October Pulse - The CEO Support System - Episode #69

Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned, and come away with actionable advice for our own journeys.

Hello everyone. Thank you for tuning in for today's Pulse episode. I want to focus on the subject of a CEO's support system. This is a very important subject that I don't think people talk about enough. When it comes down to it, being a CEO is lonely. You're carrying the weight of the world on your shoulders. You need to set the vision for your business, create the operating rhythm, hold your team accountable, build and inspire that team. You have to get in front of customers when something goes wrong, raise capital from investors, manage those investors expectations. You have to inspire confidence and keep everyone moving forward even when things are the most difficult and you don't even really know how you're going to make it through. Only you as CEO can really do all of these things and you don't feel like you can share with those around you. As one CEO said at a dinner that we host in my apartment, they said, I feel like I'm wearing a mask all day with my team, my investors, even my family. And the reality is that there really isn't work life balance in the early days and even in the later days, you have to make all kinds of sacrifices to make it all work. You end up neglecting all kinds of things in your life. Your relationship with your spouse, your kids, your own health, mental and physical health. It's hard to be a good friend while you're in this mindset and mode. And the sad truth is that no one really understands what you're going through and in many cases they don't care. Actually, I think a lot of people look at the CEO of their organization, of their company and they say, even, even their friends, I think look at them and say, I want to be in that position. It must be great to be the boss and make all the decisions. That person must make so much money.

If you're an early stage or you're a venture backed company, growing venture backed companies, some people think that when you announce the valuation of the company is 200 million, that that means you have $200 million in your pocket. Which of course that is not true. And I've had people who worked for me admit to me, they said, hey, when I was working for you, I felt like I could do your job, I wanted to do your job, I wanted to be the CEO. And it wasn't until they went and became CEOs themselves. They would. They actually called me back and said that was a lot harder, that is this is not a fun job.

And so all of this leads me to the CEO's support system. I don't think it's possible to go at this job completely alone. You need a group of people that's supporting you. And this is all very top of mind for me because it's come up a lot recently. I've had, I have to say, at least a dozen conversations in the last month about this topic and we had a CEO dinner, 10 person CEO dinner where the entire topic was support system. We spent three hours talking about it and it forced me to, to reflect on my support system and to reflect on what has worked not just for me, but from the other CEOs that I see and I talk to what has worked. And so I want to talk through what I see as a support system because I think there are elements that maybe you won't expect. So when I look at it and I look at the CEO support system, I. I'm going to start with this disclaimer. No one will ever understand what it is like to be you, specifically you, the CEO of your company in today's market with your investors and your team. That, that is a unique situation and there's only one of you. But you can surround yourself with a group of people that can help you be successful in that role, understand elements of that role and be that support system that you can do. I heard an analogy that I like which was someone was said it's like a professional athlete who surrounds themselves with a team of people that are serving very specific functions. They'll have a nutritionist, a masseuse, financial advisor, an agent, a coach, their training partners. They, they surround themselves with these people who again no one knows what it is like to be them, but they can help them in those various areas. So to me when I think about this, in the case of a CEO, the first group I think about is co founders.

Co founders are people who should be just as invested in the success of the company as you. If you're the founder, co founder and CEO, your co founder should be as invested they, they are someone who is making many of the same sacrifices. I'm not going to say all of the same sacrifices, but they should. They most likely are making many of the same sacrifices. Maybe it's their career, their, you know, the comp that they could get their work life balance and that person is motivated to have you be successful because they're very much tethered to you and the success of the company is tethered to you. So co founders is that first bucket. The second bucket is key. Executives every CEO should have, and the best ones do have at least one, at least one executive that is almost like a co founder in terms of how much they care about the company. Someone that I don't exactly describe it, but is secure enough in their role and confident enough to tell you the truth.

But also doesn't really scare easily and can hear the unfiltered truth from you about where your head is at and where the business is at. This is a critical. This takes a long time to find, but. But this is a critical part of this for me. This was Bart Hacking, who was our CFO at BetterCloud for a decade. And I spoke to him every day, multiple times a day. We put our offices next to each other so I could just literally walk next door and talk to him about whatever, five times a day. And having that was super critical because he had the context about the business, all the elements of the business, the investors, the team and, and it was such an important piece of the puzzle. Now, of course this is difficult because you have to know and trust that that person is going to be with you for the long term, that they're committed, all of that. The next is an executive assistant and, or a chief of staff. I've written a lot about this. But a great EA makes your day go more smoothly, gives you peace of mind, gives you time back. I think that a great ea, they start to learn you, understand you, your preferences better than even you may know yourself. They can help serve as the gate to keeper for meeting so you're not wasting time that in. In things that aren't important. They're making sure that when you're traveling, your logistics are taken care of and they know how you know what airline and what time of the day and where you like to stay. They're coordinating around your family obligations. This is a huge one to understand the entire calendar, especially of kids, of multiple kids, understanding that the dynamics, being in touch with your spouse, keeping track of your spouse's birthday and, and anniversaries. And I think the best ones even have a good pulse on what's happening at the company more broadly and can be a sounding board for you as you're thinking about messaging, as you're thinking about something you want to tell the broader company. And trust in this relationship is paramount. It is the most important thing. Maybe it's the Most important three things for me, I've written, like I said a lot about this. I had an EA for many years, Danny Hunt and, and the way that we work together was, was game changing for me and really made a massive difference. And you can keep going. When you start getting to more strategic, strategic and senior people, you start looking at chiefs of staff and people who are running your executive team meetings and people who are working on special projects and, and almost are an extension of yourself within the organization.

