7 Proven Practices for Becoming a High Performing CEO with Mark MacLeod, Startup CEO Coach

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So the reality is good things take time. Those kind of super fast exits do happen, but they're extraordinarily rare. And so you have to build a set of practices for yourself that are gonna allow you to not blow up and actually not just survive, but actually thrive on every level. A personal level, professional level, over as you can see in this case, in many cases well over 10 years. Because that's what's going to take. If you truly want to build a market leader, build a large transformational company. If you want to do your life's work, buckle up and settle in because it's just going to take some time. I need some traction. You need some traction.

Hey, what's up innovators? I'm entrepreneurs, visionaries and disruptors. This is your Traction podcast host, Lloyd Lobo. We're a community of over 100,000 people just like yourself on a mission to help you get the methods, the money and the madness to explode your business growth. Featuring stories and tactical advice straight from those who've done it before, like Shopify, Twilio, Asana and many more.

I need some traction. You need some traction.

For more than two decades he served as a CFO at Shopify, FreshBooks, was GP at Real Ventures, investing in awesome companies and then ran one of the top investment banks focused on SMB software, surepath and what people many people don't know and probably Mark. If you've not dropped the link, I will. Is he Mark DJs? And what I would recommend is maybe the next time we do this session we do like a social where Mark's Djang I dropped his SoundCloud link. Mark, before we get started and go into this topic, this really hot topic that nobody talks about is there is no boss or founders or CEOs right? Like everyone else gets all this coaching but founders and CEOs don't and they have this external pressure, investor pressure, team pressure and they gotta always look like they're at the top of the game and we die under this pressure. And this stress as founders.

Right.

And so before we get into that topic of how do you build high performing companies and build become a high performing founder, CEO leader, I would love to learn a little bit more of your backstory. How did you go from being CFO to investing and now doing what you're doing and all this while keeping your passion alive of belting out some awesome tunes there.

Thanks, Lloyd. Yeah, thanks for the intro and yeah, super pumped to be here folks and look forward to getting into this chat. Yeah, briefly on my background and that journey. I'm a CPA by training. I spent six years in that world, three in audit, which was as boring and painful as you can imagine. Three in corporate finance, that was better. And corporate finance was my first exposure to doing deals. And I entered the Startup World in 1999 and at the time I thought I was just really great at fundraising. Turns out anyone but a pulse was able to raise capital. But I, I had a thirst for deals and startups were just a perfect hunting ground for that because they're always burning their way to greatness and always need capital and always looking to exit. And was really enamored with venture capital and set myself a goal to become a VC within 10 years. I did it in 11 or reasons we can get into or not depending on our time. I think venture capital is overblown. It gets too much press, too much attention. It actually doesn't apply well to most companies. And I also think it's overrated even as a, as an industry. And for all those reasons, I stopped being a vc. I recognized that startup life boils down to a few big moments where having the right expertise, connections, insights, deal making capability can be literally game changing. And so felt that there was a gap in terms of advising companies on doing these deals. And I think investment banks have a well deserved bad reputation. Most investment banks and most investment bankers are useless. And so I didn't think the world needed just another generic investment bank. And I thought the only way to matter was to specialize. And so we went super deep on a space that I knew really well, which was SMB SaaS, and built arguably a leading deal maker in that space. So it's just been a natural evolution focused on a true passion for doing deals and a true passion for kind of advising CEOs, which is a thing I'm, I'm going to get into in the talk. And as for the music thing, I don't know that's a whole other thing, but that's just been a lifelong passion Something I'm going to talk about in this chat is actually the importance of fun, which I think a lot of us adults forget about. And for me, playing music, whether it's DJing back when people used to go out or whether it's producing music, it just completely feeds my soul. Like I just lose myself for hours at a time. I stop thinking. So it just, it's something I absolutely am compelled to do. And I think it's really important for us to have those things in our lives. Cause I think it gives us so much energy to bring to the other parts of our lives. So I could do a whole talk on music, but we'll save that for another time.

Awesome. Without further ado, Mark, take it away.

