An Exact Breakdown of How One CEO Spent His First Two Years of Company-Building First Round Review⁠↗

regardless of whether you’re focused on fundraising, selling, or product, as a CEO you’re responsible for the output of the entire organization. In my current role at the company, I think of myself as an information router, so my primary job is to unblock everyone else on the team to operate at peak efficiency.

You should primarily be an information router, and you need to make communication a top priority. Block off recurring blocks of time every day to process email.

Don’t treat communications as an afterthought. It’s your main job.

If you’re too focused on your own deliverables, you’re at risk of missing the forest for the trees. A specific tactical piece of advice would be if you find that you regularly have action items and deliverables assigned to you, you should try to find a way to hand those off to other people. It either means you don’t trust your team enough to delegate projects to them or you need to hire someone with the skillset needed to execute against those deliverables.

The most substantial improvement in my ability to manage my time came from using my calendar as my to-do list (and subsequently killing my to-do list). Killing my to-do list has also had the unintended consequence of substantially reducing my personal stress and anxiety — it’s been one of my biggest mental health wins of all time.

When people ask me now, “Can you have this done by Friday?” I can easily look at my calendar and respond, “I have exactly two hours open this week, so if it’s going to take more than two hours, we’ll have to change my priorities or I won’t get it done until next week.” Having this level of clarity on my time has been a huge win.

Kill your to-do list and use your calendar as your to-do list instead. If you take one action item from this piece, it should be this one.

Your job as a CEO is to build fire departments, not put out fires. If you’re regularly putting out fires yourself, you’re doing it wrong. Focus your time on how to enable others on your team to put out fires themselves.

If it’s because you have a hard time distinguishing between urgent and non-urgent problems, I’ve found that asking myself the following question tends to clarify things: If in a year we looked back on this decision, is this the decision that killed the company?

Text messages and Slack in particular can be highly disruptive because if you don’t take the action in the message immediately upon receipt, it’ll most likely get lost in the information firehose (unlike email, which is easier to triage). I recommend using asynchronous tools like email as your primary means of communication and turn off notifications for Slack and other disruptive tools. If someone really needs to get a hold of you, they can call you. I can tell you from experience, this rarely happens in practice — most things are not actually urgent. One great tool that helps with this problem for email is Mailman, which lets you batch and set delivery times for email — meaning, I only receive email in batches twice a day (2pm and 6pm). This tool helps me stay focused and it’s cured me of the habit of compulsively checking email like it’s a slot machine.

Work that is fun, easy, or energizing feels like it takes up less time, while work that is demanding or emotionally taxing feels like it takes up more time than it actually did.

As a startup CEO, you have to be good (but not necessarily great) at everything. It’s a huge asset to the company to be able to jump in and contribute to every part of the company.

Keep in mind what content replaces: taking meetings to explain the same material over and over again, emailing people, meetings, calls, seemingly endless meetings…

Open a Google Doc and just start writing. The easiest way to overcome writer’s block is to just start writing. Oftentimes, my first drafts are a barely coherent jumble of sentence fragments. But I’ve found that if I just keep going, the thought itself almost always crystallizes into something useful.

Use content to scale your time. Unless you enjoy taking calls to repeatedly answer questions like, “What’s the TAM?”, “What are the customer personas?” and “What’s your go-to-market strategy?” you should try to solve this by writing those ideas down and sharing the written content. I guarantee it will save you time in the fundraising process — and it has the added benefit of sharing context with everyone on your team!

I think one of the reasons why this is possible is that we’re diligent about getting rid of unnecessary meetings and, as a company culture, we’re highly skeptical of recurring meetings. We constantly reassess whether a given meeting is adding value, and we change things all the time depending on who is working on what project. At many companies, there’s an expectation that you need to have 1:1s with everyone you work with and that they need to be done weekly, but that’s not the case here — my co-founder Josh and I, for example, have 1:1s at most twice a month.

