My Tax Fella

09/07/2026

𝗗𝗼 𝗽𝗮𝘆𝗺𝗲𝗻𝘁 𝗮𝗽𝗽𝘀 𝗿𝗲𝗽𝗼𝗿𝘁 𝗺𝘆 𝗮𝗰𝘁𝘂𝗮𝗹 𝗽𝗿𝗼𝗳𝗶𝘁 𝘁𝗼 𝘁𝗵𝗲 𝗜𝗥𝗦?

Third-party payment apps report your gross transfers to the IRS.

Say you originally bought a couch for $1,200 and later sold it through Cash App for $400.

If you keep the record showing what you originally paid, you can prove that $400 transfer wasn’t a $400 gain. You sold the couch at a loss.

Don't rely only on PayPal, Venmo, Cash App, or whichever payment platform you're using to track things for you.

Keep the records that show what those payments actually represent.

09/04/2026

𝗛𝗼𝘄 𝗱𝗼 𝗜 𝗸𝗻𝗼𝘄 𝗶𝗳 𝗺𝘆 𝘀𝗶𝗱𝗲 𝗶𝗻𝗰𝗼𝗺𝗲 𝗶𝘀 𝗰𝗼𝗻𝘀𝗶𝗱𝗲𝗿𝗲𝗱 𝗮 𝗵𝗼𝗯𝗯𝘆 𝗼𝗿 𝗮 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀?

Getting paid via Venmo or PayPal doesn't automatically make your side income a business. The IRS looks at how you operate and whether your primary goal is making a profit.

If you keep separate books, set aside regular work hours, and take on ongoing gigs like freelancing or tutoring, you're operating as a business.

If you're just making money here and there from something you do for fun, like streaming or selling a few crafts, that's usually hobby income. You aren't really trying to make a living off it.

This distinction completely changes your tax setup. Business owners report their earnings on Schedule C and can deduct ordinary expenses to lower what they owe. If your side income is more of a hobby, you report the earnings on Schedule 1 as other income, but you can't write off any expenses against it.

09/03/2026

𝗔𝗿𝗲 𝘆𝗼𝘂 𝗮𝗹𝗿𝗲𝗮𝗱𝘆 “𝗺𝗼𝗻𝗲𝘆𝗺𝗮𝘅𝘅𝗶𝗻𝗴” 𝘄𝗶𝘁𝗵𝗼𝘂𝘁 𝗸𝗻𝗼𝘄𝗶𝗻𝗴 𝗶𝘁?

It’s the social media term for getting more value from your money, like cutting expenses or even putting rewards points to use.

𝘞𝘩𝘢𝘵’𝘴 𝘰𝘯𝘦 𝘸𝘢𝘺 𝘺𝘰𝘶’𝘳𝘦 𝘨𝘦𝘵𝘵𝘪𝘯𝘨 𝘮𝘰𝘳𝘦 𝘧𝘳𝘰𝘮 𝘺𝘰𝘶𝘳 𝘮𝘰𝘯𝘦𝘺 𝘳𝘪𝘨𝘩𝘵 𝘯𝘰𝘸?

09/02/2026

𝗪𝗵𝗮𝘁 𝗿𝗲𝗰𝗼𝗿𝗱𝘀 𝗱𝗼 𝗜 𝗻𝗲𝗲𝗱 𝘁𝗼 𝗱𝗲𝗳𝗲𝗻𝗱 𝗺𝘆𝘀𝗲𝗹𝗳 𝗱𝘂𝗿𝗶𝗻𝗴 𝗮𝗻 𝗜𝗥𝗦 𝗮𝘂𝗱𝗶𝘁?

Your strongest evidence depends on the type of audit:
• Correspondence audit: Receipts, canceled checks, and bank statements that match your return
• Office audit: Mileage logs, calendars, and meeting agendas that explain the business purpose
• Field audit: Contracts, company policies, vendor agreements, and the legal authority behind your position

The best documentation is created when the expense happens. Trying to reconstruct everything after the audit starts can make your position harder to prove.

𝘋𝘰 𝘺𝘰𝘶𝘳 𝘤𝘶𝘳𝘳𝘦𝘯𝘵 𝘳𝘦𝘤𝘰𝘳𝘥𝘴 𝘤𝘭𝘦𝘢𝘳𝘭𝘺 𝘴𝘩𝘰𝘸 𝘸𝘩𝘢𝘵 𝘺𝘰𝘶 𝘴𝘱𝘦𝘯𝘵 𝘢𝘯𝘥 𝘸𝘩𝘺?

08/31/2026

𝗪𝗵𝗮𝘁’𝘀 𝘁𝗵𝗲 𝗯𝗲𝘀𝘁 𝘄𝗮𝘆 𝘁𝗼 𝗳𝘂𝗻𝗱 𝗺𝘆 𝗹𝗶𝗳𝗲𝘀𝘁𝘆𝗹𝗲 𝗶𝗳 𝗜 𝗿𝗲𝘁𝗶𝗿𝗲 𝗯𝗲𝗳𝗼𝗿𝗲 𝗦𝗼𝗰𝗶𝗮𝗹 𝗦𝗲𝗰𝘂𝗿𝗶𝘁𝘆 𝗸𝗶𝗰𝗸𝘀 𝗶𝗻?

Draw cash strategically across three accounts to keep your tax bill as low as possible.
• Pull just enough from your Traditional IRA or 401(k) to fill up the lowest tax brackets (10% or 12%).
• Cover remaining living expenses with taxable savings or brokerage cash so you don't push yourself into a higher bracket.
• Use tax-free Roth IRA dollars for big one-off expenses with zero tax impact.

