CentsableCEO by Taxley™

Join Our Roundtable Conversations

Entrepreneurship requires far more than knowing how to do the work.

Every day, business owners make financial, operational, leadership, and tax decisions that shape the future of their businesses. The CentsableCEO™ Roundtables create space to strengthen that judgment through honest conversations and practical insights.

Every conversation is grounded in nearly two decades of helping entrepreneurs navigate financial, operational, leadership, and tax challenges.

Every Roundtable explores a different topic while building on the same CentsableCEO methodology. Join one – or join them all.

You can expect live, interactive conversations – not presentations. Bring your questions, learn from other entrepreneurs, and participate as much or as little as you’d like. Every Roundtable is complimentary and designed to help you think more clearly about the realities of business ownership.

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Upcoming Roundtables:

12

Aug – 2026

Entrepreneurship Gave Me Options, Not the Ease I Imagined

Let’s explore what entrepreneurship actually gives us, what it asks of us, and why success often looks different than we imagined when we first started.

  • Wed, 11:00 am – 12:00 pm EST
  • Online
Reserve Your Seat

02

Sept – 2026

I Know How to Do the Work. Why Is Running the Business So Hard?

Together we’ll examine why knowing how to do the work and knowing how to run a business are often very different skill sets, and why growth creates new challenges.

  • Wed, 11:00 am – 12:00 pm EST
  • Online
Reserve Your Seat
View All Roundtables Explore CentsableCEO Methodology →

What is CentsableCEO™?

CentsableCEO™ is Taxley’s proprietary entrepreneur development framework, built on one belief: entrepreneurship requires more than knowing how to do the work. Every day, business owners make personal, financial, operational, leadership, and tax decisions that shape both their businesses and their lives.

CentsableCEO helps entrepreneurs strengthen the judgment behind those decisions through honest conversations, practical education, professional guidance, and ongoing development.

CentsableCEO Roundtables and Workshops - Taxley Oversight & Guidance

The CentsableCEO™ Framework

The framework is organized around six connected pillars designed to help entrepreneurs move from doing the work to leading a sustainable business.

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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How entrepreneurs experience CentsableCEO™

Roundtables introduce the conversations. Membership creates the space to go deeper.

Complimentary CentsableCEO Roundtables help entrepreneurs explore important business realities through honest, interactive discussion. Oversight & Guidance members build on those conversations through structured workshops, Q&A sessions, and year-round guidance connected to the six pillars.

View Upcoming Roundtables Explore Oversight & Guidance

The CentsableCEO™ Methodology 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 - CentsableCEO - Taxley

    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.

    Learn More

  • Pillar 3 - Operational Infrastructure - CentsableCEO - Taxley

    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.

    Learn More

  • Pillar 3 - Operational Infrastructure - CentsableCEO - Taxley

    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.

    Learn More

  • Pillar 4 Financial Management - CentsableCEO - Taxley

    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.

    Learn More

  • Tax Account Monitoring - Taxley

    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.

    Learn More

  • Pillar 6 - Scale & Exit Readiness - CentsableCEO - Taxley

    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.

    Learn More

Next Steps

Continue Your Journey

Whether you’re looking to prevent future tax problems, resolve an existing issue, or bring these conversations to your organization, we’re here to help.

Taxley Oversight & Guidance™

Help prevent IRS and state tax problems through proactive tax account oversight, year-round Enrolled Agent guidance, and entrepreneur development.

Explore Prevention Memberships
Taxley - Tax Resolution for Entrepreneurs

IRS & State Tax Resolution

Resolve IRS and state tax problems with Enrolled Agents who understand the realities of entrepreneurship and have experience navigating complex tax matters.

Explore Tax Resolution
Taxley - CentsableCEO Coaching Tax Resolution Edition

Invite Anisha Bailey to Speak

Equip entrepreneurs with practical insights that strengthen financial clarity, leadership capacity, business judgment, and tax responsibility.

Request a Speaker