How Should You Spend Time As A CEO/Founder?

What's up, everyone? Welcome back to another episode of Founders Journal. I'm Alex Lieberman, co-founder and executive chairman of Morning Brew. Today, we're answering a very simple question: how should you spend your time as a CEO? And to answer that question, I brought in possibly the most qualified person in the world. Sam Korkos is the co-founder and CEO of Levels, a health tech company focused on metabolic health using continuous glucose monitors. Sam is what I like to call a hyper optimizer. He is obsessed with efficiency and he has gone to incredible lengths to spend his time well as a CEO. For 4 years straight, he has tracked his time down to the 15-minute increment, and he also leverages executive assistants as a major unlock for him to delegate things that he doesn't love doing or is not uniquely qualified to do. He talks about his process for tracking time and delegation on Tim Ferriss's podcast. And during our conversation today, we break down how he actually tracks his time, how he spends his time as a CEO, and how that has evolved since the early days of his business, and how you should think about spending your time as a co-founder or a CEO. So let's hop into it. Sam, thanks for joining the pod.

Good to be here.

So your article with First Round has become famous, infamous, popular, all of the things, because I've heard everything from like, this guy is incredible how closely he manages his time, to like, this guy may or may not be a serial killer with how closely he follows his time. I think it's fascinating because I've never seen empirically actually how time spent for CEOs evolves over the course of building their business. And I think it's wildly helpful for early-stage entrepreneurs who are trying to understand how should they be spending their time. So I'm just going to give you the floor with one simple question. How do you spend your time today and how has it evolved over time since starting Levels?

Yeah, I think it depends. It's going to depend a lot on the role as the CEO of the company and as one of the co-founders. I largely fill gaps wherever it's needed within the company. And so For the first couple years when I was working the most hours, things were the most busy, was during our seed round fundraise. Today, it's a lot of software development. I took almost a 2-year hiatus from the codebase, which in retrospect was a bit of a mistake, but I'm now fully back in it, getting ramped up. I think when you have a software product, I think having leadership who knows how to build software is really important. And the further away you get, from the actual building of what it is that your product is, the worse your product is ultimately going to be. So the last 2, 3, 4 months, I've been really back hands-on in the codebase. And so as growth is more of a priority, I focus more on growth. As we had a big recruiting cycle, I focus more of my time on recruiting. And so I think the nature of being a co-founder CEO is you have to be 80% good at basically everything. It's kind of a strange role. You have to be able to write a passable growth strategy and a passable clinical strategy. You have to be able to write a passable regulatory strategy. You have to be able to read and write legal docs and contracts. You don't have to be the best at it, but you have to be pretty good at it and you have to be able to jump in wherever it's needed. So yeah, over the last few years, it's varied quite a lot depending on the year.

And out of curiosity, my guess is a question that someone who's listening to this would have for you is like, Why do you have to be, let's say, 80% good at all these things if you just hire the right leaders? If you just hire the right leaders, then why would you need to spend your time on any of these things other than, you know, hiring the right people, go-forward strategy, and maintaining the right culture? Because clearly you've done more than those things over the last number of years. What would be your answer?

Yeah, I think it's— there's a degree to which that's true, but you Your ability to assess and know whether they are the right people, if you're willing to put that to luck, then sure, you can just hope that you hired the right person and you have no way of assessing the quality of their work output. If you can write a strategy, that's okay. If you have advisors, if you have people you can lean on and learn from, you can really only assess the quality of those people by knowing how to do it yourself. I've seen a lot of friends of mine who run software companies. I'm not going to throw any of them under the bus, but a lot of them are non-technical. and they criticize their engineering team. They're upset about product velocity, but they don't know how to write software. And so these criticisms are come— they come from a place out of frustration, probably frustration from their lack of knowledge on how this actually works. And so I think knowing how to do it is really important.

So one of the things you wrote in, in this article, which I've now read a number of times, I would say 3 full times through, which, which I feel proud of 'cause it's a very, very long article.

Yeah, it is.

You talked about some of the biggest surprises that you had when you went back and looked at 2 years' worth of data. Can you talk about a few of those surprises, things that you weren't expecting to see when you looked at the information?

Yeah, I think the biggest surprise, if I had to pick a singular one, is how there were things that I assumed took up a lot more of my time than they actually did. Specifically, recruiting was one where I felt like I had been spending a huge chunk of my time on recruiting. And it was actually a tiny, tiny fraction of my time. And I write a lot of memos. I write a lot of strategy. In fact, right after the end of this podcast, I'm going to be writing a strategy document. And I assumed this was 20%, 30% of my time, some very large number because the output is so high. But it was really, again, 5%, some small number. And so it made me realize that having these feedback loops and measuring things is super important. If you— I'll give a specific example. Recently, I was talking to a CEO friend of mine who was saying he probably spends 20% of his time on just board management. And that might be true. What is definitely true is that he feels like he's spending 20% of his time on board management, which means it is sucking the life energy out of him. And that alone is a problem. But he might be surprised to discover maybe it's 1%, maybe it's 40%, but he really doesn't know. how much of his time is being pulled into that because he doesn't measure it. So I think having an empirical record when you have a stated set of priorities, how you spend your time is the empirical record of your priorities.

