Tax Strategy for the ROBS (Rollovers as Business Start-ups)

Most entrepreneurs that engage in the ROBS business financing strategy want to operate the C Corporation and ROBS strategy in the most tax effective manner. There are a number of strategies that can be implemented to reduce taxes for a company and also for its business owners. 

Leading Retirement Solutions is equipped to lead these discussions with business owners, their attorneys and CPAs. Below are common examples of how an entrepreneur can reduce taxes with the ROBS business financing strategy. 

A designated Roth account is a separate account in a 401(k), 403(b) or governmental 457(b) plan that holds designated Roth contributions. The amount contributed to a designated Roth account is includible in gross income in the year of the contribution, but eligible distributions from the account (including earnings) are generally tax-free. The employer must separately account for all contributions, gains and losses to this designated Roth account until this account balance is completely distributed. 

An in-plan Roth rollover is a rollover from your 401(k) pre-tax account, into your own designated Roth account in the same 401(k) Plan. You generally include the taxable amount (fair market value minus your basis in the distribution) of an in-plan Roth rollover in your gross income for the tax year in which you receive it. In-plan Roth rollovers are not subject to the 10% additional tax on early distributions 

The plan administrator is responsible for keeping track of the amount of designated Roth contributions made for each employee and the date of the first designated Roth contribution for calculating an employee’s 5- taxable-year period. 

If you engage in the Roth conversion strategy and you have Roth monies invested in the C Corporation stock then any gain thereafter on the growth of the stock is forever tax-free. We can run through the real dollar effect of this with your accountant. For a business owner who invested pre-tax 401(k) monies into the C Corporation stock, this means that if those same monies are converted to designated Roth contributions, that the value of the C Corporation stock and earnings generated by the C Corporation stock, must be separately tracked. 

A 401(k) Roth Conversion maximizes capital returned to a participant’s retirement account for its investment. A Roth conversion, where pre-tax monies to be converted to Roth monies are currently invested in the C Corporation stock, should happen prior to the buyback of C Corporation stock, assuming the value of the stock will continue to increase and ultimately generate earnings. If you do not convert prior to a buyback of stock by the C Corporation, from the 401(k) Plan, you lose the benefit of claiming tax free earnings, assuming the value of the C Corporation stock has increased. This method extends the amount of time that the business remains a C Corporation, since the company can’t convert until all stock is redeemed. 

4. Reinvest your 401(k) money into another business venture 

There are ways to further invest the redeemed amounts in your 401(k) Plan. We work with clients who sell all or part of their business and rather than returning the sale proceeds back to the 401(k) Plan, immediately, they will use the money to finance another business venture. Are there more entrepreneur activities that you contemplate in the future where (a) you work at the enterprise, or (b) where you don’t? If so, those are priorities that should be considered.