TaxTech Talk with Nick Simpson from WorkMade | "Our standout feature is the AI-driven automation"

Intro

A month ago, Nick Simpson, founder of WorkMade, announced the official launch of the company he founded in 2022. Having raised more than seven million dollars in two rounds of funding in 2022 and 2023, WorkMade is ready to make life easier for US-based freelancers by offering banking, accounting and tax processing through its mobile and (soon) web app. We had a chance to get some more details directly from Nick.

Interview

Hi Nick, what is WorkMade and how long has it been in the making? 

Forget your taxes forever. WorkMade represents a breakthrough in financial management tailored specifically for freelancers. This platform, shaped from two decades of personal freelancing experience, has been carefully crafted over 18 months using advanced AI. It's designed to simplify and automate the often complex and time-consuming task of tax management, allowing freelancers to focus on their projects and passions. WorkMade is more than a tool; it's a partner in financial autonomy, enabling freelancers to seamlessly manage their finances with ease.

Who is behind WorkMade?

The founding team of WorkMade comes from a rich blend of technology and freelancing backgrounds, including experience at leading companies like Avalara, Affirm, Dropbox and GoDaddy. This diverse expertise is pivotal in creating a product that truly understands and addresses the unique financial challenges faced by freelancers. Our team's deep knowledge in payments, taxes, and product design has been instrumental in developing a solution that is not only innovative but also highly attuned to the needs of the freelance community.

What is the story behind WorkMade that made you start it?

The motivation behind WorkMade was born out of the financial challenges I faced as a freelancer. Recognizing that these challenges are a common thread in the freelance community, WorkMade was developed as a solution to this widespread issue. It's a platform designed by freelancers for freelancers, aiming to alleviate the burden of financial management and allow freelancers to focus more on their work and less on the complexities of taxes and accounting.

What are you doing best at WorkMade?

WorkMade's standout feature is its intelligence, AI-driven automation, specifically designed for the unique needs of freelancers. This automation revolutionizes how freelancers handle their finances, transforming tedious tasks like bookkeeping and tax filing into a streamlined, efficient process. It's not just about technology; it's about understanding and addressing the specific financial pain points freelancers face, giving them back valuable time to invest in their work.

Where are you seeing yourselves exceeding other products?

What sets WorkMade apart in the competitive landscape is its holistic approach to financial management for freelancers. Unlike other platforms that might only address one aspect of finance, WorkMade provides an all-in-one solution. It integrates banking, bookkeeping, accounting, and tax management, all tailored to the freelancer's lifestyle. This comprehensive approach, driven by sophisticated AI, makes WorkMade a unique and indispensable tool for freelancers looking for a seamless financial management experience.

Is there something that took much longer to build than expected?

Everything related to taxes - our calculation, categorization, and payment engine - was complex. Eliminating the need for an accountant wasn't easy, especially in the US where each state has a different payment infrastructure. It took us nearly a year and over 300 rounds of revisions to perfect it. The numerous circumstances that make each individual's situation unique added to the challenge.

Did you learn something that was counterintuitive while developing WorkMade?

Understanding taxes is a challenge due to frequent law changes. Therefore, we opted to create a solution that eliminates the need for traditional tax software. We intentionally avoid standard Intuit-style dropdowns, tax forms, and jargon. All processes occur in the background.

A key insight during WorkMade's development was that freelancers often find tax laws overwhelming and ever-changing, regardless of their field. This insight led us to shift our focus from just developing another tax software to creating a solution that fundamentally simplifies taxes. WorkMade is designed to handle complexities in the background. This allows freelancers to focus on their craft, rather than staying abreast of tax regulations.

How do you plan to compete with big competitors like Intuit?

Our strategy to compete with giants like Intuit lies in our agility and deep focus on the unique needs of freelancers. WorkMade is built to evolve rapidly, incorporating feedback directly from our user base to continuously improve and adapt. This approach allows us to create solutions that are highly relevant and finely tuned to the challenges freelancers face, setting us apart in a market filled with more generalized financial products.

Building traditional tax software is a futile endeavor in addressing these challenges. What's needed is a radical shift in approach: making tax management virtually invisible. By seamlessly integrating tax solutions into the daily financial activities of freelancers, we can eliminate the friction and pain points inherent in traditional methods.

This invisible approach means tax management occurs in the background, without the need for constant input or monitoring by the user. It adapts to the freelancer's unique financial situation, automatically updating with changing laws and personal circumstances. With this strategy, the focus shifts from developing software around tax management to creating a system that naturally aligns with the freelancer's financial journey, making tax time a stress-free, almost unnoticed aspect of their professional life.

How did you get the tax expertise for building your product?

To build WorkMade, we gathered a team with a rich mix of internal and external (IRS) [The Internal Revenue Service is the revenue service for the United States federal government] tax expertise, alongside our own research and understanding of freelance needs. This blend of knowledge was crucial in developing a product that is not only technically proficient but also deeply aligned with the practical realities of freelancers. Our team's firsthand experience as freelancers played a key role in shaping a platform that addresses the specific challenges and nuances of freelance financial management.

What are the next steps for you and your team?

Looking ahead, WorkMade is set to expand its capabilities to cover a wider range of freelance tax situations. We're also excited about our upcoming features. These include an enhanced tap-to-pay for iPhone experience that accepts payments and automatically sets aside and pays taxes in real time. We're launching a revolutionary web app in the first quarter of next year with amazing continuity features that transform your iPhone into a secondary screen. These developments underscore our commitment to empowering freelancers with tools that manage their finances and enhance their overall work experience.

Thank you for your time Nick and all the best for you and your team!

🤖 | TL;DR

WorkMade, created over 18 months and based on two decades of freelancing experience, is an AI-driven financial management platform designed for freelancers to simplify tax management and enhance financial autonomy.

The founding team, with backgrounds from Avalara, Affirm, Dropbox, and GoDaddy, focuses on addressing freelancers' unique financial challenges, developing a comprehensive solution integrating banking, bookkeeping, accounting, and tax management.

The platform, distinct for its AI-driven automation and holistic approach, competes against larger firms like Intuit by focusing on the specific needs of freelancers, offering seamless tax management and planning to expand with new features like tap-to-pay and a transformative web app.