# Latest **URL:** https://discussion.mainstreetbusinesspodcast.com/latest.md?page=1 [Latest](https://discussion.mainstreetbusinesspodcast.com/latest.md) · [Categories](https://discussion.mainstreetbusinesspodcast.com/categories.md) · [Tags](https://discussion.mainstreetbusinesspodcast.com/tags.md) **Page:** 2 --- ## [Trump Accounts for 15 and 17 year olds](https://discussion.mainstreetbusinesspodcast.com/t/trump-accounts-for-15-and-17-year-olds/650)
**Author:** [@gatordave2000](https://discussion.mainstreetbusinesspodcast.com/u/gatordave2000)\ **Replies:** 1\ **Last updated:** [March 11, 2026, 6:58pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/trump-accounts-for-15-and-17-year-olds/650 "2026-03-11T18:58:36Z")
Is it worth it to set up Trump accounts if your kiddos are 15 and 17? they won’t be able to take advantage of the $1000 from the gov but what else makes it worth it? I guess some philanthropist might choose to donate dow… --- ## [Paying Kids in Hawaii Business - GET?](https://discussion.mainstreetbusinesspodcast.com/t/paying-kids-in-hawaii-business-get/324)
**Author:** [@sharonmcclung](https://discussion.mainstreetbusinesspodcast.com/u/sharonmcclung)\ **Replies:** 0\ **Last updated:** [February 22, 2026, 5:43pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/paying-kids-in-hawaii-business-get/324 "2026-02-22T17:43:23Z")
Aloha! I have two kids under 18 who I want to pay in business as they are legitimately working in business. I have a Family Management Company set up as a Sole Prop that my S corp will pay to pay my kids. Here’s my ques… --- ## [Eligibility of COBRA Premiums for S-Corp Self-Employed Health Insurance Deduction](https://discussion.mainstreetbusinesspodcast.com/t/eligibility-of-cobra-premiums-for-s-corp-self-employed-health-insurance-deduction/600)
**Author:** [@Eric\_ATX](https://discussion.mainstreetbusinesspodcast.com/u/Eric_ATX)\ **Replies:** 0\ **Last updated:** [February 16, 2026, 10:09pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/eligibility-of-cobra-premiums-for-s-corp-self-employed-health-insurance-deduction/600 "2026-02-16T22:09:14Z")
I am a \>2% shareholder of my S-Corp. In 2025, I was covered under my former employer’s COBRA plan and paid 100% of the premiums (unsubsidized) from my personal account. I would like to claim the Self-Employed Health Ins… --- ## [Roth vs. Traditional?](https://discussion.mainstreetbusinesspodcast.com/t/roth-vs-traditional/654)
**Author:** [@margate5](https://discussion.mainstreetbusinesspodcast.com/u/margate5)\ **Replies:** 0\ **Last updated:** [February 12, 2026, 10:32pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/roth-vs-traditional/654 "2026-02-12T22:32:12Z")
Mark and Matt - Huge fan of both your shows! It seems that the assumption / recommendation with all the accounts we have, whether it be to invest through an IRA, 401k, etc. that it be via Roth. My question is..why so e… --- ## [Self Directed Roth 401k Eligible Investments](https://discussion.mainstreetbusinesspodcast.com/t/self-directed-roth-401k-eligible-investments/592)
**Author:** [@DevinH96](https://discussion.mainstreetbusinesspodcast.com/u/DevinH96)\ **Replies:** 3\ **Last updated:** [February 11, 2026, 8:21pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/self-directed-roth-401k-eligible-investments/592 "2026-02-11T20:21:05Z")
Hello, Mark and Mat, I am a HUGE fan of the podcast, I had a potential investment opportunity come up and I was wondering if it would be a prohibited transaction. Mat, I have a friend who has just opened a small coffee … --- ## [Employee Stock Options/Tax Strategies](https://discussion.mainstreetbusinesspodcast.com/t/employee-stock-options-tax-strategies/653)
**Author:** [@itparadigms](https://discussion.mainstreetbusinesspodcast.com/u/itparadigms)\ **Replies:** 0\ **Last updated:** [February 7, 2026, 5:27pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/employee-stock-options-tax-strategies/653 "2026-02-07T17:27:01Z")
I’m looking for guidance on tax planning related to exercising stock options and want to make sure I’m approaching this in the most tax-efficient way possible given my constraints. I work for a small tech company. To cl… --- ## [Employer Contributions for Solok](https://discussion.mainstreetbusinesspodcast.com/t/employer-contributions-for-solok/552)
**Author:** [@Collinsml3](https://discussion.mainstreetbusinesspodcast.com/u/Collinsml3)\ **Replies:** 0\ **Last updated:** [February 6, 2026, 6:42pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/employer-contributions-for-solok/552 "2026-02-06T18:42:42Z")
Hi! Matt - why wouldn’t you do the employer contribution as a business owner with Solo401k? Shouldn’t you have the employer contribution set up so you able to deduct this from the business tax return? I know you mention… --- ## [Trust Tax on Roth Earnings](https://discussion.mainstreetbusinesspodcast.com/t/trust-tax-on-roth-earnings/652)
