How Diane Hagerty Solved $898,000 IRS Bill and Helps Small Businesses Navigate Tax Nightmares
Sat Feb 07 2026
🎙️ From Accidentally Acing Accounting to IRS Enrolled Agent: Diane Hagerty's Journey Through Divorce, Starting Over, and Simplifying Tax Nightmares
Diane Hagerty, IRS enrolled agent and owner of Grassroots Taxes in Springdale, Arkansas, shares her journey from teenage musician forced into accounting class by nun with no other options available—tried failing, got hundreds instead—to discovering natural talent balancing checkbooks and explaining financial concepts, through divorce at 35 walking away with nothing starting from scratch, to solving $898,000 IRS bill reduced to zero for client with addiction issues and acres of broken-down tractor trailers. Through stories about government losing payments and forms constantly, debunking internet tax myths about putting houses in LLCs, and rising from ashes giving valedictorian speech at University of Phoenix after rebuilding life one knuckle pushup at a time, Diane reveals how consistency beats year-end panic (10 minutes weekly versus giant pile in April), make money first before expensive business structures, and finding your people plus staying busy helping others transforms adversity into superpower simplifying thousand-page legislation into actionable plans.
✨ Key Insights You'll Learn:
Accidentally discovered accounting talent: lazy teenager waited until day before school, nun said only accounting class open, tried failing but got hundreds on every assignment
Natural financial gift emerged early: balancing friends' checkbooks, reading letters, explaining concepts without studying while everyone else failed accounting
Divorce at 35 starting from scratch: walked away with nothing to avoid fighting, lost kids/business/friends, hadn't worked in years, no college degree finished
$898,000 IRS bill reduced to zero: client with addiction issues, broken-down tractor trailers everywhere, IRS made up numbers when he stopped filing, took 3.5 years solving
Government clerical errors constant: Arkansas Department of Finance loses payments, never credits forms, charges late fees despite filed extensions—just overwhelmed with volume
IRS representation requires credentials: only attorneys, state CPAs, or enrolled agents can represent taxpayers before IRS during tax issues
Tax preparation industry largely unregulated: anybody can prepare returns at big box places after taking class, no credential standards required
Consistency principle beats panic: 10 minutes weekly recording receipts/mileage prevents giant pile in April, know how business performs before accountant tells you
Make money first philosophy: test business idea before expensive LLCs/structures/fees, see if people buy product before paying state/setup costs annually
Vacation tax deduction requirements: must do business activities daily that require physical presence—meetings, networking, visiting similar businesses—not just checking email
🌟 Diane's Key Mentors & Influences:
Catholic School Nun
Ex-Spouse (14 Years)
University of Phoenix FacultyRandom Helpers Throughout Life
👉 Don't miss this conversation about accidentally discovering hidden talents when forced into discomfort, walking away from everything at 35 to start over, and transforming adversity into superpower simplifying government complexity for people scared of letters they don't understand.
🔗 Connect with Diane Hagerty:
Email: dianne@grassrootstaxes.com
LinkedIn: Diane Hagerty
Company: Grassroots Taxes
Website: grassrootstaxes.com
📄 Transcript Available: How Diane Hagerty Solved $898,000 IRS Bill and Helps Small Businesses Navigate Tax Nightmares
📺 Watch on YouTube: Inspired Stories Podcast
🌐 Our Website: The Inspired Stories Podcast
📄 Special Thanks to Anthony Codispoti & AddBack Benefits Agency: AddBack Benefits Agency - Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line Website: addbackbenefits.com
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🎙️ From Accidentally Acing Accounting to IRS Enrolled Agent: Diane Hagerty's Journey Through Divorce, Starting Over, and Simplifying Tax Nightmares Diane Hagerty, IRS enrolled agent and owner of Grassroots Taxes in Springdale, Arkansas, shares her journey from teenage musician forced into accounting class by nun with no other options available—tried failing, got hundreds instead—to discovering natural talent balancing checkbooks and explaining financial concepts, through divorce at 35 walking away with nothing starting from scratch, to solving $898,000 IRS bill reduced to zero for client with addiction issues and acres of broken-down tractor trailers. Through stories about government losing payments and forms constantly, debunking internet tax myths about putting houses in LLCs, and rising from ashes giving valedictorian speech at University of Phoenix after rebuilding life one knuckle pushup at a time, Diane reveals how consistency beats year-end panic (10 minutes weekly versus giant pile in April), make money first before expensive business structures, and finding your people plus staying busy helping others transforms adversity into superpower simplifying thousand-page legislation into actionable plans. ✨ Key Insights You'll Learn: Accidentally discovered accounting talent: lazy teenager waited until day before school, nun said only accounting class open, tried failing but got hundreds on every assignment Natural financial gift emerged early: balancing friends' checkbooks, reading letters, explaining concepts without studying while everyone else failed accounting Divorce at 35 starting from scratch: walked away with nothing to avoid fighting, lost kids/business/friends, hadn't worked in years, no college degree finished $898,000 IRS bill reduced to zero: client with addiction issues, broken-down tractor trailers everywhere, IRS made up numbers when he stopped filing, took 3.5 years solving Government clerical errors constant: Arkansas Department of Finance loses payments, never credits forms, charges late fees despite filed extensions—just overwhelmed with volume IRS representation requires credentials: only attorneys, state CPAs, or enrolled agents can represent taxpayers before IRS during tax issues Tax preparation industry largely unregulated: anybody can prepare returns at big box places after taking class, no credential standards required Consistency principle beats panic: 10 minutes weekly recording receipts/mileage prevents giant pile in April, know how business performs before accountant tells you Make money first philosophy: test business idea before expensive LLCs/structures/fees, see if people buy product before paying state/setup costs annually Vacation tax deduction requirements: must do business activities daily that require physical presence—meetings, networking, visiting similar businesses—not just checking email 🌟 Diane's Key Mentors & Influences: Catholic School Nun Ex-Spouse (14 Years) University of Phoenix FacultyRandom Helpers Throughout Life 👉 Don't miss this conversation about accidentally discovering hidden talents when forced into discomfort, walking away from everything at 35 to start over, and transforming adversity into superpower simplifying government complexity for people scared of letters they don't understand. 🔗 Connect with Diane Hagerty: Email: dianne@grassrootstaxes.com LinkedIn: Diane Hagerty Company: Grassroots Taxes Website: grassrootstaxes.com 📄 Transcript Available: How Diane Hagerty Solved $898,000 IRS Bill and Helps Small Businesses Navigate Tax Nightmares 📺 Watch on YouTube: Inspired Stories Podcast 🌐 Our Website: The Inspired Stories Podcast 📄 Special Thanks to Anthony Codispoti & AddBack Benefits Agency: AddBack Benefits Agency - Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line Website: addbackbenefits.com