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Day In the Life Of a CEO Running a $100M Company (From Home)

This is a typical day in my life as the CEO of AppSumo. I’ll go through my morning routine, how I structure my day, how my meetings go, and overall you’ll get a realistic idea of what it’s like running a 100+ team of talented people.


What Does a CEO Do? Day in the Life of a CEO

My Morning Routine as a CEO

So besides brushing my teeth, washing my face, and putting on some sunscreen (seriously guys, wear sunscreen) the first thing I do is check my Oura Ring.

These guys are awesome.

I like to check my sleep score to see how I slept that night, and based on that I’ll decide how I approach the day. If I don’t sleep so great, I’ll take it easy. But last night, I slept 7 hours, so today’s gonna be a good day.

Next is tea time. Some of my favorites are Zest Tea and the Texas Gold Tea from Texas Coffee Traders.

I think it’s nice to have a pretty tea kettle, mine’s from Fellow.

One thing you’ll notice with my morning is that everything is set up the night before. So I’ll put out my breakfast stuff so I can see it right when I get into the kitchen. Right now I’m loving Magic Spoon cereal. I also measure my cereal, so I know the exact amount of calories I’m having vs. just winging it.

I also set out my bottle of Fiji water so it’s ready to drink.

I’ve spoken about this before, but I like Fiji water because it makes me feel right. That’s why I buy it. But I don’t buy it all the time — so expensive — I usually just refill the Fiji bottle from the sink

I also put an LMNT packet out and it forces me (in a positive way) to have a good amount of water every day. Plus, Texas is hot as sh*t. So I need to drink enough water.

So when my tea’s ready, I’ll drink my tea and write on my iPad at the kitchen table.

I drink tea most days, but some days I’ll mix it up with coffee. I’m hooked on Cometeer right now (I drink their “Bold and Black” option). On Fridays I usually have a coffee and a cookie — it’s my reward for the week.

I know what you might be thinking — wow this is all so set up! It’s all so organized and planned out! But this is just weekdays. On weekends I give myself more flexibility to be relaxed.

Oh and every day, I also do push ups. I aim for 205 per day, so I’ll start that in the morning, and fit them in between meetings and other stuff throughout the day.

The one thing I think about morning routines is that I wish people could see the morning routines of the people they admire and almost be disappointed. People get really fixated on what notebook other people are using, how they’re setting up their morning, and if they meditate for 8 hours…

But really, it’s about figuring out how to engineer your own perfect day and just being intentional about it. And then realize that it’s also going to evolve over time.

Like this is not what my morning routine looked like a year ago.

A year ago, I was living in a tiny house and my morning routine was to basically just wake up and check Instagram for like 45 minutes.

Honestly, it was kinda fun then.

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How I Plan My Days

One thing I really enjoy doing is on Mondays, I’ll write down all the things I’m looking forward to for the week. It’s nice to know on a Monday all the cool stuff I have to look forward to. And if I don’t have stuff to look forward to, I know I need to plan stuff. And then on Fridays, I’ll actually compare it to see how the week actually went.

Doing this for the past few months has been a game changer. I definitely think it’s made me a better person.

One thing I do while I’m writing and planning in the morning is I don’t do anything else. So if I want to check my phone or read a book — no. Just get this done.

And I think it’s really good practice on focusing and paying attention.

After I plan, I also spend some time on my Hebrew lessons. I use Duolingo, and I also practice with a teacher a couple times per week.

My Daily Goals List

There’s a couple things I like to do/check when I’m planning every morning. I write down a list of things I need to do that day (like, Make sure to take out the trash) and I also pull up my Daily List.

It just reminds me of my values and my goals — who I am, who I want to be, and where I want to be going.

