CentsableCEO by Taxley™
CEO Development for Growth-Minded Entrepreneurs
CentsableCEO is an entrepreneur development experience focused on helping entrepreneurs expand their skillset beyond their craft so they can improve decision-making, financial visibility, and operational effectiveness.
With nearly two decades of experience helping entrepreneurs navigate tax, financial, and operational complexities, Anisha Bailey, Founder & CEO of Taxley, created CentsableCEO as a space to share honest insight and practical guidance entrepreneurs can apply to the businesses they’re building.
“Entrepreneurship Requires Knowing More Than Your Craft.”
– Anisha Bailey, EA, MSEL | Founder & CEO, Taxley
Many entrepreneurs start businesses because they are good at what they do. But building and sustaining a business requires a broader set of skills – financial awareness, operational discipline, sound decision-making, leadership, and the ability to see how each part of the business affects the others.
CentsableCEO is designed to help entrepreneurs strengthen those capabilities so they can make better decisions and build businesses that are more sustainable over time.
Experience Our CentsableCEO™ Roundtables
Entrepreneurship requires more than knowing how to do the work. It requires developing the judgment to make sound financial, operational, leadership, and tax decisions.
CentsableCEO™ Roundtables are complimentary recorded conversations that explore the realities of owning and leading a business through candid discussion, practical insight, and different perspectives.
New conversations are released throughout the year, giving entrepreneurs a simple way to learn, reflect, and strengthen how they think about the businesses they’re building.
09
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.
CentsableCEO™ 90-Day Intensive
CentsableCEO is an annual 90-day CEO development experience that helps entrepreneurs strengthen the skills needed to lead beyond the technical work of their craft.
Prepare
2 Weeks of Guided Pre-Work
Assess where you are today, identify priorities, gather key financial and operational information, and prepare to make the most of the intensive.
Immerse
5-Day In-Person Intensive
Work through the six CentsableCEO pillars through practical instruction, facilitated discussion, real-world application, and guidance from experienced professionals.
Implement
Support Through Day 90
Return to your business with ongoing group support focused on implementation, decision-making, problem solving, and applying what you learned.
The Framework in Practice
The six CentsableCEO pillars provide the structure for the 90-day experience.
Participants examine their businesses across the areas that most often determine whether growth becomes sustainable – the owner’s readiness, financial management, operations, tax responsibility, leadership, profitability, and long-term direction.
The goal is not simply to gather more information. It is to leave with stronger judgment and a clearer understanding of what your business requires from you as its CEO.
Pillar 1: Entrepreneur Readiness
Assess your readiness to lead the financial, operational, and leadership demands of business ownership.
Pillar 2: Impact
& Profit Alignment
Build a business where impact, profitability, and the life you want can coexist.
Pillar 3: Operational Infrastructure
Create processes and systems that reduce owner dependence and support sustainable growth.
Pillar 4: Financial Management
Strengthen financial judgment around cash flow, profitability, and business performance.
Pillar 5: Taxpayer Rights
& Responsibility
Understand your tax responsibilities, navigate procedures confidently, and make informed decisions early.
Pillar 6: Scale
& Exit Readiness
Build greater flexibility, value, and future options for how you grow, transition, sell, or lead.
What You’ll Build During the Intensive
Leave with more than ideas – leave with a clearer way to lead.
CentsableCEO is offered once each year in a limited cohort. Join the interest list to receive first access to dates, location, program details, and enrollment.
Meet the Founder
Anisha Bailey, EA, MSEL
For nearly two decades, Anisha Bailey has worked directly with entrepreneurs through the financial, operational, tax, and leadership challenges that often surface as businesses grow.
As Founder & CEO of Taxley, she has personally represented 500+ tax resolution matters and helped business owners navigate cash-flow pressure, tax debt, operational strain, and high-stakes financial decisions.
Building Taxley, and later Sorbailee, reinforced a pattern she had already seen in clients: entrepreneurs are often highly skilled at what they do, but must learn how to lead, manage money, build systems, and make sound business decisions in real time.
CentsableCEO was created to help entrepreneurs bridge that gap – strengthening the capabilities required to move beyond doing the work and into leading the business.
Clarity is the Entrepreneur’s Competitive Advantage
Entrepreneurs rarely struggle because they lack effort. More often, they struggle because important decisions are made without enough clarity. Better clarity leads to better judgment, better decisions, and stronger businesses.
The 90-Day Intensive is offered once each year in a limited cohort. Join the interest list to receive first access to dates, location, program details, and enrollment.