Help thinking through ROBS

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May 25, 2026

by a searcher from Lehigh Univervsity in Orlando, FL, USA

Looking for some guidance on thinking through if I should go down the ROBS path or use more liquid funds and trying to weigh the pros/ cons on this thing… Background - Need to free up north of $0.5M to fund an acquisition - Option #1: Sell stocks and pay long term capital gain tax - Option #2: Use ROBS to fund, avoid paying long term capital gain tax, and maintain more liquid assets for post-close operating flexibility - Of course could do a hybrid of the two, say 51/ 49 split Trying to think through the pros and cons With ROBs - I like maintaining more liquid assets post close and not triggering a fairly meaningful tax event. Of course those “savings” would be offset to some degree by setup cost and ongoing program cost Understand double taxation to some degree - but can leave cash in the business for the first year or two to at least delay that tax bill? Can the c-corp use those excess funds to buy-back the ROBS share? Or would I need to pay myself (double taxation) and then buy-back ROBS shared? If the first worst, then it may seem more palatable if the c-corp can by back the shares out of operating CF. Rambling here - net net looking for guidance on how to think through thins one and what I may be missing
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Reply by a searcher
from Pennsylvania State University in Miami, FL, USA
I am hearing about this for the first time with your post and now I’m in the same boat! Thanks for the question. I’m going to look into it over this week.
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Reply by a searcher
from Indiana University at Bloomington in Miami, Florida, United States
Going through the same thought process myself, interested to hear comments or discuss with you once you learn more
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