BJH: Tell us about yourself. Where are you from?
Yehuda Tenenbaum: I was born and raised here in Baltimore. I grew up on Strathmore and davened at Rabbi Goldberger’s shul. I attended TA through high school and returned to Baltimore after five years away in Yeshiva. I was lucky enough to meet my wife, who is also from Baltimore, and we settled down here.
BJH: What inspired you to pursue your career path and get involved in the work you do?
YT: Already from a young age I was business-like minded, although I didn’t realize it at the time. I ran a band back in high school called The TA Band. For our first bar mitzvah we split $150 between all four band members. This was one of my first lessons on performing customer service and marketing my talents.
When I was in Yeshiva, my mother gave me a strict budget. I tracked all my receipts in a spreadsheet on the Yeshiva computer. When I needed more money, I just sent her the spreadsheet and asked which thing I shouldn’t have spent money on. I knew then that spreadsheets would play an important role in my life.
BJH: Can you share a bit about your professional background and how you got to where you are today?
YT: My first tax return was for a camp my wife ran. Shortly after that, I became a licensed Maryland tax preparer, and over time, my side gig morphed into a full-blown profession. To level up, I became an Enrolled Agent—think James Bond, but for taxes. EAs are experts in tax preparation, with unlimited rights to represent clients before the IRS.
BJH: How is this different from a CPA license?
YT: While a CPA is tested on a broad range of knowledge stemming from financial accounting, auditing, and taxes, a CPA may not specialize in taxes at all. While working at a regional accounting firm, I was surprised to learn that some of the CPAs in the firm had no idea how to prepare a tax return because they specialized in other areas. That being said, I’m also pursuing my CPA license. I’m a Maryland notary as well, so if you need something notarized, I’m your guy.
BJH: What sets your approach apart? What unique value do you bring to your clients?
YT: Most people shudder at the idea of filling out a tax return. My goal as a tax preparer is to simplify the process for my clients, teaching them proper financial principles and tax planning along the way. My specialty is working with individuals and small businesses because I focus on giving every client the attention they need, a service not often found when working with larger firms. I run a tech-first, low-overhead business with no fancy offices or receptionists, just personalized, professional service. Clients upload documents to a secure online portal, and automation handles routine communication, allowing me to focus on the more detailed, complicated work.
BJH: What’s a particularly meaningful experience you’ve had in your line of work?
YT: Once, a new client—a therapist—came to me stressed about taxes. I told her, I’m the therapist’s therapist. Let me handle the tax anxiety so you can focus on your clients. She laughed, but it’s true. I love helping people breathe easier when it comes to money.
BJH: What’s something interesting you’ve noticed or experienced in your work?
YT: My clients amaze me with their creativity. There are so many ways to earn a living beyond the standard doctor-lawyer-firefighter trio we grew up hearing about. I get inspired daily by the unique businesses and careers people build—and I’m grateful we don’t all want to be accountants, or I’d have no one to buy meat from for my cholent.
BJH: How do you contribute to the community beyond your professional work?
YT: When I’m not knee-deep in spreadsheets, you’ll probably find me with a guitar in hand. Whether it’s singing and playing at a wedding or a siyum, music is a huge part of my life. Recently, a client asked me to do his taxes and play at his wedding—just not at the same time.
BJH: What advice would you give to someone looking to improve in the area you specialize in?
YT: Start with the basics: create a budget, set financial goals, and educate yourself. And don’t be afraid to ask for help. A good advisor can save you time, money, and a whole lot of stress.
BJH: How can people connect with you or learn more about what you do?
YT: You can visit my website at y10tax.com for more information about my services. I’m also available via email at yehuda@y10tax.com or by phone at 443-750-9606. With tax season approaching, I recommend reaching out soon—slots are filling up quickly!
