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November 9, 2018

Company Profile: AskMyUncleSam

Company Name: AskMyUncleSam

Leadership Team: Busayo Ogunsanya, CPA/MST and Jogen Shah, CTO

Website/Social Platforms:

Company Overview (provide a brief paragraph about your company and mission)

AskMyUncleSam is a digital assistant with machine learning (a subset of artificial intelligence) for the 147 million individual tax filers. 60 percent of basic tax question do not get answered when taxpayers call a live assistor. Furthermore, the IRS has not answered any tax-law questions beyond the April 15th filing deadline either on their toll-free telephone lines or in its Taxpayer Assistance Centers, even though more than 15 million taxpayers file returns later in the year. Thus, taxpayers who want to learn about how the tax law affects them are left searching 140,000 web pages on or turning to paid professionals which are costly. The AskMyUncleSam platform provides taxpayers with year-around basic tax advice.  For example, a user might ask, “I just bought a house in charlotte, what home deductions should I be aware of?” AskMyUncleSam will give the answer in conversational language. In addition, we plan on building an Alexa and Google Assistant for our market to make the process easier.

What is the inspiration for your company? 

AskMyUncleSam was inspired by founder Busayo Ogunsanya’s background as a CPA with a Masters in Taxation. In addition to AskMyUncleSam, he also runs a boutique CPA firm called BigAppleTaxReturn that serves an outsourced CFO service to entrepreneurs and medical professionals. He constantly has clients, friends, family, and random strangers ask him basic tax questions. Furthermore, most individuals are looking for quick tax answers rather than digging through the IRS website. In fact, there were 544 million visitors to the IRS website in 2017.  AskMyUncleSam’s goal is to alleviate this massive pain point.

Who is your competition and how do you distinguish your company?

We are a B2B-C platform. Taxpayers are not getting there needs met and CPAs are too busy to answer tax question. TurboTax has a platform called Smartlook. TurboTax hires live CPA and Enrolled Agents during tax season in which consumers can facetime. Our platform is available year around, get smarter over time, and more importantly we are using a component of artificial intelligence /machine line to optimize our platform. We train our platform to get smarter over time to satisfy the 147 million tax filers. We anticipate having our chat platform on accounting professional and strategic financial partner website where taxpayers can log in through their Facebook account or g-mail account. The email address is passed on to the professional and the taxpayer gets access to our platform. The target market is two fronts – tax filers (243 million tax filers) and tax professionals (75 million tax professionals). Tax compliance is a $10 billion dollar market.

What is your connection to the Carolinas and why do you operate here?

We were recently accepted to Queen City Fintech Class 9. Charlotte is the capital of the banking world and that is what attracted to us to the fintech ecosystem. In addition, we wanted to join a smaller accelerator. Since being in Charlotte, we have had senior financial and tech members from leading financial firms share their institutional knowledge on building a successful company. Based on business needs and market opportunities, we might consider operating in Charlotte post QC Fintech.  In terms of recruiting talent, it has been difficult but I believe we live in the greatest time ever to build a platform such as ours because talent can be found on, Angellist, Upwork, and

Recent Accomplishments and Challenges (share with our audience how your company has made recent progress) What is Next?… (for you, the industry, the next 5 years?)

We launched our MVP in late 2017 which was rule based. While rule-based machine learning is conceptually a type of rule-based system, it is distinct from traditional rule-based systems, which are often handcrafted, and other rule-based decision maker.  In a rule-based approach, a bot answers questions based on some rules on which it is trained. We had our platform on Slack and Facebook messenger to gather data sets. In spring of 2018, we moved our platform to a NLP (Natural Language Processing) to train our datasets (supervised learning). Currently, we are developing our API to license to CPA firms and online-tax preparers. NLP is natural language processing and can be used in scenarios where static or predefined answers, options and questions may not work. In fact, if you want to understand the intent and context of the user, then it is advisable to use NLP. We believe voice assistant is going to be huge opportunity for us. Taxpayers are looking for frictionless and simple solutions to a complex answer and Alexa/Voice Assistant is a getaway for us to meet those needs. Furthermore, we anticipate CPAs and online tax prep firms adapting our platform as lead generation to gain new clients.

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Posted by Carson Truesdell