What I'm going to talk about today is what I call 360 degree leadership. And I'll get into what that means. But really building sustainable personal practices and sustainable business practices for peak performance and peak performance, meaning across all of your roles, not just peak performance for the business, but peak performance for yourself as a human being. I'll do a super fast intro because Lloyd's covered that today. And then I'm going to get into seven personal practices that I think lead to peak and sustainable personal performance and do the same on on the business side. So 7 what I think are kind of company leadership practices for sustainable peak performance. So very briefly, Mark McLeod. I've been in the venture backed startup world since 1999. Spent 14 years as CFO for a number of venture backed software companies, most not Shopify. I was there for a brief but instrumental period through the Series A and then the internal Series B freshbooks where I led finance biz dev and Corp Dev. In between those two I was one of the original general partners in Real Ventures which was and still is Canada's largest independent seed stage venture fund. Spent five years founding and running surepath Capital Partners, a leading boutique investment bank for SMB software and for just about a year now have been serving as a coach and Advisor to the CEOs of Venture and private equity backed startups. And we've also covered the most important thing, which is I'm hugely passionate about electronic music, specifically Deep House. So let's just set the table. And before we get into these practices that I recommend, let's just talk about the context that you guys are all operating in, particularly if you've done what Lloyd and his partners have done and actually just raise some capital. Let's talk about 360 leadership as a starting point. As I mentioned at the very beginning 360 is about all of you. You know, you are not just a CEO, you are a spouse or a partner. You are maybe a parent. We're all children, we wear many different hats and they're all intertwined. If things are falling apart in your personal life, you cannot possibly show up and crush it in your work life, at least not for the long run and kind of vice versa. So it's all kind of one thing. And what I am talking about with this is bringing the same level of kind of intention and purpose and vision to all of the roles that you bring to your role as a company leader. If you look at, I've been a student of kind of high growth software companies for a long time now and what do these folks have in common? So Toby from Shopify, Mark from Salesforce, Mikael from Zendesk, so on and so on. They are all kind of original founding CEOs and have led the company from the inception of the company to now. And this is a common pattern you see, where all the biggest outcomes tend to be founder led, start to finish. So more or less a hundred percent correlation between your performance as a CEO and the outcome for your company. So the stakes are high. And this is something I've recognized pretty early in my startup career. And it's actually sort of my purpose. Whether I was like a, a CFO serving as a right hand to a CEO, trying to give that person maximum leverage. Whether I was a VC investing in CEOs or a deal maker trying to help them achieve biggest outcomes, I recognized just a huge correlation between that person's performance and the company outcome and therefore just wanted to give that person kind of maximum leverage. So this is like a, there used to be a time when I first got into the space where founders would take it so far and then the VCs were quote, unquote, bringing in professional management. And I think everyone now recognizes that's not necessarily required or even beneficial. And as they see now as the Internet has played out over a meaningful number of years, that these biggest outcomes are not the ones actually where the MBAs have been brought in, but are actually ones where the founders have scaled and transformed themselves and continued to be as relevant in the later stages as they were at the very beginning. And you know, no surprise, good things take time. You know, if we read TechCrunch too much, we think that companies go from start to finish and sell for, I don't know, 300 million bucks in, in four years. But that's absolutely not the Case these are just a few logos that I'm sure we all know. Well, Shopify has been around since 2004, freshbooks a year earlier. Even some of these companies that are still private have been around for many years. And so the reality is good things take time. Those kind of super fast exits do happen, but they're extraordinarily rare. And so you have to build a set of practices for yourself that are going to allow you to not blow up and actually not just survive, but actually thrive on every level, a personal level, professional level, over as you can see in this case, in many cases well over 10 years. Because that's what's going to take if you truly want to build a market leader, build a large transformational company. If you want to do your life's work, buckle up and settle in, because it's just going to take some time. My coaching calls I often talk about Toby from CEO and I'm guessing most of us on this call are Canadian. And so we can't help but think about Shopify as sort of the ultimate benchmark for what we can achieve. And Shopify's year over year growth is a perfect illustration of this kind of virtuous growth cycle. And what I mean by this is, you know, if all of you are, I assume many of you on this call are CEOs or otherwise in a leadership capacity in your companies and you want to transform yourselves and become better leaders, there's lots of things you can do. You can read lots of the great books, lots of great blog posts, you can listen to podcasts, you can get advisors, you can get coaches like myself. All of these things are useful. But the one thing like the single biggest thing that will transform you as a leader is unlocking revenue growth in your startup and then just hanging on for dear life. And as and this illustration where Shopify in the last five years or six years has gone from kind of 300 million in revenue to 2.9 billion in revenue is a perfect illustration of that where Toby is not the same CEO that he was six years ago and he has needed to reinvent himself many times over to be as relevant today as he was back in 2015. And Toby's going to come up a couple of times in this talk just because I can say for me, he's the benchmark. He's also the most successful CEO that I've spent time and worked with and so there's a lot to learn from him. But he has talked about for years, talked about having to re qualify for his job every year in order to be as relevant 12 months from now as he is today. And this is just this one big nugget about how you can be a better leader. It's having this maniacal focus on removing any and all barriers to increasing the rate of year on year revenue growth in your company. And lots we can get into there. But that's just one really important observation I've seen over many years. So let's get into some practices on the personal side for sustainable peak performance. The first is to have the right motivation and it's easier than ever to start companies. When I started in the startup world in the late 90s, we didn't have Amazon web services, you had to spend 3 million bucks on Oracle databases just to get going. We didn't have these open APIs. It was just there was lots of friction and now anyone can get started. In fact, you can launch things with low code or no code. It's a completely different environment, but it is, I would argue, as hard as ever. While it's as easier than ever to start companies, it is as hard as ever to go all the way and build an enduring market leading company. And every company, no matter the size, has issues. And the point of all this is that you need to have the right motivation if you're going to go all the way. And startup journey is not a straight line