What Caveday does

Caveday is a bootstrapped virtual coworking platform that runs live, human-guided focus sessions ("Caves") for individual subscribers and corporate teams worldwide. Founded in 2017 in New York City by three co-founders (Molly Sonsteng, Jake Kahana, and Jeremy Redleaf) who met at a retreat in late 2016, the company began as monthly in-person work events in NYC before pivoting to a Zoom-based virtual model in 2020 when the pandemic forced cancellation of its planned flagship brick-and-mortar Caveday Studio and the company became fully remote. The first event drew nearly 65 attendees; Fast Company later coined the team "Procrastination Nannies."

The core product is a suite of structured focus sessions (30-minute, 1-hour, and 3-hour formats) led by trained facilitators known as Cave Guides, with 20+ hours of live coverage per day, seven days a week. The technology stack is comparatively lightweight: Zoom for video, Flexbooker plus a proprietary in-house scheduling tool for reservations, a custom Member Dashboard, a Cave Squads mobile app for accountability groups, and a 24/7 Focus Lounge for on-demand body doubling. The company's IP is centered less on software and more on its published methodology (52-minute sprints, attention-residue framing, alternating work and break cycles) and its global community of over 35 trained Cave Guides. Supporting offerings include On-Demand Solo Caves, Cave Squads accountability groups, Deep Dives leadership-conversation series, The Fundamentals of Focus online course, Core Skills of Knowledge Work training, one-on-one executive coaching with co-founder Jeremy Redleaf, and a branded merchandise e-commerce store.

Caveday operates a hybrid go-to-market: a self-serve product-led motion for individual subscribers via caveday.org with a 14-day free trial, paired with a direct enterprise sales motion for corporate teams running customized training workshops. The primary revenue stream is the Starter Pass subscription at $105/quarter (approximately $35/month), with the gift card, course, coaching, merchandise, and corporate workshop lines providing complementary revenue. The company has earned coverage in major publications including NPR, CNN, The New York Times, The Guardian, BBC, Forbes, Harvard Business Review, and WIRED, and reports serving hundreds of corporate teams globally. It remains bootstrapped with no external funding disclosed.

Name

Caveday

Legal name

Caveday LLC

Website

https://caveday.org

Company type

Private

Founded year

2017

Operating status

Operating

Headcount range

1–10 employees

Short description

Caveday is a bootstrapped virtual coworking platform that runs live, human-guided focus sessions ("Caves") on Zoom for individual subscribers and corporate teams worldwide, supported by training programs, an online course, executive coaching, and branded merchandise.

Ownership category

akta.pro rank

Headquarters

HQ city

New York

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales

Revenue model

1. Subscription Membership: Monthly or quarterly recurring subscription providing unlimited access to live Caves, workshops, Focus Lounge, community forum, and planning resources
2. One-on-One Coaching: Executive coaching sessions with co-founder Jeremy Redleaf; sold as individual sessions or 5-session packs
3. Online Courses: The Fundamentals of Focus course available as a one-time purchase
4. Product Merchandise: Branded merchandise including Cave Indicator Coin, notebooks, phone pouches, apparel, candles, and posters sold via e-commerce store
5. Gift Cards: 1-month, 3-month, and 1-year unlimited membership gift cards
6. Corporate Training: Workshop programs for enterprise teams including Energy Management, Time Mastery, Flow, and Core Skills of Knowledge Work
7. Digital Downloadables: Digital products including Sprint Planner, Weekly Planning Template, Habit Tracker, and bundled MegaPack

Pricing tiers

Go-to-market motion3 records

Distribution channels4 records

Marketing channels7 records

Core offering

Caveday runs live, guided focus sessions ("caves") in which members work in synchronized work/break intervals facilitated by a trained "Cave Guide" over video. The company also sells a custom member scheduling tool, member dashboard, mobile app (Cave Squads), and structured corporate productivity workshops for teams.

Product overview

Caveday is a virtual coworking platform that operates a suite of productivity-focused products organized around its core "Caves" offering. The main product is Live Caves—structured, guided focus sessions available in 30-minute, 1-hour, and 3-hour formats running 20+ hours daily, led by trained human facilitators. These sessions alternate between deep work sprints and energizing breaks to maintain peak focus. Supporting the core Caves are the 24/7 Focus Lounge (for on-demand body doubling), On-Demand Solo Caves, Cave Squads accountability groups, Deep Dives (conversations with leaders), and workshops including Core Skills of Knowledge Work and The Fundamentals of Focus online course. The company also sells physical products (Cave Indicator Coin, Day Planning Notepad, phone pouches, candles, notebooks, apparel, posters) and offers One-on-One Coaching with co-founder Jeremy Redleaf. Corporate Teams offerings include in-person and virtual workshops for enterprise clients. The membership-based Starter Pass provides unlimited cave reservations, weekly planning workshops, and community forum access.

Differentiator

Problem solved

Functional benefit

Products and services

• Caveday Subscription

Quantifiable outcome

• Participants report getting more work done in a single session than in months
• +1 more outcomes

Named customers3 records

Segments4 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature5 records

Partnerships

Five partnerships are on record, tiered core and minor.

• ZoomcoreTechnology or IntegrationCore video platform used for all live Cave sessions; also used for internal team meetings
• StripecoreTechnology or IntegrationPayment processing for subscriptions, product purchases, and coaching services
• FreedomminorGTM or Marketing PartnerAffiliate partnership for tech blocker; Caveday recommends Freedom as a productivity tool with affiliate links
• Brain.fmminorGTM or Marketing PartnerAffiliate partnership for focus music; Caveday recommends Brain.fm with affiliate links
• NoisliminorGTM or Marketing PartnerAffiliate partnership for sound generator; discount code NOISLIXCAVEDAY for 15% off

Scale indicators8 records

Recent moves6 records

Expansion highlights6 records

Emerging players

• Forest: Pomodoro-style focus app that gamifies distraction-free work sessions. Targets the same individual productivity enthusiast that Caveday addresses with its Solo Caves and digital planning templates.
• Freedom: App and service that blocks distracting websites and apps across devices. Caveday already has a mutual affiliate relationship with Freedom, and the two are typically bundled as complementary focus tools for the same user persona.

Broad incumbents

• Headspace: Global mindfulness and mental-health platform with an enterprise B2B channel. Comparable to Caveday's enterprise motion in addressing workplace focus, energy, and burnout, though via a much wider content library.
• Calm: A scaled consumer wellness and focus/mindfulness app with a much broader content portfolio. Competes for the same 'attention and mental performance' wallet share that Caveday targets with its focus methodology.
• BetterUp: Enterprise coaching and development platform; relevant adjacent because Caveday sells 1:1 executive coaching with a co-founder and corporate workshops, putting both players in the 'coaching for knowledge workers' category.

Direct peers

• Workplaceless: Provides remote-work training and virtual coworking programs for distributed teams; overlaps with Caveday's corporate workshop motion (Core Skills of Knowledge Work) and serves enterprise buyers of focus and productivity training.
• Focusmate: Provides scheduled, 50-minute 1-on-1 virtual coworking sessions with a live accountability partner — the most direct functional substitute for Caveday's guided Caves, serving the same remote knowledge-worker and ADHD personas.
• Flow Club: Runs group body-doubling and coworking sessions on Zoom with hosts facilitating focus sprints — directly comparable to Caveday's group 'Caves' format and target use case.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights6 records

Customer concentration

• Xx.com/caveday
• Facebookfacebook.com/TheCaveDay
• LinkedInlinkedin.com/company/caveday

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Caveday