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weinstein_josh's avatar
Oct 22, 2021

Full Time RV living as a S Corp/1099 employee

First post here so thanks for any and all opinions/comments!



Long story short, I have the opportunity to sell my home and buy an RV to go travel full time while working in a virtual job. Timeframe is within the next 4-8 months. My employer is very open to the idea as we have clients nationally that need our attention, so I can plan my travel routes around our clients/needs. I have a few connections with good accountants (past employment) and have already begun opening discussions with them about how to arrange this to maximize expenses, taxes, income, etc



I have a meeting lined up on 10/25 to discuss more in depth, but thus far I have spoken to my FL accountant who suggested establishing a corporation (most likely S Corp) with a FL address and then approach my employer to discuss becoming a 1099 employee paid to my corporation.



My main questions and interest with this post center around others who may have done this and have some experience in the process as far as things to consider. Please feel free to comment and share if you have been in a similar situation or know others who may have done something like this.

23 Replies

  • Josh,

    I don't know the total ins and outs of what you are planning, but I worked out of my coach as a contractor (doing specialty work on racing sailboats) and it worked out great. This was before smartphones and good traveling internet access. I had to keep finding where (like fast food places and libraries) where I could pinch wire.

    Now, I just set the phone as a hotspot and buy the unlimited plan. When Starlink gets fully on line, that would be the cats pajamas for you. The other satellite services were too slow and very expensive.

    I used to end the year with both bunches of invoices and 1099s from insurance work, so I had to find a good accountant. If the work involves relocating at all ever during the year, then the coach expenses are deductible. Keep good records and you can win at this.

    Matt
  • YOU can become a 1099 subcontractor without the expense of S Corp ... The main reason for establishing an S Corp, or LLC would mostly be liability. They are similar, altho basically, an S Corp is a tax strategy, LLC also limits personal liability.

    If you have no liability exposure in your job, less reason to establish one. I was a 1099 Sub for years, and found no tax advantage to establishing an S Corp or an LLC ... only a liability advantage, especially if you have employees or 'assistants' ... if not, you are increasing your overhead costs. I'd weigh those costs versus the costs of operating as an independent subcontractor.

    I'm not an attorney nor an accountant, but my experience is based on operating three 'freelance' companies over past forty years.

    Tax and liability laws may be different now, but it never made sense for me to file taxes, pay accountants, and carry overhead for a company when I was the only 1099 Sub in my world - and operated independently for several 'employers' ...

    Pay can be piece work, contract fees, or hourly - never mattered.

    Recently, the Feds - and some states - are trying to eliminate freelance workers. I believe that's mainly to increase employment taxes to the state, not necessarily to assist freelancers ...

    CA and FL (maybe other states ??) attempted to force Uber and Lift drivers, writers, photographers, artists, to become employees instead of subcontractors, which would severely limit the ability for drivers or artists to create a personal work schedule around college, training, or family issues. The Feds and state argue that if you have only ONE employer, you are not freelance ... as debatable as that might become over who pays your tab.

    The question and example arose: How does a wedding photographer become an employee for every bride and groom that hires him/her for a wedding and reception.