up and to the right certainly the vast majority of the time. And so there are different kind of sources of motivation. You know, you might start something because you see a big market and so there's a big TAM and lots of money to be made. You might start something because you've built a product that you think is awesome and you want to bring it to market. I would argue that both of those motivations are not truly sustainable through all the ups and downs that you see here. If you're really just after the money, I don't think money is a sustainable source of motivation and certainly won't be for your staff, that's for sure. And if you're in love with your product, the risk there in love with the solution that you've built for the market, the risk there is start to have a closed mindset and you're just so fixated on what you've built that you don't have an open mind to evolve and kind of, yeah, iterate on what you've built to grow and evolve with the market itself. But I've found is the only truly enduring motivation is to be just completely in love with a problem you're just so fascinated by the problem and that your startup is pursuing that you just, you'll keep working at it. I talked about when Lloyd and I were chatting at the start about how passionate I am about electronic music and I just spend hours and hours on it. I'm completely fascinated by it. I can't learn enough about it, I can't spend enough time on it. It's that kind of motivation that I think gets you through all the inevitable ups and downs in the startup world as well. And there's a Japanese concept called ikigai that you may or may not have heard of. But if you find something that the is at the intersection of what you love, what you're really good at doing, what you can make some money doing, which implies is something that the world needs and you've truly found your sweet spot where you can truly do your life's work and kind of settle in for the long haul. And so I think this is just a really great aim for all of us. Again, whether we're kind of founders or even just team members within a company, if we can find work that is at the intersection of these four kind of drivers in our life, then I think it ceases to feel like work. It's just our purpose. It's just natural. This is just where we want to spend time. And so I, I really, really love this concept of Ikigan second personal practice, which is to set kind of intentional boundaries and priorities. As I mentioned before, we wear many different hats. We're not just CEOs, we're not just executives and leaders. We are potentially spouses or partners. We may be parents, we may be, we're definitely children. We all have parents, whether they're alive or not. And so there's many demands on our time. And what I have found is that work will expand to fill all available time. And if you do not intentionally carve out space for those other roles, if for instance, your marriage or significant relationship is really important to you, but you don't actually carve out time and intention and effort for it, work will just suck up all of that time. That is a hundred percent for sure. And if you look at the success rate of startups, I don't know what the actual stat is, but if you think within the whole venture model is predicated on if I make 10 investments out of a venture fund, one or two of them are going to be home runs, maybe two or three, I'll make a double or a single and the rest of the. I'll probably Lose my money, That's a pretty low success rate. And, and so for you all, as founders or leaders within companies, just recognize that, hey, this startup may or may not work out. And so at the end of it, when I look back, I have regrets about how I've spent my time. While I look back and say I put every ounce of my attention and effort and energy into this company at the cost of other things that are important to me, my primary relationship, time with family, friends, et cetera. And if so, what do I need to do now so that I don't have that regret? And I can tell you that I've lived this personally. One of the catalysts for me shutting down my investment bank and becoming a coach is I got divorced and this happens about 50% of the time. We just grew apart. But nevertheless a material event in my life. And I took the time to look back on, reflect on it and learn and figure out what I needed to learn in order to be a better human being and a better partner. And without getting into all the gory details, I think there were two big takeaways for me that informed that change. One was this notion, just this observation around work expanding to fill all available time and work life balance was just never a strength in any of my roles. Whether I was like a CFO scrambling to raise money before a company ran out of cash, a VC trying to make a first time fund a success, or by the way, investment banking. Investment banking's a super intense industry. If you've raised capital before or sold your company before, imagine doing that all the time for, I don't know, seven deals at a time. So we had offices in Toronto and San Francisco, we had clients in Europe. It was always deals on an intense stage and I was just always on. And my Air Canada status went up every year and I wasn't sustainable. And I found that even when I was home, I might have been physically home, but I was not mentally home. I was not fully present, I was checked out. I was either burnt out or stressed or thinking about the deals and planning for my next moves and the next day. And that may resonate with many of you, you may just be so consumed by trying to make a success out of your startup right now that you find you just don't have the energy and presence to give to your other roles. And I have learned myself that that's an issue. And I would say if you do decide to go all in and just commit all of yourself to your role as a startup founder, do so with intention do just own it and know, okay, I am doing this. I am intentionally setting aside these other roles that historic, historically have been important to me and may not be now. Just own it and accept it. Don't you just do it so you have no regrets and make sure that it's, it's an intentional decision. What are the things that are important to you? If you remember back when people took airplanes and there was that message before the video it plays and it talks about, hey, if you need to put on the oxygen mask, put your. Set yours on first before you put on the mask for the people you're traveling with. I think that's just a great analogy, which is you, you have to feed yourself first if you're going to truly be of service. If you're truly going to have maximum impact, you have to feed yourself first. So what are the things that feed you? Is it reading? Is it getting out in nature? Is it spending time with family? Going back to what I said earlier about work consuming all available time, if you don't intentionally make time for the things that feed you, then you'll have no time to do it because work will consume all available time. And so I would say that if you have things that feed you, do them first. And it's easy to say for me now as a coach because I'm not running a high growth startup, but even when I was running surepath and doing deals all the time, I did that. I'm a, a very passionate CrossFitter. First rule of CrossFit is to always talk about CrossFit. So great, I can check that off now I've done it. And I would go and train before I came into the office and that was just a foundational thing I found. The days where I did it, I came in, I thought I, I felt better, I thought clearer, I performed better. The days where I didn't, I didn't, I was muddier and it was just harder to think. That's just one example of things that feed you, but make really make time for that. Yeah. So let's talk about time. I hear there's like an ethos in this startup world where, hey, you know, I'll sleep when I die, or people are like bragging on Twitter about working all weekend. And I think that's a bunch of bullshit. And