When are taxes due? Tax season 2025 guide with Mark J. Kohler

As tax season 2025 approaches, we sat down with Mark J. Kohler, CPA, Attorney, and author of ‘The Tax and Legal Playbook’, to discuss what small business owners need to know about filing taxes this year.

Getting started

Taxes may be taxing, but your filing process doesn’t have to be. With the right preparation, you can transform tax season from a dreaded marathon to a manageable sprint.

“Start by getting organized and closing out your 2024 books,” says Mark. “If you’re using Quickbooks, which most do, make sure all checkbooks are reconciled, and business credit card statements are inputted into the books."

Think of this as building your tax season foundation – without it, everything else becomes significantly more challenging. It’s like trying to build a house starting with the roof – technically possible, but why make life harder?

Essential documentation and deadlines

Here are the official tax dates for 2025:

• January 27, 2025 (Monday): Official start of tax season
• April 15, 2025 (Tuesday): Individual tax returns and Q1 estimated taxes due
• June 16, 2025 (Monday): Q2 estimated taxes due
• September 15, 2025 (Monday): Q3 estimated taxes due
• January 15, 2026 (Thursday): Q4 estimated taxes due

Pro tip: Add these dates to your calendar now – your future self will thank you. Don’t forget to check your state tax authority’s website for state-specific deadlines, as they may differ from federal dates.

So, which specific tax deadlines typically catch small business owners off guard? Mark highlighted five key documents that consistently create challenges:

• Payroll reports
• Estimated Tax Payments
• State Tax Filings
• Federal and State Extensions
• Retroactive S-Election

The challenge often lies in balancing operational demands with financial obligations. When you’re deep in the day-to-day of running your business, these deadlines can feel like distant concerns until they’re suddenly urgent.

Mark emphasizes that successful tax filing isn’t just about remembering documents – it’s about understanding their importance: “Too many business owners don’t prepare any reports at all or don’t know how to read them”.

Which is fair enough – nobody started their business dreaming about financial reports.

But if you’re going to take notice of any, you should take the time to understand how and the importance of these essential documents:

• Profit and Loss Statements
• Balance sheets (based on book value and fair market values)
• Cash Flow Reports
• KPI reports

What makes a business owner successful during tax season?

Mark’s secret to success is refreshingly straightforward:

1. Reserve a fixed percentage of sales in a dedicated tax savings account.
2. Set calendar reminders for all tax deadlines.
3. Send in the estimate you determine with your Tax Advisor. If you don’t have a Tax Advisor, go here.
4. Mark also recommends maintaining a cloud-based folder system for current-year documentation. “All business documents and tax records should be kept in the cloud with strong password protection or encryption”.

And his overarching piece of advice: Never file late

Looking ahead: Digital organization

The era of maintaining physical filing cabinets is rapidly becoming a relic of the past. Modern businesses are embracing digital transformation not just for innovation but for practical necessity.

When discussing how technology has transformed tax filing, Mark offers a pragmatic perspective: “The same information is needed, just not the faxing, mailing, and cumbersome nature of paper."

While the fundamentals of tax preparation remain unchanged, shifting to all-in-one digital solutions simplifies tax season by letting you find, fill, and sign documents within one secure, cloud-based platform.

About Mark:
Mark is a CPA, Attorney, founder of Main Street Tax Professionals and author specializing in tax and legal planning for small businesses.

As a founding senior partner at KKOS Lawyers and CFO of Directed IRA Trust Company, he brings extensive expertise in helping entrepreneurs and small business owners across America achieve greater financial success.

For more tax insights, visit his website or connect with him on LinkedIn