Siobhan Says frame with a white woman with glasses and her chin propped on her fist in a thinking pose

Siobhan Says: Tax Season Readiness – How to Hire & Work with a CPA

Every spring, I see the same Detroit story on repeat: the Tax Time Rescue Mission. It starts with a trail of Cash App, PayPal, Venmo, Shopify, Square, and Toast transactions that never made it into a system, plus a shoebox of receipts that’s really a camera roll of random photos.  You juggle a lot, and taxes often fall to the bottom of the list. You’ve met the nonstop demands of your family and your business all year long but tax prep gets pushed aside until the last-minute scramble (and sometimes, the missed filing).

It doesn’t have to be that way. Whether you’re only selling to family and friends, you’re a startup, or a neighborhood staple, your numbers tell a story. Our job at DNEP is to help you move from crisis management to financial capability so that you are empowered by your finances and filing your taxes instead of overwhelmed by them.

Here are some scenarios that represent common challenges entrepreneurs face as they build and grow their businesses. You’re not alone in facing them, and you don’t have to figure them out by yourself.

Getting Started on Your Taxes Now

The secret to a stress-free tax season isn’t what you do in April; it’s what you do today. Based on our “Money Matters” workshop, here are three immediate steps to take:

  1. Understand Your COGS: Know the difference between your operating expenses (like rent) and your Cost of Goods Sold (the direct costs of making your product). This distinction is vital for accurate tax deductions and pricing strategies.
  2. End the “Commingling Crisis”: If you are still using your personal Cash App or bank account for business expenses, stop today. Open a dedicated business account. Separating these funds is the single most important step in proving your profitability to the IRS and future lenders.
  3. The 15-Minute Habit: Don’t wait until the end of the year to categorize transactions. Spend 15 minutes a week in QuickBooks (or your preferred ledger) tagging your income and expenses and organizing your financial records.

What to Look for When Hiring a CPA

When you’re ready to move beyond DIY bookkeeping and hire a professional, don’t just look for someone who is good with numbers. At DNEP, when we hire accounting consultants, we look for “Knowledge Translators.” You should do the same. Look for a CPA who:

  • Speaks Your Language: They should be able to explain a Balance Sheet as a “Snapshot” and an Income Statement as a “Story” without hiding behind technical jargon.
  • Understand the Detroit Context: You want a partner who understands the specific landscape of Detroit’s entrepreneurial ecosystem and the unique challenges neighborhood-based businesses face.
  • Is a Confidence Builder: A good CPA shouldn’t make you feel embarrassed about your past financial “messes.” They should be focused on building your financial health and capital readiness.

How to Be a Good Client

A good client wants a relationship, not a transaction. That’s when a CPA can do their best work and the client gets the most value. Put differently: the relationship with your accountant is a two-way street. To get the most value for your money, you need to be “Data Ready.”

  • Come Prepared: Use a prep checklist. Before your meeting, have your bank statements, payroll records, and a list of specific questions ready.
  • Be Honest: If you don’t know how to record a transaction, say so. It can be much cheaper and easier for a CPA to categorize a transaction correctly the first time than to fix a year’s worth of mistakes later.
  • Respond Quickly: In our programs, we’ve seen that the most successful entrepreneurs are those who respond to financial inquiries within 24-48 hours. Speed keeps your books current and your business agile.
  • Start Early: Tax documents start arriving by the end of January.  Set up a meeting with your CPA in February providing the information needed to prepare your return.  

You’re Not Alone

DNEP’s accounting program exists specifically to help you navigate these challenges, build the financial infrastructure your business needs, and position yourself for growth and funding opportunities. The entrepreneurs who succeed aren’t the ones who never face these challenges—they’re the ones who get help solving them.

Use this guide to prepare for your appointment, gather the right materials, and come ready to make real progress. While we will not do your taxes for you or give you tax advice, we will work with you to gather the information you need to get ready together.

Ready to tackle your scenario? Contact DNEP today to schedule your accounting appointment. Bring this guide, and and let’s build the financial foundation your business deserves.

Disclaimer

This article is written for information purposes only and does not constitute tax advice. If you have specific tax questions, please consult your CPA or tax advisor.