Lead with Clarity.

Build with Structure. Grow with Confidence.

The CentsableCEO™ is an executive-level forum for entrepreneurs who want to run financially sound, structurally healthy businesses.

This is not a course. This is not consulting.

Delivered through a live, facilitated roundtable, CentsableCEO™ delivers decision-level clarity for business owners who want to understand what matters, why it matters, and how to think through inevitable business scenarios – before preventable problems become expensive and overwhelming.

Join CentsableCEO™

of small businesses cite financial and operational confusion as their biggest risk (Federal Reserve)

of business failures are tied to management and decision-making gaps – not lack of effort (SBA)

EAs nationwide – advisory capacity is limited and still being developed, requiring business owners to understand more before delegating.

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

Most entrepreneurs don’t struggle because they aren’t working hard enough. They struggle because they were only given fragmented advice about money, operational structure, and growth – creating reactive leadership and forcing critical decisions without reliable frameworks or informed perspective.

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

Lead Differently

CentsableCEO: Turning Chaos into Clarity

CentsableCEO™ is built for entrepreneurs who carry real decision weight – financial, operational, and personal.

The roundtable format slows decisions down before they create downstream consequences. Rather than prescribing actions, each session sharpens how you frame problems, recognize patterns, and choose direction aligned with your actual objectives.

This forum is intentionally designed for business owners who:

  • Make decisions with real financial and operational impact
  • Want to lead growth instead of reacting to it
  • Understand effective leadership is rooted in clarity, not control
  • Are tired of the hidden costs of uninformed delegation

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

1. What’s actually driving this situation? (not just what’s visible)
2. Which assumptions or gaps are creating repeat problems?
3. What does responsible leadership require before action is taken?

You don’t leave with worksheets or tactics. You leave with clearer judgment, stronger framing, and confidence in your decisions.

This is not execution support. This is leadership calibration.

Explore the CEntsableCEO Experience

The CentsableCEO™ Framework

Six Pillars for Responsible Business Leadership

PILLAR 1

Personal Financial Management & Tax Compliance

Your business cannot outperform your personal financial discipline. Understand how budget and debt behavior, personal decisions, and compliance habits influence business outcomes.

PILLAR 2

Tax Resolution & Entrepreneur Readiness

Tax problems don’t start with the IRS, they start with misunderstanding. Learn how to assess risk, responsibility, and readiness for business ownership before issues compound.

PILLAR 3

Impact & Profit Clarity

Revenue without margin or purpose creates fragile businesses. Define what success truly means – financially and operationally – so growth and well-being are sustainable.

PILLAR 4

Business Financial Management

Learn how to interpret financial statements, project cash flow and plan for profitability, while being aware of the early signs of instability – instead of reacting to it.

PILLAR 5

Business Infrastructure

Boundaries, positioning, and process are not optional. This pillar addresses legal separation, operational structure, differentiation, and systems that reduce chaos and dependency.

PILLAR 6

Positioning & Readiness to Scale

Prepare for growth, hiring, and expansion without sacrificing stability. Scaling requires readiness and discipline – ambition alone is not enough.

See how the process works

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.

See how this fits within Taxley Join CentsableCEO™

A structured path forward

How the CentsableCEO™ Works

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

Step 1

Register

SECURE ANNUAL MEMBERSHIP

CentsableCEO™ is offered as an annual membership to ensure consistency, depth, and commitment. This is leadership development – not casual content sharing.

registration open year-round

Protects the depth, discretion, and seriousness.

Step 2

Align

COMPLETE REQUIRED LIVE ORIENTATION

To establish shared language, expectations, and readiness – all members must complete one live orientation before participating in roundtable sessions.

Live sessions – no recordings

Typically held the 4th Mondays from 10a-3p ET

Step 3

Participate

Engage in live roundtables

After orientation, members participate in weekly CentsableCEO™ roundtables – this is where judgment sharpens, leadership is strengthened, and clarity deepens.

live sessions only – no recordings

Typically held Wednesdays from 10a-11:30a ET

What’s included:

  • Annual CentsableCEO™ membership
  • Orientation to align member goals + clarity
  • Live roundtable sessions (no recordings)
  • A professional, discreet learning environment
  • 36 sessions of structured progression through the CentsableCEO™ framework
  • Q&A focused on principles and decision-making, during live sessions

We intentionally do not provide templates or tactics – because execution only works after clarity, and this forum is designed to sharpen judgment and decision-making before action.

annual Investment

$4,999

Built for entrepreneurs who understand that clarity, judgment, and leadership discipline are competitive advantages.

Secure your Seat

Frequently Asked Questions

CentsableCEO™ is a live, executive-level roundtable for business owners who want to strengthen how they think, decide, and lead – particularly around money, structure, risk, and growth.

It is not consulting, coaching, or coursework.

CentsableCEO™ is for serious business owners – whether building, stabilizing, or course-correcting – who are responsible for decisions with real financial and operational consequences.

Readiness matters more than business stage.

No.

There is no individual business advising, no implementation support, and no file or document review.

This forum focuses on decision-making frameworks and leadership judgment, not doing work for you.

Each live session centers on one pillar and applies a structured decision lens:

  • What’s really driving this situation?
  • Why do problems repeat?
  • What does responsible leadership require before action?
  • What does responsible leadership require after a problem exists?

You leave with clarity, framing, and confidence – not tasks or templates.

No business-specific consulting occurs.

Q&A time focuses on principles and leadership thinking, not individual company details. You are never required to share confidential information.

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

CentsableCEO™ is intentionally live. Presence, discretion, engagement, and judgment matter more than content libraries.

Participant recording is strictly prohibited.

Roundtable sessions are typically held weekly – on Wednesdays from 10a-11:30a ET. Exact dates will be provided upon enrollment.

  • 2 sessions per CentsableCEO pillar are discussed monthly
  • All 6 pillar are covered over a 12-week period, 2-3 times annually

Yes.  

Orientations are conducted via Zoom and typically held on the 4th Monday of each month from 10a to 3p EST, with a lunch break from 12p – 1p.

All new members must complete a live orientation session before participating in Roundtable sessions. Orientation ensures shared language, expectations, and alignment.

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.

Membership begins with 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.

Yes.

Members may join at any point. Pillars repeat on a structured cadence, and orientation ensures alignment. Serious members catch up.

Because consistency, commitment, and seriousness matter.

This is leadership development – not casual content consumption

CentsableCEO™ operates under Taxley and aligns with its mission to strengthen small businesses by improving clarity, readiness, and collaboration between entrepreneurs and professional advisors.

Annual Membership: $4,999

Includes:

  • Full year of live Roundtable access
  • Required live orientation
  • All scheduled pillar sessions for the year

No. CentsableCEO™ is a live, annual membership and is non-refundable.

Once enrollment is confirmed, your membership secures access to orientation, scheduled live sessions, and the reserved capacity of a closed leadership forum. Because participation is live, time-based, and capacity-constrained, refunds, prorations, or partial credits are not offered.

We encourage prospective members to review the program details carefully before enrolling to ensure alignment.

Clarity is a Competitive Advantage

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

Join CentsableCEO™