I don't think the solution to scaling your startup is to just keep working all the time. And I talk to many founders who work somewhere between 60 and 80 hours a week. And I would argue that our bodies and in Particular, our brains can't really handle that on an ongoing basis, and that the productivity and impact that you're having in hours 50 to 60 are less than before. And it's just like a vastly diminishing kind of rate of return. And those last hours, those 70 to 80 hours that you might be putting in a week are just garbage, useless hours. And so, you know, an hour is not an hour is not an hour. That's not actually about just putting in more hours. Now, what is the solution? Because again, easy for me to say, we'll get into some suggestions there. But just to point out, again, going back to this notion of boundaries, the solution is not necessarily putting in just ever increasing amount of hours. It's changing how you work, it's changing the scope of what you spend time on, et cetera. Third, personal practice, working on your mindset. And I'm actually going to spend a bunch of time here because it's hugely important. Perception is reality. There is no objective reality. We only experience the world through our subjective lens of perception. And do you have a glass half full mindset? Generally, do you have a glass half empty mindset that will completely color how you see the world? Two CEOs could approach the exact same situation. One of them says, oh, I have to do this. Another them says, oh, I get to do this. They're going to have completely different experiences with the exact same set of objective facts, the exact same set of circumstances. And so mindset is almost everything. And what I find is, again, because startups are never a straight line, there's always issues. But every day, no matter how hard things are, there's something to be grateful for, even it's just the opportunity to get to work on it, or the people you get to work with, or the problems that you solved that day, or the customers that signed up. There's always something to be grateful for. And gratitude is really powerful, contagious, and is something I really believe in. I'm a Buddhist, and explicit gratitude practice has been a part of my life for a long time. And according to Buddhist philosophy, the purpose of life is to be happy. That in itself is a completely separate topic. So let's park that for the moment. But for all of you, I certainly recommend carving out some time, ideally at the beginning or the end of the day or both, to explicitly acknowledge the great things that have happened in your life that day. And I've journaled for most of my adult life, many of the deals I work with feel a bit intimidated to just open up a blank page and start journaling. And so a book I've recommended to many of them is the five Minute Journal. You can find it on Amazon. As the name would suggest, it's a series of guided questions. It's meant to take you no more than five minutes, but it includes in that explicitly acknowledging the things that you're grateful for. And I highly recommend adopting that. Practice related to mindset is super important to create space in your mind. Again, as a Buddhist, I practice and meditate regularly. You don't necessarily need to do all of that, but I've included here just some apps that I've tried over time that I think are super helpful to just create some space and meditation practice to enable you to just be better at life. Create more space. We're not designed to go from meeting to meeting decision. We're not machines. And so you will actually get more productivity, have more impact on your companies by slowing down a bit and by creating space in your mind so that when you are called upon to make an important decision, you are approaching that decision with maximum clarity and maximum energy. Last thing I'll talk about is worry. Lots of things to be worried about. And Dalai Lama, no surprise, has a very wise take on this. If the thing you're worried about can be solved, then there's no need to worry. Just go ahead and solve it. And if it can't, then again there's no need to worry because you can't do a thing about it. And listen, maybe just keep that phrase in the back of your mind as you're thinking about the never ending list of things that you are maybe worried about. Practice number four it's really important to connect with your peers. By peers, I mean other founders, other CEOs. I often joke that startups are like sausages. They taste good, you just don't want to know how they're made. And the fact is, every high growth company from the newest startup to Shopify and beyond have issues. And what I have found is that technology companies exist in one of two opposite states. They are either struggling to create growth or they're struggling to keep up with growth. There's almost no, there's almost no in between. And there's no one manual. There's no one book. If there is, someone would have written it and I wouldn't have a coaching practice. And super important to get out and talk to others who are going through the same issues that you are. And the fact is, the CEO role is a super challenging role. There are very few people who get the context of that. And many of the CEOs I speak with can't necessarily share everything that they're going through with either their spouses because they don't want to worry them or even their co founders because for various reasons and so really important to have other folks to talk to. Interestingly, almost all of my CEOs are part of some sort of either formal or informal CEO peer group. And so whether that's things like pure scale here, I don't think they're across Canada, but they're certainly in Toronto or just informal networks. That's a great way to have this trusted space, meaning it's confidential. You can say what's on your mind and know that it's not going to leave the room and hear the perspective of other CEOs just super valuable. Related to this is to get support. Let's think about the stakes. I find again going back to TechCrunch, I read these headlines all the time and we're just like desensitized. Funding rounds get bigger and bigger and series A rounds today look like series B rounds a few years ago. But if you've just raised 30 million bucks, your VC is actually expecting to get a minimum of 90 million bucks in return. So the stakes are super high. And so the way I think about this CEOs of these high growth venture backed companies is they're almost like professional athletes. And if you're like LeBron James or whoever else like you have a team around you, you've got physical therapy coaches, strength coaches, nutrition coaches, sports psychology coaches, you have a whole team around you that is designed to help you achieve maximum performance. And I think it's a similar, a mindset and a similar investment that's required to get the most impact for yourself as a CEO of a venture backed company, you again, you have to grow faster than your company. You have to transform yourself many times over. I strongly encourage getting a coach, having advisors, those are two separate things. And in many cases getting seeking therapy. These are all interrelated and mutually supportive things. And, and to really recognize you're not alone. Like a thing that comes up a bunch in my conversations is imposter syndrome. A feeling like hey, I'm faking it, I don't really deserve to be here. People can see through me and see that I don't know what I'm doing. Many founders are intimidated by the notion of hiring VP or senior C level people who are truly subject matter experts in their specific domain. And the fact is, and maybe this is cold comfort, but imposter syndrome is universal. Even folks that are have achieved massive amounts of success experience it. Because by definition if you are out there doing something new and you, if you are out where you have never been before, then it's new and it's intimidating and you're always going to feel a little bit of that. But just to recognize