**Author:** [@edricketts](https://discussion.mainstreetbusinesspodcast.com/u/edricketts)\ **Replies:** 0\ **Last updated:** [February 5, 2026, 9:29pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/trust-tax-on-roth-earnings/652 "2026-02-05T21:29:01Z")
I wish to make my Revocable Family Trust (RFT) the beneficiary if the Roth IRA. My granddaughter is beneficiary to 20% the Roth, but if the RFT is the beneficiary, the earnings that are not withdrawn are subject to trust… --- ## [Small Business](https://discussion.mainstreetbusinesspodcast.com/t/small-business/611)
**Author:** [@Muggs338](https://discussion.mainstreetbusinesspodcast.com/u/Muggs338)\ **Replies:** 0\ **Last updated:** [January 31, 2026, 2:50am UTC](https://discussion.mainstreetbusinesspodcast.com/t/small-business/611 "2026-01-31T02:50:01Z")
So I have to refer back to the S-corp. As Ive mentioned before you guys are great, I enjoy your information and commentary. My wifes LLC nets around 200k. I’ve asked by the S-election, but this particular question is abo… --- ## [Real estate and S Corp](https://discussion.mainstreetbusinesspodcast.com/t/real-estate-and-s-corp/630)
**Author:** [@dsservices](https://discussion.mainstreetbusinesspodcast.com/u/dsservices)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 3:15am UTC](https://discussion.mainstreetbusinesspodcast.com/t/real-estate-and-s-corp/630 "2026-01-29T03:15:09Z")
thank you for your great podcasts and YouTube videos. my question is about potentially buying real estate and how to make it a business write off if it’s even possible The business is an S Corp. We are looking at a co… --- ## [Equipment Depreciation](https://discussion.mainstreetbusinesspodcast.com/t/equipment-depreciation/645)
**Author:** [@tgreimann](https://discussion.mainstreetbusinesspodcast.com/u/tgreimann)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 3:02am UTC](https://discussion.mainstreetbusinesspodcast.com/t/equipment-depreciation/645 "2026-01-29T03:02:28Z")
I bought an a excavator for my farm business back in 2019, and since it has been fully depreciated. The entity that I bought the equipment under ceased to do business in 2023.. In 2025 I created a new company. I would… --- ## [S-corp benefit and reasonable comp](https://discussion.mainstreetbusinesspodcast.com/t/s-corp-benefit-and-reasonable-comp/607)
**Author:** [@Muggs338](https://discussion.mainstreetbusinesspodcast.com/u/Muggs338)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 2:58am UTC](https://discussion.mainstreetbusinesspodcast.com/t/s-corp-benefit-and-reasonable-comp/607 "2026-01-29T02:58:53Z")
I’ve been listening to the Main St podcast for over a year and live your information. My question is how you both live the S-corp election if net income is over $50k. My wifes LLC has netted almost $200k and we pY max F… --- ## [Sellf settled irrevocable trust](https://discussion.mainstreetbusinesspodcast.com/t/sellf-settled-irrevocable-trust/637)
**Author:** [@Markmat1](https://discussion.mainstreetbusinesspodcast.com/u/Markmat1)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 2:50am UTC](https://discussion.mainstreetbusinesspodcast.com/t/sellf-settled-irrevocable-trust/637 "2026-01-29T02:50:36Z")
Is this trust worth getting with a net value of 4 million --- ## [Capital Gaines](https://discussion.mainstreetbusinesspodcast.com/t/capital-gaines/649)
**Author:** [@Michael](https://discussion.mainstreetbusinesspodcast.com/u/Michael)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 2:46am UTC](https://discussion.mainstreetbusinesspodcast.com/t/capital-gaines/649 "2026-01-29T02:46:35Z")
I will be selling a collectable through an auction in two months, I’ve had this for over 40 years and it is estimated to bring in over $1M. How can I set up something (LLC, C-Corp), anything, to avoid being raked over th… --- ## [Non-profit](https://discussion.mainstreetbusinesspodcast.com/t/non-profit/648)
**Author:** [@shasnain7](https://discussion.mainstreetbusinesspodcast.com/u/shasnain7)\ **Replies:** 1\ **Last updated:** [January 29, 2026, 2:33am UTC](https://discussion.mainstreetbusinesspodcast.com/t/non-profit/648 "2026-01-29T02:33:07Z")
We are high income w2 married couple. We have been taking care of small animal for last 3 years. We are planning to open a non-profit that will rescue and rehabilitate small animals from our home (we have dedication arou… --- ## [Business associated with a business](https://discussion.mainstreetbusinesspodcast.com/t/business-associated-with-a-business/608)
