We caught up with the brilliant and insightful Jessica Streetman a few weeks ago and have shared our conversation below.
Jessica, appreciate you joining us today. What was the most important lesson/experience you had in a job that has helped you as a business owner?
I feel like this is a loaded question….my previous job is my blueprint on how not to run my business. One of the biggest lessons I have taken away from that job that has helped me as a business owner, enrolled agent and an accountant is to put money back into your business. We all want to be wealthy (some more than others) but by putting some money back into your business to purchase technology, education and at least one association you can also buy time. To me, time is worth more than money.
I worked from and accounting assistant to office manager at my previous job. When I was hired there was no advertising, education offered, and the only technology was basic software necessary to get the work done. With a great deal of effort I was able to find every free way to bring the company into the current year. Once we began seeing an increase in clients the owner felt comfortable spending some money on an upgraded office software. Still no education or technology that helps with the actual work being performed day to day. I was there for about seven years. I took education on my own and taught myself new software that the company was not interested in using. CPA’s and accountants never stayed long.
I will say that when I started my own business I was able to utilize all of the free services I found at my previous job. I am still growing my tech stack to not only make my life easier, but my clients as well. Education is very important to me and I am shocked that any accounting and/or tax office does not offer it to their employees or at the least let them know where to find it.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I have been happily married to my husband for the past 23 years, have two children in college and a playful pup. I enjoy gardening which sounds super boring but it is a really good stress reliever during tax season. I am a Volunteer Ambassador for the Gulf Coast Center for Nonviolence and volunteer with VITA every tax season.
Accounting has been something I have always enjoyed and been good at since high school but I did not get into tax (aside from my own) until 2017. After spending years running an accounting and tax company for someone else (the story of countless other entrepreneurs) there came a moment that was the “final thing” that pushed me to go out on my own. As cliche as it sounds, it was truly the best thing I could have done for myself and my clients. I take triple the amount of education each year, I look for technology that helps me and my clients, and I love my work again.
The majority of my business is remote so that I can work with clients throughout the United States. outside of the United States and at times that are convenient for them. It can be difficult for a business owner or an individual to just drop what they are doing and have a meeting in the middle of the day. I make it so that they can meet after work if needed via video call, phone call, etc. I do have in person meetings for those who request them. I have a secure portal so that my clients can upload, access or sign documents at their convenience.
I work with a lot of clients who are just starting out, trying to get “caught up” from years of neglected books and/or returns, or just need someone to get them on track business wise so they can see where their money is going. Being able to help someone grow a business, even from the background, is a very fulfilling thing.
Any stories or insights that might help us understand how you’ve built such a strong reputation?
My ability to work with those with short attention spans, especially those in the creative realm who are constantly on the move. You can’t put a person on the bottom of your to do list because they don’t get you information back on your time. It can be exhausting sometimes, but it is doable.

What’s worked well for you in terms of a source for new clients?
Yourself and word of mouth. Everyone says it and I did not want it to be true. I am an introvert so the thought of social events is not at the top of my list. I decided this year that I would change that and business has picked up. If you do not market yourself then know one will know who you are or what you do.
Contact Info:
- Website: https://www.streetmantax.com/
- Facebook: https://www.facebook.com/StreetmanTaxServices
- Linkedin: https://www.linkedin.com/in/jessica-streetman-ea-013418147/
- Yelp: https://www.yelp.com/biz/streetman-tax-services-gulfport

