The Secret to Running a Billion-Dollar Venture Group | Roy Heldshtein, COO & CFO Team8 (Podcast 446)

Believe it or not, I don't know. If I may say so, we're not using Slack. That gives you the answer. I'm trying to keep the schedule of my people as free as possible because I know that they have their own meetings and their own tasks and their own fire drills, and I'm trying not to add more fire drills into their pot. I'm trying to do it only once a week. And when there's a, you know, an urgent thing, it happens from time to time, but that shouldn't be the regular course of business.

Today's guest is Roy Heldstein, the COO and CFO of Team8, a leading venture group with nearly $2 billion in exits and over a billion dollars in assets under management. Company is based over in Tel Aviv, Israel, an area that I'm fascinated with and have been to a couple of times. Team 8 partners with top tier investors like Microsoft, Walmart, AT&T and MasterCard to incubate and invest in early stage companies across cybersecurity, AI, fintech and digital health. As the COO and cfo, Roy oversees finance, HR operations, legal and marketing, ensuring smooth operations and strategic alignment. Before Team 8, he excelled in finance leadership roles at the tech sector and earned an MBA with high distinction from the University of Michigan's Ross School of Business. You're going to love this episode. We will see you on the inside and make sure you share this one too. You can also watch all of our second in command podcasts on our second in command podcast YouTube channel. So Roy, welcome to the second in command podcast.

Oh thank you for having me. Great to be here.

Really looking forward to this. I think you are the second or third company that I've interviewed that are based in Tel Aviv and I would love to get more. I'm completely fascinated by the region. I'm fascinated by Tel Aviv itself. I think it's one of the most beautiful and livable cities in the world. But I have been kind of enamored with the Tel Aviv tech scene for 25 years. I was living in Seattle back in 1999 and Tel Aviv was already starting to get a bit of a buzz about it. And I had been to Tel Aviv in 1991 when I was backpacking around the world. I think I was one of the only Catholic kids to end up on a kibbutz at Ian Gedi and I spent time on kibbutz and got to see Tel Aviv back then and the people banging around with the rackets out on the beach fell in love with the city. But Then I realized that you guys are a massive, massive tech hub. Why is that? Why is Tel Aviv the tech hub that it's known for today?

I think it's a great question. First of all, let me refer to how fun it is. I think Tel Aviv is one of the cities where the gap between what you think about Tel Aviv and what you feel when you come to Tel Aviv is probably one of the highest in the world. It's really a party city. It's a nice city, great food, great atmosphere, great climate. So all the things that you are looking for in a city, I think that's, that's number one. As for the texting, that's an interesting question because I would refer this not necessarily to how fun is Tel Aviv, but more to the culture of a typical Israeli. So I'm not sure, I'm sure that you probably heard or read the Startup Nation and other books about this, but there is something about the way we're being raised and born that make us more techie and more entrepreneurial in nature. That's how I see it. And we can elaborate on this, but I guess that the combination of the vividness of the city and this culture make this more of a techie city.

I think that's interesting. So it's probably more the convergence of the entrepreneurial DNA of the Israeli matched with the coming of age of the computer. You know, the computer was starting to become. The Internet was starting to open up. So you have this very, very entrepreneurial Israeli matched with the technology, and it just bloomed and blossomed from there. Is that kind of your read on it too?

It's, it's a great read. And in a way I would also connect it to the innovation that we have in the idf. So idf, which is an obligatory place that the Israeli Defense Forces, you see that when you work on something in the IDF in the years to come, it's kind of one step ahead of the industry. And then you see a lot of people that are mastering. You know, it used to be chips and then it was security software, and now we're talking about AI and in the future, maybe quantum. So you actually see the correlation between what we are working on and the industry. And this match also supports, I guess, the ecosystem.

Interesting. All right, I'm going to ask you about the brand in a second and the business that you're building, but I'm curious more about your particular COO role. One of the things that I've noticed, certainly in the fact that we've interviewed about 430 coos. Now for the second in command podcast. And then we have an organization called the COO alliance, which is a global network of CEOs. One was called Multiply Me, which is actually from Tel Aviv. Their COO was a member a few years ago. Is that only about 30 or 40% of the COOs tend to have finance report to it and you actually have the CFO rolling up into you. Do you have a finance background or is that kind of like an MBA style acumen where you learned it? Where does the finance, I guess, area fall into your sweet spot?

