AI Assistants

Built-in help when you get stuck

Every BossWorks account includes six AI Assistants. Each one is focused on a specific part of starting a business and uses your business context — type, city, stage, plan — so answers are specific to your situation, not generic advice.

6Assistants
24/7Available
$0Extra cost
How they work
Context-aware answers, not generic advice

Each Assistant reads your business plan as context before answering. A bakery owner in Brooklyn and a freelance designer in Phoenix asking the same question get different answers, because the Assistants factor in your business type, city, stage, and what is already in your plan.

Answers come with sources where available. Recommendations link directly to the next step inside your plan — a permit application, a supplier directory, a pricing template — so you can act on the answer without leaving the platform.

Ask any of them a question and you get an answer in seconds. When a question needs a licensed professional, the Assistant will say so and tell you what kind of professional to talk to.

Frequently asked questions

No. All six are included in the $20 per month or $200 per year subscription.

There is no hard limit on questions during normal use.

No. They give you information, options, and trade-offs. You make the call.

Yes. For anything that needs a licensed lawyer, accountant, or specialist, the Assistant will say so directly.

Ready to launch your first business?

BossWorks gives first-time founders a complete plan, city-specific launch checklist, funding matches, and six AI Assistants — all in one place.