8 min 41 sec

“Productivity Nannies” Dig Concentration Caves for Modern Workers

Fall into a hole and don’t come out until your work is complete! These three friends create daylong, distraction-free zones for the masses.
Co-Working Problems & Solutions Service Unique Ideas

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What It's About

Three friends nanny workers needing to unplug and focus.

Business Model
Skills Required
Coordination & Organization
Profit Potential

Words of Wisdom

If you’re struggling on making progress with your own side hustle, you could also make your own Caveday—or even a Cave Morning or Afternoon to work without distraction.

You don’t have to check your phone every 10 minutes. The Pomodoro method can be really helpful in forcing you to move forward on something you need to do but keep resisting. I use a version of it myself with an app called Be Focused.

Fun Fact

Jake recommends defining co-founder roles as early as possible. It doesn't help for everyone to do everything and for every decision to need everyone making it. Playing to people’s strengths is a key factor in maintaining harmonious roles...something Jake and his friends are practicing every day.

Notes from Chris

Episode 644
Have you ever been caught in the loop of checking your messages, then Facebook, then Instagram, then back to Facebook to see what you missed in the past 30 seconds? And you think to yourself… since you’re already on your phone, you might as well check another platform, too, even though you haven’t used it in months?

It’s a cycle of distraction that keeps you from doing your work efficiently and productively. And it was a problem that Jake Kahana, a freelance graphic and user experience designer from New York City and two of his friends knew a little too well.

They all had interesting projects in the works. They were working on things they were passionate and excited about, but they were also getting desperate. None of them seemed to be able to finish anything they started. It’s not because they didn’t love what they were doing—they just all seemed to be too distracted to make enough progress to get it over the finish line.

One of the friends felt like they could all be more successful at finishing something, anything if they could just shut away somewhere. A magical place without phones, notifications, apps, or someone knocking at the door with a question that had a Google-able answer. A cave, almost—just not as dark.

So, the three friends decided to make a cave for a day. They got together at 9 am, holed up in Jake’s apartment, put all of their phones in a basket by the door (so they wouldn’t be tempted), set up a series of Pomodoro timers that would serve as ‘sprints,’ and settled in.

By the end of the day, they had all made more progress on their individual projects in one day than they had in months. Pretty soon, they were doing this every weekend and adding in more friends as they showed interest.

It was when enough other people wanted to join, and they started to run out of space, that they realized that not only were they not alone in their search for increased productivity… but that there could people out there who would pay for a Caveday of their own to help them be more efficient.

Never one to shy away from unconventional ideas, Jake got to work and set up their first public Caveday for January 15, 2017. They teamed up with a local co-working space, put up some flyers, made some Facebook ads, told their friends, and hoped for the best. Within a week, they had sold out all 60 spots for their first event at a price of $40 each. This price included two meals, snacks, coffee, and a handful of work-related services like access to the space.

A few events later, Jake and his two friends had a legitimate side hustle helping people get away from their distraction-filled life to focus on what they really want to create.

Jake and his friends now bring in around $1,400 a month in profit. Although they started with an individual, pay-per-event model, they’ve since shifted into a membership model. They have chapters in New York and LA, and have also incorporated remote days that allow users to meet on Zoom (a video conferencing platform) for a three hour, “deep work” intensive on Fridays and Sundays.

They’re currently training 3 new Cave Guides in New York City so they can test outgrowing their offering in new ways. From there, assuming it works, they plan on creating a program where they can train other hosts in other cities. And then they can take over the world… but first, they’re going back in the cave.


  • Caveday: Learn more about this highly focused side hustle over on their website!
  • Zoom: The video communication platform that this trio used with their clients
  • Be Focused: If you're having trouble focusing, give this app a try—it will help you find some focus


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"We started Caveday because we realized that no one ever taught us how to actually work. We all have different and dysfunctional relationships with technology, and we needed to be trained in how to use (and not use) that technology to serve all of the projects and work we had going on. We created a side hustle to solve our own problem, and it worked!"
—Jake Kahana #SideHustleSchool

Sponsors & Gratitude


This week, Side Hustle School is brought to you by Crazy Enough to Work, a popular podcast and film series. 📈

When the rest of the world is still zigging, some companies know when it’s time to zag. Elizabeth Banks has teamed up with State Street Global Advisors to make a series of podcasts and films that uncover the bold moves mid-cap companies make to thrive and survive.

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To infinity and beyond,

Chris Guillebeau