that you can grow faster than your business and again, to recognize that everyone has experienced this at some point in their life is comforting. I find practice number six, I've touched on this a little bit, prioritizing physical health. The fact is these things, startups are not sprints, they're marathons, they take a long time and often we think of ourselves, we identify just with our brains. There's so much mental chatter going on and we just think of us as these thought and decision making and communication and machines and we forget that the brain is a really small part of our body and that most of our body is that it's a physical body and they need to be used in that proportion. So what does that mean? It means getting some form of physical exercise every day, eating real whole foods, getting a proper sleep. Kind of somewhat obsessed with sleep primarily because I'm genetically predisposed to have poor quality sleep. So whether it's. There's lots of apps on an Apple watch, if you have them. The Oura ring is something I've tried before. Sleep is a thing that can be measured and, and tracked. If you're really fascinated by this, there's a book I recommend called why we sleep and then not drinking too much alcohol. I live in the real world, don't recommend that you don't drink at all. I find my alcohol consumption has gone up during these crazy times that we live in. I'm not getting carried away with it because it really does have a negative impact on sleep and has other kind of consequences as well. But again, we are not robots. We are not kind of machines producing widgets in a factory. And because the startup journey is going to take a long time, we will only be able to thrive over the long term if we take care of ourselves physically. Last personal practice is to explicitly make time for fun. And maybe this sounds indulgent and if so, that to me just highlights even more the need to do that. When's the last time you explicitly made time to just truly have fun? I recognize in the current environment we can't get out, we can't really spend time together. So that's a thing. If you think back to the last time you did that, I'LL back you. It felt really great. I'll bet you it was energizing and just melted away stress and tension and you just felt better. And the true play, experiencing true joy. I think it's just so restorative and so essential. It is not an indulgence, it is not a luxury. It's an absolute essential. And so it's something I think has to be built into a schedule on the regular. And to the extent that you do this, I think that it is a thing that actually gives you more energy, more passion to more happiness to bring to all of your other roles. I think you will be a better CEO, a better spouse, a better parent, a better child if you are truly happy and truly energized, which making time for fun can do. For me, there's things that I've done for that. CrossFit's one of them. Music is another. Hugely passionate about music. Have been for my entire adult life. And when I settle in to make a track or do a DJ set, I just completely lose myself. I forget about everything that's on my plate and it's just so energizing. Toby again, let's go back to Toby from Shopify. Toby's built a company that did 2.9 billion in revenue last year all by. By being a really passionate gamer. And he's always made time for gaming every step of the way. And it's just. That's his thing. And, and it, I would argue that he's, it has been part of what has made him a happy, productive human being and obviously a hugely successful CEO. Let's maybe switch gears a little bit and get into some company practices. First and foremost is to get the right people on the bus. And by this, what I'm really talking about is the senior leaders that report to you directly. There's a journey that you go through from founder to CEO, where you go from succeeding through individual heroics to succeeding through your team members. And so your senior leadership, that's your leverage. And there's a huge difference between good versus great leaders. When you have great leaders, first of all, they give you more leverage, more impact. As a CEO, you can spend more time on your things and not have to worry about their functions that much. But I think more fundamentally to the scaling of the business, really great leaders are like magnets for talent. They raise the bar and then really great people want to work for and work with them. And conversely, if you settle for a good leader, an okay leader, they're less of a magnet for talent. And guess what talent is super smart and they can tell when someone's not an A level leader. And whether you realize it or not, settling for that person, you are sending a message to your entire company that good is okay, that it's okay to just have someone who's good and not to hold out for someone that's great. And in the same way that you need to grow faster than your business every year, you've seen your leadership team does as well. So I cannot overemphasize the importance of this in my coaching relationships. Once we onboard and get the current state of the union of the CEO and their business and kind of deal with any burning fires, the next thing we turn our attention to is assessing the senior leadership team and figuring out if there are any changes that are need to be made. It's literally the first thing we get to after the initial onboarding. Second is to align a second company. Practice is to really invest in aligning your leaders and your company. And there's a different difference between alignment and agreement. Agreement is we literally all agree to take the same decision. We all have the same point of view. Alignment is we have these differing points of view and we express them and there's a debate. But then at some point a call is made and we align behind that, whether we fully agree with that decision or partially agree with it or don't agree with it. And the only way to move forward with velocity is to have alignment versus holding out for agreement, because it's hard to get that all the time. And values and mission give us purpose. I think more than ever, people are looking for purpose. They're looking for meaning. I think this was true even before COVID but now with COVID and most companies being remote first talent is more portable than ever. And so I think all else being equal, they want to work for a company that has true meaning, true purpose. And so really making values and mission and vision come to life and be real for your company is hugely important. I'm going to talk about values a little bit in a second. I actually find that most, the root cause of most conflict or disagreement in a company is actually unarticulated or conflicting values. And so for most companies, values are just like these cheesy posters that we had in walls back when we went in offices and they weren't truly being lived. But I think the companies that really transform, that really scale the values are lived every day and become hugely important. This is an exercise you could do in your spare time. Here's just like a list of Values, it's not exhaustive a thing you could do where you circle what's important to you personally and maybe have your co founders do the same. And then, okay, how does that align with the values that we have set for our company and what conclusions do we draw from that? Like first of all, as a co founding team, do we have complimentary and consistent values or are our values totally different? Here's an example of maybe values and priorities. Someone may look be looking to achieve, build a market leading company, go quote unquote all the way. And to do that person wants to raise capital, another co founder may be very happy just building a small profitable business. And there it's much more about having a nice lifestyle. You can't achieve both. They're, they both want two different things from life and as a result want two different things from the companies. And explicitly articulating that and capturing that in values