What Skippers does

Skippers is a private, Estonian-registered (Live Skippers International OÜ) coliving and coworking operator running a single 5000m2 property in Diani, Kenya, founded in 2023 by two former liveaboard sailors, Duncan and Camilla. The core offering is long-stay accommodation in six air-conditioned en-suite rooms (Basic at €500/4 weeks, Standard at €700/4 weeks) bundled with 8-desk air-conditioned coworking, a fully equipped gym, plunge pool, on-site Neapolitan pizzeria (ranked #1 in Diani), poke bowls, weekly meal boxes, and a community experience managed by a dedicated 'Head of Fun.' The property runs on triple-redundant infrastructure (Starlink + fibre internet, solar + generator + grid power) targeting the digital nomad segment's core pain points of connectivity reliability and workspace quality in East Africa.

The business runs a direct-to-consumer, WhatsApp-led distribution model with no OTAs or intermediaries, using a 'vibe check' to qualify guests; deposits (€150-€300) are taken online with balance on arrival, and a 10% returning-guest discount and 20% low-season discount support retention. Beyond physical hospitality, Skippers has developed three proprietary technology products — POS Forecast (F&B predictive analytics), Askari Macho (security facilities management), and Skippers Delivery (multi-location ordering with iOS/Android apps) — targeted at the broader East African hospitality market, with licensing positioned as a potential revenue stream.

The company is bootstrapped (no disclosed external funding), operates a small team of ~10 named staff plus community-management contractors, and signals intent to expand to additional Kenya and East Africa locations. Marketing is content-led (blog, Instagram, Facebook, 920+ subscriber newsletter) and word-of-mouth-driven, with a 4.6/5 Google rating across 67 reviews indicating strong community satisfaction despite the small physical footprint of 12 guests maximum.

Name

Skippers

Legal name

Live Skippers International OÜ

Website

https://teamskippers.com

Company type

Private

Founded year

2023

Operating status

Operating

Headcount range

1–10 employees

Short description

Skippers operates a coliving and coworking property in Diani, Kenya, serving digital nomads and solo travelers with long-stay rooms, coworking, meals, and community programming, while also developing hospitality technology products for the East African market.

Ownership category

akta.pro rank

Headquarters

HQ city

Tallinn

HQ country

Estonia

HQ region

Europe

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Accommodation Rental: Primary revenue from coliving room rentals. Two room types offered: Basic (€500/4 weeks) and Standard (€700/4 weeks). Short-term weekly rates available at €196-245/week. Minimum 4-week stays preferred to maintain community culture. Additional room service tiers available (Deckhand included, First Mate $14/wk, Captain $20/wk).
2. Food & Beverage: On-site restaurant serving Neapolitan pizzas (ranked #1 in Diani), poke bowls, and meal boxes. Meal boxes priced at 600 KES (~$4.68) each, targeted at ~450 calories. Communal kitchen available for self-catering. Breakfast included in room rate.
3. Coworking & Meeting Space: Air-conditioned coworking space with 8 desks, monitors, and whiteboard. Bookable meeting room available. Revenue from meeting room rentals and as amenity included in accommodation.
4. Hospitality Tech Products: Skippers develops proprietary hospitality technology products (POS Forecast, Askari Macho, Skippers Delivery) which may be licensed or offered as products to other hospitality operators in East Africa.

Pricing tiers

Go-to-market motion2 records

Distribution channels1 record

Marketing channels6 records

Core offering

Skippers operates a sustainable coliving facility in Diani, Kenya, offering long-stay air-conditioned rooms (Basic and Standard tiers), coworking workspace, meal plans, gym, plunge pool, and an on-site Neapolitan pizzeria for digital nomads, solo travelers, and small remote teams. The company also develops and sells proprietary hospitality technology products (POS Forecast, Askari Macho, and Skippers Delivery) targeted at hospitality operators in East Africa.

Product overview

Skippers operates a coliving hospitality business with two product lines: (1) Core coliving accommodation comprising Basic Rooms (~20sqm, €500/4 weeks) and Standard Rooms (~50sqm, €700/4 weeks) with coworking, gym, pool, and dining; and (2) Three hospitality technology MCPs (Multi-Channel Products) developed in-house — POS Forecast (predictive analytics for F&B), Askari Macho (security facilities management), and Skippers Delivery (multi-location ordering system with IOS/Android apps). The coliving includes on-site pizza restaurant, poke bowls, and meal boxes as food & beverage offerings.

Differentiator

Problem solved

Functional benefit

Brands

• POS Forecast: A predictive analytics dashboard aimed at helping retail and hospitality F&B better predict and track growth trends.
• Askari Macho
• Skippers Delivery

Products and services

• Skippers Coliving Accommodation Sustainable coliving facility on Kenya's coast in Diani offering air-conditioned private rooms, coworking workspace, meal plans, gym, plunge pool, restaurant, and community programming for solo travellers, digital nomads, and remote teams.
• Basic Room

Quantifiable outcome

• 4.6/5 Google rating from 67 reviews
• +2 more outcomes

Named customers1 record

Segments3 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

One partnership is on record.

• Local Academy (Kenya)minorStrategic or Co-development PartnerPartnered with a local academy for potential training facilities and student recruitment for the digital nomad scholarship program. Still in early stages with details being finalized.

Scale indicators7 records

Recent moves7 records

Expansion highlights6 records

Direct peers

• Common: Coliving operator with private rooms, shared kitchens and member community in city locations, serving professionals on month-plus leases. Direct peer on coliving mechanics; differs from Skippers on city vs beach destination.
• WiFi Tribe: Membership-based coliving community that moves groups of remote workers between destinations on rotating schedules, with strong community mechanics (Slack groups, group leaders). Highly comparable to Skippers' community-led, long-stay positioning.
• Roam: Curated coliving spaces in multiple countries offering private rooms, coworking and community for long-stay remote workers. Closely matches Skippers on long-stay format, workspace integration, and dispersed-coliving-network strategy.
• Outsite: Network of coliving houses in surf/beach/cultural destinations designed for remote workers, with shared workspaces and community programming. Directly comparable to Skippers on customer (digital nomads), product (coliving + coworking) and destination-led model.
• Selina: Global lifestyle hospitality brand operating hostels, hotels and coworking spaces in beach/tourism destinations, explicitly targeting digital nomads and solo travellers. Closest direct peer to Skippers' coliving-plus-coworking-plus-F&B proposition, only at vastly larger scale.

Broad incumbents

• WeWork: Global coworking and flexible-office incumbent serving freelancers, startups and enterprise teams. Broad incumbent comparison for the coworking leg of Skippers' offering, though at vastly larger scale and without lodging.

Emerging players

• Anternative Ælla: Early-stage coliving/coworking community with locations in Africa including East Africa, focused on sustainability and impact — overlaps Skippers on geography (East Africa), audience (nomads) and impact narrative.
• Impact Hub: Global network of impact-focused coworking and innovation spaces, several in East Africa. Comparable to Skippers' digital-impact programme and coworking leg, though without lodging and with a different member profile.
• Remote Year: Subscription program that takes cohorts of remote workers to multiple countries for month-long stays with curated housing, workspace and community. Comparable to Skippers on the remote-worker subscription/community thesis and long-stay destination model.

Regional players

• Sands at Nomad: Boutique beachfront resort located in Diani, Kenya, directly competing for the same tourist and remote-worker demand in the same micro-market as Skippers but operating a traditional hotel model.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/liveskippers
• Instagraminstagram.com/liveskippers
• LinkedInlinkedin.com/company/teamskippers

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Subsidiaries1 record

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 Skippers