For example, in the past it’s looked something like this:

  • Work:
    • $50 million for AppSumo
    • 250,000 YouTube Subscribers
    • Finish Million Dollar Weekend Book
  • Workout:
    • Bike Across America
    • 75,000 push ups
  • Personal:
    • Complete pilot’s license
    • Go on 52 dates
    • Spend everything I make or give it away
  • Living:
    • Buy a house I love in Austin
    • Make Austin house my own
  • Travel:
    • Do 1 week of solo travel
    • Cruise with Tynan
    • Spain/LA Summer
    • Trip with parents and brother

I love seeing this almost every single day — it’s pinned at the top of my notes.

What I’d recommend for you is to make it something you see all the time. Keep your goals in eyesight. Your goals, your values, and fun things you want to do for yourself.

How I Start My Workday

So now the workday starts.

And it starts with even more planning.

Either at night or in the morning, I use my 305 index cards and my Pilot G2 pens (these are game changers) to make a list of all the different things that I really want to get done that day.

And I’ll also go through my calendar. It’s actually color coded:

  • Orange = Fun
  • Green = Workout
  • Yellow = Learning

This gives me a quick snapshot of what my day and week look like.

The way to win your week, I think, is to spend 1-2 hours on a Sunday (plus I also do this with the head of staff, Anna) going over your priorities.

For example, my priorities at AppSumo are recruiting and getting more partners on our marketplace — those are the two major things I’m helping the company with — so I want to look at my week and see how much time I’m actually spending in those zones.

Today for instance, I’m really diving into those two things. And again tomorrow and Thursday.

Today is also our leadership meeting day. Every Tuesday from 10-11, we do our leadership meeting. Before that happens, I’ll check my text messages, Instagram, and Slack.

AppSumo launched new products today. So Jared and Genevieve will talk about that in the Slack channel, so I like to check in on that.

I basically just like to do a quick dial-in with all channels before the meeting.

One thing I don’t do (besides emails — I don’t really check email too often these days) is I don’t wake up and look at our stats right away.

That’s something I used to do, especially early on, just to make sure everything was looking good. But I try to look more at the things I can control in terms of the metrics. And then also just checking in on how people are doing.

How I Structure My Workweek

So since today is Tuesday, Mondays and Tuesdays are really just one-on-one days.

The way I structure my week is Mondays and Tuesdays are one-on-ones with the people on my team, and then Wednesdays and Thursdays are about my priorities. So Wednesdays, I’m focusing a lot on recruiting right now, and then Thursdays are for alignment to the company’s strategy and the things that we’re doing at AppSumo.

Time for Meetings

So today I had three meetings:

  • Tactical team meeting
  • VP of operations
  • Therapy meeting

One thing I need to work on is giving myself a little bit more space. Today was just meeting, meeting, meeting, meeting, meeting…

Because that gets hard.

But if it was easy, I wouldn’t be here. I could just go get a day job making donuts or something. But the truth is, all the things that we really appreciate in life — or at least the things I really appreciate in life — come with some work.

Later in the day I also had a last-minute team member call, and we talked about some hard stuff

Being the CEO of AppSumo, there are hard decisions all day long.

It’s nice to have someone who’s going to call you on your sh*t but also come up with a solution for how we can move forward. Sometimes in business, it doesn’t feel linear. You go forward and you go back, but ideally it’s going in some level of curvature that is progressing nicely.

And I think part of that is, whether you’re running your business by yourself or with other people — do you have people holding you accountable and giving you feedback. Like here’s what’s going well and here’s some sh*t I didn’t see you do.

It helps when people give you feedback in real-time so you can make course corrections.

Afternoon Break

I think it’s good to take a bit of time to recharge and get re-centered and then be able to come back healthy.

Like if you’re uncertain about something, just give yourself some space. Sometimes you need to change it up.

Today, I called up my friend Nick Gray and we headed out to the water. Which was exactly what I needed.

Reflecting on My Workday

There’s a lot of room for me to grow up.

Today was interesting. I thought meetings would go differently, then I took a break, and now I’m feeling a lot more optimistic.

It’s also interesting being a CEO because I’m trying to find the balance between do I tell people exactly what I want them to do or do I listen and let people make their own decisions.

I’m still figuring out where that line is.

