA

Mark MacLeod on Coaching, Advising & Investing in CEOs & CFOs of high growth technology companies

Posted on: 10/27/2020

Mark MacLeod

Mark MacLeod

Coach, Advisor, Investor - Mark MacLeod: Coach, Advisor & Investor

Mark MacLeod of Mark MacLeod: Coach, Advisor & Investor - Podcast Summary

Mark MacLeod talks about his new Executive Coaching practice. We talk about how Mark’s favorite part of his previous role at SurePath was the advising and coaching he did alongside fundraising & M&A advice. Mark gave up SurePath to focus on Coaching and is having more fun and more impact.

Mark MacLeod of Mark MacLeod: Coach, Advisor & Investor - Podcast Transcript

Scott: Hey, welcome to Founders and Friends, and I just want to do a quick intro for my awesome conversation with Mark Macleod that you’re going to hear in a second. Mark has just been a longtime friend, been on the podcast a bunch of times. And he did a really cool leg transition, so instead of being a Tech Exec at Shopify or in Fresh Books, and instead of being a Venture Capitalist and then, instead of running his own MNA shop, he actually became an Exec Coach for startups. And you’ll hear in the conversation how happy he is, how great he’s doing. There’re so many great things that came from this, but one of my favorite ones was learning how to work without stress, which sounds cheesy, but really cool, really impactful. And then, he’s got a couple other really good sayings, where he talks about how a founder of a startup has to actually grow faster than the company, which I actually really believe. And, I know in times where I haven’t been growing fast enough, not only myself, but the company struggled a little bit. Probably same with Vanessa. Then, he also talks about the importance of unlocking growth in the organization, both for the founder to put them in kind of that growth position, and help force them to change and force them to grow. But also, all the benefits that come for the company. So, this is a great conversation. Mark’s a really good friend. It’s a longer podcast, but I kept it long because there’s so much here and there’s so much to unpack. And I think this might be one you can listen to a couple different times. So, hope that helps, hope you enjoy it. And thanks again Mark, for doing the podcast. (singing)
Singer: It’s Kruze Consulting. Founders and Friends, with your host, Scotty [Orn].
Scott: Welcome to Founders and Friends podcast. This is Scott Orn at Kruze Consulting. And today, my very special guest is Mark Macleod. Welcome Mark.
Mark: Thank you Scott, so happy to be here.
Scott: Well, it’s great to see you. You are, I’m going to blow your talking points here, but former Tech Exec, then MNA Expert, and now, you are living the good life. Do you want to tell people what you’re doing now?
Mark: Yeah, very brief. I’ll go from the beginning, but go super-fast. So, 14 years as the CFO for a bunch of companies. Most notably Shopify and Fresh Books. Three years as a GP in a venture fund, five years running an investment bank. And just this year, kind of pivoted to focus on being a coach to CEOs of institutionally funded companies, so venture funded and PE funded companies. That might sound like a little bit of a pivot, but if I look at all of my roles, whether it was a CFO acting as a right hand to a CEO, or a VC investing in CEOs, or when you think about selling your company, especially if its founder led, hugely personal decision. Throughout all these roles, very, very intimate relationships with the CEOs that I’ve served, and that coaching and advisory aspect was the thing that I loved the most. So, now I’ve just gotten rid of the distraction and now, I’m just doing what I’ve always loved to do the most.
Scott: Yeah, I second that. I know there’s a bunch of things I do at Kruze, and at Lighthouse before that, but the conversations helping people and helping them work through really tough things, and helping them enjoy the good moments and make their dreams come true is by far my favorite point too. We kind of monetize through accounting and taxes, but really, I love that advisory and just, I think you probably share the same feeling, like building those relationships, they’re super long-term relationships. We just had Fleet Smith get bought by Apple, and I still remember when Zack called me on the phone when they were a two-person company. You know? So, this kind of things, and I think before we turned the mics on, you were also saying that this is maybe the most rewarding position you’ve had in your whole career.
Mark: Without a doubt, yeah. The personal impact already has been so huge, and yeah, really, really so rewarding. I’ll share one anecdote, just in my onboarding, I always do an onboarding with new CEOs just to kind of get the current state of the union of the person and the business. And for founder led business, often for better or worse, those two are inseparable.
Scott: Yeah.
Mark: That’s debate whether that’s good or bad, or not. But it is what it is. And, one of the questions I always ask is, kind of rate your level of satisfaction of your relationship with your significant other on a scale of one to five. And this person gave me an answer, kind of four out of five. And I was just like, “If I was talking to your spouse, and asked her the same question, what do you think she would say?” And, he was like, “I don’t know. I’m going to ask her.” And he did, and turns out it was a one out of five.
