Welcome to our exclusive interview with Dionne Cheshier, a seasoned tax resolution specialist whose journey from aspiring anesthesiologist to tax expert reveals a deep commitment to service and a nuanced understanding of the IRS.
Dionne, can you tell us a bit about your background and how you became a tax resolution specialist?
My original goal in life was to be an anesthesiologist. My mother, who was a 40-year veteran of the SBA and a pioneer for women and minorities in business, allowed me to ride her coattails and follow her to literally every event growing up. As an admirer of these women in AWED and NAWBO (Association of Women Entrepreneurs of Dallas and National Association of Women Business Owners) it was only natural that I wanted to become one of them. I chose a woman who became the first licensed Hispanic anesthesiologist in Dallas and modeled myself around her advice to pursue science and medicine. In 1995, a mere two classes away from a degree in Biochemistry my father was diagnosed with lung cancer and my life was completely changed forever. While in the surgery waiting room, as they performed a partial lung removal on my father, I sat there with the CFO of the company where my father worked. In this crossroad meeting, he asked me if pursuing medicine was really what I wanted to do. To pursue medicine would have meant to go off to medical school and not spend what may have been my father’s last days with him. In that meeting with the CFO and my parent’s personal accountant, he asked me if I wanted to pursue a career in tax. He stated that if I took the proper courses, then he would send me all the clients I could ever handle. With that, I made the decision to take the fork in the road, and I have never looked back. I later went back to school to pursue a bachelor’s degree in Accounting and graduated with honors. My need to serve the public is still very much alive I just help with taxes instead of medicine! After 21 years in accounting and tax work I saw a growing need with people having issues with the IRS. I began by referring clients to an outside firm. When they weren’t being served in a manner that I felt was “up to par,” I pursued a new set of education credentials to become a Certified Tax Resolution Specialist and an Enrolled Agent and take my practice to a whole new level.
Can you explain your process for handling a new client’s case from the initial consultation to resolution?
In Cheshier Tax Resolution, we have developed a system we refer to as the “Road to Resolution”. Literally, every case takes different twists and turns on this road; however, the process generally remains the same. Clients start out with a mandatory compliance check. In this stage, we assess the client from both the client’s and the IRS’ point of view to understand the full scope. From here, we are able to make a decision on which winding road the client is best suited. From the compliance check, we take a turn to direct them to our sister company (both owned by Dionne) to close any gaps in their filing history. Before the IRS will negotiate a client must be in a compliant status with the IRS. Having no missing back filed returns or estimated payments, we achieve compliance. Once the client is compliant and we know the debt we are looking at we take a third turn to perform an in-depth financial analysis to determine if the debt can be settled, paid or maybe the client is just not collectible at all and we pursue the appropriate road from there. Upon the 4th turn and rounding out the collection phase of the resolution we bring the client across the home plate with the resolution that suits their financial capabilities.
You have an impressive record of maintaining a 100% acceptance rate in resolving cases with the IRS. How do you achieve this?
100% comes with caveats. We have had clients give up in the process and we have had them withdraw because they are not happy with our proposed outcome. Clients hear these misleading national advertisements and automatically think that everyone qualifies to settle their debt, which is simply a false belief system created by the media. Every client that we have pursued a resolution and taken the case through collections, sometimes appeals, and even assisted with handling the case through the tax court has received an outcome as initially proposed or better. We have never had a case returned as frivolous or an intentional delay of collection. In other words, the IRS has always seen fit to work with us and find the perfect resolution to the case at hand. When we interview clients we are very thorough and we make sure that the cases we take on are qualified for the programs the IRS is offering. If we take out the clients who quit during the process or decided the IRS was taking too long, then yes, we have absolutely and unequivocally never lost a case. We provide quality work within the criteria and standards of the IRS, and when this happens, the IRS typically (not always) does not have discretionary approval capabilities. The numbers speak for themselves when done properly.
Can you walk us through a particularly challenging case and how you successfully resolved it?
I have had the fortune of helping many clients and we have resolved more than $500M in cases. I have completed settlements and audit cases that were equally challenging. The IRS is trained to be misleading and lead clients down a road that will trap them into answering questions and putting them in positions that are hard to get out of. I had a case one time where the client was making payroll and never turning over the tax money to the IRS each pay period. They stated that their accountant advised them they could use this money “temporarily” to grow their company, and once they were big enough, then they could pay the IRS. Well, the IRS considers this money “trust fund” money. In other words, the IRS is trusting the employer to collect and turn over this money every pay period. This is one of the only ways the IRS can break through a corporate veil. It is also a fast track to possible criminal investigation and even jail time in certain circumstances. This client hired me after the IRS had come out to interview them. In the interview, the IRS somehow managed to get the client to state his father was the “general manager”. Mind you, the father literally came in to hang out and feed the dogs. He was elderly and just didn’t want to sit at home all day. This trust fund not only comes with assessments for taxes withheld and not turned over, it is also sometimes called the 100% penalty. It is the only penalty, once assessed, that can break through the corporate veil and be assessed to the owners and ANY OTHER person involved. Beware of this penalty, because if you are a payroll processor or a signer on the account or any person of authority in the company (I.E. the General Manager as mentioned above!!), you could very well be held liable. This is what happened to my client. My client’s company was assessed with the $6M debt as well as the sole owner and his “general manager” dad. In the end we were able to settle the corporate debt for just around $246K. The owner was able to settle for $462K, and the father was relieved of all liability. This means that we settled a $6M debt for 11.8%. Prior to being referred to my firm for help, this client was told by many that he should just close his doors. We were able to keep him in his business and teach him the proper way to handle payroll, and today, he is out from under this debt and able to thrive.
