Philip B Hebner, CPA, EA

06/05/2026

Some great low-start-up cost business ideas in here, but remember... Starting a business also means bigger tax responsibility. Let's talk about what the IRS expects of you as a business owner and how to set you up for success with the right tax structure.

https://www.inc.com/chris-morris/7-small-business-ideas-you-can-start-for-less-than-10000/91349155

06/05/2026

Do You Get Better Tax Breaks For Being Married, Santa Cruz County Couples?

Do you get better tax breaks for being married? Discover how tying the knot changes your taxes, unlocks massive savings, and boosts retirement.

06/04/2026

𝙒𝙝𝙖𝙩 𝙙𝙤 𝙄 𝙙𝙤 𝙞𝙛 𝙄'𝙢 𝙗𝙚𝙝𝙞𝙣𝙙 𝙤𝙣 𝙢𝙖𝙠𝙞𝙣𝙜 𝙢𝙮 𝙚𝙨𝙩𝙞𝙢𝙖𝙩𝙚𝙙 𝙩𝙖𝙭 𝙥𝙖𝙮𝙢𝙚𝙣𝙩𝙨?
Your first step you want to take even before making a payment or setting up a payment plan is to get the full picture of your situation. To do that, you'll need to gather the following:

• IRS notices
• State notices
• Prior-year tax returns
• Proof of estimated payments
• W-2 withholding records
• Any payment plan paperwork you already have

This will help you figure out what you really owe, for which years those payments are owed, and whether you have accumulated penalties and interest as part of your balance.

If you'd rather have an experienced tax specialist look at this for you, that's where we come in. Comment 𝗧𝗔𝗫 𝗛𝗘𝗟𝗣 below if you want to set up a time to talk this one out and get a plan of action for moving forward.

06/03/2026

𝘿𝙤𝙚𝙨 𝙜𝙚𝙩𝙩𝙞𝙣𝙜 𝙢𝙖𝙧𝙧𝙞𝙚𝙙 𝙡𝙤𝙬𝙚𝙧 𝙢𝙮 𝙩𝙖𝙭𝙚𝙨?
Getting married changes how the IRS views your finances, but it doesn’t guarantee a lower tax bill.

For some couples, filing jointly can open up planning options. For others, filing separately may be the better option, especially when one spouse has high out-of-pocket medical expenses or other complications to their tax situation.

Getting married can change your...
• Filing status
• Tax bracket
• Credits you qualify for
• Deductions you can take
• Retirement savings options
• Workplace benefit choices

Want to talk through whether filing jointly or separately is the best option for you? Or just see if there are ways to lower your tax bill now that you're married?

Comment MARRIED below to request an appointment to talk this through.

06/02/2026

𝙒𝙝𝙖𝙩 𝙝𝙖𝙥𝙥𝙚𝙣𝙨 𝙞𝙛 𝙮𝙤𝙪 𝙥𝙖𝙮 𝙦𝙪𝙖𝙧𝙩𝙚𝙧𝙡𝙮 𝙩𝙖𝙭𝙚𝙨 𝙡𝙖𝙩𝙚?

If you miss a quarterly estimated tax payment, the IRS treats it as an underpayment. Meaning you may owe an added charge for paying late, plus interest that keeps building until the amount is paid.

So no, one missed estimated payment doesn’t mean the IRS is going to send you a notice, but they do start to keep track.

Quarterly tax payments may apply when you have income that isn’t covered through regular withholding, such as self-employment income, investment income, rental income, retirement income, or passthrough income.

If you missed an estimated payment, don’t ignore it until it's time to file your taxes. Paying late before the tax deadline will still be better than waiting until you file.

06/01/2026

𝙃𝙤𝙬 𝙙𝙤 𝙮𝙤𝙪 𝙥𝙧𝙚𝙛𝙚𝙧 𝙩𝙤 𝙧𝙚𝙘𝙚𝙞𝙫𝙚 𝙛𝙚𝙚𝙙𝙗𝙖𝙘𝙠 𝙤𝙧 𝙧𝙚𝙘𝙤𝙜𝙣𝙞𝙩𝙞𝙤𝙣?

Some people appreciate a quick note. Others value a private conversation, a public shoutout, or clear next steps they can act on.

The same goes for recognition.

A simple “thank you” can mean a lot, but it means even more when it’s given in a way the other person actually receives well.

So here’s a good question to ask your team, your clients, or even yourself:

When someone wants to acknowledge your work, what feels most encouraging to you?

05/29/2026

2026 Guide to Short-Term Rental Taxes for Santa Cruz County Airbnb & VRBO Hosts

Hosting for the 2026 World Cup? Get the facts on short-term rental taxes, from the 14-day tax-free rule to maximizing your 100% bonus depreciation.

05/29/2026

𝙒𝙝𝙖𝙩 𝙖𝙧𝙚 𝙤𝙘𝙘𝙪𝙥𝙖𝙣𝙘𝙮 𝙩𝙖𝙭𝙚𝙨?

If you rent out your home, apartment, or spare room to guests, income taxes may not be the only tax issue on the table.

Occupancy taxes are taxes charged on the rental price paid by your guest. They’re sometimes called tourist tax, hotel tax, room tax, or lodging tax.

They’re different from income tax, which is based on your profit.

The confusing part is that occupancy tax rules can change depending on your city or county. And if the tax isn’t collected and sent in correctly, the penalties can be a real problem.

Have a short-term rental or thinking about starting one? Comment “RENTAL” to get help with the tax obligations.

05/28/2026

𝘾𝙖𝙣 𝙢𝙮 𝙨𝙩𝙪𝙙𝙚𝙣𝙩 𝙡𝙤𝙖𝙣𝙨 𝙗𝙚 𝙙𝙞𝙨𝙘𝙝𝙖𝙧𝙜𝙚𝙙 𝙞𝙣 𝙗𝙖𝙣𝙠𝙧𝙪𝙥𝙩𝙘𝙮?

Yes, student loans can be discharged in bankruptcy, but it’s not automatic like credit card debt.

You have to prove that repaying the loans would create an undue hardship for you and your family.

For federal loans, your financial records may be reviewed before you ever go to trial. If the Department of Justice agrees that your situation meets the hardship standard, they can agree to the discharge.

Before filing, gather your records and know what kind of loans you have:
• Federal loans
• Private loans
• A mix of both

If you want to talk further about how discharged student loans affect your tax situation, comment "HELP" below.

05/27/2026

Google's updates to its search bar are really interesting: https://www.techbrew.com/stories/google-it-while-you-still-can

And you might be tempted to ask all kinds of tax questions with the new features. And the thing is, the answer might sound definitive in the results but actually still be wrong for your situation.

Tax questions need details that AI agents don't think to ask for.

Maybe your income changed. Maybe you got an IRS notice. Maybe you’re asking about a deduction, but the real issue is how your business is set up.

Don't rely on quick answers from Gemini when it comes to your IRS obligations.

Ask a professional you can trust (we're right here).