Scott: Oh wow. Yeah.
Mark: And just been kind of holding off, and just kind of sucking it up and supporting him because he’s an entrepreneur and that is what it is. But it sparked a whole bunch of great conversation and a re-gigging of his priorities. And I’m not going to say it saved his marriage, because I don’t know if it was on the brink. But had a hugely positive impact. So, that’s just awesome, you know? I really love that.
Scott: And you changed two lives there, or maybe many lives with kids.
Mark: Yeah, they got kids too.
Scott: Also, that positive cycle of like if that executive kind of re-jiggers their priorities but becomes a happier person.
Mark: Yeah.
Scott: And a more balanced person, that actually can really… I think that’s the big thing is what I’ve really learned, is it really translates to the whole organization and everyone that works at that company is just happier and does a better job.
Mark: 100%, and people often think, “Oh no, I can’t carve out more time. I need to put 80 hours into work.” But an hour isn’t an hour, isn’t an hour. I don’t presume all of those 60 or 80 or whatever number of hours that you put in are of equal value and equal impact. I did not become a coach to project my issues on to other people. But, one of the big catalysts for this decision to finally become a coach, and I would say I actually bought my first book on coaching in 2002. Wisely concluded I lacked the gray hair and moral authority to really crush it as a coach. So, I kept grinding for a while. But, it’s something that’s called to me for a long time. Also, as an aside, I’m Buddhist. Being of service to other human beings is a huge thing for me, and it always has been. So, very much been called to do it, but the thing that drove the decision, a big thing that drove the timing, was my marriage ended last year. And, these things happen at alarming frequency. Over 50% of marriages end, but I took the time to unpack kind of why that happened, and what I could do to be a better human being and better partner in the future. And two big conclusions, why I’m getting into all of the dirty laundry, one is what we just talked about already. I’ve kept a journal for years, and I reread a bunch of years last year as I was unpacking, kind of doing a postmortem on myself, and saw that the days I was most excited about were the days where I had one of those one-on-one coaching advisory conversations that I felt had impact. But, going back to this notion of 80 hours, or whatever, the other big catalyst was work/life balance. Never a strength, through all my roles, whether I was a CFO scrambling to raise money for a company before it ran out of cash, a first-time fund manager trying to get a first time fund to be successful, or by the way, investment banking, that’s not an industry that prizes work/life balance in any way, shape or form. And you know because you’ve been one.
Scott: Yeah.
Mark: Well, the more success that [inaudible] Capital had, the worse it got. And every year, whatever my reward status, with the airline went up and it was stupid. It was really clear to me that I could not both achieve the vision and potential of that investment bank and be a good husband or partner, right? It was one or the other, and COVID was actually the thing that gave me the space to think through that and have the courage to pull the trigger and pivot.
Scott: That’s really amazing. Yeah, going back to the hour per hour thing, where people think they need to work 60 or 80, and I think we were certainly, and speaking for Vanessa too, certainly like that too. But as you kind of strip… I think one thing we’ve… And we’ve, by the way I told you this before turning the mics on, but we go to Visage, which is kind of a peer coaching group.
Mark: Yep.
Scott: With a coaching lead, and it’s been a huge game changer for both Vanessa and I. So, I highly recommend that to people. And it’s helped us carve out our own role and then, delegate more and also, just prioritize. But, simple stuff that I’ve learned, like now I just block off two hours in the afternoon or two hours in the morning almost every day just to think. Or, do something creative, like write my scripts for videos, or things like that. You make space for yourself and you can just become better at your job, and do it in less time, and be a more giving person and help other people. So, I think what you’re doing is, not to be cheesy, but it’s like God’s work. You’re making other people happier, more successful, and you’re starting that like kind of visualizing when you throw a rock into the pond.
Mark: Yeah, yeah, yeah.
Scott: Those little waves go out, and helping a lot of different people.
Mark: Totally.
Scott: So, kudos to you.
Mark: Thank you. I will say, for what it’s worth, that you would make a great coach.
Scott: Aw, thanks man.
Mark: Yeah, the reason why-
Scott: I’ve actually told Vanessa I want to do it when we’re done with Kruze someday.
Mark: Yeah. I say that for [inaudible] reasons. One is you have varied experience, right? You have deployed capital, you’ve been a deal maker, you’re now exposed to hundreds of companies through Kruze. So, there’s just a whole bunch of pattern matching, but the most fundamental thing is you genuinely love people. And, that sounds cheesy, but it’s a prerequisite and you have a very deep curiosity. It’s very clear. I’ve listened to many of these podcasts, and you really enjoy asking questions. It’s never routine. You just love it, and that job is to ask questions. Right? So, very clear to me you’d be a great coach.