Yeah, so the finance falls into my sweet spot. Both based on my academic background, I had a Bachelor of Econ and finance and strategy and then MBA at the University of Michigan. But I guess the second part of it is that I based my career on the data part. So I'm coming from a data world and the data world is highly connected. It led me to take on financial worlds and from there I actually got to the CEO. So I didn't start as a CEO. I started as a CFO and as a finance guy. And I added the, you know, the capabilities of being a CEO. So I'm kind of doing it reversely.

Interesting. I love that question for you. On the, on the finance side and on the data and analytics side, do you believe that analytics the data, I used to call it mis, management information systems. Do you believe that the data side of the business should roll up through finance or should it roll up through operations?

Wow, that's. That's a great question. I really see the pros and cons to each I'm coming from. It really depends on how you define the finance role and the CEO role in each one of the organizations. The advantage of having the data sits under finance and operations is the objectiveness of the data. So you can come to a room and when the product guys and the sales guys are debating now about what's the truth. You have one source of truth. And I find, at least in my career, I found that this having one source of truth saves a lot of time because now you start talking about the real problems and about strategy and you stop the conversation about who's got it right. One of the sides, it may be more problematic.

That makes a lot of sense. I think I heard a saying years ago, I believe it was from Google and they said, you know, when they're in a meeting and somebody says I think something, they said, I don't care what you think, what's the data say? And I believe you're Right. That operations needs. It's hard because many operational CEOs don't have the acumen of the finance side of the business. But I believe that finance is better capable at overseeing the metrics and analytics side of the business. The fact that you actually can speak both removes that bridge between the two. Is that kind of right for your.

It's totally right that when you're bringing this Google story, it reminds me my Checkpoint story. I spent big chunk of my career at checkpoint, almost 13 years. And in Checkpoint, they called it Gill Shui, the founder and former CEO and many others, they called it, I'm just translating from Hebrew, they called it waving hands. So they said when someone came and said something about what they think, they said, stop waving hands. Let's talk about data. So I can totally refer to this, this concept.

I love that. What do you think has made you a good CEO? Because you're running a real business, legit. We're going to talk about it again in a second. What do you think has made you a good CEO? Is it your mba? Is it your finance background? Is it just some of the operational skills you've learned along the years?

You know, it's very hard for me to talk about myself, but I guess the easy answer to say it's a combination of all things. But I'll do give you an answer. I think that after you accumulate the academics and the experience and the knowledge about what you do, I think that the most important things, the most important thing after you have the basics is the people. So once you are able to look at the people in front of you, and I mean, you know your customers as well as your employees, as well as your colleagues, as well as your managers, if you have. That's, I guess, what makes a good CEO more than another CEO, if you will.

I would agree. I think, I think the people side is so, so critical. It's one of the reasons why I believe that, you know, the COO role is almost one of the last that could get replaced by AI is because there is some soft skill there that, I mean, currently, maybe, maybe we're out of a job in six months because AI is improving so quickly. But yeah, it feels like I would agree with you on that. Tell us about Teammate. What's the core of the business? And I'm going to talk to you about how you got into the role of COO there.

Sure. So Teammate is a very unique beast in the venture world. Teammate is now a $1.2 billion develop venture entity. And I'm Trying not to say venture capital because venture capital is only part of the deal. So Teammate is a venture creation as well as a venture capital vehicle. And venture capital is pretty straightforward. We know what it is, we make money, we invest it in things that we know and in companies that we believe in. But Teammates started as a very unique idea of venture creation. Venture creation from the concept of actually taking, looking at the world, trying to estimate and to look how the world will look like in five to 10 years and start to create Thesis in the place and in the areas that we work in. After we have Thesis now we see which products can meet these market Thesis. And once we have a good idea for a product, then we move these revalidation processes, both technological and market verifications. And only then at this point, and it's totally counterintuitive to guys who are working in the VC world only at the point that we are convinced about the thesis, about the product validity from a technological point and about the market potential only there we take, we found the right founders and we build up a company around this idea. So that's, I'm giving you a very, very brief. But that's, that's the idea behind the venture creation of Teammate.

