We’ve been saying for months that the current era of money being thrown at accounting firms and all these capital-fueled AI “firms” popping up reminds us so much of the dot com boom of the late 90s/very early 2000s. The press release we’re about to share with you definitely isn’t helping change that view. Alright, let’s see what’s going on with this “AI-powered tax firm” and the giant pile of money they just got.
OLarry, an AI-powered tax firm for the next generation of high-net-worth individuals and businesses, today announced that it has raised a $10 million Series A round led by TTV Capital and joined by Walkabout Ventures and Marin Sonoma Impact Ventures, bringing the company’s total funding to $14.5 million. OLarry bridges the gap between DIY tax preparation and ultra-high-net-worth, hourly tax advisory, empowering thousands of clients to gain access to personalized tax strategies for an all-inclusive annual fee. With AI at its core, OLarry automates client onboarding, document preparation, and data extraction, enabling CPAs to focus on what they do best: provide proactive advice to clients with complex financial situations.
“Proactive tax planning has historically been reserved for the ultra-high-net-worth – those who can afford the most elite tax firms in the country. We built OLarry for the next generation of high-net-worth individuals and businesses, who need personalized tax advice but are underserved by TurboTax or their current tax advisor,” said Eric Rachmel, Co-founder and CEO of OLarry. “OLarry uses AI to streamline workflows, freeing up CPAs to focus on what they do best: provide holistic tax advice year-round, not just during tax season. In doing so, we enable our clients to make smarter investment and life decisions because they can understand how it will impact their taxes.”
They go on to say that OLarry will use this capital to “continue building out the company’s proprietary tax data classification and extraction model,” “advance the development of predictive scenario planning tools to help clients optimize tax outcomes in real-time,” and “create an agentic, AI-powered client experience to support seamless communication, education, and advisor interactions.” On top of that, they’ll be looking to merge in existing firms with revenue up to $6 million (got that part from their website, not the news release) and recruit “nationally recognized, top-tier CPAs.”
This is what they’re offering those top-tier CPAs and tech talent on their careers page:
According to Glassdoor, the median total pay for tax directors in the United States is $225k per year. Here’s what they list for tax director jobs at PwC, CLA, and RSM for comparison:
Founder and CEO Eric Rachmel, who is not a CPA, but rather has a background in venture capital and investment banking, explains on their website what inspired the creation of OLarry:
COVID changed people’s lives in many ways. For me personally, it meant the sudden loss of my father, Larry, who was a sole proprietor running a successful CPA practice. We often overlook what our parents do for a living, as it is so ingrained in our lives that we don’t see the opportunity. I grew up with an entrepreneurial father who ran a tax practice for two decades.
Suddenly, in the midst of tax season, my sister and I found ourselves navigating the complexities of running and ultimately selling our father’s business. At this point, the two sides of my life came together. I recognized the industry’s opportunity and vast potential for improvement, with a critical need for enhanced services and the integration of modern technology.
The inspiration for this new venture arose from a reflection on my interactions and experience with accountants, both professionally and personally (oddly, many of whom were also called Larry!). Different messages from different CPAs, a disconnect in understanding the information their clients meticulously gathered, and the frustrating limitations of old and clunky systems highlighted the dire need for a better way. A way forward that places the skills and knowledge of CPAs at its core, not merely relying on technology. The pain point that exists today in the accounting world is colliding with the macroeconomic view that over 72 trillion dollars will be passed down from boomers to their heirs in the next 20 years. There is a huge opportunity to ensure this tax strategy and advisory are done correctly.
It will be interesting to see if high net worth individuals embrace this new generation of tech-forward startups or stick to the tried and true if overpriced traditional big firms. We’ll be watching.
“I believe the available market is smaller than the bulls believe it to be and that Green Mountain has already penetrated a good chunk of it,” Einhorn, president of Greenlight Capital Inc., said today during his so-called “GAAP-uccino” presentation at the Value Investing Congress in New York. “The market is limited,” he said. The company also has a “litany of accounting questions,” Einhorn said, adding that it has reduced transparency and needs to improve disclosure. [
Anyone who works for companies such as these and Intuit is an absolute scab to the profession and deserves to be shamed out of it. The future of the profession isn’t big firms or big tech – it is what made our profession as trusted as it is, and that is being hands-on advisors to businesses. VC and PE is a cancer to America