How JustAnswer Works:

  • Ask an Expert
    Experts are full of valuable knowledge and are ready to help with any question. Credentials confirmed by a Fortune 500 verification firm.
  • Get a Professional Answer
    Via email, text message, or notification as you wait on our site.
    Ask follow up questions if you need to.
  • 100% Satisfaction Guarantee
    Rate the answer you receive.

Ask jgordosea Your Own Question

jgordosea
jgordosea, Enrolled Agent
Category: Tax
Satisfied Customers: 3026
Experience:  I've prepared all types of taxes since 1987.
3653323
Type Your Tax Question Here...
jgordosea is online now
A new question is answered every 9 seconds

Turn my stock investing hobby into a business per IRS

Resolved Question:

I would like to setup a business structure, where I can buy/sell dividend and income bearing stocks/ETFs/funds and use the income as "revenue", while deducting expenses such as health premiums, health expenses, miscellaneous home office expenses, and retirement contributions. I also want the resulting business to make my wife and I eligible for group small business health insurance. Finally, I want the assets of the business to remain in the joint revocable trust my wife and I have set up. What is the best structure to achieve this?  Note, the income from this business will be my only source of income, and I want to avoid double taxation on that income.  There will be no employees, except myself and my wife.

Submitted: 10 months ago.
Category: Tax
Expert:  jgordosea replied 10 months ago.

Greetings,

 

The likely best entity for accumulating portfolio income and deducting fringe benefits is a C corporation.

 

From http://www.nysscpa.org/cpajournal/1999/0899/features/F40899.HTM

"10. When can a C corporation be recommended?

The following are the three most advantageous situations:

 

* There is a need to reinvest profits for reasons such as capital expansion. Limited income splitting can occur, resulting in the C corporation obtaining the benefit of the 15% and 25% tax brackets on the first $75,000 of taxable income.

In addition, there is the availability of excluding 70% of the dividend income of publicly-traded stocks as a result of the dividends received deduction. This is beneficial for nonappreciating securities being held for investment by the corporation (e.g., preferred stock).

 

* The full deductibility of the type of fringe benefits (principally health insurance including dental, optical, and long-term care or nursing home coverage) is not available to the owners of partnerships, S corporations, and LLCs having more than a two percent interest.

 

* A corporation formed in a state without a corporate income tax (e.g., Nevada) can be funded with money and assets in order to lend (in a secured manner) or lease to a corporation in a state where business operations are being conducted. This can reduce the corporate income taxes in the latter state by shifting income in the form of deductions such as interest and lease payments, or perhaps royalties and licensing fees, to the corporation in the state without taxation.

 

This strategy can be utilized provided a bona fide corporate office presence exists in the tax-free state (e.g. a Nevada corporate resident agent headquartered in Carson City). Though the implications of any applicable unitary tax must be considered, Federal law prohibits states from taxing interstate commerce when activity (such as from the corporation formed in the tax-free state) is limited in the high tax state to such activities as the solicitation of orders. This concept was expanded in 1992 by the U.S. Supreme Court case Wisconsin Department of Revenue vs. Wrigley, in which the Court ruled that "solicitation" includes ancillary activities such as recruiting, training, and evaluating an in-state sales force."

 

Especially in regard to your desire to be eligible for and able to deduct group health insurance the C corporation is the only entity. Owners of partnerships, S corporations, and LLCs having more than a two percent interest are not permitted to deduct fringe benefits in the same manner as C corporation employees.

Likely the best arrangement for office expenses would be an accountable plan to reimburse the employee for the business use of the home (and other expenses).

 

Having the assets remain in the revocable trust is problematic as the entity has to be the owner of the assets in order to claim the income from the assets. The trust is a separate entity and ownership does have to transfer to the entity as the income can not be assigned from the trust owner to the entity.

This goal is not compatible with an entity that owns the assets and has income for tax purposes from those assets.

 

Although the provisions of the trust would have to be examined and adhered to there may be a possibility of having an entity (such as a C corporation) be paid fees from the trust to manage the assets of the trust and retain asset ownership by the trust along with the deductions by the corporation. Issues relating to registration and security laws would need to be checked to ensure the entity, or the employees, need not be subject to licensing or other regulation as a manager of investments.