**Author:** [@Muggs338](https://discussion.mainstreetbusinesspodcast.com/u/Muggs338)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:45pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/business-associated-with-a-business/608 "2026-01-14T19:45:06Z")
I’ve chimed in before, been watching you guys often. My question here is, my wife has a small business in the medical field. We spend hours doing medical billing, a lot of the rates out there to outsource are 6% of month… --- ## [Paying the kids](https://discussion.mainstreetbusinesspodcast.com/t/paying-the-kids/642)
**Author:** [@Nz2123](https://discussion.mainstreetbusinesspodcast.com/u/Nz2123)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:42pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/paying-the-kids/642 "2026-01-14T19:42:32Z")
So I have a question in regards to paying the children I understand if you pay him under the standard deduction they do not have to file but does that just negate the rule of paying anybody cash over the allotted amount … --- ## [Solo 401k to keep or not?](https://discussion.mainstreetbusinesspodcast.com/t/solo-401k-to-keep-or-not/569)
**Author:** [@Bjohnsonjr](https://discussion.mainstreetbusinesspodcast.com/u/Bjohnsonjr)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:38pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/solo-401k-to-keep-or-not/569 "2026-01-14T19:38:24Z")
Hi Matt I have a solo 401k with directed. I started it in 2024. At that time I just had my s corp with no employees and several other llcs with passive income. In October I purchased an llc filing with s Corp status an… --- ## [Start-up Expense Dedcutions](https://discussion.mainstreetbusinesspodcast.com/t/start-up-expense-dedcutions/646)
**Author:** [@dr.dave](https://discussion.mainstreetbusinesspodcast.com/u/dr.dave)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:35pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/start-up-expense-dedcutions/646 "2026-01-14T19:35:57Z")
I retired from dentistry in December 2025 but during 2025 I started my new venture as an RV technician, including attending the NRVTA and signing up for the SmallBizRVer course. When I asked my tax accountant about dedu… --- ## [Multiple LLC or one with multiple REPT](https://discussion.mainstreetbusinesspodcast.com/t/multiple-llc-or-one-with-multiple-rept/644)
**Author:** [@B3N\_Koh](https://discussion.mainstreetbusinesspodcast.com/u/B3N_Koh)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:30pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/multiple-llc-or-one-with-multiple-rept/644 "2026-01-14T19:30:44Z")
Please compare and contrast the following strategies with an eye towards the ability to simplify bookkeeping and scale; A) Use one WY LLC holding company holding multiple state-specific LLCs (not serial), each holding o… --- ## [How much can I deduct if I am a sole proprietor and not an LLC?](https://discussion.mainstreetbusinesspodcast.com/t/how-much-can-i-deduct-if-i-am-a-sole-proprietor-and-not-an-llc/641)
**Author:** [@Scott\_Newlun](https://discussion.mainstreetbusinesspodcast.com/u/Scott_Newlun)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:25pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/how-much-can-i-deduct-if-i-am-a-sole-proprietor-and-not-an-llc/641 "2026-01-14T19:25:23Z")
Hello, my question comes from the fact that I do multiple (things) to try and generate funds. For instance I have purchased Domains in hope of selling them for profit, tried to set up affiliate sales, traveling around th… --- ## [For tax year 2025, after the OBBB changes, does a Marketplace Bronze plan qualify for an HSA 2025?](https://discussion.mainstreetbusinesspodcast.com/t/for-tax-year-2025-after-the-obbb-changes-does-a-marketplace-bronze-plan-qualify-for-an-hsa-2025/639)
**Author:** [@Sandy](https://discussion.mainstreetbusinesspodcast.com/u/Sandy)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:14pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/for-tax-year-2025-after-the-obbb-changes-does-a-marketplace-bronze-plan-qualify-for-an-hsa-2025/639 "2026-01-14T19:14:35Z")
This is question is from my Husband. For tax year 2025, after the One Big Beautiful Bill changed, does a Marketplace Bronze plan that (a) has an out-of-pocket maximum of $9,200 (above the $8,300 HDHP limit) and (b) charg… --- ## [Hottest topic for 2026 taxes](https://discussion.mainstreetbusinesspodcast.com/t/hottest-topic-for-2026-taxes/610)
