Year-end Tax Planning for 2022 (Part 2 of 2)

As we exit the first "post-COVID year," it's time to start thinking about 2022 tax filings this coming April. As always this time of year, I'm indebted to my good friend John D'Aquila, a certified public accountant and head of D'Aquila and Company LLP in Jacksonville, Florida, ( for sharing some of his year-end tax tips with...Read more

Year-end Tax Planning for 2022 (Part 1 of 2)

As we reach the end of the first "post-COVID year," it's hard to even think of another income tax deadline in three to four months.

But as Mark Twain once observed, the only two things you can count on in life are death and taxes.

The good news is that the post-COVID "return to normalcy" means your small business probably had a better year ...Read more

Preparing Your Cap Tables the Right Way

"We have kind of a 'good news, bad news' problem in our business.

On the one hand, a local angel investor has offered to buy 15% of our company for $300,000.

On the other hand, we don't know exactly who owns our company. My brother and I inherited my father's 80% share in the business when he died last year, and the remaining 20% is owned by...Read more

School's (Almost) Out ... Time for Tutoring!

"I'm a retired teacher, and I'm thinking about buying one of the 'after-school tutoring' franchises. The franchise agreement says that I'm responsible for complying with all state and local laws but doesn't give any guidance as to what I need to look for. Can you give me an idea of what I will need to do?"

It's amazing how many startup ...Read more

Dealing With Taxes When You Sell Your Stock

"I invested in a small business corporation several years ago. The investment hasn't worked out the way I thought it would, and now I'm looking for the exit door.

Is there any way I can recoup some of my investment by taking a deduction on my taxes?"

The short answer to this question is "maybe."

First, take a look at the corporation's books...Read more

When an LLC Makes a 'Subchapter S' Election

"I have operated a service business for the past few years as a limited liability company (LLC) and have been quite successful.

My accountant is recommending that I change my LLC so it's taxed like a subchapter S corporation. I understand she is trying to save me money on taxes by doing this, but I'm confused by what I'm reading on the ...Read more

Are You Giving Advice, Guidance, Feedback or Something Else?

As a columnist, expert and blogger on legal and tax issues affecting small businesses and entrepreneurial companies, you can bet your bottom dollar I get a ton of emails, phone calls and text messages asking me for my opinion on various matters -- just about every day.

Whenever I receive a question -- either from a reader's email or from the ...Read more

When Posting on Social Media, Consider Your 'Political Opponent'

"If one writes in a secret Facebook group something not very complimentary about another Facebook member, and that person finds out and prints a screenshot of the posting, does one need to be concerned about legal liability?

Also, if said person wants to write an apology, would a lawyer recommend that this was an OK way to prevent a lawsuit? ...Read more

When the IRS Sends You a Letter

Few things in life are more unsettling than getting a letter from the IRS -- especially if you don't think you did anything wrong.

The recent Inflation Reduction Act allocated nearly $80 billion to the Internal Revenue Service to close the enforcement gap between what the IRS is collecting and what it should be collecting. Right now, even as ...Read more

Why Your Kid Should Major in Philosophy

Maybe it's the change of seasons (I've always been a big early fall fan), maybe it's because I am now pushing 70, but I've been spending more time than usual reflecting upon my past.

Whenever you reflect on "things you should have done differently," you almost always end up going back to your high school and college years. A lot happened ...Read more

'If You Can't Convince Them, Confuse Them'

"I run a small contracting business. I have been hired as a subcontractor on a large construction project -- a 40-story downtown office building.

I am told there are more than 70 different contractors who will be working on this project. My company will be responsible for only a small piece of it.

The subcontract they want me to sign is ...Read more

Getting Started in an Occult Business

"I am in the process of watching one of your YouTube videos and I was wondering what your thoughts are on spiritual/New Age stores.

I do know that it is best to have a business location that has some sort of draw, and I am located in between two cities with retail shops like this, making it, what I feel, a good place to locate a shop like ...Read more

Going for the Handyman Special

"I am a general contractor and builder whose business has gone downhill with the current housing downturn. I have decided to start a local handyman business to help ride out the storm. I would greatly appreciate your opinion of this business in this market."

With new home construction winding down due to higher interest rates and a shortage ...Read more



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