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I grew up in a family business myself. We owned a popular barbershop and convenience store. My family worked very closely with the Small Business Administration (SBA). They have leaders that are committed to help Americans start and grow businesses. The SBA has staff located in various cities that carry out the mission of building business each day. They work collectively to advocate for small businesses and empower the spirit of entrepreneurship within the community. It is their main goal to help small businesses succeed.

A sole proprietorship is an unincorporated business that has just one owner who pays personal income tax on profits earned. Minimal paperwork and low set-up costs are two major benefits of having a sole proprietorship. According to the SBA, it’s the simplest and least expensive business type you can establish. A disadvantage of a sole proprietorship is that it rarely survives if the owner dies or is incapacitated. While a corporation is legally a separate entity from its owners and can be taken over by someone else, a sole proprietorship must be run by its owner.

A sole proprietorship can be turned into a Limited Liability Company (LLC). However, if the dad dies while still operating as a sole proprietor then the company dies with him. To transfer ownership, the dad must transfer ownership of relevant assets to his sons. The sons can begin a partnership with the sons by contracting them as sub-partners. However, the partnership can still die as with a sole proprietorship. 

Sole proprietorship cannot shift its owner. Therefore, it is best to change it to LLC and sell all shares to one of his sons. 

If someone wants to pass their successful one-person business to their two sons, they need to change the business type to allow shared ownership, usually to a general partnership or LLP. They'll create a partnership agreement that lays out what each son does and how much they own. They transfer the business assets and let everyone know about the change. They should also consider the tax impact and decide if the handover happens all at once or over time.

To transfer the business to his sons, the father can convert the sole proprietorship into a partnership. This involves creating a new partnership agreement, transferring business assets, and allowing the sons to co-own and operate the business.

The father can also convert the sole proprietorship into an LLC or corporation. This involves registering the new entity, creating a legal document outlining ownership and responsibilities, and transferring business assets. This option offers tax and liability benefits and provides a structured transition plan for family succession.

As another option, the father can gift or sell the business assets to his sons. After dissolving the sole proprietorship, they can start a new business entity. The transfer can be structured as a sale for tax purposes or a gift for a non-monetary transfer.

In a nutshell the father has three options: he can transfer assets to his sons so they can establish a new company or LLC, or he can turn the company into a partnership. Each option provides a way to ensure continuity of the family business, with varying levels of complexity and legal issues. The best course of action is to speak with a legal or tax expert.

From what I learned in my own family business this is a tricky process. Although they did not own sole-proprietorships after doing research I found there are some ways to work around this. Convert to an LLP and then workout the ownership between a legally binding contract and the two inheritors. This way there is no confusion, and no assets will be lost.