Scott: I appreciate it. Well, I will be working for Mark Macleod Coaching, hopefully, in 10 years or something like that. But no, I appreciate it, and that’s super nice. In my book, that’s like the nicest thing someone could say to me, expect that I’m a great father and a good husband too. So, I appreciate that. Let’s talk, let’s jump in. So, one of the things we talked about in a couple different ways before we turned the mics on was how the role of CEO and just how it evolves.
Mark: Yep.
Scott: And we have a couple little bullet points. But, do you want to kind of introduce us to that topic? And then, we can go through some of the bullet points. Or, we just cover the bullet points organically?
Mark: Yeah, I mean, maybe I’ll just kick it off with-
Scott: Yeah.
Mark: … A sentence or two. But I think my observation is anyone can start a company and call themselves a CEO. And back when I was at Steed Stage VC, I’d have a five-person company with three founders come in to pitch me. And three people with C Level titles. It was bonkers. And there’s a huge difference between calling yourself something and actually really being the full potential of that role. What it means to be a CEO changes over time. I think at the highest level I think of sort of two stages in the life of a startup. Kind of pre-product market fit, and post-product market fit. So, pre-product market, all you should be doing is figuring out whether your product deserves to exist in the market. Nothing else. No board meetings, none of this bullshit. 100% focused on nailing the value proposition, and the target customer, and again, figuring out, like I say, whether you deserve to exist. And ideally doing it in as compressed a timeframe as possible, because you’re burning with nominal or no revenue. It’s a huge funnel, right? Maybe half of Steed Stage companies go on to raise an A, half go on to raise a B, right? So, there’s a big drop off at every stage. So, the faster you can figure that out the better. Then, once you’re in the post-product market fit, that’s when actually all the issues and opportunities of being a CEO start to present themselves. That’s when you start building a leadership team, trying to find repeatable channels. So, there’s tons that’s been written about this, but you should be sort of successively putting yourself out of jobs. Right? Because you’re the doer number one, everything, right? The most strategic things to the most mundane things in the start as a founding CEO. But over time, you go from… If I use an orchestra analogy, you go from playing the cello to being the conductor. And that’s actually a huge struggle for many founding CEOs who either don’t want to relinquish product, or who they’re just creators, so they love the startup stage. But then, you get into, whatever, the teams, 10/15 million in ARR. Now, it’s boring. So, you’re thinking about the next shiny new thing. So, how do we reorient so everything that you got as a creator, all the fulfillment, all the energy. Is there a way for you to maybe think about your company as the product, and architect the user experience for new staff? How you on board, how you do culture, communication. There’re tons of things that can leverage all of those instincts and strengths, right? And by the way, there’s nothing wrong if you conclude like, “I’m just an early stage person.” There’s nothing wrong with that, but it’s just really kind of exploring it until you reach the decision that really reflects your core, versus an instinctual kind of gut reaction decision. I think the CEO role, at scale, and by the way, I’ve realized now I’ve said more than a couple of sentences. I’m going to shut up-
Scott: No. Keep going. Keep going.
Mark: Fred Wilson wrote, I think, The Canonical Post, on this back in 2014, where he boiled the CEO role down to like three things. Setting and repeating a vision, and mission, et cetera. Hiring and retaining great talent, particularly at the senior management level. And making sure you don’t run out of cash. It’s those three things.
Scott: Yeah, it’s beautiful. I haven’t heard it put as succinctly as you said it, which making the company your product eventually. Because you’re totally right, the people who like to start companies or do this kind of stuff, see it as a creative outlet. I see it as a creative outlet, and I think Vanessa does too. But then that fear of putting yourself out of jobs, whether you recognize it’s a fear or not, I think it is for most people and I know it was for me. But then, turning your… There needs to be this pivot point where, and through coaching this is how it can happen, you start seeing like, I know the way I visualize our company as the product now. And I can see, “Oh, our technical team is part of the product, and our accounting team, and our tax team, and the leadership.” And how people work, it’s actually incredibly fulfilling to me. It took me probably a while, but I somehow made that pivot too. And now, it’s like I really enjoy… I feel like I’m in the workshop, hammering in the nail on something and sawing something else. But really, all I’m doing is constructing like a vessel with a group of amazing people that we’re tackling something together. And it’s not about inventing a new way of doing accounting or things like that anymore. It’s about making our service really good, and making life really good for the people that work at Kruze.
Mark: Yeah, I love it. That’s great. Yeah, you should switch altitude from working [crosstalk]-
Scott: Yeah, that’s what I’m saying. It helps [crosstalk]. Yeah.
Mark: … Working on the business, right?
