Executive Development for Entrepreneurs

As Your Business Evolves, So Do Your Responsibilities

Business ownership is more than building a successful company. As your business evolves, the financial, leadership, operational, and tax responsibilities you carry evolve with it.

CentsableCEO Advisory reinforces the entrepreneur’s ability to carry the evolving responsibilities of business ownership by strengthening entrepreneurial judgment through the CentsableCEO Framework, ongoing guidance, and proactive tax visibility.

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Anisha Bailey, EA, MSEL — Founder of Taxley

“Clarity is the entrepreneur’s competitive advantage.”

– Anisha Bailey, EA, MSEL | Founder & CEO, Taxley

The longer you’re in business, the more connected your decisions become.

A hiring decision affects payroll. A pricing decision affects profitability. A tax issue affects cash flow. A personal financial decision affects the business. What appears to be one decision often creates consequences somewhere else.

Clarity helps entrepreneurs recognize those connections earlier, evaluate decisions more intentionally, and respond before small issues become larger obstacles.

CentsableCEO Roundtables

Join complimentary discussions exploring financial clarity, business leadership, tax responsibility, and entrepreneurial decision-making.

Wednesdays • 11a – 12p EST • Online

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Guidance for the Responsibilities Ahead

CentsableCEO Advisory is Taxley’s ongoing advisory relationship for entrepreneurs seeking continued guidance as the responsibilities of business ownership continue to evolve.

Grounded in the CentsableCEO Framework, advisory combines Framework Discussions, Office Hours, and proactive tax visibility to reinforce entrepreneurial judgment and help entrepreneurs remain proactive as new opportunities and responsibilities emerge.

Rather than waiting until challenges require Strategic Analysis, Tax Resolution, or implementation support, CentsableCEO Advisory helps entrepreneurs stay engaged, informed, and prepared between major decisions.

CentsableCEO Advisory is delivered through these four integrated experiences, each designed to strengthen entrepreneurial judgment over time.

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Framework Discussions

Participate in live, group discussions exploring how entrepreneurs evaluate business decisions through the CentsableCEO Framework and its six interconnected pillars.

Office Hours

Continue the conversation during interactive Office Hours designed to deepen understanding of the framework, discuss broader entrepreneurial questions, and reinforce practical application.

Proactive Tax Visibility

Stay informed through ongoing tax account monitoring, compliance visibility, notice support, and proactive awareness designed to help you address tax responsibilities before they become larger issues.

Additional Strategic Support

When greater support is needed, Taxley provides Strategic Analyses, Tax Resolution, and implementation services tailored to the entrepreneur’s situation.

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You Don’t Have to Navigate Entrepreneurship Alone

Entrepreneurs engage with Taxley in different ways. Some come because they have an urgent tax issue. Others begin with a Strategic Analysis to better understand their business, financial position, and entrepreneurial responsibilities.

Many simply want an ongoing advisory relationship that helps them remain proactive as their responsibilities continue to evolve. CentsableCEO Advisory is designed for those entrepreneurs.

The CentsableCEO Framework

Business ownership isn’t one responsibility – it’s many. The CentsableCEO Framework helps entrepreneurs strengthen their judgment across six interconnected areas that influence every major business decision.

Pillar 1: Entrepreneur Readiness

Evaluate the personal, financial, and leadership capacity required to successfully carry the responsibilities of business ownership.

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Pillar 2: Impact & Profit Alignment

Build a business where the impact you create is supported by long-term profitability and the life you want it to sustain.

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Pillar 3: Operational Infrastructure

Create processes, systems, and operational discipline that reduce owner dependency and support sustainable growth.

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Pillar 4: Financial Management

Strengthen financial judgment by understanding the numbers that drive cash flow, profitability, business performance, and better business decisions.

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Pillar 5: Tax Responsibility & Resolution

Understand your ongoing tax responsibilities, navigate tax procedures confidently, and make informed decisions before small issues become larger problems.

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Pillar 6: Scale & Exit Readiness

Build a business that creates greater flexibility, value, and future options – whether you choose to grow, transition, sell, or lead differently over time.

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Explore the Complete Framework

The CentsableCEO™ Framework In Action

These six leadership pillars help entrepreneurs build businesses intentionally – from the first decision to long-term sustainability, scalability, and future opportunity.

Pillar 1: Entrepreneur Readiness

Format: Online

Evaluate the personal, financial, and leadership realities influencing your business so you can make stronger decisions, manage risk more effectively, and prepare for the increasing responsibilities that growth inevitably creates.

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Pillar 2: Impact & Profit Alignment

Format: Online

Build a business where the impact you create is supported by long-term profitability, personal priorities, and a business model designed to sustain both your mission and the life you want to build.

