Boring Tax: How Juan and Thomas Are Revolutionizing Tax Advisory with AI
Volume #22 of "Happy Bootstrapping" Newsletter
Juan and his co-founder Thomas launched Boring Tax in February 2024 and have already acquired 100 clients. The bootstrapped startup from Berlin automates accounting and taxes with AI, offering everything for €198 per month – including annual financial statements. An honest insight into building a legal-tech startup that lives up to its name: taxes should be boring so founders can focus on what matters.
This is a summary of Episode 133 of the “Happy Bootstrapping” Podcast (German).
From Idea to MVP in Six Months
The founding story of Boring Tax begins with a simple realization: "People shouldn't have to deal with these topics," Juan explains. After eight years in legal tech, he saw Generative AI as the perfect answer to the industry's challenges. Together with Thomas, with whom he had worked for over ten years, he programmed the first MVP from September 2023 to February 2024.
What makes their approach special: Both founders are full-stack developers who understand the domain. "Understanding the problem and the technological possibilities are combined in one step and then directly implemented," Juan describes the crucial advantage over larger players like Lexware or Sevdesk.
The Business Model: Service as a Software
Boring Tax deliberately positions itself not as pure software but as a comprehensive service. For €198 monthly (up to €250,000 annual revenue), customers get:
Ongoing bookkeeping with automatic document matching
VAT returns
Annual financial statements
Direct communication with real tax advisors through the platform
"We're not Software as a Service, we're Service as a Software," Juan emphasizes. The technology works in the background: receipts are automatically linked to transactions, an algorithm books automatically, and an accountant from the partner firm checks everything.
The Technology Behind It
The tech stack is deliberately kept lean: Java, React, Python – "nothing fancy," as Juan says. The real innovation lies in the data architecture, designed from the start for AI applications. All data is processed in Germany, and they plan to build their own LLMs based on open-source models in the medium term.
A clever detail: customers can submit receipts via email and even WhatsApp. "That's just obvious," says Juan about features missing from competitors.
Marketing and Growth
With just two full-time developers, Juan and Thomas currently manage 100 clients. Customer acquisition runs through various channels:
Google Ads (the starting point)
LinkedIn outreach
Reddit ads (yes, that works!)
Meetups for expats in Berlin
"It's so much easier to exchange directly with founders because they understand... the conversation quickly becomes informal and open," Juan describes the advantages of direct exchange.
Bootstrapping Challenges
Both founders still live off their savings and don't pay themselves salaries. The biggest challenge wasn't the product itself but internal coordination: "There were a few moments where I thought it could really fail now because we couldn't agree."
The tax advisor shortage is both a curse and a blessing: while it's hard to find partners ("They're not so easy to find"), it also validates the business model. Boring Tax is currently looking for an employed tax advisor for their own firm.
Learnings from a Legal-Tech Founder
Timing is everything: "There aren't enough tax advisors. Gen.AI just came out and existing players can't adopt it like this"
MVP mentality: Six months for a functional prototype in the sensitive tax sector
Direct connection: Personal onboarding calls instead of self-service – "It's also important for us to briefly get to know people"
Stay lean: "Our obsession is to stay lean and efficient and small"
Focus: Clear pivot from "legal and tax" to pure tax and accounting focus
What I Learned as an Interviewer
Juan's radical transparency impressed me – from internal conflicts to concrete customer numbers. I was particularly fascinated by the conscious decision against investors despite many inquiries: "Fundraising costs tremendous opportunity costs." The combination of technical know-how and domain knowledge in both founders shows how important it is to truly understand the problem before solving it.
Happy Bootstrapping is a German podcast where I interview bootstrapped founders, indie hackers, and solopreneurs about their startup journeys.
Over the years, I've connected with many successful entrepreneurs who have built e-commerce shops, SaaS platforms, mobile apps, content businesses, or hybrid models.
Furthermore I am a bootstrapper myself and growing my DevOps-as-a-Sercice and Web Operations Company “We Manage”.