Scott: That’s really cool. So, is it worthwhile kind of going through the stages by fundraising stage? Or how do you… What’s a good way of thinking about this as a CEO’s role changes?
Mark: We definitely can do that.
Scott: I’m just throwing it out there. By the way, we’re friends. So, normally, audience, I would have a boom, boom, boom. But Mark and I have talked so many times that I’m really kind of interested in pulling out, not making on a boiler plate, and having a more coaching. It’s because I don’t know how to be a coach, that’s what’s interesting about this conversation to me.
Mark: Right. Yeah, my only hesitation there was like, if you read Tech Crunch all the time, you think every company is funded. But actually, the vast majority of startups are not. I notice this in Sure Path, right? We focused on startups that served the S&P software market, and over five years a full half of our clients got to north of $10 million in revenue with no funding.
Scott: Totally.
Mark: And so, it’s actually more head counts. There’re frictions in head count where everything changes. The first 10 people, you’re all in the same room, you’re eating pizza, you’re working all the time. You’re all wearing the same really smelly hoodie. And I realize I’m making a male stereotype there, which is not intentional. But in any event, 10 to 20 is when maybe everyone doesn’t know everyone as well. So, there’s a more explicit need to create those bonds, to create a homogenous culture, which doesn’t mean it’s a board. It doesn’t mean everyone’s the same. But it does mean we’re starting to work on culture. And I think that kind of moves along nicely until you get to 50 people. And, around 50 people, there’s some ARR number that corresponds to that, but you’re starting to figure out scalable channels of acquisition. You’re starting to maybe build your senior leadership team. And these are maybe not true C Level people, but it’s head of this, head of that. You’re now starting to think about, “How do I succeed through others? How do I enable others? How do I relinquish decision making capability?” A lot of the founding CEOs I coach sort of really miss the point in the company where they knew literally everything. There was no question that could be asked that they could not answer, right? And I think north 50 people, that just starts to happen. If you try to be in the weeds of everything you’ll just blow up.
Scott: Yeah.
Mark: And, that can coast along now. So, you’re starting to succeed through others. There’s sort of a gap of 50 to 100 people. And north of 100 people, first of all, you’ve probably iterated your senior leadership team at least once along-
Scott: I was going to ask that question. How do you know if…? Because you’re building your leadership team, but you may find some great people and they just hit the ground running. But other people may need some coaching, and other people just maybe aren’t a fit. How do you make those determinations? How do you know something’s not working?
Mark: Yeah, I mean there’s no one way because you’re dealing with human beings and they’re all different. The context, and more importantly, it’s not that one person in isolation. It’s that person thought of in the context of the broader management team. Right? So, there isn’t one way. But, Toby from Shopify often talked about himself having to re-qualify for his job every year. So, that’s just a really interesting mindset. Right? Particularly important, right, if a company is growing rapidly, as a leader you have to grow at least as fast as that in order to remain relevant and crush it in the way you might be crushing it today. So, a lot of it is really thinking about the same way you think about a product road map. What is your leadership road map? What is your role going to look like 12 months from now? And what things do you need to be doing now so that you deliver that set of leadership capabilities, that set of leadership functions and features 12 months from now?
Scott: Yeah.
Mark: So, it’s just like you are the product.
Scott: Getting out of the way if you can’t deliver that. That’s kind of the, getting out of the way, if you look at that list of the things you’re supposed to deliver and you know you won’t be able to deliver it, then either plug in the gap. Or, just getting out of the way.
Mark: That’s right, and having a lot of very open and honest conversations, right? Particularly with yourself, which is super hard, right? It’s hard. Nothing in life is experienced truly objectively. Everything is experienced through our perception, through our lens. So, this is actually where coaches can be tremendously helpful, right? To be detached. I’m not your venture investor. I may, as a venture investor, I have tons of value to add. I’ve seen a lot. I’m supremely networked. I can help, but I have a vested interest, right? I want you to become a home run. As a CEO, maybe you can’t confide everything in me, because I’m also on your board of directors, right? So, there’s just a-
Scott: And that venture capitalist has pressures on themselves.
Mark: Absolutely.
Scott: You might be their only good company out of their last five investments. So, they really need you to work. Or, you may not be one of their top companies, and so they care a lot less. So, understanding where they’re coming from is super important. But yeah, the other thing I find about, like my version of coaching is slightly different than what you’re doing. But being able to, because we do this exercise where we share challenges that we’re going through and where we need help. And just the process of articulating that, and kind of forming it for the group, oftentimes gives me half the answer.
Mark: Yep.
Scott: Because I had never had that peer pressure to really sit down and set the structure for it, you know?
Mark: Mm-hmm (affirmative).
