Jun 26

I got a great question from Sahil

Here is a typical day for me as the CEO of Treehouse. As many of you probably know, we work a 4-day week.

Monday - Thursday

  • 4:54 AM - Wake up. I use the ‘Crickets’ alarm on my iPhone and turn the volume down to 1.
  • 5:00 AM - Eat a cold slice of chicken or ham. Make a coffee or mix up a Goodness Greens glass. Eating right away starts my metabolism and gets my body burning calories. Goodness Greens is just more green veggies in my system, which can never be a bad thing.
  • 5:05 AM - Make a point of appreciating all that is good about my life, instead of immediately rushing into my day. I often take a deep breath and sit out on our deck for a few minutes.
  • 5:10 AM - Sit down at my iMac and open up Chrome. Three tabs auto open: Trello, Google Calendar and Team Gantt
  • 5:10 AM - 5:30 AM - Go over my todos in Trello and allocate things to my ‘This Week’ list. I wrote a detailed post about managing my todos if you’re interested (see #2).
  • 5:30 - 7:00 AM - Examine our company road map in Team Gantt. I’m a big-picture person so I need to see the overall goals, if we’re missing anything and how we’re progressing. This is a deep-thinking session. I need the quiet of the morning to completely focus on this. I believe this is one of the most important jobs of a CEO.
  • 7:00 - 7:30 AM - Bring coffee up to my wife Gill (who’s just waking up) and sit in bed and chat while the boys run around for a bit. I love this time.
  • 7:30 - 9:00 AM - Shower, eat breakfast and prep the kids for their school
  • 9:00 - 9:30 AM - Crank through todos
  • 9:30 - 11:00 AM - Hop on my bike and head to the gym. I work out for an hour and the bike ride takes 15 minutes either side.
  • 11:00 AM - 12:00 PM - Meet with Alan, our Chief Product Officer and plan out the tasks for the Product Team for the week. We also chat about Road Map and make adjustments accordingly. As the Founder and CEO of Treehouse, I really need this time to bounce ideas, fears and questions off someone. This meeting with Alan is great for this.
  • 12:00 - 12:30 PM - Lunch with Gill and the kids (I work at home)
  • 12:30 - 3:30 PM - Crank through todos or do meetings
  • 3:30 - 4:00 PM - Product meeting over Go to Meeting. These often involve UX discussions and wireframing
  • 4:00 - 6:00 PM - Finish more todos or meetings
  • 6:00 - 7:00 PM - Put the kids down to bed. Put them in the bath and then read stories. I love the stories part. We’re starting to read fun books now like Trouble for Trumpets (my favorite book of all time).
  • 7:00 - 10:00 PM - Dinner with Gill and chill-out time. We often watch TV or spend time reading books or blogging.
  • 10:00 PM - Hop in bed and try to not get sucked into reading blogs on my iPhone (I use Reeder).


Most of my work days are like this. There are slight variations on the other days based on when I work out (Mon, Tues and Thurs) or what meetings I have.

I usually meet with one of my managers on each day …

  • Monday: Product
  • Tuesday: Video and Teaching
  • Wed: HR and operations
  • Thursday: Sales and Marketing

On Thursdays we also have a meeting with the entire management team, which is around six or seven people and we do this over Go to Meeting. We each go through what our teams are working on to make sure everyone is on the same page.

We used to do a company-wide meeting on Mondays but it got unworkable over Go to Meeting, once we hit 25+ people. I think the whole company needs to hear from me more often though, so I’m thinking about sending a video update every week to the entire company so they know what’s going on in the big picture. I’ll probably just record that with Photo Booth on my iMac.

What I focus on

When Treehouse was <25 people, I actually did a lot of execution. I’d write newsletters, sketch wireframes, answer support emails, start marketing campaigns, etc.

Now that we’re about to hit 50 full-time employees, I spend all my time ‘steering the ship’. Essentially thinking about our Road Map, checking on growth, communicating our Mission, researching solutions and managing people. I’d say 80% of my time is doing meetings and talking to people now.

That’s me! Would love to hear about your schedule in the comments.

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    We used to do a company-wide meeting on Mondays but it got unworkable over Go to Meeting, once we hit 25+ people. I...
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    of… Eso suena como una rutina bastante épica, cómoda y saludable :O
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