And then you have board members and I want to say board members, investors, the right investors and board members. And I'm going to say it again and underline that. The right investors and board members can be an important piece of your support system. Like anything else, it takes the time to build the relationship and the trust. But they can give you perspective because in many cases they're board members on multiple companies, they're investors in multiple companies. So they can give you perspective that is hard to get otherwise. And they should be, if you've got the right ones, they should be equally motivated like a co founder. They should be equally motivated for you to be successful because that makes the company successful. It's about finding that right investor, understanding that you, that that trust exists and making sure that they are someone you want to open up to, feel comfortable opening up to. But, but the right ones can be really powerful. For me, this was our executive chairman at BetterCloud. His name was John Hallett. And he wasn't only a major investor, but I had known him for many years. I had worked for him. He was my boss at one point at a previous company. And in the beginning, I mean I was speaking to him every four, you know, three, four days. I mean I was talking to him every, all the time. And probably the most influential person in my career in many ways. And then there's a different group which is the advisors. And this is important, which is these are advisors that are not board members. I think there is an important distinction when you have a board member and not a board member, what you can tell them and, and the dynamics there and how they're really working for you specifically. And so this is one that when I talk to founders and CEOs, a lot of people talk about how this advisor didn't work out. I don't think advisors are useful. I shouldn't give equity to advisors. They should give me money and they should invest in the company. And if they don't invest in the company, they shouldn't be an advisor. I, I've seen a Bunch of different structures, some that work, some that don't work. When it works, advisors are super impactful. I've had, I think across all the companies, six maybe. Yeah, six. Six official advisors. And if I'm being honest, three were pretty useless and three were, were really, really important to the company and, and helped us with our success. And my lesson there with the ones that were successful was to be first of all to speak on a regular cadence, to have some. Because everyone gets busy, busy. The advisors get busy, you get busy having a standing meeting with those people, being very specific about the project or the problem or the opportunity area where they're helping you. And I believe in doing these things one at a time. Hey, we now have this project. You have experience with this, you've helped other companies go through this, you went through this as an operator. Help me solve this problem. For example, it could be operating rhythm of the company, it could be board management, it could be a fundraise, it could be changing from a product led motion to having enterprise sales. But it's having this very specific project and goals for that advisor to work with you on and with your team on. And when you have that, it's great. We had two of the best advisors I've worked with. One was Alex Estevez who I've talked about a lot on the podcast. He really made a big difference on me. I've tried to model myself after him when I advise companies. And he was an example where he came in and, and helped us with the entire operating rhythm of the business, from planning to leadership team meetings to board management, all of those things. And that was really powerful. And then the other one was Krista Kopperman who helped us really with our customer success account management motion. And she had crazy experience at Okta and Salesforce and just amazing resume and had done it and had been in the weeds and came in and helped us with everything from comp to how we do QBRs to how we structure the team. And it wasn't just that they impacted me, but in, in those cases, they impacted the other executives they worked with at the company. They impacted the entire company and how it operated. And a little trick here is to have, when you have great advisors, leverage them to, to speak to the whole company, put them in front of the whole company, let them share their experiences. A lot of times it helps to have a third party talking about these things, talking about running the business and all that. So another topic, this is one, another group, another group that I don't really have so much Experience with IS therapists. The CEO dinner that we did on the support system therapist was a huge part of that conversation. We probably 4 out of the 10 people talked about how they had therapists and they swore by them. One person, the way it stuck with me. One person said, I spent all week with people bringing me their problems. I have to talk to these customers. I have to get on the call with the investors. I have to hold it all in when I'm really frustrated about something, but I don't want to show it. And I need 45 minutes to talk to someone, have them listen and not judge me. And the other element that we got to at that dinner that has been with me is that a lot of the challenges we face as CEOs, they push into our personal lives, like I said before, because of the sacrifices that we're making and because of the stress that this puts on ourselves and our relationships. And having a therapist who is trained and who is an expert in this and who can talk to you about that element, not the they can talk to you about what's happening at work, but they can talk to you about how that's bleeding into your personal life and can help you with that. That's a really big deal. I find. Not all. Not all, but many founders and CEOs I talk to have a lot of guilt about the sacrifices that they're making. Even if they're just making it to themselves and their own mental and physical health, they have guilt. And having someone to speak to about that who's not judging you is a big deal. And so that was, for me, that was eye opening, actually, the therapist conversation was. Was eye opening. I have not been to a therapist, but I can see and kind of wish that I had gone to one in some of those years that were the hardest at Better Cloud. The next one is an important one. Your spouse or your partner. And I think that if you do not have alignment with your spouse, if you don't have support from them, especially if you have children, then you're going to have a really hard time being your best self at work. A really hard time. And if we're being fully transparent, the, the, the reality is usually your spouse is the one who gets the short end of the stick. They're the ones that you take for granted first. They're. They're the ones filling in for the parent duty. They're the ones that have to hear you complain all the time. I had conversations with my wife over the years where I would talk about people that I wanted to let go from the company. And she would say this is the 98th time that you're telling me this and why don't you actually do something about it? And that's exhausting.