up front can save folks a lot of time and a lot of heartache. And values ultimately are the things we're not willing to sacrifice as individuals and as a company. They're things that are super important to us. And so I think really spending time to explicitly acknowledge them, capture them, and then live by them is really important. Related to the third company practice, and this is very much related to getting alignment on vision, mission, values, et cetera, is to just really invest in communicating. And as your company grows, your job will just more and more be a communications job. You may think it's a nuisance, it's not. It's the job, period, full stop. And when you're in hypergrowth mode and you're hiring new people every week, if people haven't heard from you in a month, then there's like a whole chunk of people who've like literally never heard from me. And so as a leader, it's super important to always be reinforcing why we're here, what matters to us, what are our values, what are our priorities so that everyone is aligned and approaching decisions in the same way that you are. And basically, if you are sick of hearing yourself saying the same things over and over again, then you may be just possibly communicating enough. Um, that's how high the bar is here. Practice four. Operating at the right altitude. Many CEOs, when they come to work with me, it's because they're just, they've reached the breaking point and they can't possibly scale anymore and they're just blowing up. And there's lots of reasons for that, but I would argue in many cases they're contributing to this. And either they are unable to let go of things that they used to do and are going back to what I was saying earlier about the importance of your senior leadership team, they don't have the right leaders in place and as a result they are having to get more involved than they should be. And Fred Wilson from Union Square Ventures many years ago articulated what I believe to be just the best definition of the role of a CEO. And I've put it here, it's really just doing three things. First is to set the overall vision and communicate that over and over again. Second is to build the best team possible. I would actually refine that further just to hiring the best senior leadership team possible, I. E. Just focusing on the people that report directly to you. Because if you do that and you hire the absolute best possible people for your stage and resources, they will be a magnet that will bring in really great people beneath them. And then the third thing a CEO does is just making sure that they never run out of cash. And an ideal world, once you're into scaling, all of your time should be in one of these three buckets. And if it is, then you truly can scale yourself as CEO, which brings up kind of scaling, decision making. Your calendar may look something like this where it's meeting to meeting. Sometimes you're double booked, there's almost no kind of break time and you're working through lunch. And of course this doesn't even count the extra shift that you put in the evening doing all the emails that you didn't get to during the day. If you are operating at that right altitude, if you're just focused on reinforcing vision, mission values, if you are focused on building retaining the strongest senior leadership team that you can and making sure you don't run out of money, your schedule shouldn't look like this. One of the big benefits of investing so much time in communicating vision, mission, values, priorities is it gives the entire company context so that they can make decisions in a way that is consistent with how you would if you were in the meeting. Meaning you don't have to be in the meeting. And so this is something that gives you maximum or just higher leverage. Often I find CEOs are like back to back in meetings. So let's take, I don't know, product review meetings. And so they're in hour long sessions. But I would argue a CEO doesn't need to be involved into that level of detail. I think if any important project the CEO, I think of a barbell analogy. The CEO should Be involved upfront to define what does success look like for this project, for this product launch, whatever it is at the end of the project to to be the ultimate kind of arbiter of did we achieve those success criteria. But in that middle, the CEO should not be involved unless it's there's exceptions or issues. So if there really are, if it's well run, you've got the right leadership team, then there's this whole messy middle where the CEO doesn't need to be involved and doesn't need to be in those big hour long mid project status updates. As an example, this is again related to operating at the right altitude, but an analogy where how much time are you spending working on the business versus working in the business? So at the beginning you're working in the business, right? You're writing code, you're selling to customers, you're taking out the garbage, you're doing everything. But over time, as the company grows, I guess you know, to use a music analogy, right, you go from playing the instrument to being the conductor. And this is the right orientation. And so really maybe just the thing to check in periodically. Like how much time am I spending working on the business versus working in and if I am spending time in looking at that and why, what is causing me to have to work in the business here? Do I have a gap in process? Do I have a gap in people? Or do I just need to change some of my habits and extract myself from that so that I can work almost exclusively on the business? Last recommended company practice is in the same way that you have a roadmap for your product, define a roadmap for yourself as leader, who do you need to become? What skills do you need to acquire so that you are as relevant a leader 12 months from now as you are today? And some of that's going to come out of if you've got a financial model and there's a certain scale that's implied in that, maybe there's certain new initiatives that are implied in that. That kind of sets the path for kind of understanding who you need to become as well as maybe talking to others, talking to peers. If you're running a 50 person company today, talking to people that run a hundred person companies and understand, hey, what happens between here and there? What did you learn? Who did you have to become? Lessons learned, scar tissue, et cetera, there's lots of different sources. We all come in all shapes and sizes. And is this notion of superpowers, maybe we have this notion of the stereotypical CEO all singing, all dancing, swashbuckling, charismatic person. And the fact is, CEOs come in all shapes and sizes. And once again I'll point to Toby as a great illustration of that. Toby was not the original CEO of Shopify. He's super introverted. But he has built a company and built a CEO role in his own image by recognizing what he is best at, which is product and technology and long term vision and not trying to become great at business development as an example, not trying to be a great public speaker. He has just doubled down on his superpowers and that's definitely an approach I recommend for folks. Hire around your weaknesses rather than investing time to fill them out. I started to try and teach myself how to code back in the day and I realized I'll never be the best developer. But back when I was operating I said I'm going to double down and become the best possible CFO that I can. So I really recommend focusing on that and really taking the time to think about who you need to become one year from now so that you are as relevant then as you are today. I think wrapping up here once again, I'll just wrap up with Toby. His mantra is how do I grow 1% better each day? This is a practice he's had for years. If you graph that over the course of a year, 200 working days, that's a 7x improvement in your performance. So very dramatic and so really powerful practice. That's it. Thank you so much. These are the various ways to reach me.