It sounds, it sounds like you're operating almost like a hybrid of an incubator with a venture capital firm. Then would that be accurate? Are you operating as an incubator where you're taking the idea and kind of building it out and looking for the team?

I, I, I fully agree. That's, that's a very easy way to, to explain it. But if you go into the details, you'll see that it's a lot more than any, any incubator. Just to give you a glimpse of how big we are. Yeah, we are, you can, you can say a $1 billion fund, you can say if it's small or big. But 100 people working in a $1 billion fund, that's a very untypical and unorthodox thin. So we have 100 people internally intimate that are doing this venture creation process. And I haven't talked about what happens once we build a company, because once we build a company, this route isn't over yet because then you have the marketing people that helps you to tell your story. You have the business development people that help you gets the first leads for your company. And you have HR people that are bringing you the talented finance people, Eagle and Ops. So this is a very, very extensive play in the areas we work in.

What, what areas do you like? And I Was just thinking I'm going to turn to Rachel from your team later after we get off our interview and get some introductions to some of the companies that, that you, I guess, have built out on the venture creation side because we should get their CEOs, a few of the good ones, onto the podcast later too, and hear their story almost from that early embryonic stage to where they are today and how they've worked with a group like yours. Tell me about the industries that you like, the products that you like, what's the space that you are, I guess, as a company most interested in.

So first of all, great idea about the CEOs of our companies in terms of the fields that we work on. We have to remember teammates started with three people coming from the 8200 unit in the IDF. So 82 unit is the parallel to the NSA in the United States. And they brought the attacker perspective from the cyber world. And they said, we're not going to do any more attack work, but we know how attackers are thinking, so we will do the defense work. So teammate started as a cyber venture creation vehicle and the first few companies that we built were only in cyber. But the interesting thing that happened was that once we realized that we have some sort of a recipe or a machine that knows how to replicate this process that I just described, we said, why should we limit ourselves only to the cyber world? We know how to do it in the cyber world. We have, we already did it, I don't know, 5, 10, 15 times. Let's try to do it now in the fintech world. And then we built a fintech vehicle that does exactly the same. We did also the same play in data and the same play in digital health. So today we're working in these fields of cyber data, fintech and digital health. We are building companies on these fields. And from a certain point of time we also realized that since we have so many good ideas, but we're only able to build one to two companies a year, you know, building a company, it's a hard thing to do. So once we realized that we have more ideas than ability to build, we also created a regular plain vanilla, if you will, VC that actually invest in these ideas, but have the muscle that can allow them to validate the idea in a better way. So that's how these are the things that we do in general.

Super interesting on the cyber side. Is this kind of like the hacking side of the, of the industry? Is that what the cyber was or what cyber actually.

On the contrary. So this is the side that blocks hackers from entering your company. And we do it in many, many different ways and in many different verticals. So we do it on the cloud, we do it in remote places. So it depends what vector do you look at? But since we know how the hacker will address the hacking task, we believe that we have the capability to build companies who know how to defend in the best way.

I love that. So another core part of your business then is, is the finding of people. I think most venture capital firms tend to wait for the ideas to come to them. They vet all the ideas, they bet on the ones that they like and at best they might be trying to put a few of their key executives into it or board seats into it. Are you looking for these early stage leaders of businesses too? Are you, are you that kind of early stage or Definitely?

Definitely. If I think about the three things that makes us successful and just between you and I, no one, no one will listen. It's not recorded. Right. But we are so far pretty successful relative to the industry. We just, you know, when, when we summarize and we look at ourselves, we think that it happens because of three reasons. One is definitely what I just described. It's called the platform. So the teammate platform, the way we do things, et cetera, the replication, the, the machine, what we call the machine. Then you have the village, which is hundreds of professionals that surrounding us in each one of the vectors that I just described. So you know, in the cyber world These are the CISOs. In the FinTech world, these are fintech experts. Same for digital health, same for data. So we are surrounded by industry experts. I'm talking about top notch industry experts that help us to do the validation. Sometimes they help us to do the POC and even sometimes they are our initial customer, the first customers of our companies. But the third leg is the one that you mentioned. So we are enthused about finding the right entrepreneurs at any, you know, any day, any time. So, and I'm using this platform as well to say if anyone hear about, you know, here, our proposal, the way we work and they say we have a great idea or we are up to hear your ideas and your thesis and want to work together. We are open to get anyone that wants to join the, join the team.

