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.

View All Roundtables Explore CentsableCEO Methodology →

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 →

Upcoming CentsableCEO Roundtables

Each Roundtable explores a different aspect of entrepreneurship through practical discussion, real-world experience, and the CentsableCEO methodology. Attend one conversation – or continue learning throughout the year.

  • Entrepreneurship Gave Me Options, Not the Ease I Imagined

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

    Learn More & Reserve Your Seat

  • 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.

    Learn More & Reserve Your Seat

  • CentsableCEO Roundtable - Taxley

    The Business is Making More Money but I Still Feel Broke

    Together we’ll explore why business growth doesn’t always create financial stability, the warning signs entrepreneurs often miss, and how stronger financial awareness supports better decisions.

    Learn More & Reserve Your Seat

  • Taxley - Tax Resolution for Entrepreneurs

    The IRS Notice Didn’t Create the Problem. It Revealed It.

    Together we’ll explore why entrepreneurs develop tax problems, the realities that commonly contribute to them, and why lasting resolution often requires understanding more than tax debt.

    Learn More & Reserve Your Seat

  • Is My Business Creating the Future I Actually Want?

    Together we’ll explore how today’s business decisions shape future opportunities, flexibility, and success – and whether your business is creating the future you actually want.

    Learn More & Reserve Your Seat

Bring These Conversations to Your Organization

Taxley’s Founder & CEO, Anisha Bailey, EA, speaks to organizations, associations, and professional communities on entrepreneurship, business leadership, tax responsibility, and financial clarity. Request a Speaking Engagement →

What is CentsableCEO™?

CentsableCEO™ is built on one belief: entrepreneurship requires 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.

CentsableCEO exists to strengthen the judgment behind those decisions through practical conversations, professional guidance, and ongoing development.

The CentsableCEO™ Methodology

Entrepreneurs strengthen judgment across six areas through CentsableCEO Roundtables and member-exclusive workshops.

Pillar 1: Entrepreneur Readiness

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

Learn More

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.

Learn More

Pillar 3: Operational Infrastructure

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

Learn More

Pillar 4: Financial Management

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

Learn More

Pillar 5: Tax Responsibility & Resolution

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

Learn More

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.

Learn More

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.

Tax Problem Prevention Membership

Prevent IRS and state tax problems before they begin through proactive tax account oversight, ongoing professional guidance, and entrepreneur development.

Explore Prevention Memberships
Taxley - Tax Resolution for Entrepreneurs

IRS & State Tax Resolution

Resolve IRS and state tax problems with an experienced Enrolled Agents who understands the realities of entrepreneurship.

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 compliance.

Request a Speaker