Yep.

You can wave your hands and say that you have a set of priorities, but what you spend your time on is the record of your priorities. And so, it's really useful to have that reflection and feedback loop to know how you've tracked on what your stated priorities are.

I should have asked this in the beginning, but I'll ask it now. Why did you decide to start tracking things so methodically by the 15-minute? And for people who are listening that maybe want to embark on this maniacal journey like you, how does one actually go about tracking by the 15-minute over an extended period of time?

You know, it's— it started out of necessity. I was doing a lot of consulting work, software development, contracting work, and I just had to keep track of what I was spending my time on in order to build the right people. And so it came out of necessity. Just, I spent 30 minutes on this project. I spent 90 minutes on this project. And being able to retroactively go back and bill those people the correct number of hours was ultimately what started this. And then I started to realize, I started adding more and more of what I was doing to my list. And so knowing how I'm spending my time, some of these things, like I keep track of how much time I spend with my wife. And some people find it weird that I have that in my calendar, but it is a real priority for me to know that I'm spending an appropriate amount of time. And I mean that in the positive way.

Totally.

You can get a whole week and see, holy cow, I only spent 3 hours with her this week. That's really bad. I need to change my priorities. So knowing how you're spending your time and having a record of that allows you to just live the values that you have.

Yeah. I love that. And as it relates to actually putting this into action, because I love what you do in concept, but maybe this is a story that I tell myself, but it feels like a lot of work. It feels like it'll take a lot of time to track your time.

Yeah.

One, is that the case? And 2, if I wanted to start doing this, like, what is the system for tracking in the way that you do?

I think one is starting by being proactive. Which is the biggest thing to do is to get rid of your to-do list and put all of your action items on your calendar. Block off the amount of time that you think it's going to take. You have a to-do list. Everyone has a list of things that they want to do. And just translate all of that into time on your calendar. And then as the day progresses, check your calendar, see what you're supposed to be doing right now. There are a lot of failure modes with this. One, from somebody I was talking to recently is he found that when the time came to do task X, he just didn't feel like doing it. And then he would bump it to the next day and then he wouldn't feel like it and he bumped it to the next day. I think that's not a problem of the process. That's a problem of you trying to force yourself to do something that you don't want to do. This is a— you're trying to solve an upstream problem with tactics. Really, if you don't like doing a certain thing, like writing investor updates, it means that you should probably have somebody else do it because clearly, you're not a reliable person on this specific type of task. I tell my team this all the time when they ask me like, hey, Sam, we need you to do X, Y, or Z. I say, look, I can do it once, but you cannot rely on me to do this because I'm going to find this really taxing and you're probably better off finding somebody else to do it.

Totally.

So I think being proactive about it, Putting your to-do list on your calendar, also retroactively updating the amount of time that it took. That's probably the first step. I use an EA to manage the— they put all this stuff in a spreadsheet. They do all the calculations for me. A lot of the analysis happens later. They send me a weekly and a monthly report, which gives me a little bit more visibility into it. But the stuff that actually takes time, and it's probably single-digit minutes per day, Is putting things on the calendar. The first thing I do when I wake up in the morning, I open my calendar. I look at what my agenda, what my to-do list is today, which is all in the calendar. So that's, that's probably it. It really does not take that much time.

Super interesting. And so basically it's like your to-do list is in your calendar. It reminds me of, uh, I read, uh, Nir Eyal's book Indistractable, right? And he talks about time blocking and your time blocks are just in line with your values. And the issue with a to-do list is you never feel like you get to the end of it. But, you know, when you're time blocking things, you're quite literally mapping the time you have in your day to the tasks you want to do. It sounds like you basically just keep an updated record of that. And then is your EA just responsible for basically exporting your calendar and putting it into kind of like buckets, the 10 buckets that you've categorized?

Yeah.

As what you spend your time on.

That's exactly right. I try to limit it to about 10 buckets. You can always get more granular, but at a certain point, it's not useful. So figuring out what's useful in terms of the buckets of time that you want to be spending. And my, yeah, my EAs do most of the heavy lifting there. So the stuff that really does take time, which is the categorization, the analysis, if I had to do it, it probably would just not get done. It's too much effort. The ROI is not there for me to be doing it. But if you can create a process for that, it works really well.

Totally. So when I look at your analysis, right, I'll just read out for everyone kind of what the buckets are that you've put things into. It's engineering, sales and marketing, operations, strategy, investor relations, recruiting team, information processing, and network. And now I'm looking— and again, this isn't updated. You sent me an updated one yesterday. I didn't have a chance to really dive in, but at least from 2019 to midway through 2021, when I look at the distribution of time, obviously things vacillate, but by and large, the 2 biggest buckets look to be network and then information processing. Can you talk about what those actually mean in practice, like what you're actually doing in those buckets and why they're worthy of that much time?