I love that. What's your, what's your kind of process for building companies? If you were, I guess, you know, advising a group of people that maybe had an idea, they had funding, they had some people, what would you give them as the top three to five Things to do kind of foundationally, like building a home. What are the foundational things that you would have them start with or do you approach it that way?

Yeah, of course. That's exactly the way we approach it. After we have a good idea, we have a sanity check about the market and about the technology. And we have founders, the exact thing that you just described. We're going with our founders through several, we call them milestones, but we go through several milestones in this process. So the first milestone will just be a first conviction that we have something to work about. Like the idea works well, the thesis work well, etc. Then the, the second milestone will be a technological milestone where we will have our founders meeting this village, the people on the industry and our partners, which the majority of our partners are people who really build companies. So unlike other VCs, when you see most of the partners will be investors, in our case, most of the partners will be people that actually built unicorns, built companies that went through IPOs. So they know the drill of how to go through this cycle. And the first will be about technology. We will want to make sure that the product can work, the technology is valid. And don't get me wrong, when I'm saying a milestone, you probably hear two hours discussion where you come to present what you have and everyone clapping hands and telling you how great you are. Not at all. Our milestone is a bloodshed. It's like if, if you don't get out of the milestone at least 5, 10, 15 problems that are crucial and your company will not be successful if they remain. We didn't have a good milestone because that's my belief. Our belief is that when you do the fine tuning at the beginning, at the first few years, when you only have 5, 10 employees, you can change, you can revisit, you can do a turnaround. But when you do it, when you're already with 200, 300 employees and we have customers and you have obligations, then it becomes tricky. So we are trying to do the beginning. So the first one is the trip technology. The second one is product market fit. It's a PMF milestone, same drill, same bloodshed. But you're going from these two, you are ready to go and then it's becoming easier for you and we truly believe that then your chances to have a successful startup are increasingly high.

Then I guess it comes down to kind of the operational milestones and the P and L like the budgeting and cash flow stuff, right?

Great.

It's interesting the, the I, I love that Approach. I also love that we used to do that years ago, 20 odd years ago, I was part of a tech company in Seattle and we were part of nine companies that were acquired as this public company. And every quarter we would have to meet and present our plan and our numbers and our milestones to the group. And man, we, we prep for that thing and we got shredded and we all had to present the same idea. But we loved it because it raised our bar every. So we called it our bar meeting because it had to raise our bar. You know, it was a business area review. But I like that. I think A players like that, right. I think C players run away. Right. The, the average employee thinks that's a horrible environment. They hate that. But a players like give me that all day long, right? It raises their game.

I hear you. I ask you a question, Cameron. When, when you prepare for these quarterly meetings, at least that's what I'm hearing from our founders. They are telling me, you know, the preparation for this meeting was worth at least 50% of the benefit of the meeting itself.

For sure. Yeah. Especially because they gave us a format to present in that we had to review the numbers, we had to review our goals, had to review our milestones, had to review our people, we had to go in with our plan and we had to think of it from different perspectives and be there, ready and also be willing to go. Huh. Never thought of it that way. So we never took any of their critiques as against us. We just took that feedback as, as opportunities to grow. So we used to say that feedback was the breakfast of champions. Right. That we wanted that feedback every morning. And then as Jim Collins in Good to Great said, it's about confronting the brutal facts. So sometimes you need to have somebody hold up the mirror and make you look into it too. Right.

I can't agree more. As you know, as an FBA guy, it's, that's how I started. It's, it's definitely. I, I love both boats.