**Author:** [@Muggs338](https://discussion.mainstreetbusinesspodcast.com/u/Muggs338)\ **Replies:** 1\ **Last updated:** [January 14, 2026, 7:09pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/hottest-topic-for-2026-taxes/610 "2026-01-14T19:09:49Z")
So Matt & Mark, what would you place on the top of the list for 2026 in a small business for tax strategy and investment growth based on the recent IRS rules changes, especially the car loan interest deduction for Americ… --- ## [Workaround](https://discussion.mainstreetbusinesspodcast.com/t/workaround/609)
**Author:** [@Muggs338](https://discussion.mainstreetbusinesspodcast.com/u/Muggs338)\ **Replies:** 0\ **Last updated:** [January 1, 2026, 5:59pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/workaround/609 "2026-01-01T17:59:36Z")
Second Circuit denies SALT cap workaround Final regulations prohibiting a federal charitable deduction for contributions to a state or local fund for which the donor receives a state or local tax credit are upheld under … --- ## [Cost segregation](https://discussion.mainstreetbusinesspodcast.com/t/cost-segregation/643)
**Author:** [@drgi](https://discussion.mainstreetbusinesspodcast.com/u/drgi)\ **Replies:** 0\ **Last updated:** [December 21, 2025, 6:06pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/cost-segregation/643 "2025-12-21T18:06:34Z")
I have been doing cost segregation on single family homes for last year. As the value of each property is lower, less than 200 k, I have been using automated computer cost seg assessment. Using company, KBKG. there has… --- ## [Tax liability resolution for 2025 tax year](https://discussion.mainstreetbusinesspodcast.com/t/tax-liability-resolution-for-2025-tax-year/640)
**Author:** [@StrykerBiz](https://discussion.mainstreetbusinesspodcast.com/u/StrykerBiz)\ **Replies:** 5\ **Last updated:** [December 10, 2025, 3:18am UTC](https://discussion.mainstreetbusinesspodcast.com/t/tax-liability-resolution-for-2025-tax-year/640 "2025-12-10T03:18:08Z")
Finishing the end of the year and looking at the 2025 tax year, I have 1099 income from my business and seeing there’s a possible tax amount owed of $50,000 what is the best thing for me to do in an investment or somethi… --- ## [RMD after death](https://discussion.mainstreetbusinesspodcast.com/t/rmd-after-death/638)
**Author:** [@Laurachristofk](https://discussion.mainstreetbusinesspodcast.com/u/Laurachristofk)\ **Replies:** 0\ **Last updated:** [November 19, 2025, 2:44pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/rmd-after-death/638 "2025-11-19T14:44:29Z")
My 89yo mother recently passed (in November). She had not yet made her RMD for 2025. Because her taxable income kept her easily in the 12% tax bracket and I am in the 22%, I obviously want to tax shelter as much of her … --- ## [HSA loophole/strategy](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/636)
**Author:** [@Benrhilton](https://discussion.mainstreetbusinesspodcast.com/u/Benrhilton)\ **Replies:** 0\ **Last updated:** [November 11, 2025, 10:12pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/636 "2025-11-11T22:12:54Z")
Mark n Mat. No joke, instead of Metallica, I listen to you guys at the gym. Pumps me up. Quick question. I heard Mat talk about this loophole, I mean strategy, in 2024. I just need an HSA qualifying plan for the month … --- ## [HSA loophole/strategy](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/635)
**Author:** [@Benrhilton](https://discussion.mainstreetbusinesspodcast.com/u/Benrhilton)\ **Replies:** 0\ **Last updated:** [November 11, 2025, 9:28pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/635 "2025-11-11T21:28:05Z")
Mark n Mat. No joke, instead of Metallica, I listen to you guys at the gym. Pumps me up. Quick question. I heard Mat talk about this loophole, I mean strategy, in 2024. I just need an HSA qualifying plan for the month … --- ## [Self-rental sublease](https://discussion.mainstreetbusinesspodcast.com/t/self-rental-sublease/634)
**Author:** [@Ralica](https://discussion.mainstreetbusinesspodcast.com/u/Ralica)\ **Replies:** 0\ **Last updated:** [November 7, 2025, 2:24pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/self-rental-sublease/634 "2025-11-07T14:24:50Z")
Can you sublease 50% of your self-rental, do a cost segregation and still take advantage of the grouping election to offset your active income?Will the passive loss limitations apply if the rental income from the subleas… [Previous page](https://discussion.mainstreetbusinesspodcast.com/latest.md) [Next page](https://discussion.mainstreetbusinesspodcast.com/latest.md?page=2)