Speleogenesis

Molly Sonsteng recently left a career in arts administration and was designing & hosting unique event series.
Jake Kahana was a creative director at an ad agency and was leading the “You’re Better Than Brunch” community.
Jeremy Redleaf was on the heels of his film directing debut, and running a monthly “mystery guest” dinner series.

We got to know each other as friends at a retreat in October 2016. Conversations kept circling around getting stuff done and spending our time well. We compared notes and realized that nobody had ever taught us how to work. We also had lots of friends in NYC who would complain about never having enough time to make progress. Over a few coffees and work sessions, we decided to do something about it.

We set a date for Sunday, January 15, 2017 as the first Caveday– a full day for getting things done among community. After countless hours of research learning how our brains work, the psychology of productivity, and science of focus, we designed a methodology full of rituals, work sprints, and energizing breaks.

The first Caveday sold out. With nearly 65 people, we packed a coworking space in NYC. People not only got more work done in a day than they had in months, but many actually made progress on projects they’d been putting off for years. They left feeling accomplished and energized.

So we planned more. The next one was in March. Fast Company came and coined us “Procrastination Nannies.” Partners began approaching us.

Caveday became a monthly event that a growing community started to look forward to.

After a stellar first year, with a building community and some press coverage, we wanted to grow.

We started designing workshops and training programs to work with corporate teams. Our schedule of Caves expanded into the work week and monthly membership was introduced.

Additionally, we made our first hires. Boyuan Gao and Jahan Mantin became our newest Cave Guides and began leading Caves in Summer 2018.

Most notably, we began experimenting with what an online Cave experience could look like. What began as a SlackBot quickly turned into Zoom sessions where we tweaked the format to make Caves work remotely. People from all over the world began joining.

This year, we were all about building towards a more complete solution to workplacelessness:

More fun than a library,
more community than a coworking space,
and more focused (and more outlets) than a Starbucks.

Moving from full 8-hour Caves towards 3.5-hour Caves, our experiences were designed to feel like our Cavedweller community was getting as much done in a half day as they would in a normal day anywhere else. We continued to hire as we expanded our schedule to offer Caves 6 days a week.

Our international members were growing as we continued to refine our remote offerings and membership.

Finally, we developed a modular corporate workshop program, designing trainings in new topics like Energy Management, Time Mastery, and Flow. Using that base of knowledge we also started writing monthly newsletters with insights, stories, and recommendations.

While we came into this year expecting to open a flagship brick-and-mortar Caveday Studio, the world had other plans for us. As everyone around the globe went into lockdown, many people were struggling to find focus at home and felt lonely.

In March 2020, we updated our schedule to facilitate every Cave remotely. We went from 8 Caves a week to 24 in a matter of weeks and began hiring internationally. Our community was growing month-to-month and we continued to listen to what people needed.

The 3.5 hour Caves quickly switched into 3-hour blocks to make scheduling simpler, and after hearing from parents and other people who needed more flexibility, we added in 1-hour Caves.

We also began to offer partnerships and collaboration with other communities.

In 2021, we continued to hire and currently have over 35 Cave Guides around the world and expanded our coverage to nearly 16 hours a day 5 days/week.

We introduced an affiliate program to reward those that spread the word about Caveday.

We refined our accountability program, Cave Squads, and built a mobile app for it.

After 15 months of running our company remotely, the Caveday co-founders had their first in-person planning meeting. We’re always refining our product.