Talk to me about the, the internal operations at Teammate. So you're on the leadership team, you're coo, you work with the C suite, you work directly and I guess report to the CEO. How do you and the CEO interact day to day? And how do you debate them or you know, argue for the good of the company? But how do you argue and debate? I don't imagine you show up saying, okay, yeah, I'll do it your way all the time. Can you walk us through that?

Sure. So in Teammate, it's slightly different because It's a partnership. But so every time someone else wears the CEO hat in a way, because they lead a project or an initiative and then I'm acting as the CEO. But I can tell you about these interactions and also my interactions in backing Checkpoint, which, you know, I was the VP Finance. I was in many, many situations like this. I think that the CEO, in my role as a CEO and CFO needs to provide some sort of a pocket if I'm taking a turn from the football world. A pocket to the CEO. If the CEO is the quarterback, I think we need to give them the ability to take a decision with, you know, in a specific way to let them, you know, give them the time to think, give them the data and information and the recommendation of what we think is the right thing based on data, but not less important, what should they do from a legal perspective or technical perspective. So just giving some sort of a rails, if I can use that term, to the CEO to take decisions. I guess that's the best way I can describe it.

Makes a lot of sense. It's funny that you're using an American football analogy. And then I remembered that you actually went to the University of Michigan. What years were you at? What years were you at the U of m?

It was 2007 to 2009.

Okay, so maybe a little bit late, but did you ever know the name Jay Feeley, the kicker for the University of Michigan? Do you ever know that name?

I know the name, unfortunately, I was in the years of Chad Henney and others that I saw on the field.

But I think Jay was a little bit before you. Jay was a family friend of ours back when I was living in Scottsdale, Arizona. We stayed at his place up in the Upper peninsula of U of M. I was always enamored as a Canadian with the University of Michigan. What a great opportunity to go to a. What was that like? What was it like for an Israeli kid to like, go to school at one of the biggest culture football colleges in the US Mind blowing.

It was a mind blowing experience. I would lie to you if I would tell you that starting day one, I realized everything. I understood everything. I came, you know, a bit, A bit, you know, from Israel with, with some lack of cultural knowledge and some lack in other things. But the great things about the University of Michigan community is that they know how to digest people like me and how to get us realize things fast. And believe it or not, football was one of the first things that helped me to realize and understand the American culture. Just take me through one tailgate and I can tell you everything.

After Glenn tailgate, I almost, I was going to ask you about culture in a company. Do you think you picked up anything from the culture of being at the University of Michigan culture that you bring into the business culture today?

No doubt at all. Even the, even the question you asked me before about what makes a CEO better than others and me using the term of people, that's one of the greatest things that I learned about University of Michigan. It's all about group work, it's all about collaboration, it's all about being together. It's a great. So you don't see anything about one competing with the other. Of course there is some competition when you want to get your summer internship or your full time position, but it's really on the sides. I think the main thing about being a U of M guy is being a teamwork player and I love it.

Curious about MBAs for a second. This is a bit of a side question, but we're in an era right now where it feels like universities are being massively disrupted. My youngest son is finishing his fourth year of university. He decided to go and do an exchange in Singapore to get more global experience. But he's like, dad, I'm making so much money running my own business right now, it's pointless to be in university. And I told him, yeah, it kind of is, but you're almost done, you may as well get it. Do you have a bias against or for MBAs these days? Knowing that you have one, knowing that you grew up in it, do you have a bias for and against now.

It'S a very hard question to answer, but I'll tell you this in my story. I could not have sit in front of you now without going to University of Michigan. I think University of Michigan, not only from the academic perspective, like taking a young kid from Israel, talented or not, you know, people will say, but going to a top notch university opened so many opportunities for me that I can't see any other way that there would have been an open for me. At the same time, the reason I'm saying this is a very hard question to answer. The world is changing. The world is changing. So, you know, expecting what will happen in five to 10 years, it may not be necessary. Maybe someone from Israel can just apply or from any other country for, for the sake of discussion can just apply to it to work. And they will, you know, their AI will meet, you know, the other AI and they won't speak. And that will be enough to say they have enough, enough talent and potential. And we'll send you a training, an AI training to your computer. Just let's see how you are after two weeks. We'll send you an exam and then we'll be it. I don't know. It's, it's, it's a. The world. One thing that we both can agree on, the world is changing dramatically over in the past few years. Yeah.

