Tax Resolution & Integrated Business Advocacy

Lead with Clarity.

Build with Structure. Grow with Confidence.

CentsableCEO™ is an executive-level decision forum for entrepreneurs who want to lead with clarity, structure, and intention – before momentum locks them into the wrong path.

This is not a course, a mastermind, or consulting.

This is leadership calibration.

A disciplined space for decision framing – so you manage money smarter, run your business better, and collaborate with advisors before mistakes get expensive.

of small businesses fail within the first five years (SBA – Bureau of Labor Stats)

of small businesses report financial or operational challenges (Federal Reserve)

of an employee’s first-year earnings is the average cost of a bad hire (Dept of Labor)

You Don’t Need To Do More. You Need To Lead Differently.

Most entrepreneurs don’t struggle because they lack effort. They struggle because decisions about money, structure, and growth are shaped by fragmented advice – leaving leaders exposed when clarity, context, and disciplined judgment matter most.

CentsableCEO™ exists to provide a decision framework most business owners were never given – before avoidable mistakes become expensive.

Explore the Framework

CentsableCEO™: From Chaos to Clarity

CentsableCEO™ is built for experienced business owners, founders navigating growth or change, and serious prospective owners who want to understand what responsible ownership actually requires – before committing capital, time, or authority.

The roundtable format is a structured environment designed to strengthen how decisions are framed before action is taken – so execution aligns with reality instead of urgency, and professional advice can actually be used effectively.

This forum is designed for leaders who want to lead growth intentionally, reduce the hidden costs of uninformed delegation, and operate from clarity instead of control.

How Decisions Are Framed

Each session centers on one core pillar of the CentsableCEO Framework and applies a disciplined decision lens:

1. What decision is actually being made?
2. What assumptions or gaps are shaping it?
3. What does responsible leadership require before action?

You don’t leave with worksheets, templates, or tactics. You leave with clearer judgment, stronger framing, and confidence in your decisions – so delegation and execution happen from a position of clarity.

This is leadership calibration.

Attend an info session

The CentsableCEO™ Framework

CentsableCEO™ provides a six-pillar, progression-based decision framework you cycle through year-round to build clearer thinking around money, structure, compliance, and growth. This isn’t a one-time “assignment” – it’s a repeatable leadership framework because the decisions don’t stop.

PILLAR 1

Personal Finance & ENTREPRENEURSHIP Readiness

Unexamined personal financial pressure shapes how owners frame business decisions, distorting risk tolerance, pricing, and growth.

PILLAR 2

Tax Compliance & Resolution

Misunderstood tax obligations and resolution options frame decisions through fear, leading to reactive and costly outcomes.

PILLAR 3

Impact & Profit Clarity

Misalignment between impact and profit drives growth decisions that feel meaningful but cannot sustain the business or owner.

PILLAR 4

Business Financial Management

Limited financial understanding shapes decisions that feel reasonable short-term but undermine cash flow and growth capacity.

PILLAR 5

Business Infrastructure

Unclear legal and financial separation shapes misinformed decisions, increasing personal risk and complicating delegation and growth

PILLAR 6

Scale & Exit Readiness

Unexamined assumptions about growth and succession limit intentional expansion and future exit options.

Learning more effective decision-making skills is cheaper than fixing avoidable mistakes. CentsableCEO™ exists so experience doesn’t have to be your most expensive teacher.

Meet the Founder & Facilitator

Anisha Bailey, EA, MSEL

Anisha Bailey is an award-winning entrepreneur and federally licensed Enrolled Agent with nearly two decades of experience inside the financial, tax, and operational realities of small businesses.

Through years of representing entrepreneurs in complex tax and financial matters, she observed a consistent pattern: business failure is rarely caused by lack of effort – it is caused by lack of clarity, structure, and readiness for ownership responsibility.

Rather than continuing to solve problems one business at a time, Anisha focused on building what the system lacked. She created the nation’s first federally registered workforce development pathway for Enrolled Agents – establishing structured standards for developing advisory-ready professionals at scale.

She also created CentsableCEO™ as a leadership forum designed to strengthen how entrepreneurs think, decide, and collaborate with advisors, as she transitioned away from consulting.

CentsableCEO™ reflects a simple belief: strong small businesses require both capable advisors and capable owners – and both must be developed intentionally.

Join CentsableCEO™

Clarity is a competitive advantage

Join the CentsableCEO™

A disciplined membership experience for business owners who value clarity, structure, and informed leadership.