Scott: Then, I mean, I know the audience might laugh at this, but just hearing the answer out of other peoples’ mouth, it adds so much credibility and weight to that. It’s just really powerful. And you’re kind of vulnerable, you’re putting yourself out there. So, having people respond to you knowing you’re in a vulnerable place in a constructive way is like, it’s just magic. It really works.
Mark: Yeah, it helps you let the guards down, and also, realize you’re not alone.
Scott: Yeah.
Mark: So many people, like a CEO is a pretty lonely job. You don’t get a ton of feedback, or if you do, it’s negative. Everyone wants a piece of you. You, for better or for worse, your identity is intertwined with the company, especially as a founder. But even execs in big companies, whatever, Fortune 500 companies, it’s a different issue. Their identity is tied up in their power and their title, and their status. So, they’re inseparable from the role, and then they get terminated and they go into depression. Totally generalizing, but there’s all of these things where being able to talk this through and realizing you’re not alone, and you can get through this, and everyone’s facing this. Often, we have this stereotypical notion of what a CEO should be, and they’re confident and charismatic and they make rain happen. And they’re deeply strategic. The fact is, everyone’s got imposter syndrome. Everyone has issue. Every single company has warts, I guarantee you that, right? So, helping you realize like, “Oh, I’m not insane. I’m not alone” is super helpful.
Scott: Yeah. How do you break down, because I know I’ve experienced it in this group way, but when you start working with a new person, do you have…? How do you get them to kind of confide or relax, or trust you? Or is it that you know that by them coming to you, you know they’re ready to do it? Or, how does that process work for people who are thinking about getting a coach?
Mark: Yeah, no, it’s definitely not automatic because they’re coming to me. It’s obviously helpful, but I think of it, in many ways, the way I used to think of potential founders when I was a venture investor. Where the thing, one of the biggest attributes that I was looking for, was self-awareness and an openness to learning. Because of this observation that the founder would have to grow faster than the company in order to remain relevant, right? For me, there’s a very high, almost 100%, correlation between founder success and the CEO role, and company outcome, right? All the biggest outcomes are founder led, kind of start to finish.
Scott: Yeah.
Mark: As a CEO, as I said, you have to grow faster than the company each year. So, the benchmark for me on this is, again, Toby from Shopify. I had the privilege of serving there as an intern CFO through the Series A and the Series B, spent a bunch of time with Toby. And, Toby is not your charismatic, stereotypical CEO persona. He is as introverted as it gets. He was a reluctant CEO. He was not the original CEO of the company. But going back to self-awareness, introverts are very often very highly self-aware. He was off the charts on that, and he learned very rapidly. There was a whole bunch of other things we can get into, but anyway, just self-awareness is a big thing that I look for. I think the fit has to be there, because coaching is deeply personal. And again, I’m not a therapist. I, ironically, do have a couch in my room, so if people want to lie down on the couch, awesome. But I’m not a therapist, but there has to be a level of trust there. I think, for better or worse, anyone can call themselves a coach, and there’s a lot of, let’s call them, so-so coaches out there. And, there’s maybe a couple of more prevalent personas. One is someone who hasn’t operated but is a credited coach. And, they’ve got all the tools in their toolkit to be a coach. They just don’t understand your context. Startups are not normal, right? So, they just don’t really have an appreciation for your reality.
Scott: Yeah.
Mark: On the flip side, you maybe got a former CEO, and so they understand your reality. It’s just like they understand it with a very small sample size. One company, two companies, at most three companies. And again, if I generalize, many of them come at it with [inaudible] pride and ego, right? “This is what I did in the past, and this is what you should do. It worked for me.”
Scott: That’s what I was going to say. Yeah. They suggest the two things that worked for them in the exact same situation.
Mark: Right. Meanwhile, it was like 10 years ago, context is totally different. So, in many ways, I feel like I apprenticed for this role for 22 years by doing a whole bunch of different things. And being sort of on every side of that journey from start to exit. So, I come at it, like I think what my clients like is, first of all, I’ve been in their shoes. I’ve operated, I’ve invested and I’ve exited businesses. But there’s a large N, like the sample size of companies I’ve been exposed to is large. And I’m not-
Scott: That’s a great-
Mark: I’m not a former CEO, so I don’t have my ego and my identity wrapped up in that. It’s always been about being at the right hand of CEOs, and enabling them, and being of service to them. So, it’s just not about me. That helps me be really objective.