 

An arrangement that I have seen used for family assets is a limited partnership with the individuals (along with others such as children and grandchildren) as limited partners and a corporation as the general partner. The corporation is wholly owned by the grantor parent and the health insurance is paid by that corporation. There is not much difference in using an S corporation or C corporation for that purpose in my experience. This structure can be effectively used to gift partnership interests to the child and grandchild partners each year up to the annual gift exclusion.

 

Hopefully this provides some possible choices for structure that you can discuss with your tax practitioner that can advise, with all the facts, what may be best in your case.

 

Please ask if you need more discussion or clarification.

Thank you.

Customer: replied 10 months ago.

Thanks for your answer. If I understand it correctly, I can minimize the double taxation by keeping assets and resulting dividend income to a small amount above the total deductions allowed, further cushioned by being able to shelter 70% of the dividend income from taxation. I am not interested in the Nevada complexity. Are the dividends from the C corp to me treated as qualified dividends? If so, the main downsides are not keeping assets in the trust, but I can get around that if the shares in the C corp can be in the trust? The other downsides are the cost of setting it up and the state annual license/tax as well as the cost/hassle of making my wife and I employees in the C corp for the purposes of getting corp insurance. Just for completeness, my understanding is that as a sole proprietor business, hiring my wife as an employee, my business can pay for my wife (and her dependent husband - me) individual health plan premiums and deductible/co-payments and deduct those costs under a Section 105 HRA. Is this not true? If true, can I set my investment business up as a sole proprietorship business?

Expert:  jgordosea replied 10 months ago.

Hello again,

 

Are the dividends from the C corp to me treated as qualified dividends?

Since this is not a foreign corporation and if the holding period is met then so long as the dividend is not "of the type listed later under Dividends that are not qualified dividends " they will be qualified dividends.

See http://www.irs.gov/publications/p550/ch01.html#en_US_2012_publink100010086

Yes, these can be qualified dividends when not in those excepted types.

 

If so, the main downsides are not keeping assets in the trust, but I can get around that if the shares in the C corp can be in the trust?

 

Presumably the trust agreement is written such that the shares could be held by the trust. There is no general rule that would prohibit such ownership so only trust restrictions would prevent such ownership.

 

...as a sole proprietor business, hiring my wife as an employee, my business can pay for my wife (and her dependent husband - me) individual health plan premiums and deductible/co-payments and deduct those costs under a Section 105 HRA. Is this not true?

This is true.

If true, can I set my investment business up as a sole proprietorship business?

No, individual investor (as contrasted with a trader) is not in a trade or business.

 

For more on investor versus trader see http://www.irs.gov/taxtopics/tc429.html

"To be engaged in business as a trader in securities, you must meet all of the following conditions:

  • You must seek to profit from daily market movements in the prices of securities and not from dividends, interest, or capital appreciation.
  • Your activity must be substantial, and
  • You must carry on the activity with continuity and regularity.

 

The following facts and circumstances should be considered in determining if your activity is a securities trading business:

  • Typical holding periods for securities bought and sold.
  • The frequency and dollar amount of your trades during the year.
  • The extent to which you pursue the activity to produce income for a livelihood, and
  • The amount of time you devote to the activity.

 

If the nature of your trading activities does not qualify as a business, you are considered an investor..."

 

From your description your activity ("buy/sell dividend and income bearing stocks/ETFs/funds" would not qualify as a trade or business for tax purposes.

 

Indeed you need to consider the cost (time, trouble, and expense) of using any such structure against the benefit in your circumstance. Besides payroll implementation and taxes there will be additional income tax returns for the corporation. For example, in California there is often a minimum annual franchise tax due.

 

Hope this clarifies for you in order to consult a local tax practitioner with all the facts.

 

Please do continue to ask if you need more help on this question.

If you would like more assistance on another question please use my name within the question to alert other experts.