Set the expectation that the cadence of meetings like 1:1s is subject to change as responsibilities change. I recommend revisiting all recurring meetings at least once per quarter. I’ve found it helpful to frame changes as an experiment to reduce the emotional cost. For example, “Let’s try changing our 1:1 cadence from once-a-week to every-other-week for a month and see if we notice any difference.”

I started tracking my time more seriously after I installed an app and, to my horror, discovered that I was spending more than three hours per day on social media and several additional hours consuming news. This was especially surprising because if you had asked me how much time I was spending on these things, I would have guessed probably 20 minutes a day. It nudged me to make some serious changes with how I spent my time.

I’ve found that by tracking my time rigorously, I’m constantly taking the pulse if I’m spending the appropriate amount of time on the areas most critical for the business.

regardless of whether you’re focused on fundraising, selling, or product, as a CEO you’re responsible for the output of the entire organization. In my current role at the company, I think of myself as an information router, so my primary job is to unblock everyone else on the team to operate at peak efficiency.  If the company is a steam engine, my job is to be the lubricant — I don’t have any real deliverables other than to make sure all the other parts are running smoothly.

Depending on the responsibilities you have within your company, there’s a good chance you’ll end up with a list that’s different from mine. My only recommendation is to limit the number of categories to no more than 10 — otherwise, things get out of hand pretty quickly.

There’s no shortcut here. The only way to learn who your customers are and deeply understand what problems you can solve for them is to hear their stories first-hand.

For example, it was in these conversations that we learned that most of our early members spent meaningful time listening to health and wellness podcasts and that they regularly use Google to search for health-related information. This is what led us to lean into podcasts — we’ve done 200 podcast appearances in the last 12 months — and content via SEO, because we knew that we would be able to reach the right kinds of customers through those channels.

Even though we’re two years in, I still do monthly calls with our members to get their first-hand experience. We call them “community calls” and it’s typically me and 6-8 members from our community for at least an hour. I listen to their experiences, their pain points, and I use it as an opportunity to float new ideas to see how they resonate with our members. Don’t underestimate how important it is to keep a pulse on how people are experiencing your product!

It’s okay to build systems that are not scalable in the early days. The goal is to learn what’s working and what’s not. Spreadsheets and Google Forms are great places to start. We didn’t have a proper database set up until a year after we started the company.

One thing that I started doing in 2020 that’s been immensely helpful is a quarterly “Think Week” with my brother Chet. For Think Week, I don’t take any meetings or calls and just spend time thinking and writing. I’ve found that taking a Think Week is a great way to force me to take a step back from the day-to-day and think more holistically about company strategy.

Having done a few of these, here are some tips on how I do them effectively: Block off time in your calendar well in advance. I often block off the entire week on my calendar 2-3 months in advance. Bring other folks with you. I have a hard time staying motivated when I try to do Think Weeks by myself. Set expectations with the people you’re doing a Think Week with and let them know that there are no set schedules and that group dinners etc., are all optional. If you’re in a flow state, don’t break out of it due to feelings of social obligation. Set an OOO reply for email, put your phone on airplane mode, use website blockers to block email, Slack, Twitter, or anything else you think might distract you. No calls, meetings, or expected communication during the week. I usually check emails each morning for <1 hour in case I need to unblock something, but then I turn it off for the rest of the day.

Many CEOs treat email like a second-class citizen and squeeze it into their time between other tasks without recognizing how much pain it causes the rest of their team. Block off time specifically for communication.

Having a strong network is a critical piece of being a startup CEO, and being good at following up and asking for the right things from the right people is a superpower. Be respectful of other people’s time, and be organized. I follow up with close to 100% of the people I talk to, and I send an email to the person who made the introduction thanking them for making the connection. Make time for follow-ups — very few people do and it makes a huge difference.

Always have a list of “asks” ready. At the end of a lot of meetings, people will ask you, “How can I be helpful?” and most of them genuinely want to help. Personally, I’m terrible at coming up with these things on the spot, so having a list of asks in my back pocket makes a huge difference. Some of the most important, serendipitous events in company history came from being prepared to answer the question, “How can I be helpful?”