Scott: Yeah. Those two things, the large N, is such a great point. Because even at Lighthouse, I just saw so many companies come through and we had a higher velocity model than a typical VC firm. So, we would have 150 companies in our portfolio that I could see grow, and mess stuff up, but fix it. And then, at Kruze, it’s like even more turbo charged, because we’re almost up to 300 clients now. And those are just clients we have right now. We’ve had a bunch of those get bought, or unfortunately go out of business. So, that big N, I really believe in that too. And, I just wrote a note to one of our founders last week, who’s in a tough space, and getting just hammered in the travel space. I just gave him a little note of confidence because I remember all the… They got so big that I stopped working with them a lot, mostly just our controller. But I remember getting so much from him, even though I was the service provider or the helper. That large N allows you to do that stuff. Then, being able, like the other point you made about just being the right-hand person, and not having your ego tied up in it. It is a different mindset. You’ve seen, from that perspective, you’ve helped a bunch of CEOs. So, I think both those points of view are incredibly valid. And maybe it’s because I share a lot of that with you.
Mark: Yep.
Scott: But, it makes so much sense to me.
Mark: Awesome.
Scott: So, then after you have that foundation and trust, do you guys tackle specific issues? Or, do you put them on… We talked about the company being the product. Do you put them on a plan, or goals? Or how does everything work?
Mark: There isn’t like the Mark Macleod 10 step method, or anything of that bullshit. I do the on boarding up front to just get the state of the union of the person, and the business. Out of that discussion comes usually a set of topics we’re going to work through together. And people often use the term kind of coaching and mentoring and advice sort of interchangeably. But they’re very different things. So, coaching is really about me asking you questions, me probing, me taking the conversation in a certain direction where you generate your own insights, and your own actions. Whereas, advice and mentoring is more about, “Well, here’s what I’ve seen. And here’s what’s worked in the past, and what do you think about trying these things?” So, there’s a role for both, but the foundation is coaching, right? It’s much more about that. And so, the nature of the dialogues will depend on the topic. So, one is like, “I’m preparing for Series B. I need to know what the bar looks like for Series B.” That’s much more in the advice camp, because there’s an objective bar for being Series B ready, which I’ve just seen a lot, so we’ll talk through it. Whereas, if it’s more about like, “I’m struggling with imposter syndrome, and I’m completely stressed out, and I’m not present at home. So, I’m being a shitty whatever, partner, and father, or mother. And, that’s impacting my work.” That’s absolutely a coaching conversation. So, the nature of the interaction changes, I would say, from session to session. But, while I don’t have, like I say, the 10-step program, I do have a thesis, which is you can read all the blog posts, you can read all the books. You can have all the coaches and advisors. But you will not transform as a leader, and until your company goes through revenue growth and you hang on for dear life. And, I will once again go back to Toby at Shopify as a great illustration of this, right? Toby would not be the CEO that he is if Shopify hadn’t… If he hadn’t been gone through all the growth that Shopify has gone through to become a multi-billion-dollar company. Shopify wouldn’t be the company that it is without having Toby as its leader. So, there’s this virtuous, ever expanding cycle. So, I’m not a former growth hacker, I’m not a former CMO, I’m not sitting there, tweaking conversion funnels. But once we’ve put out any of the fires for the person or the business, a huge focus of the conversations is on how do we unlock growth? For all the reasons I mentioned. It will just… The single biggest driver of enterprise value, all else being equal, is you’re on your revenue growth rate. And like I say, that is the thing that will transform the person, and it’s a thing that will deliver all the optionality. If you are growing like stink, all the investors will want to fund you, companies will want to buy you. People will want to work with you, they’ll want to partner with you. It’s a virtuous cycle. So, how do we unlock that, right? So huge focus on that.
Scott: That’s beautiful. And you said a couple different times that for a company to grow, the founder has to grow faster. Which I’ve never heard that ever, but I totally agree. Because I look at times where Vanessa or I was not growing fast enough or not seeing the writing on the wall fast enough. And things either stagnated or we had problems. It’s almost like a kid will let you know when you have a problem, you know? We were having that kind of stuff.
Mark: Mm-hmm (affirmative).
Scott: So, being in that mindset of continually improving is so valuable. And in terms of the company, you’re totally right. Unlocking that growth does lead to a bunch of different good options for more capital, bigger exit. I think the one thing that people don’t quite understand, that I underestimated, was growing allows you to attract really good executive team members.
Mark: 100%.
Scott: And makes your life easier. So, one of the things we had to unlock was how do we get big enough to be able to afford good executives to work with us? And we hit that point and we finally, we worked with Heely and some of the other people, Bill, and Lorena, a really great team, Alex. But some of those people we honestly just couldn’t afford until we got to a certain size. So, for us, there was this uncomfortable push to get to a certain revenue number and a certain growth rate so that we could then hire really amazing people. Which then, made our lives better, and made the whole company better. You know?
Mark: Yep.
Scott: So, that’s a good example of what you’re talking about.
