Alumni Business Spotlight: Anisha Bailey on Leading with Clarity in Entrepreneurship
Half of all new businesses don’t make it past five years. Champlain College Online graduate Anisha Bailey, EA, MSEL, is motivated to change that.
“The reason we do what we do, and the foundation of our work, is really to help drastically reduce the five-year 50% business failure rate. And the way that we do that is by helping entrepreneurs make better decisions by understanding how they think through them,” shared Bailey.
Bailey left her role at Deloitte to found Taxley, an advisory firm focused on helping entrepreneurs build stable, well-structured businesses through disciplined decision making. She later became an Enrolled Agent, the federal government’s highest licensure in tax law, and earned her Master’s in Executive Leadership from Champlain College. With nearly two decades of experience working with entrepreneurs, she came to a consistent conclusion about why so many businesses struggle — one that is frequently overlooked in today’s fast-paced world of work.
The Real Problem
While doing tax resolution work, helping business owners navigate IRS and state tax problems, Bailey saw consistently that the tax issue was never the real problem, but a symptom of something deeper. “The issue has always been that they are making decisions without structure. Critical decisions about money, compliance, hiring, and growth are often made under pressure, without a clear structure to guide them.”
Her clients, across industries and revenue levels, understood their craft. What was missing was clarity on how to run their business and how to make sound decisions when things got complicated. That observation is what led her to create the CentsableCEO Framework, the foundation of Taxley’s advisory work.
The small business failure rate that Bailey cites has remained consistent in U.S. Small Business Administration data for years, and financial management is often identified as one of the leading contributing factors. Bailey’s work addresses that specific gap.
CentsableCEO: Slowing Down to Make Better Decisions
CentsableCEO is a decision-making framework created by Bailey that underpins Taxley’s advisory work. Unlike many programs on the market, Taxley’s approach is not self-paced or template-driven. Everything is live and centered on applying structured decision-making in real time. Engagement begins with a 90-minute working consultation, where the business and the founder’s personal and operational realities are assessed through the CentsableCEO framework. From there, ongoing advisory work focuses on implementing that framework in practice, and additional experiences such as the CentsableCEO Roundtable provide deeper application.
“The decision framework approach came from seeing so many people doing the wrong things very well,” Bailey explained. “Most business programs teach execution. They don’t teach you how to slow down and understand the environment you’re operating in, so you can make structured decisions.”
Her work focuses on preparing leaders to think through the framework before they execute decisions that lead to expensive problems.
“Most business programs teach execution. They don’t teach you how to slow down and understand the environment you’re operating in, so you can make structured decisions.”
A recent client example shows how this work plays out in practice. A business owner with two locations came to Bailey with a complicated tax matter he had been unable to resolve on his own. Part of the challenge was external: the IRS was not doing what it needed to do, and part of it was a lack of proper guidance.
After reviewing his numbers and considering his goals, Bailey identified that the real issue wasn’t just the tax situation, but how the business was structured. Her recommendation was clear: close one of the two locations.
It wasn’t an easy decision. “He took some time to process it,” she said. “But when he came back, he realized it was the right move. It really took some weight off his shoulders, which he didn’t realize was going to be the case.” Once the decision was made, execution followed. Within five months, the change was fully implemented.
For Bailey, the outcome was about more than resolving a tax issue. “Sometimes people just need clear guidance they can trust.”
Developing the Enrolled Agent Workforce
One of the major themes across Bailey’s work is that entrepreneurship is not just an individual concern. When small businesses fail, the effects extend outward, to employees, families, and the local economies that depend on them.
Through her work, she identified a broader gap: it is not just entrepreneurs who need better support, but the professionals who serve them. Traditional pathways into the Enrolled Agent profession do not consistently train practitioners to support entrepreneurs in a structured, advisory capacity.
In response, Taxley created ApprentEA, the first registered apprenticeship program for the Enrolled Agent profession, designed to establish a new standard for how practitioners are trained. The program focuses on developing Enrolled Agents who can operate within Taxley’s advisory philosophy and the CentsableCEO framework.
The goal is to equip professionals with both technical tax expertise and the ability to help entrepreneurs make structured, well-informed decisions. “Most advisory environments separate business strategy from the personal reality of the founder. In practice, they are inseparable,” Bailey explains. “If we’re not helping entrepreneurs navigate both, we’re not setting them up for long-term success.” By building a workforce trained in this approach, Taxley aims to expand access to high-quality advisory support, help more entrepreneurs operate with clarity, stability, and confidence.
For Students and Aspiring Entrepreneurs
Bailey’s advice to people considering entrepreneurship is consistent with everything she builds into her programs: take it seriously, and take your time.
“Entrepreneurship is not easy. Second to parenting, it can be the most challenging thing you ever volunteer to do.”
She encourages people to think carefully about what they actually want their business to accomplish. “Your business should fuel your personal goals. Be intentional about setting them so you can be the kind of person who can achieve them.” Bailey continues this message, sharing, “Entrepreneurs don’t fail because they lack effort. They fail because they are making decisions without structure.”
For Bailey, the work has always been practical: give entrepreneurs the context to make better decisions, and step in when IRS and state tax issues threaten stability — so they can stay focused on leadership. That focus, steady across nearly two decades, is what continues to drive her forward.
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