CentsableCEO™ Roundtables
Start with a Conversation
Most entrepreneurs build their businesses while simultaneously learning the profession of entrepreneurship.
The complimentary CentsableCEO™ Roundtables create space for honest, interactive conversations about financial clarity, leadership, business decisions, and the realities of entrepreneurship.
Every discussion is grounded in nearly two decades of helping entrepreneurs navigate financial, operational, and tax challenges.
Whether you’re navigating growth, uncertainty, or increasing responsibility, each Roundtable is designed to strengthen entrepreneurial judgment before small challenges become larger ones.
05
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.
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.
What to 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.
Engage with us
Continue the Conversation
When you’re ready to go beyond the discussion, explore the next step that best fits your goals and business.
CentsableCEO Advisory
Continue strengthening your entrepreneurial judgment through ongoing Framework Discussions, Office Hours, and proactive tax visibility.
Strategic Analysis
When you need deeper insight, evaluate your business, financial position, and tax responsibilities to determine the right next steps.
Invite Anisha Bailey to Speak
Bring practical discussions about entrepreneurship, financial clarity, and tax responsibility to your organization or professional community.