The CEO Business Startup & Scaling Playbook was created to help entrepreneurs ask the right questions before launching or scaling their businesses. Written by attorney and consultant Alessandra Cortina, this guide helps founders better understand the legal, financial, and operational considerations that often get overlooked in the early stages of business.
Instead of navigating these decisions blindly, this playbook helps you walk into conversations with your attorney, accountant, insurance advisor, and other professionals prepared, confident, and informed.
Inside, you’ll find a practical CEO founder checklist along with essential questions to ask professionals about:
- Business structure and legal protection
- Taxes, bookkeeping, and financial systems
- Contracts and intellectual property
- Hiring, payroll, and employment compliance
- Business insurance and risk management
- Launching and protecting digital products
- Structuring partnerships and collaborations
Whether you’re launching your first business or preparing to scale an existing one, this playbook helps you build your business with clarity, protection, and intention.
Because successful businesses aren’t built by guessing, they’re built by founders who ask the right questions.

