Small Business Leadership Development

Lead with Clarity.

Build with Structure. Grow with Confidence.

CentsableCEO™ is an executive-level decision forum for entrepreneurs and leadership teams who want to lead with clarity, structure, and intention – before momentum turns into expensive mistakes.

This is not a course, a mastermind, or one-on-one consulting.

It’s a live executive forum designed to sharpen decision framing before execution.

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

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 and leadership teams navigating growth or change, and serious startups and prospective owners who want to understand what responsible ownership actually requires – before deeply committing capital, time, or bandwidth.

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 chaos.

How Decisions Are Framed

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

1. What rules govern the issue at hand?
2. What assumptions or limitations are shaping the decision actually being made?
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.

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 missing opportunities or fixing avoidable mistakes. CentsableCEO™ exists so experience doesn’t have to be your most expensive teacher.

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Meet the Founder & Facilitator

Anisha Bailey, EA, MSEL

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

Through years of helping entrepreneurs navigate IRS and state tax pressure, cash-flow strain, and high-stakes operational decisions, she saw a consistent pattern: failure is rarely caused by lack of effort. It happens when pivotal decisions are made under pressure – without a shared framework to evaluate tradeoffs, risks, and responsibility.

CentsableCEO™ was created to solve that upstream problem: a live decision forum designed to strengthen how entrepreneurs and leadership teams frame decisions, align internally, and collaborate with advisors – especially when the stakes are high and the consequences are real.

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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
A professional, discreet decision forum
Guided Q&A decision framing sessions
Exclusive access to CentsableCEO™ business vault
Post-Session Debrief notes – decision framing anchors
Exclusive access to CentsableCEO™ Certification path

Annual Investment

Seats are assigned to named participants and may not be shared. Each seat must be held by the owner/founder or an authorized executive decision-maker (e.g., COO/President) representing the business.

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

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

This isn’t just better thinking. It’s demonstrated leadership.

CentsableCEO™ equips owners to lead with clarity, control, and credibility across the realities that determine long-term stability – so perception aligns with performance.

Demonstrating Leadership

CentsableCEO™ Certified

Exclusive to active CentsableCEO™ members, certification is awarded to businesses that meet our defined standard of leadership and stability. The process is rigorous and evidence-based. More than a marketing label, CentsableCEO™ Certified signals verified clarity across financial, structural, and framework realities.

The CErtification process

Step 1

Assessment

We assess your business against the CentsableCEO™ framework to confirm what currently meets the standard – and what is not yet verifiable.

Step 2

Verification + Evaluation

We verify IRS and state tax compliance and risk factors, and evaluate whether leadership and structure align with the full CentsableCEO™ standard.

Step 3

Certification

Members who meet the standard earn CentsableCEO™ Certified status, renewable every three years, with active membership required to maintain the designation.

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Frequently Asked Questions

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

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.

It is not a training course and not a one-on-one advisory service. It’s a structured environment that builds disciplined thinking, judgment, and leadership clarity over time.

CentsableCEO™ is for entrepreneurs and leadership teams 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™ is a live, facilitated decision forum. It does not include one-on-one consulting, coaching, document review, or implementation work. Sessions focus on decision framing inside the six pillars, so leaders can evaluate tradeoffs clearly and execute responsibly.

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.

No—sessions are live only and not available for replay.

After each session, members receive Debrief Notes (a short written set of decision-framing anchors for reference). Debrief Notes are not a transcript, not minutes, and not a recording.

We may record internally for quality control, but recordings are not distributed.

Participant recording is strictly prohibited.

No. CentsableCEO™ is not a case-by-case advisory service. Sessions teach the rules, tradeoffs, and decision logic within the six pillars—so you can apply them in your business and lead from clarity, not dependency. If you need a business-specific designation, the CentsableCEO™ Certified path is the appropriate next step.

This is leadership calibration. You bring real context, but the work is learning how to frame decisions responsibly: what to ask, what to verify, and what tradeoffs you’re actually accepting – so your execution (and your advisors’ execution) becomes more effective.

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 Wednesday of each month from 10a-12p 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.

Yes. Seats may be sponsored for a delegated executive decision-maker (e.g., COO/President/CFO) authorized to represent the business in the forum. Seats are assigned to named participants and may not be shared.

Sponsors do not attend roundtables, office hours, or gain access to weekly briefs unless they purchase their own seat.

For CEOs who want visibility without full participation, an optional annual Sponsor Add-On is available at registration and includes:

The CentsableCEO™ Sponsor Pack (framework overview + standards)
Two CEO briefings per year (online group setting) to stay aligned with what your leadership team learning

No written summaries, 1:1 support, or business-specific guidance are included. All sponsor access must be elected at the time of registration or renewal – no prorating or mid-year additions.

Roundtable sessions are typically held:

Jan. – Mar., May – Jul., and Sept. – Nov.
1st – 4th Wednesdays
Live sessions: 1:30 – 3PM ET, Office Hours: 3 – 4 PM ET

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.

You don’t need to be perfect—you need to be responsible. CentsableCEO™ is for owners who are willing to slow down decision-making, verify what’s true, and lead with discipline. If you’re looking for fast answers, tactics, or someone to “take this off your plate,” it won’t be a fit.

Members gain clearer judgment, stronger decision framing, and better advisor collaboration across the six pillars, so leadership decisions are made deliberately, with fewer preventable consequences. CentsableCEO™ isn’t a promise of results; it’s the operating standard that protects growth.

CentsableCEO™ Certified is a formal designation available to active members whose business meets the CentsableCEO™ standard of leadership and stability. It is evidence-based and includes verification to confirm established compliance, standards, and leadership clarity. Certification is renewable every three years, and active membership is required to maintain the designation.

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.

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