Your clients are often referred to you by third parties such as mortgage lenders and attorneys. What expertise and experience do you have that goes beyond the counsel of a regular attorney?
As an Enrolled Agent I am directly licensed by the US Treasury (which the IRS is a division of) and often preferred by many of the IRS employees due to my specialized knowledge and pursuit for the end solution. As an enrolled agent, my entire career has been based on tax and tax resolution. My test was a four-part test involving every aspect of tax. I have a reputation amongst mortgage lenders and realtors for being able to get liens discharged or subordinated in a very rapid fashion allowing them to close on more loans. The underwriting process is often a challenging one when processors are not able to timely pull transcripts holding up loan closings. We are able to assist and sometimes pull the transcripts instantaneously. We are sought out by Tax attorneys because of our reputation, level of expertise and ability to be shrewd negotiators with the IRS (a skill learned from my father!!) We also work with other Enrolled agents and CPA’s who do not care for this type of work. To negotiate with the World’s largest collection agency takes a specialized skill set that I have now spent years mastering.
What common misconceptions do people have about dealing with the IRS and back taxes?
This is a loaded question for sure and can be approached in many ways. Here are a few thoughts. First there are those who receive notices and just pay them. The IRS makes many mistakes and erroneous letters are amongst them. If you get a letter, do not jump to pay the amount, especially if it doesn’t “feel” right. If your tax preparer has stated that you have a refund and you get a letter that the IRS has changed your return, take the time to investigate that you actually owe. Second, do not go at it alone. The IRS is trained to phish for information and lead taxpayers down a bunny trail to collect way more information than necessary. To the innocent taxpayer, the IRS will attempt to solicit information beyond the scope of their assignment. Third, EVERY TAXPAYER has rights. Thanks to Nina Olsen (past taxpayer advocate) we now have Publication 1 the Taxpayer Bill of Rights. Taxpayers have a set of rights. The Right to Representation is perhaps the most valuable right. Once invoked, the IRS cannot communicate with the taxpayer, as long as the representative is completing tasks requested of the IRS in the allocated timeframe. If the representative does not cooperate with the IRS or causes intentional delays of collection, the IRS does have the right to invoke a bypass, so beware that the representative hired is a reputable one. There is also the Right to pay your fair share of tax. This means that the IRS cannot arbitrarily make assessments. There must be proper substantiation for the assessment, thus the previous advice to not pay these arbitrary notices of “proposed” tax due. Next the Taxpayer has the right to finality. This means the IRS cannot drag their feet on and on, they must have an end goal in mind as well. If the “right” representative is hired, they will know the taxpayers rights and hold the IRS responsible to achieve the proper resolution. Finally, it’s not advised to go to court without proper representation; therefore “Why would you want to go up against the “World’s largest collection agency” without proper representation?”
What advice would you give to individuals or businesses currently facing significant tax debt, especially regarding the stress and uncertainty of dealing with the IRS?
I have trademarked the tagline “Frontline Defender for the Distressed Taxpayer”. I take this tagline very seriously. My job is to defend taxpayers from the sometimes unfair practices of the IRS. My job has many facets, among them are: to defend the taxpayer at all times, to know when the IRS is “phishing”, to know when they delaying collections, to hold them accountable when necessary, and press them to finality. Most taxpayers are reactive to the IRS and succumb to the scare tactics, unknowing of the tools provided to bring the proper defense. Our job is to be a “Wall of China” between the IRS and taxpayers, so they can rest peacefully knowing we are on guard. Knowing also that we are here to defend and protect so their tax account reaches a zero balance and their life is restored to sanity.
What do you find most rewarding about helping clients resolve their tax issues?
The most rewarding experience is having a client in my office who starts out full of anxiety and uncertainty and we are able to bring them to a state of confidence and relaxation, knowing every case has a solution. There is no such thing as a perfect case but there is always a path to resolution. The level of appreciation and gratitude received by a client who can again relax is very rewarding.
Finally, what keeps you motivated and passionate about your work in tax resolution?
Tax is an everchanging and growing field. It is impossible to know it all. I have always been a person who seeks knowledge and constant learning. I am a firm believer that if at any time, a person does not get up excited to go to work and check out what the day brings, is maybe not in the right field. 15 years after that CFO in the hospital advised me to take the fork in the road one of his previous clients ended up in my office by mere chance. She was so worried because her CPA had passed away, and three years had gone by without her filing a tax return. She came to my office full of anxiety and lost. I was able to get her returns filed and get her compliant. In the process, I noticed that the CPA who had passed away happened to be the CPA who was mentioned in the first question, which led me to take the fork in the road. I knew in that moment of my life coming full circle, I was right where God had intended me to be. Knowing I am serving God everyday in my profession to assist people with tax returns and tax resolution keeps me motivated. It is this motivation that drives my passion and affords a happy life with my children.
Dionne Cheshier was awarded Tax Resolution Specialist of the Year for the Finance Monthly Taz Awards 2024
