TrulySmall is a specialized software brand launched by Kashoo Cloud Accounting Inc., a Vancouver-based fintech company with over 15 years of experience in the accounting sector. Following its acquisition by the DataTax Group in early 2024, TrulySmall has become the cornerstone of a broader mission to provide high-accessibility financial tools to the 'truly small' segment—businesses often ignored by enterprise software giants. The brand's philosophy is rooted in eliminating the 'accounting anxiety' that small business owners feel. By focusing on essential tasks like invoicing and expense management, TrulySmall positions itself as a partner in growth, offering a streamlined path from simple billing to full-scale automated bookkeeping. The company maintains a strong reputation for user-centric design and human-first customer support, differentiating itself from the robotic interactions common in the SaaS industry.
The foundation of TrulySmall is deeply linked to the history of Kashoo, which was co-founded in 2008 by Jim Cook and Casper de Jong in Vancouver, Canada. Jim Cook, an experienced entrepreneur with a background in SaaS scaling, and Casper de Jong, a software architect, initially built Kashoo as a simple web-based alternative to bloated desktop accounting software. As the market matured and enterprise tools became increasingly complex, the team observed a growing gap for micro-businesses that found even modern cloud accounting too difficult to navigate. In 2020, they launched the TrulySmall brand as a specialized suite for freelancers and solo-entrepreneurs. This shift was a strategic pivot to return to the company's 'simple is better' roots, culminating in the release of the TrulySmall Invoices mobile app which prioritized speed and ease of use over complex accounting logic.
Before being integrated into the DataTax Group family, Kashoo (the developer of TrulySmall) successfully navigated several rounds of institutional and angel funding. Notable milestones include a Series A round in 2011, which raised approximately $2.5 million from lead investors like Real Ventures and a syndicate of private angels. This capital was instrumental in transitioning the company from a web-only platform to a mobile-first provider, allowing them to compete with larger incumbents. Over the years, the company maintained a capital-efficient growth model, focusing on product-led growth and high retention rates. In March 2024, Kashoo and its TrulySmall brand were officially acquired by DataTax, a dominant player in financial services and software. This acquisition provided the necessary resources and financial expertise to expand the TrulySmall ecosystem, including enhanced AI integration and broader international tax compliance support.
The TrulySmall product portfolio is built as a modular ecosystem that allows business owners to pay only for the functionality they need. TrulySmall Invoices is the lead offering, providing the primary billing engine. This is complemented by TrulySmall Expenses, a dedicated application for receipt scanning and automated expense categorization using OCR technology. For users requiring the full spectrum of accounting, TrulySmall Accounting serves as the flagship, offering double-entry bookkeeping, bank feed synchronization, and comprehensive financial reporting (Profit & Loss, Balance Sheets, etc.). The genius of the offering lies in its interconnectivity; data flows seamlessly between the mobile-first Invoices and Expenses apps into the central Accounting dashboard, creating a 'Smart Inbox' where transactions are reconciled automatically. This tiered approach allows a freelancer to start with free invoicing and eventually upgrade to a full financial management suite as their revenue grows.
TrulySmall has leveraged the global reach of the Apple App Store and Google Play Store to expand far beyond its Canadian headquarters. While its primary markets are the United States and Canada—where it offers localized tax settings for IRS and CRA compliance—the software is utilized in over 100 countries worldwide. The multi-currency feature is a core component of this expansion, supporting billing in almost every major global currency. Under the new DataTax flagship, the company is intensifying its focus on international markets, particularly the UK and Europe, by ensuring alignment with evolving regulations like Making Tax Digital (MTD) and GDPR. While the core team remains in Vancouver, the expansion strategy includes building a network of localized 'financial experts' through the DataTax group to provide regional support and specialized tax advice to TrulySmall users globally.
In the last 18 months, TrulySmall Invoices has seen significant evolution, particularly in its integration capabilities. A major update in 2024 introduced a seamless 'Direct Connect' between TS Invoices and TS Accounting, allowing users to automatically sync invoice payments with their bank ledger. Other recent feature launches include 'Color Themes,' allowing for better visual branding on PDF invoices, and a new 'Invoice Voiding/Cancellation' workflow that maintains a clean audit trail without deleting records. The development team also enhanced the 'Payment Recovery' feature, which allows businesses to automatically calculate and add convenience fees to credit card transactions. On the mobile front, recent updates have focused on 'Offline Mode,' ensuring contractors can draft estimates in areas with poor connectivity and have them sync once they return to a network, a critical update for field-based services.
The culture at Kashoo/TrulySmall is defined by an 'entrepreneurs helping entrepreneurs' ethos. Based in the tech hub of Vancouver, the team prides itself on being small and agile, much like the customers they serve. The company maintains a hybrid work environment that values technical excellence alongside a deep sense of empathy for small business struggles. This is reflected in their support policy; unlike many competitors who hide behind chatbots, TrulySmall maintains a staff of 'real human beings' who are trained in both technical support and basic bookkeeping. This culture of accessibility permeates the product design, which eschews corporate jargon in favor of plain language. Internal values emphasize transparency, continuous improvement, and 'radical simplicity,' ensuring that every developer and designer is focused on removing friction from the end-user's day.
TrulySmall fosters an active community of micro-business owners through various digital channels. The primary hub is the 'TrulySmall Small Business Community' on Facebook, where thousands of freelancers and contractors share tips on scaling, tax advice, and general entrepreneurship. This forum is also a direct line for product feedback, with TrulySmall product managers frequently engaging with users to prioritize upcoming features. Beyond social media, the company maintains a robust 'Resources' blog that provides educational content on topics like 'When to Send Invoices' and 'Accounting Mistakes to Avoid.' They also participate in small business webinars and local entrepreneur meetups in the Vancouver area. This community-centric approach helps transform a utility software into a supportive network, which is particularly valuable for solo-entrepreneurs who lack a traditional office support system.
TrulySmall Invoices
By Kashoo Cloud Accounting Inc. (DataTax Group)