 

Thank you for the opportunity to be of service.

jgordosea, Enrolled Agent
Category: Tax
Satisfied Customers: 3026
Experience: I've prepared all types of taxes since 1987.
jgordosea and other Tax Specialists are ready to help you

JustAnswer in the News:

 
 
 
Ask-a-doc Web sites: If you've got a quick question, you can try to get an answer from sites that say they have various specialists on hand to give quick answers... Justanswer.com.
JustAnswer.com...has seen a spike since October in legal questions from readers about layoffs, unemployment and severance.
Web sites like justanswer.com/legal
...leave nothing to chance.
Traffic on JustAnswer rose 14 percent...and had nearly 400,000 page views in 30 days...inquiries related to stress, high blood pressure, drinking and heart pain jumped 33 percent.
Tory Johnson, GMA Workplace Contributor, discusses work-from-home jobs, such as JustAnswer in which verified Experts answer people’s questions.
I will tell you that...the things you have to go through to be an Expert are quite rigorous.
 
 
 

What Customers are Saying:

 
 
 
  • I really was impressed with the prompt response. Your expert was not only a tax expert, but a people expert!!! Her genuine and caring attitude came across in her response... T.G.W Matteson, IL
< Last | Next >
  • I really was impressed with the prompt response. Your expert was not only a tax expert, but a people expert!!! Her genuine and caring attitude came across in her response... T.G.W Matteson, IL
  • I WON!!! I just wanted you to know that your original answer gave me the courage and confidence to go into yesterday's audit ready to fight. Bonnie Chesnee, SC
  • Great service. Answered my complex tax question in detail and provided a lot of additional useful information for my specific situation. John Minneapolis, MN
  • Excellent information, very quick reply. The experts really take the time to address your questions, it is well worth the fee, for the peace of mind they can provide you with. Orville Hesperia, California
  • Wonderful service, prompt, efficient, and accurate. Couldn't have asked for more. I cannot thank you enough for your help. Mary C. Freshfield, Liverpool, UK
  • This expert is wonderful. They truly know what they are talking about, and they actually care about you. They really helped put my nerves at ease. Thank you so much!!!! Alex Los Angeles, CA
  • Thank you for all your help. It is nice to know that this service is here for people like myself, who need answers fast and are not sure who to consult. GP Hesperia, CA
 
 
 

Meet The Experts:

 
 
 
  • Wallstreet Esq.

    Tax Attorney

    Satisfied Customers:

    570
    10 years experience
< Last | Next >
  • http://ww2.justanswer.com/uploads/KU/KUMI95/2013-9-30_195031_kumar.64x64.jpg Wallstreet Esq.'s Avatar

    Wallstreet Esq.

    Tax Attorney

    Satisfied Customers:

    570
    10 years experience
  • http://ww2.justanswer.com/uploads/CU/Cuttinggirl/2011-10-29_03719_wcrop2.64x64.jpg Wendy Reed's Avatar

    Wendy Reed

    Enrolled Agent

    Satisfied Customers:

    3052
    15+ years tax preparation and tax advice.
  • http://ww2.justanswer.com/uploads/CATax/2009-08-04_204548_Mark.jpg Mark D's Avatar

    Mark D

    Enrolled Agent

    Satisfied Customers:

    985
    MBA, EA, Specializing in Business and Individual Tax Returns and Issues
  • http://ww2.justanswer.com/uploads/IN/insearchoftheanswer/2013-8-16_0233_attorney.64x64.jpg Richard's Avatar

    Richard

    Tax Attorney

    Satisfied Customers:

    3229
    29 years of experience as a tax, real estate, and business attorney.
  • http://ww2.justanswer.com/uploads/MY/MyVirtualCPA/2012-7-5_44024_cookmegan1.64x64.jpg Megan C's Avatar

    Megan C

    Certified Public Accountant (CPA)

    Satisfied Customers:

    6121
    Licensed CPA, CFE, CMA who teaches accounting courses at Master's Level
  • http://ww2.justanswer.com/uploads/JG/jgordosea/2012-6-7_43138_GordosVeritas.64x64.jpg jgordosea's Avatar

    jgordosea

    Enrolled Agent

    Satisfied Customers:

    2783
    I've prepared all types of taxes since 1987.
  • http://ww2.justanswer.com/uploads/OZ/ozaukeecpa/2012-6-7_193219_Picture1croppedandshrunk.64x64.jpg MequonCPA's Avatar

    MequonCPA

    Certified Public Accountant (CPA)

    Satisfied Customers:

    2231
    CPA, Over 30 yrs experience w/individuals and small businesses. Masters in Tax.