Yeah, network is a tricky one because it's, it's in many ways a catch-all for interpersonal engagements that don't have a specific agenda. So like I met with a founder this morning and we were just talking about industry stuff. I might be able to connect him with a couple other people who are looking for their next roles, but there's no specific agenda there. A lot of those, if I was to retroactively update this, which would just be way too much effort, But if I was to retroactively do this, it might turn out 20% of those are actually recruiting in retrospect because they ended up joining, or 15% ended up being investor relations because in retrospect, I now know that that person became a Levels investor. And so it's sort of an ambiguous bucket of no real intent.

Yeah, it basically sounds like the things that don't have an obvious immediate result. They could down the line, but you just don't keep track of those things down the line.

That's right. They're interpersonal interactions that don't have an immediate deliverable. I've just realized over the course of my life that so many of the best things that have happened to me in both life and in work just came from being in touch with more people and just being real with people. Yep.

And then information processing. Can you talk about that? Yeah.

So that's the sort of catch-all for internal comms, company communication, email processing as well. It's text message processing is part of information. Any sort of information that I need to process around async communication, I bucket into that. So again, I could get really granular and figure out what percentage of that time that was spent. is actually on investor relations or on other things. But yeah, it's a lot of— yeah, it's on a whole bunch of different categories.

Yeah. But I think what's interesting, at least around that bucket, is I feel like a lot of it is related to unblocking. And one of the things that you talk about as you look at your time is you say that unblocking is a top priority. Can you talk about what that actually means and why it's so important for you to be the one to unblock?

Yeah. The CEO ultimately is the final decision maker on anything that needs to be done at the company. And so having the flattest structure possible while still being able to manage effectively. I was asked recently if I could have dinner with anyone in the world and learn something from them, I would pick the CEO of Nvidia because he has a very interesting management structure. He has something like 40 direct reports.

Wow.

Which is crazy, but he does it in such a way that it's not super burdensome. And the intent behind it, from what I understand, is that the closer you get to the ultimate decision maker, the faster decisions get made. The fewer committees that you have to form, the faster your company will go. And so figuring out how he managed to build that type of structure, I find very interesting. So whenever there's a tie, whenever things need to be collaboratively escalated, when there's a misunderstanding or disagreement, the faster that gets to a decision point, the better. And the CEO is always the tiebreaker in any discussion. If the CEO says we're going left, then we go left and there's no further discussion. So that's really the underlying intent there.

Love it. One last question for you is what your mental model is for how to prioritize your time and what you should spend time on moving forward, because all of this is backward looking. And it's interesting because I think even in how you presented the way in which you spend your time in the beginning, you talk about it, how it's basically vacillated on the most important thing, from fundraising to recruiting to, you know, actually building software. And I think that may actually feel different from how a lot of entrepreneurs, maybe when they read an article online or they talk to other founders, the way they hear it, which is generally like, Early days, you're focused on building the product and getting the product to product-market fit. And then later days, it's company building, which is like hiring leaders, managing leaders, setting long-term goals. And that's kind of what you do. So how— what is— what is your model by which you decide, say, for the next 3 to 6 months, how you are going to bucket your time?

It's a matter of whatever is the top company priority. And so right now, most of our major priorities are ultimately within the software org. On changing our go-to-market, shifting our core product strategy. And so a lot more of my time is going towards that. Recruiting is a much lower priority right now. We're probably not going to be doing another round of hiring for several more months. So that's just low priority. Fundraising is probably still 6 months away from that being a real push. So I don't need to prioritize that. Uh, some amount of my time always goes towards fundraising and keeping those relationships warm. You'll see in the chart, there's always some amount of time on investor relations, but those come in waves. I think the challenge with these fundraise conversations is that you want everyone to have all the context and you have to make a decision within a very constrained period of time. So it really is a sprint to set clear expectations because As soon as somebody gives you a term sheet, they usually give you some deadline. They don't want you to shop around and wait for 3 months to see if you can get a better deal. They want you to make a decision quickly. And so the more people that you have in the loop, the better it will be for the company. So I think one of the things that I do tactically that I have found incredibly helpful on time is I I block off one week per quarter. I just directly stole this from Bill Gates to do a think week where I don't engage in email, I don't engage in comms. I just focus on thinking about strategy. And it often takes me 2 or 3 days to see the forest and not just the trees, to zoom out, to think more holistically about where we're going as a company. I often end up pushing them because of priorities that come up and I always regret it. And every time I do it, I think I need to do more of these, maybe monthly, because you always end up with the best ideas when you have that separation. So when I finish writing one of these strategy documents, I'll think through what are the major priorities and then how can I positively impact those?

Love it. an absolute masterclass in just how to think about spending your time as a CEO. And also, from my vantage point, how to be in control of your time versus having your, your time or people who are on your calendar controlling your time. So, Sam, really appreciate you joining the conversation. I hope you enjoyed this episode of Founders Journal. If you like this new format where I curate world-class entrepreneurs and investors to answer the most important questions for early-stage entrepreneurs, Shoot me an email to alex@morningbrew.com to suggest a future question or challenge you want answered, or a specific expert that you would love to see come on the pod. As always, thank you for listening and I'll catch you next episode.