Small Businesses and the IRS

by | Jan 2, 2018 | Toby Talks Tax

Uncle Sam’s sniffing around in your affairs is not limited to your private emails and cell phone conversations. Your small business’s paper and electronic trails may be leaving behind the heady scent of money strong enough for Uncle Sam to track. And Uncle Sam does...

Travel and Taxes

by | Sep 9, 2017 | Toby Talks Tax

I hear yelps from the Water Cooler Area that the Boss plans to have me accompany her to a dog show in New York for fun. That means I might be out of the office for a few weeks, as I’ll need to put on the dog a bit before the big event.  So the big question is:  Can...

Employment Tax Deductions

by | Jul 17, 2017 | Toby Talks Tax

I’ve been working this same job as Assistant Office Manager my entire life, so last week I decided it might be time to sniff out some other possibilities. Not that the perks at Law Offices of Christy Lee, P.C., aren’t much appreciated, you understand – those...

Gambling and Taxes

by | May 20, 2017 | Toby Talks Tax

I think I look good sitting around the poker table in Vegas.  There I am, all spiffed out in a diamond collar, groomed nails, and a satin vest.  (Ix-nay on the cigar, whiskey, and entourage of fluffy line dancers all named FiFi.  The boss doesn’t like it when I bring...

Early Withdrawal of Retirement Funds

by | Mar 24, 2017 | Toby Talks Tax

The Boss frequently treats me to discounted rates for a sound advice.  But lately I’ve faced a few problems with my financial planning that I don’t want to discuss with her – if I confess that I’m thinking about digging into my retirement accounts to fund a few...

Roth IRA

by | Feb 23, 2017 | Toby Talks Tax

I have to figure out if it’s a good idea to risk paying taxes now on funds that I will be stashing away for later, which I can enjoy “tax-free” at the time of withdrawal.  The big question is:  What if I don’t live long enough to take out and spend tax-free all the...