Caveday
Business Case Study

THE PROBLEM

So many people in NYC are doing amazing work ineffiently.
They’re working alone.
They procrastinate.
They’re distracted.

THE BRIEF

How can we build a community around deep work
and make it a transformative, energizing, experience?

MY ROLE

Co-Founder, Head of Brand Experience

My cofounders, Jeremy Redleaf and Molly Sonsteng, and I wanted to build community around deep work.

Yellow flyer for Caveday event with black text, a pencil on the top left corner, listing date January 15, 2017, in NYC, and sponsors including Impact Hub, Sweetgreen, Harmless Harvest, EXO, and Runa.

We researched the science of productivity and IRL experience design to build the first ever Cave Day– a full day of deep work where we commit to our most challenging tasks, take breaks together, and celebrate our progress at the end of the day. Our first event on January 15, 2017 sold out.

Multiple smartphones placed in wooden slots, viewed from the front.

Large screen on a stand displaying a welcome message to 'CAVEDAY' with a blurred background of a laptop and indoor plants, against an exposed brick wall.

A smiling woman wearing a headlamp and a Halloween bat-shaped pin stands in an elevator, holding a small bowl with food inside, with signs on the wall behind her.

Group of people gathered in a spacious room with brick walls, standing and sitting in a semi-circle, listening to a speaker with a bald head wearing glasses and a dark shirt. There are snacks and drinks on a table at the front.

Event flyer with a hand on a white computer keyboard, and a computer mouse in the top right corner. The flyer reads '[CAVEDAY] January 15, 2017' and the website 'caveday.org' at the bottom.

Round stickers with the text 'I am outside the cave' in black and white, scattered on a glass surface.

Group of people in a room, some with hands together as if praying, some observing, with curtains in the background.

People working at desks in a modern office space with an exposed brick wall, some of them wearing headphones and working on laptops.

I designed the first round of our brand with a very simple style.

Yellow background with two gray pencils in the top left corner; text reads '[CAVEDAY] January 15, 2017' and website 'caveday.org'.

A person's hand holding a pen and writing on a piece of paper on a wooden surface, next to a cup of coffee.

Two months later, we were featured in FastCo as the future of work.
I went “into the Cave” to develop an ownable brand as we were developing an event into a full-on business.

Text outlining the mission and values of the Cave, a company focused on productivity, innovation, and redefining work in the 21st century.

A promotional collage for Caveday featuring swimming and underwater images of people in blue tones, with text about a productivity training event on July 30 and June 25.

About 9 months in, we were starting to realize that this business had potential to be bigger than just a monthly 50 person events. We started documenting our process and soon after, trained other facilitators and launched Caveday chapters in Los Angeles and DC.

Group of people standing in a circle on a green rooftop with a city skyline in the background.

Black and white photo of a busy city street in New York City with tall buildings, pedestrians, and cars. Large, stylized text overlay reads 'NEW YORK CITY' in gold letters.

We started asking our customers about their needs and pain points.

Event tickets turned into monthly membership.
Full day events evolved into half day Caves.
We updated our format to include novelty in its structure.
And added in some workshops to help people manage their time and workload.

Screenshot of a virtual meeting with 13 participants, each in their own video window, some wearing headphones, with backgrounds including bedrooms, living rooms, and offices.

Two round coasters on a wooden surface, one black with white text that reads 'I'M INSIDE THE CAVE' and one white with black text that reads 'I'M OUTSIDE THE CAVE', with a piece of paper partially visible in the background.

Black and white photo of a basketball court with palm trees and a sunset, overlaid with the text 'CAVE DAY LOS ANGELES' in yellow font.

A man giving a presentation to a diverse group of people seated around a conference table in a well-lit room with a large screen displaying a slide titled 'Two Types: Block Off Time' and other points.

It became a tool that I used to build out our corporate training program.

Announcement about new caves opening in NYC, with the hours 9:30 am to 1:00 pm.

A group of people attending a meeting or workshop in a conference room, with a presenter standing and a large screen displaying the SMART goal acronym.

We heard people across the world were interested in joining.
So we started experimenting with Remote Caves in 2018.

I also developed Caveday’s first workshop to teach people about the benefits of deep work and flow.

Over the years, we’ve worked with some amazing partners.

A collection of company and platform logos on a black background, including Facebook, Spotify, The New York Times, Pinterest, Gensler, WeWork, TED, and others.

In January 2020, we were aligned on raising money to open up the first ever work studio. Think: Soul Cycle, but for Work.

Ahead of our fundraising, I led a brand redesign.
We hired our first photographer and designer and created a more sophisticated and dark look and feel for Caveday.

Silhouettes of five people in different lighting settings, some with backlighting creating a halo effect, others with side or front lighting, all with contemplative or thoughtful expressions.

Then the pandemic hit.
We found ourselves running an IRL events business.

We pivoted the business to a virtual coworking community.
The category didn’t really exist before, so we started making up the rules.
We began with generosity: offering free workshops on how to WFH.

A promotional graphic for a webinar titled 'How To Make Remote Work, Work' scheduled for Monday, March 23 at noon EST. The background features a collage of people working remotely in various settings such as home offices and outdoor spaces.