That was fantastic. Some great insights there. One of the best ones I've found is you gotta grow yourself faster in the business and make time for fun. There's a couple questions that I want to take and maybe one of them is just coaching. You're a leader in the company, but of course you're reporting up and you have a CEO. How do you coach up? Coach the CEO. So Janine says, I agree with everything you're saying, but how do you make time for yourself, for fun, for your spouse, for networking? When your boss is the CEO or the CEO demands and the expectations, how do you level set with the CEO in terms of what's doable? And this is like the whole venture capital of Silicon Valley seen as created this culture of hustle porn which is a recipe for burnout worry. Yeah. What are your thoughts there? What's your advice for Janine?

So first of all, like I say, a great talent is more portable, more employable than ever. And I talked earlier in the chat about how the meaning and purpose, purpose of the company are important, but also I would say is qualifying for fit with values and priorities. Right. So if you are, if having that personal time, if going hiking on the weekends, actually having time on boundaries between work and other things is important for you, but in the process of interviewing you feel that's not important to the leadership. And in particular, the CEO. Culture starts from the top and comes down. And it's not what people say, it's what they do. If the CEO has no boundaries and if the CEO is, I don't know, had three spouses or whatever, their life's falling apart, then expect you're going to be out of alignment and maybe look for companies who have a much better fit with your values. I really, it's basically don't compromise on values and priorities fit. Don't feel like you, if you join that company and going in that the CEO has zero work life balance. Don't expect to have work life balance. I find this sort of this, this sad reality where CEOs are just like overburdened, overwhelmed, have too much on their plate, too much responsibility, and then staff are sitting there dying for like more responsibility, give me more work. It's just tragic. And so I think part of the solution to this, even before you've built your senior leaders, is like switching gears as founders and pushing everything down. Even though you might be better at it. The best way for you to grow your team is to expose them, help get them to put the reps in. Right. You become great at something by being shitty at something and keeping going. Right. And so I did the same thing at surepath. Like, I was by far the oldest person in my company. I had the most experience. I could have easily built the most accurate models for our companies, but I'd never built a model. I got the team to put the wraps in. So I think it's as CEOs you have to recognize that begin with the end in mind and recognize that individual heroics will not scale. So the only way to scale is to invest in growing your team at all levels, not just at the level it directly reports to you from day one.