I just had lunch today with the CEO of an AI company. I will not use their name because it's not quite public yet. It will be by the time this comes out, but just in case Sequoia knocked on their door a month ago and said, we want to invest in your company, and three weeks later is a $15 million Series A, like AI is crazy and exploding. Are you guys looking at that space? It wasn't something that came up when you said cyber and fintech and data. Is AI just going to be everywhere now?

Exactly, exactly. I think that someone who said, I'm investing in AI, it's okay, but basically it's almost redundant because, by the way, four years ago when you looked at our lpa, we said cyber, data and AI. So we talked about AI exactly as we should as a fund. We looked into the future and saw that today such a, you know, it's such a commonality.

Yeah.

Our companies, it's in our cyber companies to defend from, you know, malicious things that you can do in AI. It's in our feeder companies to know how to work with AI to make the software better. So it's, of course, in digital health. It's everywhere.

Yeah. It's Almost like in 2000 you said you were in digital marketing and now you're like, that's just marketing. Now it's just marketing.

Same exact.

What do you think has been your area of growth as a CEO? What have you focused on in growing your skill set over the years?

I think that the main thing that I try to grow on and I still have a room to go, is to take a hairy problem. And it may be hairy because it's complicated. It may be hairy because it's very urgent and there's a need to act fast and as a CEO, to formalize this problem, to make it a process and to act fast upon it. I guess the best CEOs I worked with were very, very good on this. So we act fast and in a very, very methodological way. And I'm trying to be as good as I can in this, but that's my growth area.

Interesting. What area Are you growing on today? Is there an area that you're still working at?

So other than this one? I made a big career switch about three years ago coming from the cyber world, working at Checkpoint Software and their VP of Finance, becoming the CEO and CFO for Team 8. So, you know, moving from, you know, a big public company to a, to a fund, it's a big change. So for me, the growth area now is to, you know, keep learning the language, understanding the big challenges, preparing for the future. I'll even describe it to you. When I came in, Team 8 was only, not only, but it was, but it was $500 million size of a fund. And my partners that gave me the offer told me, look, in two years we will be more than one billion dollar fund. And this is like a complicated play. We had a bunch of venture creation, venture capital and a lot of partners, a lot of employees. So it's a big company also. And you know what, we are running very, very fast. It's a great ride, but we feel that the wheels are kind of shaky. And if we keep riding that in that velocity, it will get to the 1 billion in the same place. The wheel will just fall apart. So we won't be able to keep everything, all the reports and all the people and all the processes as is. And please, if you want to join the ride, that's number one. Number two, that's your role, try to help us with this. So I guess that's a great, that's a great analogy or explanation of what they did over the past three years with my teams, of course, and with my great people work with me, is to make sure that these wheels are keeping intact, the machine or the vehicle is sliding and keep riding as it is. And I enjoy doing that. And that's probably what I'm going to do in the next three years.

My guess, and I'm going to say that I'm, I'm almost, I would put almost 100 certainty that my guess is going to be correct on this. My guess is that your answer is going to be yes. When you came in and started to put all those operational systems and processes and stuff in place, my guess is that you continued to go just as fast as you were going. You didn't try to slow it down, did you?

No, not at all. So your guess was correct. Even. Even so, the entire fight that I think a good COO will have is how to fix all the things without adding two more layers. And I'm cautious here. Too many layers of bureaucracy or things that holding. So in one way, process and rules, it's something that helps keep things together. But this is a very delicate. You can testify for yourself. I know your background, you think things like this in, in your past. But the delicate, you know, play between putting too many rules and hold the horses and putting too less of too, you know, lacking rules and having a mess, this is the play of the CEO, in my opinion.

I think it's one of the biggest plays for sure. We used to say that if you feel like you're going too fast, step on the gas. From that was from a race car driver, driver Mario Andretti. And then we also used to say that it's more important to focus on outcome over process. That we. And I'm, I'm a big systems process guy. I built franchise organizations, so we had to have systems that all of the franchisees could execute on. But if I was so worried about the minutiae, I was missing the big picture. So how do you get yourself to stay focused on that big picture versus majoring in the miners?

