Meet OLarry: Bridging the gap between tradition and innovation for tax advisory

With great excitement, we announce the founding and first institutional round of capital for OLarry . Becky Hobbs , Corey Heldreth, CPA , and I have partnered with @Walkabout Ventures (leading the financing), Point72 Ventures, and other strategic angels, for a $4.5m equity financing round. 

OLarry wants to change how you think about your relationship with your accountant. Tax advisory is the core pillar to financial success, and over time, we seek to earn your trust in many aspects of wealth creation. We believe having a responsive professional equipped with the right technology who truly listens, understands, and explains different tax strategies, is paramount to the right approach for you and your family's financial well-being. 

As someone who has spent 15 years in venture capital, investment banking, and building companies, my passion drives me to look towards uncharted territories—areas where a large market awaits, underserved by current technology or processes. This guiding principle led me into mortgage servicing in 2017 and to found Brace, a business we built from the ground up that was acquired in 2023. Brace partnered with the nation's largest banks and mortgage originators, helping over 100,000 people stay in their homes when faced with financial hardship during and after COVID. 

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. 

Starting a company is not just about a vision; it's about the people who drive it. Our founding team embodies determination, passion, and a shared vision for change. 

Originally from the UK, Becky has spent over 20 years helping to disrupt and modernize industries with user-friendly technology. She shared her frustrations with the U.S. tax process. The process's inaccessibility and the significant risk of taking the wrong step or advice is the opposite of the consumer-first, transparent world we are moving towards. She believes it is time for a cultural change in how we think about taxes and how families plan for their future. 

Corey has spent 15+ years working closely with high-net-worth individuals and businesses as a CPA and trusted tax advisor. His background as a collegiate and professional athlete taught him the value of consistent collaboration and the need to adapt to an ever-changing environment. On the cusp of hitting the ground running with his own tech-forward, collaborative tax practice, Corey serendipitously met Eric and Becky. His unique perspective further solidified our collective belief that the business of tax (and beyond) can be done in a way that better serves customers and provides an exciting career path for aspiring professionals. 

Through our collective experiences, OLarry was founded to leverage technology to enhance the traditional accounting business. Together, we are embarking on a journey to revolutionize financial management and guide wealth across generations.