How do you ensure, like, when you add these senior leaders, they're aligned on the culture, how to identify areas of work before they actually ruin the culture. No boundaries in sending communication at any time, et cetera. Like, how do you set these things in place here?

Yeah, there's no, there's no substitute for spending meaningful time with people. Back when I was at Freshbooks, Rambiz, Dev and one of our big partners was Augusto, payroll company in the US and spent lots of time with Joshua, the CEO. And whether it was executives he was looking to hire or even VCs that he was thinking of partnering with, he would go for multi hour hikes with them. He invested really serious time to make sure that there was alignment on that dimension. And so that's a big part of it. And then going back to values. Right. If you're truly living your values, then you need to explicitly discuss them with candidates with potential senior leadership hires and have them convince you not just through their words, but through their prior actions at other companies that they live and operate in a way that is consistent with those values.

We'll close it out with the last question with Michael because Michael was the first person to welcome us. See, you're that great talent that could help a CEO. How do you vet that? The CEO is the right mindset, has the right mindset like you've described. Is there a telltale sign that this is not a sociopath CEO?

I don't know. There's usually pretty telltale signs if somebody says I all the time versus we. I did this, I built this product, I raised this money, I achieved this success. To me that's a massive red flag, I think, versus something talking about we built this product. So I think where it's all about the individual versus the team. That for me is a red flag for sure. And I think you have to really like the person. So you're going to spend, if you're on the senior leadership team and you're reporting to that CEO, you're going to spend more of your waking hours with that person than with your spouse or partner? I always talk about the Tokyo test. Would I get on a flight to Tokyo with this person and look forward to it or be like cringing and like taking, I don't know, something to like knock me out for 14 hours. That to me is a telltale test of whether I truly want to work for this person.

Yeah. Great achievements and companies are a result of many and the best leaders succeed by enabling the success of others. One last question here to close it out. We're a little over the top of the hour. If looking back on your career, what do you wish you did more of and what do you wish you did less of?

Man, awesome question. I don't know. I. It's all been a journey. I wouldn't want to be any place other than where I am now. Ironically, I bought my first book on coaching in 2002 but concluded I lack the gray hair or moral authority to really crush it as a coach. So I kept grinding for a while. But I'm super grateful for being where I am now and I'm happy. I've been on every side of the equation from an operator to a VC banker and now this. If I was just thinking about dollars and cents, I should have stayed at Shopify. I shouldn't have left to go to Real Ventures, that's for sure. But still a very happy shareholder at Shopify. And listen, I think this is my purpose. I was offered CEO roles back when I was operating and turned it down in three seconds flat because I knew how hard it was. And so being at the right hand of a CEO is the reason why I get up in the morning. So there's not much I would change. Honestly. It's been you learn from everything, even the failures. In fact, primarily the failures. Right. I've been part of Startup where we raised 10 million bucks and achieved absolutely nothing. And I learned a lot from that. Right. So it's all. It all moves you forward.

Awesome. That was fantastic. Great insights. Thanks so much Martin for joining us.

Thank you.

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