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Pillar 3: Operational Infrastructure

Format: Online

Build the systems, processes, and accountability that reduce owner dependency, improve consistency, strengthen professionalism, and create a business capable of operating successfully beyond you.

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Pillar 4: Financial Management

Format: Online

Learn to interpret financial and operational information so you can anticipate challenges, strengthen cash flow, and make informed business decisions before today’s numbers become tomorrow’s problems.

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Pillar 5: Tax Responsibility & Resolution

Format: Online

Understand how tax responsibilities, business decisions, and IRS procedures work together so you can reduce risk, respond confidently to challenges, and protect what you’re working so hard to build.

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Pillar 6: Scale & Exit Readiness

Format: Online

Build a business that creates greater flexibility, enterprise value, and future opportunities by increasing scalability, transferability, leadership capacity, and long-term optionality.

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Choose the Advisory Relationship That Fits Your Stage of Growth

CentsableCEO Advisory provides an ongoing advisory relationship that grows with your responsibilities as an entrepreneur.

Personal

$1,999 / year

– Best Value –

(or $199/mo. for 12 months)

For individuals preparing for business ownership by strengthening their entrepreneurial and financial readiness.

Includes:

Entrepreneur Readiness

Complete the mandatory New Member Orientation & Advisory Foundation.
Build entrepreneurial readiness through quarterly Entrepreneur Readiness Framework Sessions
Apply what you learn during quarterly Office Hours
Receive practical session summaries with key takeaways

Ongoing Tax Visibility & Support

Continuous monitoring of one personal IRS tax account (Single or MFJ)
IRS and state notice support
Proactive compliance reminders
Annual estimated tax or withholding review
Submit tax visibility questions through your member portal

Grow With You

Add state tax notice support
Request a Strategic Analysis
Engage Tax Resolution services

Choose Personal

Pro

$4,999 / year

– Best Value –

(or $499/mo. for 12 months)

For solo entrepreneurs with no employees building businesses or managing a small owner-operated business.

Includes:

Entrepreneur Development

Everything included in Personal
Build entrepreneurial capability through monthly CentsableCEO Framework Sessions
Apply the framework to your business during monthly Office Hours
Receive implementation-focused session summaries

Ongoing Tax Visibility & Support

Everything included in Personal
Continuous monitoring of one business tax account
Review personal and business tax notices
Proactive compliance reminders
Semiannual estimated tax or payroll withholding review
One monthly Tax Visibility Support Call

Grow With You & Your Business

Add Leadership Seats
Add additional business tax accounts
Request Strategic Analysis
Engage Tax Resolution services

Choose Pro

Enterprise

$9,999 / year

– Best Value –

(or $999/mo. for 12 months)

For entrepreneurs leading growing organizations with employees or increasing operational complexity.

Includes:

Executive Development

Everything included in Pro
Quarterly Executive Roundtables
Executive implementation strategy discussions
Annual Life & Business Alignment Review
Executive session summaries and strategic insights

Ongoing Tax Visibility & Support

Everything included in Pro
Payroll tax notice monitoring
Enhanced compliance visibility
Two monthly Tax Visibility Support Calls

Scale With Confidence

Add Leadership Seats
Add additional business tax accounts
Add sales tax visibility
Request Strategic Analysis
Engage Tax Resolution services

Choose Enterprise

Tax visibility support calls are limited to questions related to your tax visibility and support services: tax notices, account activity, and compliance visibility. Calls do not include tax planning, tax preparation, tax resolution, business advisory, or other professional services.

What Happens After You Join

Your membership begins with onboarding that establishes your advisory relationship, activates tax visibility services, and prepares you for your first sessions.

Step 01

Complete Onboarding

Establish your membership, configure proactive tax visibility, and prepare your personalized workspace.

Step 02

Stay Connected

Participate in Framework Discussions, Office Hours, and ongoing proactive tax visibility throughout the year.

Step 03

Gain Confidence

Apply what you learn as your responsibilities evolve, and engage Taxley whenever deeper analysis or implementation is needed.

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Need More Than Ongoing Guidance?

Most questions can be addressed through ongoing advisory. When significant tax matters, financial uncertainty, operational challenges, or major business decisions arise, Strategic Analysis provides the comprehensive analysis needed before recommendations are made.

You’ll receive a personalized roadmap with recommendations that may include Tax Resolution, continued CentsableCEO Advisory, implementation with Taxley, implementation with your existing advisors, or a combination of these approaches.

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Frequently Asked Questions

CentsableCEO Advisory is Taxley’s ongoing advisory relationship for entrepreneurs who want continued guidance as the responsibilities of business ownership evolve.