Mark: Yeah, I mean I often encourage folks to wait as long as possible before hiring true C Level people. The difference, I’ll take a CFO, just because I was one forever. The CFO you will get for a $5 million revenue company is totally different from the one you’ll get for a $20 million company, right? So, this is why I like head of functional area for as long as possible, versus chief of functional area.
Scott: Yeah. I totally agree with that too. Have there any things that surprised you as you started the coaching business, or the coaching practice? Things you learned about yourself or things that your clients, like there was patterns amongst the CEOs that you can share with us?
Mark: The biggest surprise for me, personally, was spending the first two months of this practice, I only launched it full time three months ago, I guess. Learning to work without guilt, or without stress rather. And feeling guilty about not having stress. I’ve been in the startup world since 1999 now, and for most or all of that time, have worked with a blatant kind of just consistent level of stress. To be clear, a lot of that was self-imposed, but nevertheless, it was a pervasive part of my reality. And now, I’m not stressed. So, there was a whole thing around just understanding and accepting that, and getting over the guilt of it. Then, realizing how amazing that is. And also realizing, when you give yourself space, like look at your anatomy. I’m six feet tall. Most of that is body, not brain. The brain is a small part of that. But we walk around thinking that we’re just brains, and it’s like, “I’m thinking. I’m on all the time.” [crosstalk]-
Scott: That’s it. Yeah.
Mark: [inaudible] being. Giving yourself room to exercise, to sleep properly, to eat properly means that when you do need to turn your brain on, you’re going to deliver better. We were talking about this, I think, before we went on air, or maybe it was when we were on air, either way, but many of the CEOs I talk with who work 60 to 80 hours per week, I don’t assume every hour is of equal impact and value. An hour is not an hour, is not an hour. My fundamental belief is if they took the time to feed themselves first, exercise, sleep, nutrition, I’m not going to make everyone meditate, but I think they should meditate. I hate the word should, by the way. I just used that word. We can talk about that. Should is a four-letter word, even though it has five letters. But, if they feed themselves first, they will have way bigger impact. And work expands to fill all available time. If you give it 80 hours, it’ll take 80 hours. This is extreme, but I would argue that if you gave it 40 hours, you could still crush and deliver 80% or more of what you’re delivering in the 80 in those 40 hours.
Scott: Yeah, I agree. There’s something, I always think about this, this is one of the ways that got me to slow down, or take a step back, or just create room. Not a perfect analogy, but when you’re doing the 60- or 80-hour weeks, a lot of your decision making or the way you work with people is kind of reactive.
Mark: Oh yeah.
Scott: And I always think like the crocodile brain, the reptilian brain. Because you’re so tired, or you’re just so unfilled or whatever it is, you’re not really who you are and thinking clearly. So, you tend to make reactive decisions instead of being more inquisitive and slowing down, and thinking. And that’s all stuff I’ve been trying to work on quite a bit, like slowing down, taking time, asking questions, things like that. So, you get in this reptilian decision-making method, which I think is kind of addictive because it satisfies this weird, you know the reptilian brain. So, it feels okay. It feels good, that you get some adrenaline because you’re making decisions. And it feels like you’re moving fast. But you’re not moving… I think you move a lot faster when you do feed yourself, like you said, and just take time. And ask the why more often.
Mark: That’s right. I mean, the key word there is just reacting. Right? Work is happening to you, not by you. Right? And you feel good, it’s busy, like, “Oh, I’m adding value.” But you’re not intentionally, right? Just what you talked about earlier, right? You’re taking the first couple of hours of your day to create, right? You’re carving out that space. If you tried to fit it in between meetings, it probably wouldn’t happen or it wouldn’t be as creative. So, you’re being intentional, at least with that part of your day. So, taking the time, again, to be intentional. What is it that I need to achieve? How can I add the most value? And then, moving with intention, versus reacting is absolutely the more powerful way, right? And there is a dopamine hit. Every time you get an email or [inaudible], there’s a little hit of dopamine in your brain, right? It’s a thing. So, it’s [inaudible]-
Scott: Yeah, [inaudible] brain really craves that dopamine. Whereas, the kind of happy, content brain doesn’t need it as much. You know?
Mark: Right.
Scott: That’s why I think it feeds on itself.
Mark: Yep.
Scott: We only got a few more minutes but let’s talk about should, because I think I know where you’re going with that. And, I’m guilty of that too.
Mark: Right.
Scott: So, talk about why should is a four-letter world.
