About Me

Thanks for joining me!

My name is Trudy M. Howard, and I’m the small business tax lady better known by the hashtag #smallbiztaxlady, and I’m here to help you on your entrepreneurship journey! I am the founder of Howard Tax Prep LLC, which is an independently owned tax agency located in the South Loop of Chicago, Il. Howard Tax Prep LLC specializes in preparing small business tax returns, freelance worker tax return, and 1099 worker tax returns. Although I’m physically located in the South Loop of Chicago, I offer nationwide tax services, and nationwide business services.

You can research my tax preparation & tax resolution credentials on IRS.gov Directory of Federal Tax Return Preparers with Credentials and Select Qualifications. I hold an IRS AFSP record of completion, which allows me to represent my clients before the before IRS revenue agents, customer service representatives, and similar IRS employees, including the Taxpayer Advocate Service. In addition to my tax specialist credentials, I am also a licensed insurance broker certified to sell life, health, home, commercial, auto, and Medicare part C health plans. Should you ever need the services of a notary, I’m also an Illinois registered notary.

Over the last 16 years I’ve owned several business ranging from an inventory based candle business (in which I used raw materials to manufacture the product), to an incorporated insurance agency (ALEM Agency Inc.) that specializes in covering the hard to insure. In 2012 my mother was diagnosed with stage 4 cervical cancer, and within 3 months I had to bury her; however, as an ongoing form of therapy, later in 2012, I decided to found a tax exempt non profit 501(c)(3) organization Senior Resource Group Inc.  Senior Resource Group Inc. help seniors (and those that are  disabled) find low cost drugs & understand their Medicare options. As you can see, I’m not only experienced, but I’m also very knowledgeable in many areas!

#Smallbiztaxlady came to fruition when the “gig economy” started, and I noticed that I had more friends/clients/family asking me questions regarding their 1099 form(s). Unfortunately, many of the self proclaimed “tax professionals” are unable to assist clients with: Uber driver tax questions; Lyft driver tax questions; Doordash taxes; Airbnb taxes; first time 1099 forms; real estate investor taxes; real estate professional taxes; small business owner taxes; payroll tax penalties; and home based business taxes. In an effort to assist my fellow entrepreneurs I began posting tips, “how to’s”, and answering questions on my personal Facebook page, twitter, Instagram, and in entrepreneur groups. More recently I decided to reach a broader audience, and thus, the #smallbiztaxlady website was born.

I am here to answer your questions regarding: small business tax planning; small business insurance; new home owner tax preparation; college student tax preparation; business compliance; entity creation; retirement plans; college savings plans; tax resolution (tax problem help); and tax planning for individuals. My goal is to assist small business owners in every area of their business, and to make the appropriate referrals when necessary. If you have a tax question, insurance question, or business entity question, please email me at questions@howardtaxprep.com

P.S. For wealth building and tax reduction tips, please join Howard Tax Prep LLC  newsletter!