Whittaker General Contracting
I had been operating as a sole proprietor for 8 years and finally got tired of the personal liability. File.Business formed the LLC, set up the right insurance partners, and walked me through the Florida CILB license transfer.
Tom Whittaker, Founder · $2.2M revenue · 9 employees + 6 sub crews · Formed 2023
The situation
Tom operated as a sole proprietor general contractor for 8 years. After a near-miss accident on a project site, he decided he needed liability separation.
What File.Business did
Formed Floridan LLC. Transferred Florida CILB (Construction Industry Licensing Board) license to the LLC. Set up Florida sales tax and employer withholding. Coordinated commercial general liability insurance (~$8K/year) and workers compensation through partner broker. Created subcontractor agreement templates.
The outcome
Personal liability separated from business. Insurance premiums tax-deductible at LLC level. Subcontractor agreements protect against misclassification claims. $2.2M year-1 revenue post-LLC.
Key facts
| Industry | Construction |
|---|---|
| Entity structure | Floridan LLC |
| Year formed | 2023 |
| Scale at story point | $2.2M revenue |
| Team | 9 employees + 6 sub crews |
About this case study
This is a representative composite case study based on patterns we see across many similar customers. Names and identifying details have been changed. The structure, services, and outcomes described are typical of customers in this segment.
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- What is it
- Whittaker general contracting: how a construction business set up with file.business is a regulated business process governed by federal or state agencies. File.Business handles the paperwork, filings, and tracking for you.
- Why it matters
- Doing this correctly the first time avoids penalties, late fees, and personal liability exposure for owners.
- Who needs it
- Any US business that has triggered the relevant requirement - usually based on entity type, state, or business activity.
- When it is due
- Deadlines vary by agency and state. We track your specific dates and remind you ahead of any filing window.
- How it works
- Tell us what you need, review the prepared filing, and we submit through the agency's official channel.
- What it costs
- Pricing is shown on this page with state and federal fees disclosed separately from our service fee.
- Risks of skipping
- Penalties, administrative dissolution, loss of liability shield, blocked transactions, or audit triggers depending on the filing.
- Alternatives
- File directly with the agency yourself, hire a law firm, or use a competing service. File.Business is the fastest premium option.