Mark: Yeah. I mean, I always tell people like, “Stop shoulding all over yourself.” Right? It’s just like, the external expectations. Often, we impose them on ourselves thinking that this is what others do, right? Again, going back to this stereotypical notion of, “Well a CEO does this. I should do this.” Who says? Who wrote the manual to say that is the thing? And by the way, CEOs come in all different shapes and sizes. If you’re a technical introvert, the path for you to succeed and thrive is very different than an enterprise sales leader who is now a CEO. So, you have to… The path to success is molding the role, according to your strengths, your superpowers, what feeds you. There’s this Japanese concept called Icky Guy, and it’s the intersection of what you’re good at, what you love, what the world needs, and what you can be paid for. If you can connect the dots on all of that, you can have huge impact and never feel like you’re working a day in your life.
Scott: The other thing I think about should is that it’s easy for people to say to you.
Mark: Oh yeah.
Scott: Without having any of the responsibility. It’s like, I don’t know how to… I’m not going to articulate this perfectly. But, it’s easy to give a recommendation, but not fully… you’re giving, kind of back to what you were saying, you’re bringing your own history to that recommendation and things like that. It’s the classic like, you’re giving a recommendation but you’re not 100% vested in it because it’s not your company or your life, or your relationship. So, that should carry… You got to be careful. Don’t let that should carry a ton of weight when it’s coming from other people. It’s much better if you can generate it yourself.
Mark: And again, I’ll go back. First of all, I totally agree with that. But I’ll go back to now distinguishing between coaching and advice. So, often that should be advised. Here’s a thing that you should do. With coaching, I would be asking questions, so that the person generates their own should. They’re not using the word should, but they’re coming to an insight and action. But it comes from the inside, so it’s not being opposed. But that should, that advice thing, like the thing I always tell people about advice, even when I give advice, it’s all just input. Right? So, you ultimately have to decide. I had a coaching call today with a CEO running a vertical specific SAS business. We were talking through strategy direction that’s specific to his industry. And I asked a bunch of questions, trying to diagnose where things were at, and I offered some suggestions at the end on this strategy. It was around whether to acquire a company, and the implications of that on product strategy. At the end I was just like, “You’ve spent years thinking about this. We’ve just spent an hour. So, take it for what it’s worth. It’s input. I’m not telling you, you should do that. Keep replaying back what you’ve told me. These are the conclusions I draw, right? But it’s just input.”
Scott: [inaudible] told you about speaking in front of the group, that CEO is running the stuff by you. Part of the benefit is just them running it by you, and then, also you re-articulating your advice is probably incredibly helpful to that person, because they’ve been going back and forth in their brain, probably, a ton. So, just getting out of your brain.
Mark: But no one they can talk to, right? Because they may not want to talk to their venture investor until it’s fully baked. They may not want to talk to all of their management team because they’re going to get distracted by all the shiny new thing, and drop the ball on the thing that they’re actually running.
Scott: Totally. I love it. First of all, this has been awesome. Thank you so much, and I’m so happy for you. I didn’t get a chance to comment too much on it, but working without stress is a really amazing goal. I’m glad you got there, and I have to say, I’m getting pretty close. I’m really enjoying it, so I’d mark that as a win in my column too. So, I hope people who listen to this just kind of… I wouldn’t have thought that was possible three years ago.
Mark: Right.
Scott: So, if you’re listening to this and you think it’s not possible, then we can tell you it is. And if you need a coach, Mark is the man. I’m really excited that your practice is going so well.
Mark: Thank you so much. I love it, and it’s hugely rewarding. And again, I’ll just go back to Buddhism for one second. A premise of that is the purpose of life is to be happy. We are seeking happiness. And the way I think about that is all I have are my days. So, is each day happy and rewarding? Or not? And the absence of stress is a huge contributor to each day being happy. So, yeah, I’m loving it.
Scott: Beautiful. What URL or how do we get in touch with you if we want to work with you?
Mark: Yeah. So, I’m now in the world of least scalable business. It’s just me. So, very simple, MarkMacleod.me. Macleod is, M-A-C-L-E-O-D. So, MarkMacleod.me. I put some blog posts up there pretty regularly. I love to write. I learn and clarify my thinking through writing. Again, my job is not to prescribe, even though a lot of those blog posts are in the form of advice. But at least allows people to see how I think, and if they resonate with how I think, then we should have a chat.
Scott: Love it. MarkMacleod.me. Thank you, Mark, and looking forward to the next time we talk.
Mark: Thank you so much, Scott. Really enjoyed being here. Keep well. (singing)
Singer: It’s Kruze Consulting. Founders and Friends with your host, Scotty Orn.

Kruze Consulting offers solid financials to help de-risk your startup’s next venture capital round. Work with a startup expert! Kruze bookkeepers will help your startup have accurate, up-to-date financial statements that you can use to manage your business’ growth and cash flow.

Explore podcasts from these experts

  Talk to a leading startup CPA