Wonderful question. We call it the North Star. That's how we call it in Team eight. We actually have a term for that. So our North Star is very, very clear. And I hope that if I ask any of my colleagues or managers or employees and teammates, wake them up at night and ask them, what is our North Star, they will say, what I'm going to say now. The North Star is making our companies successful. That's it. So now, talking about processes and everything, no press on the gas, but make sure, no matter if you go this way or that way, make sure that the way that you go improved the way one or many of your companies will look like tomorrow. That's the way we think about it. And now people know if they have a consideration, do I work on a lead to one of our companies or do I know, work now on something in the. As you said, the minutia on the, on the back burner, you will go and help the company 10 times before you do anything else.

Yeah, I learned this lesson the hard way. Years ago, one of our franchisees came to me and he said, you know, Cameron, you major in the minors. And I said, what do you mean? He said, well, you've been all over us that our email signatures aren't the right format for all the franchisees. He said, you're right, but you're missing the point that we have 100 franchisees who don't even have a marketing plan or a marketing calendar, a marketing budget. You're worried about something so tactical. I'm like, whoa, what like, what a massive like mindset shift for me. How do you, how do you prevent yourself from getting sucked into the day to day when you could be in on every meeting, in on every decision involved in so much? How do you know what to stay focused on in that CEO CFO role and what to not get pulled into and, you know, not let them put the monkey on your back.

Wow. I would say that I don't always know that that will be my first reaction because that's a daily, if not an hourly challenge to know how to divide and conquer. But I do few things that help me out. First of all, I keep myself with specific times in the week when I know that I can work for myself. So working either the Excel if it's relevant for the finance world or the, the Word document that I'm working on or the process that I'm kind of fleshing out. So first of all, I'm leaving, you know, a few timeslots. Second, I'm trying always to look ahead and look at my calendar and make sure that there is a healthy balance between, you know, high level things that I'm involved in and the day to day. So I'm very into the day to day because that's my role and I want to have weeklies with my people and make sure that people are happy in the office and they don't get problem. But at the same time I have to be out there. So I have to be, you know, in conventions, I have to meet, you know, industry people and I have to also, you know, be in podcasts like this one. So I'm really trying to keep it balanced.

I'm going to ask you in a second about the business life balance and how you kind of keep that work life integration. But you just said something about your weeklies with your team and I want to ask you about that directly. How, how does your weekly one on ones with your direct reports work and how is your weekly team meeting with your direct reports work? Can you walk us through kind of the overall agenda or system that you use to run each of those?

We are trying as the meeting. First of all, we're trying to keep a limited amount of meetings with a limited number of people in each one of the meetings. We're not always successful, but that's at least what we're aiming for as the meeting is wider. We're trying to have an agenda before the meeting, send to the extent possible, send materials before so people can be Educated, read them and be opinionated when they sit in the room. It's never the same when people are coming to the room and learning about the topic as we go, it's always less effective. And as meeting is becoming more towards a one on one meeting, then I'm trying not to interrupt too much between meetings to the people. I let them work. But as topics are being being accumulated, I'm just keeping them. For each one of my reports, I keep a list of things that are totally live. It's a live list. Some of them are moving from one week to another, some of them are new. And then when we meet, we know that each one of us. I always start with my managers, they start, I always go second. But they asked me all the questions, all the open items that they have for me. So they know that they have at least one hour every week that all theirs. And then they don't, you know, wait for things during the week. They're not. They know that they have this time and they keep everything. And I do the same.

That really folds into the exact format that I outlined. One of one of my books was called Meetings Suck. And I wrote a book about the reason meetings suck is we suck at running meetings. So I talked about how to run meetings, how to attend meetings, how to get people to participate, and one of the meeting styles I talked about is our one on one meetings with direct reports. And that's the way I used to do it too. I keep that running list of all the stuff to talk about. I let them go first and then I'd get to my list. I'm like, well, that was stupid. I don't need to ask you about this one. This one solved itself. Instead of messaging them all day long and every day and all week, by the time that that meeting actually happened, most of the stuff was either stupid or redundant or it solved itself and them doing the same. So do you try to kind of orbit the giant hairball of slack and get more done in Those highly effective FaceTime meetings with your team, or do you work with both?