Through the CentsableCEO Framework, Framework Discussions, Office Hours, and proactive tax visibility, members remain connected to the guidance and perspective needed to make stronger decisions over time.

CentsableCEO Advisory is designed for individuals preparing for business ownership, entrepreneurs actively operating businesses, and business leaders who want ongoing guidance as their responsibilities continue to evolve.

The right membership depends on where you are in your entrepreneurial journey and the complexity of your responsibilities.

Personal is designed for individuals and married couples preparing for or exploring business ownership.

Pro is intended for one entrepreneur operating a business without employees.

Enterprise includes the primary business leader and allows additional leadership participants as outlined in the membership.

If your business structure changes over time, we’ll recommend the membership that best fits your evolving responsibilities.

No. Many members join simply because they value ongoing guidance and proactive tax visibility. Others continue their relationship after completing a Strategic Analysis or Tax Resolution engagement.

Proactive Tax Visibility combines IRS account monitoring, notice guidance, and ongoing awareness to help you identify potential tax issues earlier, understand their implications, and make informed decisions throughout the year.

IRS Account Monitoring: With your explicit authorization via Form 8821, Taxley monitors your IRS tax account throughout the year to identify changes, notices, and activity requiring attention.

Notice Guidance: We’ll review IRS and eligible state notices submitted by members according to their membership level, explain what they mean, discuss your options, and recommend appropriate next steps.

This service does not include direct communication with the IRS or state tax authorities. Representation before a taxing authority requires a separate Tax Resolution engagement.

Submit the notice through your member portal. Based on your membership level, we’ll review it, explain what it means, discuss your options, and recommend the most appropriate next step.

If representation before the IRS or state taxing authority is needed, we’ll discuss the appropriate Tax Resolution services before any additional work begins.

No. CentsableCEO Advisory is designed to strengthen your entrepreneurial judgment over time – not just answer questions. Framework Discussions, Office Hours, proactive tax visibility, and Session Briefs help members recognize opportunities, avoid preventable issues, and make stronger decisions as new responsibilities arise.

Framework Discussions and Office Hours are live, online group sessions with access to the meeting link through your member portal.

Because discussions often involve real business situations, sessions are not recorded, and members are required to participate with cameras on in a professional environment.

After each session, members receive a concise Session Brief summarizing the key concepts, discussion themes, and practical takeaways.

These sessions provide ongoing guidance in a group setting rather than private consulting.

The CentsableCEO Framework is designed to help entrepreneurs strengthen judgment by learning alongside other business owners facing similar responsibilities.

Framework Discussions, Office Hours, and Executive Roundtables create opportunities to ask questions, hear different perspectives, and apply the framework to real-world situations. When individualized guidance is needed, Strategic Analysis and implementation services are available separately.

Members may contact Taxley regarding the proactive tax visibility and support included with their membership, such as IRS account activity, IRS and state tax notices, compliance visibility, and related questions.

Guidance related to business strategy, leadership, financial decisions, or entrepreneurship is delivered through Framework Discussions, Office Hours, Executive Roundtables, or separate Strategic Analysis engagements.

A Strategic Analysis is appropriate when you need a comprehensive evaluation of your tax responsibilities, financial position, business operations, or entrepreneurial priorities before making significant decisions or addressing complex issues.

No. CentsableCEO Advisory provides ongoing guidance, Framework Discussions, Office Hours, and proactive tax visibility. When Strategic Analysis, Tax Resolution, or implementation services are appropriate, they’re recommended separately based on your specific situation.

Yes. As your responsibilities evolve, your membership can evolve with you. If your business grows beyond the scope of your current membership – or your needs become simpler – we’ll recommend the membership level that best aligns with your situation.

Tax visibility and advisory participation are handled separately.

If you’re enrolled as Married Filing Jointly, your spouse is included in the tax visibility services provided under your membership.

Entrepreneurial guidance through Framework Discussions, Office Hours, and Executive Roundtables is reserved for the enrolled entrepreneur.

This structure keeps discussions focused while ensuring the appropriate tax accounts receive proactive visibility.

You may enroll either monthly or annually.

Annual membership offers the best value and includes onboarding at no additional cost. Monthly membership provides a lower barrier to entry but includes a one-time onboarding fee and a higher monthly rate.

This flexibility allows entrepreneurs to begin receiving support without requiring a large upfront investment.

Annual memberships are non-refundable. Monthly memberships renew each month and may be canceled before the next billing cycle.

No. CentsableCEO Advisory is an ongoing advisory relationship that helps entrepreneurs strengthen judgment and maintain proactive tax visibility throughout the year.

Tax preparation involves preparing and filing tax returns. Tax Resolution addresses existing IRS or state tax problems. When those services become appropriate, they’re recommended separately based on your specific situation.

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