And I've Talked to some CEOs recently, a number three in the last couple of weeks, who shared with me that they, they are or are getting divorced because of their job and because of the company. And, and it's, it really could put a lot of stress. And so having that alignment and spending that time making the time with your spouse and not talking about work, like all of that is important. But, but they're in this with you and having that, that's a huge part of your support system. For me, if it wasn't for my wife, my wife Jess, I wouldn't have been able to build better cloud. I wouldn't be able to build. Not another CEO today.

Was, she was the, the pillar for me in that period and, and is again now. And this, this can extend to other family members. I know for a lot of the people I've interviewed on the podcast, their parents were entrepreneurs. In my case, that, that was, that's my father and I, he's been a big, big part of my support system and a sounding board for 20 plus years. Hasn't built technology companies, hasn't built very large companies, people wise but, but has been through all the ups and downs of entrepreneurship and, and can be that loving sounding board. And so the family side of it is important. And then there's one group that does understand or closely understands the job that you're in, and that is other CEOs. And this is an area where I wish I was more deliberate over the years. It's an area where it's almost always bidirectional. Both, both people in the relationship or all the people in the relationship of CEO to CEO or getting something out of the conversation, even if they're at different stages, even if they're in different businesses, there's something about being around other people who are going through this that is.

Therapeutic. It's important, it's special. And for me, over the course of my career, the events that I love the most were the ones where every person in the room was a founder and, or a CEO. And I can remember those events. Every single one of those. I would have at least, at least one meaningful conversation that either taught me something, gave me an idea, made me feel better that I wasn't the only one dealing with some kind of a challenge. And I met hundreds of these founders and CEOs and actually many of them were at venture capitalists that had invested in the company and was at their, their annual founder CEO summits. And in the beginning I didn't know if I should go to those. I don't have time. I'm very busy. But getting together with those people was so powerful. I just wish that I had turned those into regular conversations, ongoing conversations with those same people. And it's hard because we are all busy and we do have a lot of things pulling for our attention. But I though the CEOs that I leaned on, that I spent time with, really they helped so much. And, and the list is. Is too long to list all of them, but I've tried to feature many of them on the podcast, get them on as guests because, because it's. There's something special about that. So I.

This is a subject close to my heart. And I think it's important that people take away from this, that you have to be intentional about building your support system and that that support system is critical. It will give you more energy, it'll give you better ideas. It'll reduce your stress. Not to zero, but it will reduce your stress and it will help you be the best leader that you can for everyone around you and for your team and give you the best chance of success. And to be clear, this will cost money for some of these people. It will cost equity. It will take time. It's going to take time upfront to find these people in your support system. It's going to take time on an ongoing basis to, to work with them. But the value is is there. And that for us, Nick and myself, that's we want not another CEO to be part of your support system. This is something that I hope that the podcast, the articles on the substack and all that, that that's helping people who are going through this and who are on this journey because I. That's. That that's what I've tried to create specifically when I have the conversations on the podcast of just as if you were speaking to the guest and as if they were sharing these big challenges that they face and the things that they've overcome and how they did that so that you can get that even if you're not meeting with them one on one. And we are going to continue to push this forward. We are evolving how we are part of your support system. A big thing that happened in September is that we are now. We announced that we're now running founders club NY. It's a community it's a WhatsApp based community in New York City. We have about 400 founders in the group, and these are people who are all helping each other, answering each other's questions. We've been doing these dinners, we've been doing poker nights and happy hours and barbecues at people's houses on the weekend. And it's about bringing this group together and having them learn from each other and, and help each other. And this is the first one of these communities. We want to do more of this. We are in talks in a couple of other cities to either start or in some cases take over existing founder communities in those cities. And we feel like community is, is the next chapter of Not Another CEO. And it's this next evolution of what we're doing. And if you have ideas, if you know of communities that we should be looking at, if you are running a community that you want help administering and managing, please reach out to us. You know, this, like I said, this is such an important subject and it's something that really can change not just people's companies, but people's lives. And that's what makes us so passionate about it. So with that, I hope this was helpful. And if you ever have any thoughts, feedback, suggestions, people you think we should get on the podcast, please reach out. We'd love to hear from you. And you'll hear from me again for the next Pulse. Thank you. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast.com we'll see you next week. Weekend.