What Chaos Software does

Chaos Software Group, Inc. is a privately held, bootstrapped software publisher founded in 1992 and headquartered in Plano, Texas, that develops Windows-based customer relationship management (CRM) and personal information management (PIM) applications targeted at micro/small businesses and individual users. The product portfolio centers on three desktop applications: Time & Chaos (contact and calendar manager priced at $49.95 per user), Chaos Intellect (full CRM with an integrated email client and auto-linked email history per contact, priced at $59.95 per user), and Legal Billing (time, expense, and UTBMS-coded billing software for attorneys, priced at $49.95 per user). The core architecture is local-first: data resides on the user's own Windows computer with no cloud required, and shared databases on a local area network can be used by multiple simultaneous users without dedicated server hardware or software. Optional extensions add cloud or device-to-device synchronization: ChaosHost.com provides cross-device sync over Chaos-operated servers ($9.95/month flat for an entire team), while Chaos DesktopSync offers direct Wi-Fi/local-network sync for users unwilling to use any third-party cloud. Native mobile companion apps (Chaos Contacts, Calendar, Tasks, and Billing on Android; ChaosTasks and ChaosBilling on iOS) extend the database to smartphones. Add-on utilities integrate with Microsoft Outlook, Google Contacts/Calendar, Microsoft Phone Link, OAuth-authenticated Gmail and Microsoft 365 accounts, CompanionLink, Docs2Manage, and TAPI-based dialers.

The company sells exclusively through its own secure online e-commerce store with immediate electronic license delivery, supported by a 21-day fully-functional free trial on all products, a free Chaos University video training platform, a knowledge base, and a low-volume product-news mailing list. Pricing is one-time perpetual licensing per user (not per computer), with two years of upgrade protection included; recurring revenue is limited to the optional ChaosHost.com subscription. Customer testimonials reference micro-businesses and solo professionals across legal, accounting, real estate, healthcare, coaching, and training services, with no disclosed enterprise or anchor accounts. The business operates with 1–10 employees, has never raised external funding, and was rebranded from iSBiSTER International, Inc. in July 2003 under the same founders (Bill and Dave), who continue to lead ongoing product development — most recently Chaos Intellect 10.7 in January 2026.

Name

Chaos Software

Legal name

Chaos Software Group, Inc.

Website

https://chaossoftware.com

Company type

Private

Founded year

1992

Operating status

Operating

Headcount range

1–10 employees

Short description

Chaos Software develops Windows-based CRM and personal information management applications for micro/small businesses and individual users. It sells perpetual-license desktop software including Time & Chaos, Chaos Intellect, and Legal Billing, with optional ChaosHost.com cloud sync subscriptions.

Ownership category

akta.pro rank

Product category

Contact Management and CRM Software

NAICS

Software Publishers (5132)

SIC

Services-Prepackaged Software (7372)

akta.pro primary industry

End-User Device Management (UEM/MDM, Desktop/Laptop/Tablet) (BPAEAIAB)

Keywords

• Contact management software
• CRM applications
• Personal information management
• Time and billing software
• Email client software

Headquarters

HQ city

Dallas

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B and B2C

Offering type

Software

Cost components

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

Revenue model

1. Software Licenses: One-time perpetual license purchases for Windows desktop software products. License by user, not computer. Includes two years of upgrade protection with free updates to new versions released within that period.
2. ChaosHost.com Subscription: Optional monthly cloud synchronization and data hosting service. Enables cross-device sync, mobile access, and team collaboration. Sold as optional add-on to desktop software.
3. Sync Add-on Tools: Additional sync utilities including Chaos DesktopSync ($19.95 one-time), Google Sync ($25.00 one-time), ChaosSync for Outlook ($29.95 one-time), and Address Swiper ($17.95)

Pricing tiers

Go-to-market motion2 records

Distribution channels1 record

Marketing channels4 records

Core offering

Chaos Software develops Windows desktop CRM and Personal Information Manager (PIM) applications for micro/small businesses and individual users. Its core product line includes Time & Chaos (contact relationship manager), Chaos Intellect (business CRM with integrated email client featuring auto-linked email history per contact), and Legal Billing (time and billing software for attorneys). All products install locally with local data storage, support shared databases on local networks without server hardware, and can be extended with the optional ChaosHost.com cloud synchronization service and mobile apps for Android and iOS.