Step 1

Annual membership ensures depth, consistency, and commitment.

Step 2

Orientation

One required live orientation establishes shared language, expectations, and readiness.

Step 3

Live Roundtables

Live sessions sharpen judgment, leadership clarity, and advisor collaboration over time.

What’s Included:

Annual CentsableCEO™ membership
Orientation to align member goals + clarity
36 live roundtable sessions (no recordings)
A professional, discreet decision forum
Guided Q&A decision framing sessions
No templates, tactics, or homework

Annual Investment

Individual

Seat

Limited Time

Founding Member

First Year Rate*

$4,999

~~Standard: $7,499~~

Includes 1 non-transferable seat

Leadership Team

Block

Limited Time

Founding Leadership Team

First Year Rate*

$14,999

~~Standard: $22,499~~

Includes 3 non-transferable seats

This investment is intentionally priced below the cost of common leadership mistakes – including a single mis-timed hire, a reactive tax fix, or a missed growth decision.

One seat must be held by the owner or primary decision-maker. Additional seats are for named key leaders.

*Founding Member rates reflect a limited-time scholarship for early participants. Standard membership rates apply at renewal.

Join CentsableCEO™

Frequently Asked Questions

CentsableCEO™ is a live, executive-level decision forum designed to strengthen how entrepreneurs frame decisions about money, structure, and growth before execution creates avoidable consequences.

This is not an educational program or advisory service. It is a structured environment that builds disciplined thinking, judgment, and leadership clarity over time.

CentsableCEO™ is for entrepreneurs and their leadership team who carry – or are preparing to carry – real ownership responsibility.

This includes experienced business owners, founders navigating growth or change, and serious prospective owners who want to understand what responsible ownership actually requires before committing capital, time, or authority.

Readiness and seriousness matter more than revenue or business stage.

No.

CentsableCEO™ does not provide one-on-one coaching, consulting, implementation guidance, document review, or tactical advice. It is also not a peer mastermind or networking group.

This is a facilitated decision forum focused on how leaders think, not on telling members what to do next.

Each live session applies a disciplined decision-framing process within one of the six CentsableCEO™ framework pillars.

Discussions focus on:

What’s really driving this situation?
What decision is actually being made?
What assumptions or gaps are influencing it?
What does responsible leadership require before action?

Members leave with clarity and framing – not checklists or assignments.

CentsableCEO™ is not a case-by-case advisory forum.

Members may reference scenarios for context, but the focus remains on decision logic, not on diagnosing or solving individual businesses concerns. This protects confidentiality, keeps the room executive-level, and ensures value is not dependent on whose situation is being discussed.

CentsableCEO™ is intentionally live. The value comes from presence, real-time thinking, and a discreet environment where leaders can engage without concern that discussions will be replayed or shared.

We ONLY record sessions for internal quality control – recordings are not shared outside of our internal team or stored long-term.

Participant recording is strictly prohibited.

Yes.

All members must complete one live orientation before participating in roundtables. Orientation establishes shared language, expectations, and participation standards so the forum remains focused, disciplined, and valuable for everyone in the room.

Orientations are conducted via Zoom and typically held on the 4th Monday of each month from 1p-4p ET.

The first available orientation, after you register, dictates your membership start date. Delaying orientation does not extend your membership period, but it will delay your ability to participate in the roundtables.

We encourage you to register when you carve time out of your schedule to participate in the orientation session.

Decision-making skill compounds through repetition, not one-time exposure.

CentsableCEO™ is structured as an annual membership to ensure continuity, depth, and shared context across the full decision cycle business owners experience throughout the year. This is not a drop-in or transactional experience.

Roundtable sessions are typically held:

Jan. – Mar., May – Jul., and Sept. – Nov.
1st – 4th Wednesdays

Exact dates are listed in the CentsableCEO Guide and will also be provided upon enrollment.

Membership begins the date you have access to the next available live orientation, based on your registration timing.

Your annual membership term and renewal date are anchored to the date of the first orientation you have access to.

Roundtable participation unlocks only after orientation is completed – no exceptions.

Membership time does not pause, defer, or extend due to delayed participation in orientation.

CentsableCEO™ is designed for leaders who value disciplined thinking and long-term clarity. If you are looking for fast answers, tactical fixes, or passive content, this forum will not be a fit.

A Clear Path Forward

Choose Your Next Steps

If you’re tired of reacting, guessing, or learning the hard way, this is where you strengthen how you lead – before decisions cost more than they should.