Believe it or not, I don't know. If I may say so, we're not using Slack. So that gives you the answer. I'm trying to keep the schedule of my people as free as possible because I know that they have their own meetings and their own tasks and their own fire drills. And I'm trying not to add more fire drills into their pot. I'm trying to do it only once a week. And when there's a, you know, an urgent Thing. It happens from time to time, but that shouldn't be the regular course of business.

Yeah, I'm seeing, I'm actually seeing a shift for companies right now starting to pull away from Slack. And I'm really curious if this is a bit of a canary in the coal mine, whether companies have found that there's just too much miscellaneous all over the place. It's too much busy work and too much distraction versus working on the critical few things. Talk to me about, about business and like work life integration, work life balance. I always say it's like an elephant on a teeter totter. It can never be perfectly balanced. You kind of go back and forth a little bit. But how do you manage this stuff?

It's always a challenge, definitely for finance people and CEOs, I guess, that say no. These are very intensive roles and things are urgent and you get things that you know. When you're a product guy, you have some highs and lows, but you can plan ahead. When is the release, what you need to do? Of course there is a stretch towards the release here. It's kind of a day to day basis. But I am trying to be as flexible as I can. I think that since COVID I think life for many of us have changed. I'm actually taking this podcast right now. This is Thursday. I'm taking Thursday from home and I'm working remotely. I'm coming four days a week to work. That's how usually most of our people are coming three to four days a week to the office and working from home on the other time. So that's a big change because you save traffic in and out and it saves you three hours of magic time every week. But other than this, I think you need to be attentive to the things that are crucial to your family. And I will say this. When there's something that is crucial for my wife or for my kids, no matter what, I'll apologize, but I'll be there and I'll work hard before or maybe wake up before or maybe work after. But. But I will really try to make myself available. It's not always successful, but I'm trying to make myself available for things that are crucial and also, you know, try to keep weekends out. But that's. I don't think I'll tell. I'll say anything that you haven't thought about before.

No, but it's also for the audience, for the person listening right now. You know, I've always said that the to do list that we have does not have Our name on it. You know, your to do list doesn't say Roy's to do list. And even if you got, even if you got the whole list done, you're going to add to it tomorrow or next week anyway. That working nights and working weekends to catch up is a lie. I think you've got that.

I hear you, I hear you.

But it's hard at times too, right? Roy, I want you to go back and give the 21 or 22 year old some advice. What advice would you give the younger you that you know to be true today?

Be real, work hard. You know, it's. I know I can't give advice and don't be generic, but I have to say that because I think, you know, sometimes generic things are actually works. So I think the work hard, play hard thing is true. And invest in education. I think these are the years when you set up your foundations. I don't know. I'm trying very hard to keep learning all the time, but when I compare the amount of things I learned today versus what I learned when I was 21, 22, that was the real thing. So 21, 22. Run as much as you can. Don't look back. I know, you know, these years are, I'm always saying, you know, being 25, being 30, these are the hardest years in your life. Having, you know, young kids at home usually and trying to make sure that you, you do well at work. But the thing is that's when you have to use your, the sentence you said before, when it's getting faster, you know, push the, the paddle or you set it back on the gas, put on the gas. So that's the best thing I, I can recommend. Don't look, don't look back. Don't try out. Understand that it will be painful. Understand that it will be hard. But remember, when it's painful, that's when you are growing up. When you are, when it's not painful, you're not growing. And that's, I guess, the, the best thing I can say to them.

I love it. We've got Roy Holstein, the COO for teammate. Thanks so much for sharing with us on the Second In Command podcast. Really appreciate you.

Thank you so much, Cameron. It was a great conversation. Thank you for having me.

I'm here because of going down that software route, but I mean, software is extremely tough to get into because once you start, you can't stop or it stops. That's unfortunate. And a lot of people who want to get into it don't understand that yet. So again, me preaching that to people, it's like, be careful. If you're going down that route, it's just resist resilience.

It really.