Balancing your withdrawals this way keeps your overall tax rate low and can even unlock 0% capital gains rates.

08/28/2026

𝗔𝗺 𝗜 𝗮𝗰𝗰𝗶𝗱𝗲𝗻𝘁𝗮𝗹𝗹𝘆 𝘀𝗵𝗮𝗿𝗶𝗻𝗴 𝘀𝗲𝗻𝘀𝗶𝘁𝗶𝘃𝗲 𝗱𝗮𝘁𝗮 𝗲𝘃𝗲𝗿𝘆 𝘁𝗶𝗺𝗲 𝗜 𝘁𝘆𝗽𝗲 𝗮 𝗽𝗿𝗼𝗺𝗽𝘁 𝗶𝗻𝘁𝗼 𝗔𝗜?

You could be. Time to fix that.

(We already make sure all privacy settings are enabled for any AI tools we use here.)

Worried about your personal AI chats being exposed? Here's how to tighten your privacy across several major chatbots.

08/27/2026

𝗪𝗵𝘆 𝗰𝗮𝗻'𝘁 𝗜 𝘀𝗲𝘁𝘁𝗹𝗲 𝗺𝘆 𝘀𝘁𝗮𝘁𝗲 𝘁𝗮𝘅 𝗱𝗲𝗯𝘁 𝘂𝘀𝗶𝗻𝗴 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝗽𝗿𝗼𝗴𝗿𝗮𝗺𝘀 𝗜 𝘂𝘀𝗲 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗜𝗥𝗦?

Because state tax agencies generally enforce much tighter guidelines than the IRS.

States often cap payment plans at 12 to 36 months (compared to 72 or 84 with the IRS). Many states have no settlement program at all or enforce stricter criteria.

First-Time Penalty Abatement exists federally, but states rarely waive penalties and almost never waive interest. And state appeal windows run just 30 to 60 days from the notice date.

𝘊𝘩𝘢𝘭𝘭𝘦𝘯𝘨𝘦: Take 5 minutes today to check the dates on any state mail sitting on your desk. Opening state mail as soon as it arrives and prioritizing it in your budget early will help keep extra fees from stacking up.

08/26/2026

𝗪𝗵𝗮𝘁 𝘀𝗵𝗼𝘂𝗹𝗱 𝗜 𝗱𝗼 𝘄𝗶𝘁𝗵 𝗺𝘆 𝘁𝗮𝘅𝗲𝘀 𝗯𝗲𝘁𝘄𝗲𝗲𝗻 𝗹𝗲𝗮𝘃𝗶𝗻𝗴 𝗺𝘆 𝗷𝗼𝗯 𝗮𝗻𝗱 𝘁𝗮𝗸𝗶𝗻𝗴 𝗦𝗼𝗰𝗶𝗮𝗹 𝗦𝗲𝗰𝘂𝗿𝗶𝘁𝘆?

A core strategy we suggest during this retirement gap is a Roth conversion staircase:
• Move funds from your traditional IRA into a Roth IRA when your income sits in lower tax brackets.
• Pay taxes today at low rates so that money and its future growth stay 100% tax-free.
• Convert in stages each December to fill your target bracket line, instead of moving a single lump sum that spikes your tax bracket.

𝘖𝘯𝘦 𝘤𝘳𝘪𝘵𝘪𝘤𝘢𝘭 𝘳𝘶𝘭𝘦: Pay the taxes using cash outside your IRA, such as a high-yield savings or taxable brokerage account. Withholding tax money directly from the IRA reduces your tax-free shelter and triggers a 10% IRS penalty if you're under age 59½.

If you recently left your job or plan to step away soon, DM us to find out how to map out your retirement gap.

08/25/2026

𝗦𝗵𝗼𝘂𝗹𝗱 𝗜 𝗽𝗮𝘆 𝘁𝗵𝗲 𝗜𝗥𝗦 𝗼𝗿 𝗺𝘆 𝘀𝘁𝗮𝘁𝗲 𝘁𝗮𝘅 𝗯𝗶𝗹𝗹 𝗳𝗶𝗿𝘀𝘁 𝗶𝗳 𝗜 𝗼𝘄𝗲 𝗯𝗼𝘁𝗵?

State agencies act much faster than the IRS. A lot of states send just one notice before putting a levy on your bank account or they garnish your wages within weeks.

Not only that, but they also connect directly into local systems like the DMV to flag your account immediately.

The IRS enforcement timeline is anywhere from 3-6 months because of the required notice cycle.

08/24/2026

𝗪𝗵𝗮𝘁 𝗶𝘀 𝗼𝗻𝗲 𝗺𝗼𝗻𝗲𝘆 𝗼𝗿 𝘁𝗮𝘅 𝗿𝘂𝗹𝗲 𝘆𝗼𝘂 𝗵𝗮𝗱 𝘁𝗼 𝗹𝗲𝗮𝗿𝗻 𝘁𝗵𝗲 𝗵𝗮𝗿𝗱 𝘄𝗮𝘆 𝗮𝘀 𝗮𝗻 𝗮𝗱𝘂𝗹𝘁 𝘁𝗵𝗮𝘁 𝘆𝗼𝘂 𝘄𝗶𝘀𝗵 𝘄𝗮𝘀 𝘁𝗮𝘂𝗴𝗵𝘁 𝗶𝗻 𝗵𝗶𝗴𝗵 𝘀𝗰𝗵𝗼𝗼𝗹?

Whether it's how W-4 withholdings work, how interest adds up, or how credit scores are calculated, we've all had that moment. Drop yours below!