Ask Terry Archives

My hubby and myself are in our late 70s and each have 2 managed funds. One is an S&P 500. I have been considering switching to one of the index funds that follow the S&P. Is there a website I can see a comparison between the 2 for say 5-10 year period? Do you have…

Hi, Terry have watched you for a long time on WGN. My daughter is halfway thru her Junior year of college. I had planned to sell stock upon graduating in May 2019, to payoff her Stafford and our parental student loans. We currently claim her as a dependent and itemize deductions. With the looming changes…

Are funds raised through "Go Fund Me" pages taxable? Recently it was reported on the news that some young woman had started a "Go Fund Me" page for a homeless veteran and (at that time) had raised nearly $400,000. Does she have to pay income taxes on the money raised? I realize that if the…

Hello Terry . I watch you all the time on wgn in the morning and try to follow your advice as best I can. Unfortunately in the past year I have found myself in a bit of a financial crisis. I have accumulated about 5300 dollars in debt due to credit cards and a loan.…

My daughter graduated college in May and now her student loan grace period is over. She’s got over $140,000 in loans of which $105,000 are from private lenders because my husband & I have had our own financial troubles and our credit has suffered. We did not qualify for the Parent Plus gov. loans. Our…

Hi, Terry, I listen to your advice on wgn radio and love your energy and wonderful suggestions. My 22 year old son just started his career in engineering and will be getting his first paycheck soon. He is living at home with me and my husband for a bit to save up money. He has…

My daughter has around $15,000 in credit card debt and making minimum payments. She worked as a NICU nurse at Rockford Memorial Hospital but has had to go on disability due to horrible migraines. She has migraines 5-7 days a week and was not able to tend to the little premature babies. She also has…

With news of the College Illinois 529 program being halted again, I was hoping you can advise what families should do who have already started investing in this program. Luckily our child is only in 4th grade so college is not in the immediate future. We have about $17,000 saved in the program to date.…

a friend is asking me to invest in bitcoins with him. Is this safe and legal ? Or is it a pyramid type investment?

When doing a revocable living trust what is included or necessary within the trust? Seems when you talk to attorneys they attempt to sale you all these additional services that add up and before you know it you are several thousand dollars into the process. What would be the most economic way to have one…

I have 2 stocks that are losers Green Hunter Energy and Bretburn Energy. Can I sell them and get a write off on my taxes? Should I sell just one or both to get the tax write off? Should I do it now before the possible new tax laws?

My first question was the other day what was the name of the website for people that can invest with no minimums. Well I found out that it's stockpile.com I've called different locations regarding the stockpile gift card most people are dumb phone and have no idea what it is. Is that what we're supposed…

Hello, and thank you for your time. I have 2 small businesses and was looking at offering insurance. I saw your article on the small business special enrollment period. When I go to the site you reference, I do not see "find insurance for your business" I see find plans, then small business and then…

How to get your free financial organizer

My husband is 72. He has been paying approximately $1000 a year for Whole Life insurance. He had to purchase it when we purchased the house - to cover the loan. The house is now paid for. Is it still practical to continue the Whole Life? OR - change to a different insurance policy? I…

Hello Terry. I am new to your site but not new to listening to you. Are commercial mortgage bridge loans a good thing? Thanks. Jennifer

I retired early at age 62 and need to choose new health coverage. I can get my employer's retiree plan for 3 years with a very high premium, or COBRA at a lower premium but only for 18 months. That would then push me towards ACA. With so much uncertainty about the future of ACA,…

Good day Terry, My wife (age 47) owns her own business selling agricultural land in southern CA and is currently is getting health care through the ACA paying full premium and no discounts. She has no employees. Are there any better financial options. We appreciated your Small businesses get a break on insurance article this…

I have an older 403B plan from a previous employer. The balance is less than $50,000. I am retired and currently in the 15% tax bracket for the next few years as I am not yet drawing my pension. Since I am in the lower tax bracket for now, I was thinking of converting my…

My wife is currently covered under my job's insurance. August 2018 she will be 65-even though she will still be under my job insurance do she still need to enroll in Medicare? My retirement plan is another 6 years away. I work for a small firm with 20 employees. Thank You