Product overview

Chaos Software offers a suite of CRM and Personal Information Management (PIM) desktop applications for Windows, with optional cloud and mobile extensions. The core product line includes Time & Chaos (basic contact manager at $49.95), Chaos Intellect (full CRM with integrated email client at $59.95), and Legal Billing (time and billing software for legal professionals at $49.95). All desktop products support local data storage with optional network sharing and can be extended via ChaosHost.com cloud sync service, Chaos DesktopSync local sync, or mobile apps for Android and iOS. The company also offers add-on sync tools for Google and Microsoft Outlook. Pricing is one-time purchase per user with two years of upgrade protection included.

Differentiator

Problem solved

Functional benefit

Brands

• ChaosHost.com: Cloud data hosting and synchronization service for Chaos Software desktop products, allowing sync with mobile devices and multiple Windows computers
• Chaos University
• Chaos Labs
• Time & Chaos
• Chaos Intellect
• Legal Billing
• ChaosFree

Products and services

• Time & Chaos Award-winning Windows contact relationship manager with calendar, tasks, appointments, and shared database support on local networks. Designed for users who want contacts and calendars without the business email features. Priced at $49.95 per user with perpetual license.
• Chaos Intellect Top-of-the-line business CRM email software combining powerful contact management with integrated email client, auto-linked email history per contact, personalized group messaging, and OAuth-authenticated IMAP/SMTP mail handling. Priced at $59.95 per user with perpetual license.
• Legal Billing Time and billing software designed for busy lawyers and legal professionals. Includes time slips, expense logging, invoicing, payments tracking, and a built-in address book. Works standalone or integrated with Chaos Intellect and Time & Chaos. Priced at $49.95 per user with perpetual license.
• ChaosHost.com Optional cloud synchronization service enabling data sharing across multiple Windows computers, smartphones (iPhone and Android), and web browsers. Includes 30-day free trial and team pricing at $9.95/month total. Keeps data off Microsoft, Google, and Apple servers.
• Chaos DesktopSync Local network synchronization program enabling direct sync from a Windows computer to a smartphone over local Wi-Fi without internet or cloud. $19.95 one-time purchase with no annual fees.
• Google Sync

Quantifiable outcome

• 30+ years in continuous operation since 1992
• +3 more outcomes

Named customers12 records

Segments4 records

Ideal customer profiles3 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration15 records

Feature9 records

Scale indicators2 records

Recent moves7 records

Expansion highlights5 records

Broad incumbents

• Microsoft Outlook: Default contact, calendar, and email client shipped with Microsoft 365 and Windows. The most direct free substitute for Chaos Software's contact-management functionality, especially for SMBs already in the Microsoft ecosystem.
• HubSpot CRM: Dominant SMB/mid-market CRM with a robust free tier that directly competes with Chaos Software's price-sensitive micro-business segment. Comparable on contact management core, vastly broader on marketing automation, sales hub, and ecosystem.
• Zoho CRM: Broad small/mid-business CRM suite with a free tier and tiered subscription. Overlaps with Chaos Software on SMB contact management and CRM but offers a much wider portfolio of business apps and a cloud-native delivery model.

Direct peers

• Bitrix24: SMB CRM with free and low-cost tiers including contact management, tasks, and team collaboration. Comparable to Chaos Software in targeting SMBs with affordable contact/CRM features, though delivered as a cloud platform.
• Act! (Swiftpage): Long-standing SMB contact and CRM platform with desktop heritage and ongoing subscription pricing. Directly comparable to Time & Chaos in target market (small business contact management) and product category (desktop/Windows-friendly CRM).
• Maximizer CRM: SMB-focused CRM with both cloud and on-premise options serving similar small-business and professional-services verticals. Directly comparable to Chaos Software's CRM and contact management positioning for SMB and individual users.
• Pipedrive: Modern SMB CRM focused on sales pipeline management and contact organization for small teams. Directly comparable in target market (SMB) and contact/deal-management functionality, though delivered as cloud-native SaaS rather than desktop.
• eM Client: Windows and macOS email client with integrated contacts, calendar, and tasks. Comparable to Chaos Intellect in combining an email client with PIM/contact management features for individual and SMB users.
• GoldMine: Established SMB CRM with a long history in Windows desktop deployments. Directly comparable to Chaos Intellect in offering small-business contact management, sales pipeline tracking, and on-premise/hosted deployment options.

Others

• CompanionLink Software: Existing Chaos Software integration partner offering sync to BlackBerry, Android, iPhone, and iPad. Adjacent ecosystem player; relevant because it extends Chaos's reach to mobile devices without Chaos itself investing in native mobile CRM.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/ChaosSoftware
• LinkedInlinkedin.com/company/chaos-software-group-inc.

Compliance2 records

Revenue estimate

Valuation estimate

Number of profiles

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 Chaos Software