IRS & State Tax Resolution for Entrepreneurs

IRS & State Tax Problems Require Calm Strategy

When tax pressure escalates, reactive decisions often make the situation worse. Our enrolled agents help entrepreneurs assess exposure clearly, stabilize the situation, and determine the most responsible path forward.

With nearly two decades of experience representing entrepreneurs with tax problems, our advisory-based approach addresses both the immediate tax issue and the broader pressures contributing to it.

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Request a 15-minute Clarity Call

A private discussion designed to assess your situation, determine fit, and identify the most appropriate next step. This conversation is intended to provide clarity and direction – not legal or tax advice.

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Behind many tax problems is an entrepreneur carrying too much pressure for too long.

Tax problems rarely begin with the IRS. They often develop slowly through operational pressure, cash flow strain, reactive decisions, and inconsistent compliance over time.

At CentsableCEO™, we evaluate and resolve tax matters in consideration of the broader realities affecting the entrepreneur – including operational structure, financial pressure, compliance exposure, and long-term decision-making.

Tax Problems Rarely Exist in Isolation

For many entrepreneurs, tax problems are often connected to broader patterns developing beneath the surface – operational pressure, cash flow strain, rapid growth, unclear visibility, or prolonged reactive decision-making.

That is why our enrolled agents approach tax resolution differently.

Our work is designed not only to address the immediate IRS or state matter, but also to help entrepreneurs better understand the conditions contributing to the issue so they can move forward with greater stability and control.

What this often includes:

Clarifying the root causes contributing to the issue
Evaluating operational, compliance, and cash flow pressures
Establishing a structured resolution strategy

The goal is not simply resolving the immediate tax matter with a payment plan, hardship request, or Offer in Compromise. The goal is ensuring your rights are protected, while helping you move forward with clarity on how to run and grow your business more sustainably.

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857+ Clients Served Nationwide

Every tax situation is different. Outcomes depend on the facts of the case, financial realities, compliance history, and the willingness to address the situation proactively.

IRS liabilities $722,000 + state $109,966 → dual OICs approved for $14k and $25k
Liens released and operational pressure reduced
Firefighter & Entrepreneur
Wilmington, OH
$76k IRS balance → lien released + home refinance approved
Passport reinstated; Cash flow increased by ~$2,000/mo.
Retired Educators
Lithonia, GA
$4M+ payroll tax liabilities and active levies → $0/month (hardship status)
No further threat to business continuity or enforced collections
Healthcare Company
Lanham, MD
5 years unfiled + ~$400K exposure (incl. TFRP) → compliance restored + ~$50K penalties abated
Levies released; operations simplified; CNC secured; cash flow improved
Entrepreneur | Multi-location Auto Business
Marietta, GA
$2M+ including Trust Fund penalties → $207,228 OIC approved
Federal liability resolved; no further risk of levy
Executive Director
Bowie, MD
$184,279 + unfiled returns + Social Security levy → $500 OIC approved
Compliance restored; retirement income protected
Retired Doctor
Highland, IN
$153,086 state tax debt; harsh levies → state balance eliminated
Levies released; peace of mind restored
Married Couple
Racine, WI

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Sustainable Resolutions Requires More Than Negotiation

Resolving a tax matter is important. Preventing the same patterns from creating future exposure matters just as much.

That is why CentsableCEO™ approaches tax resolution through both representation and advisory support – helping entrepreneurs address the immediate issue while strengthening the business decisions and operational habits surrounding it.

The goal is not simply getting through the tax problem. The goal is helping entrepreneurs move forward with greater confidence and control.

start with a Private Clarity Call

How Tax Resolution Works

Our process is designed to establish clarity, verify the facts, and determine the most responsible path forward.

Step 01

Private Clarity Call

The process begins with a private conversation designed to understand the situation, assess immediate concerns, and determine the most appropriate next step.

step 02

Investigation & Evaluation

Our enrolled agents conduct a formal investigation with the IRS and state agencies while working with you to evaluate the operational, financial, and personal pressures contributing to the situation.

Step 03

RESOLUTION & Stabilization

We manage the tax resolution process while helping entrepreneurs strengthen the financial habits, systems, and visibility needed to move forward more sustainably.

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Meet the Founder & Lead Enrolled Agent

Anisha Bailey, EA, MSEL

Anisha Bailey is a federally licensed Enrolled Agent who founded Taxley in 2008, has specialized in IRS and state tax resolution since 2012, and established the CentsableCEO™ in 2025.

Through nearly two decades of working with business owners, she has seen firsthand how tax problems develop – and how disciplined strategy can resolve them.

Her approach emphasizes clarity, disciplined decision-making, and resolution strategies grounded in the broader realities affecting the entrepreneur as a whole.

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Common Questions

The Clarity Call helps determine whether tax resolution support is appropriate and whether the situation aligns with our approach. This conversation helps us understand the urgency, concerns, and broader pressures affecting the entrepreneur before formal investigation begins.

Our enrolled agents conduct a formal review of IRS and state tax records while evaluating the operational, financial, compliance, and decision-making pressures contributing to the situation. This phase establishes clarity and helps determine the most strategic path forward.

Our work is designed to create clarity and control – not simply establish payment plans or file paperwork.

When entrepreneurs come to us with serious tax problems, there are often broader pressures affecting decision-making, operations, compliance, and financial stability behind the scenes.

While we manage the tax resolution process itself, we also help clients strengthen the structure, visibility, and habits needed to move forward more sustainably.

Depending on the situation, that may include strategic guidance, implementation support, or operational recommendations designed to reduce future instability.

The goal is not simply resolving the immediate issue. The goal is helping entrepreneurs regain stability, confidence, and control – long-term.

Yes. As federally licensed enrolled agents, we are authorized to represent taxpayers before the IRS and manage communication with the appropriate tax authorities throughout the resolution process.

Traditional tax resolution firms often focus only on settling the immediate tax issue. Our approach combines strategic tax representation with advisory support designed to strengthen operational structure, financial visibility, and long-term decision-making, so entrepreneurs can move forward with greater stability and control.

Every case is different. Timelines depend on the complexity of the matter, responsiveness of the taxing authorities and client, documentation requirements, and the entrepreneur’s financial and operational situation.

During the evaluation phase, we establish realistic expectations, and outline the most appropriate next steps.

Tax resolution services are delivered within a structured engagement under a formal service agreement; nothing on this page modifies or supersedes those legal terms.