But I feel like the universe hooked me up today, I have my CEO coaching call in a few minutes. It feels like I need to talk to him about some of these things like our strategy for goal setting and some of the team dynamics and how I can be a better CEO.


Watch this video to find out everything I’ve learned from spending $100,000 on a business coach.


One thing I noticed that I was doing today, I was writing to people when I was tired or frustrated and that’s the moment you need to hit pause on send.

Take a quick time-out, take a step back, maybe go jump in the water, or just go for a walk.

Know when to stop.

Wrapping up the Workday

So I have my 4pm snack and then I have a few more meetings.

I’m going to revisit things with Ilona who is the VP of Operations, she helps run the day-to-day of AppSumo. We’re going to revisit some of the things we talked about, get back to being connected and grounded with her, and then finish the day strong.

End of the Day

It’s 8:39pm.

I started the day at 8am and I literally just finished.

It was back-to-back. My Mondays and Tuesdays are normally pretty intense like that.

I signed up to run AppSumo, and it’s hard work. There are days where it’s easy — we have all these amazing people and we have great customers and great partners, everyone else is making all the decisions and I get the easy stuff….

And then there’s days like today where there’s a lot of difficult conversations and a lot of mistakes that I’ve made.

But there were also some good decisions.

Thinking back on the day, we had some lack of clarity in the leadership meeting and I didn’t feel comfortable or ready to actually say, No, here’s what we’re doing. I felt like it might be rude or overstepping.

I’m still learning as a CEO where I should be saying something, and where I should let the team say something.

And today was also a good reminder for me that when I’m coming into these meetings, remember two things:

  • Be prepared for them
  • If the meeting isn’t productive, pause

Or really try to narrow down what you’re trying to solve.

I noticed for myself and others on the team, we sometimes get sidetracked with different debates and we need to recognize if it’s helping us move forward or not.

Another thing that happened is my flight instructor came over to help me study (I have a big test on Sunday) but he could tell I had a long day so he was like, Hey, do you wanna just move it? And I hadn’t even thought of that.

So that was a good reminder to move things around and rejig your calendar to what suits your priorities and what you really want to be accomplishing.

The other good decision of the day was changing up the scenery after the tough call.

Don’t just sit in your sh*t, you know?

If you’re feeling tired or low-energy or if you have something bad happen, it’s really easy to invite everyone to our pity party — but uninvite yourself. Go outside to the FUN party. Just go for a walk, go play basketball, go jump in the water, go do jumping jacks, go do push ups, whatever it is.

Moving around and changing up the scenery changes up your vibe.

And it’s amazing how that flipped a switch and shifted my day, and then I went into my other meetings a lot more productive.

So What Do CEOs Do?

There are a few things that come to mind when I think about what CEOs do on a daily basis.

Yeah, you see these CEOs that make a lot of money, and it looks like they just sit around all day, but it’s a tough job. A lot of times, the role of the CEO is to deal with the problems no one has solved yet.

It’s the unknown — which is really mentally taxing.

I’m also going to be straight though. I’m super lucky to have the people that AppSumo’s former CEO, Ayman, hired and built around the company. I’m very lucky that there’s an amazing group of people who really support me.


Check out my podcast episode with Ayman where he talks about growing AppSumo from $4M to $85M.


But when you find work that you enjoy and it’s really tough, there’s something beautiful in the process of it and the outcome of it. But I also need to be mindful of like, can I do this for 10 years if it’s like this every day?

Probably not.

My Takeaways from Today

I learn a lot from days like today.

I’ll review each meeting and figure out what my takeaway was from each one, and I’ll work on my schedule again with Anna and we’ll figure out how to adjust the meetings so they’re more effective.

My main takeaways from the overall day are:

  • Some meetings are just tough. I tried to bring positive energy to every meeting today, but as the CEO, it’s not always going to be hunky-dory
  • Everything is fixable. Even when I make a mistake, I can always correct it

I definitely wanna improve as a CEO and I like to have mentors and get feedback, but sometimes, you just have to trust yourself and the process, and just be you.


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