Three people sitting inside separate soundproof booths with black walls and glass doors, working on laptops and smiling, in a modern office or collaborative workspace.

It certainly was a weird time.

Screen capture of a virtual presentation titled "How to Focus" featuring a digital illustration of a human brain with glowing neural pathways. A video thumbnail shows a smiling man named Jake Kahana speaking, surrounded by other participants in a virtual meeting.

These workshops became a perfect marketing tool for new members.
I led over 75 workshops in 2020.

Our mailing list started to grow quickly.
By the end of 2020, we had 10x’d our membership.

Poster with the title 'Values' and sections labeled Focus, Humility, Energy, Discipline, and Accountability, each with a brief description and an icon above the text.

This little side hustle was actually becoming a full-on business serving a global audience. And yet, our back end felt like it was kept together with duct tape and staples.

A collage of logos of various business and communication tools including Mailchimp, Squarespace, Zoom, Circle, FlexBooker, Slack, MemberSpace, Zapier, Sendinblue, WhatsApp, and Homebase, each with a description of its primary function like email marketing, web hosting, video conferencing, member messaging, scheduling, operations communications, membership management, automation, CRM and emails, staff communication, and staff scheduling.

Q4 2020 was spent updating, integrating, and migrating our systems.
We began getting really good with list segmentation and email marketing.
I started writing biweekly newsletters offering productivity tips and insights.

Our new systems for booking and membership management unlocked a new tool:

DATA

A dashboard showing various statistics including paid members, trial members, free members, page views, link views, saved amount, recovering funds, revenue analytics, and site navigation options.

Screenshot of a webpage from Caveday featuring podcast episodes and articles, including a photo of Tina Roth Eisenberg smiling, wearing glasses, and a striped shirt, with a background that appears indoor with warm lighting.

Screenshot of an email marketing platform dashboard showing contacts, email and SMS campaign stats, previous campaigns, and options to create new campaigns.

This, combined with segmenting, allowed us to amplify our marketing, tailor our messaging, and continue to grow our membership at a healthy rate.

Click here see more of how I led the redesign of our booking experience.

We began expanding our schedule of Caves to offer more start time for people working with us from around the world.

The image appears to be a screenshot of a dark web browser with a list of clickable links at the top, but the specific content and details of the links are obscured or blurred.

This forced us to get really good at delegating. Including our training process.
Which was helpful as we hired 30+ facilitators in 2020-2023.

Close-up black and white headshots of eight diverse people, with their names and locations written below each image.

A screenshot of a virtual meeting with 31 diverse individuals, each in their own video frame, some smiling, waving, or making gestures.

Black beanie hat with the words "MONO TASKER" embroidered on the front in white letters.

A woman in a gray sweatshirt holding a black tote bag with the words "Stay focused out there" printed in white and yellow.

A few of our facilitators we call “Cave Guides”

We wanted to increase word of mouth marketing.
Our strategy was to launch an affiliate program and create buzz-worthy merch.

Metal coasters with the words "Outside the Cave" and "Inside the Cave"

White candle in a transparent glass holder with a lit flame, featuring a minimalist label that says "focus" and "start your Cave with a ritual."

A woman with curly hair smiling while wearing a white hoodie with the word CAVEDAY printed on it, standing against a geometric gray and white background.

Young woman with long, wavy blonde hair wearing a white baseball cap with yellow text and a graphic, and a white t-shirt, standing against a light wall.

Screenshot of a weekly planning worksheet with sections for previous week and next week, including prompts for setting goals, priorities, and tasks, and a note about a free Google Doc template.

500x

our customer base

We started Caveday because we know the power of
community + deep work.

We wanted to serve people. Not spend our time writing emails.
So we’ve spent a lot of time creating

workflows and automations.

It’s not a very visual thing to show in a case study, but worth mentioning that learning to create email drips for new members, marketing automations, and cancellation winback flows has saved the company tens of thousands of dollars and weeks worth of time.

A screenshot of an email automation workflow showing steps to add contacts to a newsletter list, wait for three minutes, and send a welcome email. The interface includes options to add entry points and activate automation, with icons representing each step.

Creating automations also gave us the bandwidth to focus on creating our first in-person retreat, and first in-person event in 4 yeras.

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Silhouettes of people working on laptops in a modern conference room with large windows and ceiling lights.

Group of diverse women standing in a room with lockable storage lockers, raising their hands during a workshop or training session.

RESULTS

In 8 years, we’ve had some impressive success.
It became a bootstrapped, full-time job for my cofounders and I.
Plus, we hit some huge milestones

$80K

monthly recurring revenue

56

staff members hired and trained

An illustration of a laptop screen with a virtual meeting in progress, surrounded by colorful office supplies and confetti, celebrating with emojis like hearts and thumbs up.

75+

corporate clients

20k

newsletter subscribers

475

avg bookings per day

and got tons of press

Logos of various media outlets including Fast Company, CNN, NPR, Harvard Business Review, the New York Times, The Guardian, Bloomberg Businessweek, Forbes, and BBC.

Sunday NYT Business section feature in July 2021