Bootstrapped Giants

My Weekly Schedule

Published 2 months ago • 4 min read

A newsletter reader said, "I'm struggling to keep up with one business. How do you find the time to run multiple companies, while being a present father and keeping up with your health?"

My short answer: I have an incredibly routinized schedule.

But you subscribe for depth, so let's take a deep dive into my week in hopes that it serves as inspiration or gives you ideas for how you can spend your time.

Before we go there: WHY even have a weekly schedule?

I started doing this in 2015 after my son was born. It was clear that if I wanted to make time to be with him regularly, I would have to schedule it.

Having done this for 9 years, I wish I started scheduling properly in 2009, when my company, Ampush, was born.

Startups are so intense and so involved emotionally, intellectually, and physically. So if you don’t have some kind of system or schedule for yourself, guess what, you’ll always default to working.

So what's wrong with that?

As I tell all the Gateway X CEOs: Your to-do list will grow faster than your ability to get things done. Said differently: you CANNOT outwork building a company.

So you must prioritize your time. One simple trick to prioritizing: create a constraint. When establishing your schedule, create time to work and time not to work. It will make you more productive.

Also for context: I’m married, have an 8-year-old son, a 6-year-old daughter, and a newborn. My wife is home with the kids & we have an au pair in the house (which I highly recommend, if you have an extra room, it's <$300 a week for 45 hours of time, we used the agency Au Pair Care).

Now that you know my rationale, let's look at my weekly schedule:

I usually sleep between 11-Midnight and wake up at 7-8 am

Morning - Family time, kids activities, Gurudwara, etc

Afternoon - I exercise and spend 3+ hours working, mostly catching up on emails, prioritizing the calendar, and planning the week.

Evening - We have family dinner and I handle bedtimes, then relax with my wife and watch a show.

Morning - Personal training and get fully up to speed on reporting, emails, and priorities. Usually, leave this time unscheduled.

Afternoon - Take meetings for all of Gateway X + each company to see where things stand. Also, Adriane (CEO of GrowthAssistant) gets time.

Evening - Family dinner by 630pm and I handle bedtimes, then relax and work for 1+ hours after my wife sleeps.

Morning - I do school dropoffs and get in a little early. I have my days split across the companies at Gateway X so Tuesday AM is Carolyn’s time (CEO of UnCo)

Afternoon - Tuesday afternoon is Kasey’s time (CEO of Aux).

Evening - Tuesday is a late day for me so I usually work until 7 pm and/or grab a biz dinner. Then I play tennis at 8 pm.

Morning - I work on content creation (like writing this) and LinkedIn/X content.

Afternoon - It's Aux Time.

Evening - Home by 6, Spend some time with the kids then leave at 7 pm. Deepika (my wife) and I have a standing date night. Usually, it's a nice dinner spot followed by Target (married people understand). I might work after she sleeps. Often, I take a long 1+ hour walk alone or with a friend.

Morning - Same as tuesday.

Afternoon - Same as tuesday.

Evening - Same as tuesday.

Morning - I work on content creation.

Afternoon - Mostly networking and catching up on calls with old friends.

Evening - I try to end Fridays by 5, if not earlier, so I can hang with the kids and we always do pizza and movie night. I do bedtime.

Morning - Exercise

Afternoon - Kids activities, I will sneak in work sometimes here.

Evening - Another date night with D.

This was helpful to write out and reflect on.

A few themes worth noticing:

  1. Work -I’m guessing I’m underestimating how much time I work and the number is closer to 60 hours per week than 50.
  2. Kids/Family - Sometimes I feel guilty that I still work so much, even though I don’t have to. But I enjoy my work and get some quality time with the kids nearly every day. Combine that with a lot of weekend time and vacations and it feels right for them and me. Speaking of vacations, I’d estimate I take roughly 3-5 weeks off per year.
  3. Exercise - This has been the hardest one to nail over the years but I’ve been on this schedule for 2+ years!
  4. Friends/Social Life - We usually combine this with our date nights or kid activities e.g., birthday parties. This is an area that feels a bit light but OK for our stage of life.

As my friend Alex Lieberman noticed: it's VERY routined. The funny thing about me is I’m NOT organized at all. I show up to the airport late, I don’t carry bags with me usually, and I don’t keep a to-do list.

So in some ways, this amount of structure is insane.

On the other hand, it really works! Each member of my family has their own version of this. It gives us predictability and an opportunity to get all the things we want done.

To be clear: it's not set in stone. We will often swap days, or adjust because of travel. But even then, it's a helpful baseline to work from.

I encourage anyone reading this (even if you don't have kids/aren't married), to try and get on some weekly schedule. There are enough unpredictable things for us as entrepreneurs, don’t make your week one!!


PS - reply and tell me about your schedule or any suggestions/ideas you have for me! I’ll share the best ones back with everyone and give you credit.

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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