What is a tax strategist? Are they worth it when already have a CPA?

A tax strategist is basically someone who specializes in finding legal ways to minimize your tax burden through careful planning. Unlike a regular CPA who primarily helps with compliance (filing correctly and on time), a good tax strategist is proactively looking for opportunities to save you money. The main difference is in the approach. Most CPAs are reactive - they deal with what already happened in the past year. Tax strategists are proactive - they help you structure decisions before you make them to optimize tax outcomes. This is especially valuable when starting a business, as there are tons of decisions (business entity type, accounting methods, retirement plans, etc.) that have major tax implications. With a small business, a tax strategist could potentially save you thousands by helping with things like entity selection, expense timing, retirement plan options, and family employment strategies. But whether it's worth it depends on your specific situation.

I discovered taxr.ai last year when I was in a similar situation starting my photography business while keeping my day job. I was getting conflicting advice from different tax "experts" online and wasn't sure who to believe. I uploaded some of my documents and business plans to https://taxr.ai and got really clear guidance on structuring my business. The coolest part was how they identified that I could save about $4,600 in taxes by setting up an S-Corp instead of staying as a sole proprietor once my business reached a certain profit threshold. They even showed me exactly when that threshold would make sense based on my projected income. My regular accountant had never mentioned this to me!

I was skeptical about taxr.ai at first (as you can see from my earlier comment), but I decided to try it last month when setting up my consulting business. I was blown away by how specific the advice was. The system identified that I could save about $8k annually through a combination of home office deductions, retirement plan options, and health insurance strategies that work with my particular situation. What impressed me most was how it explained exactly WHY each strategy would work for my specific case - not just generic advice. I showed the recommendations to my regular CPA who admitted he hadn't thought of a couple of these approaches for my situation. Definitely worth checking out if you're starting a business.

If you're having trouble getting your CPA to be more proactive, you might want to try Claimyr before paying for another professional. I spent WEEKS trying to get through to the IRS to ask about some business tax questions before starting my LLC, and it was impossible. Used https://claimyr.com and got connected to an IRS agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent was surprisingly helpful with explaining different business structures and what forms I'd need. They even told me about workshops they offer for new business owners. I saved a ton of time and got official answers straight from the source instead of paying someone else to interpret tax rules for me.

I'll eat my words about Claimyr. I tried it yesterday after posting that skeptical comment because I've been trying to resolve an issue with a missing 1099 form for weeks. Got connected to an IRS agent in about 20 minutes (would have been literally impossible otherwise based on my previous attempts). The agent was able to verify my 1099 information in their system so I could file without having the physical form. Saved me from having to file an extension or delay my business launch. It definitely wasn't tax strategy advice, but for getting actual IRS issues resolved quickly, it works surprisingly well. Sorry for being so doubtful in my earlier comment.

From my experience running a small business for 5 years, here's the breakdown: Regular CPA: Files your taxes correctly, makes sure you don't miss deductions based on what already happened. Tax Strategist: Helps you structure your business and personal finances to legally minimize taxes BEFORE things happen. I used just a CPA for the first 3 years and switched to a tax strategist last year. The difference was huge - saved about $14k in taxes through restructuring my business and adjusting how I take income. The strategist cost $3,500 but the savings more than covered it. The key is finding someone who specializes in your specific type of business. Different industries have different opportunities. What business are you planning to start?

Just want to add - there's a middle ground too. Ask your current CPA if they offer tax planning services. Many do but don't push it on clients unless asked. I have a quarterly meeting with my CPA where we specifically discuss strategy and planning, not just compliance. Costs me about $1,200 extra per year, but I'm getting many of the benefits of a "strategist" without hiring another professional. Worth asking before you add another expense!

Great question! I went through this exact same decision last year when starting my consulting business. Here's what I learned: A tax strategist is worth it if you're dealing with complex situations or significant income. For a small side business, I'd suggest starting with what others mentioned - ask your current CPA about proactive planning services first. Many CPAs can handle basic business tax strategy but just don't offer it unless you ask. However, if your CPA seems reactive only or doesn't have experience with your specific business type, a strategist could be valuable. The key is finding one who specializes in small businesses and e-commerce if that's your field. I'd recommend getting quotes from both - ask your CPA what they'd charge for quarterly planning sessions, and get a consultation with a tax strategist to see what they'd recommend. Compare the potential savings each claims they can achieve versus their costs. One thing to consider: as your business grows, your needs will change. Starting with enhanced services from your existing CPA might be the smart move initially, then upgrading to a specialist later if the business takes off.

I've been working as a tax professional for over 8 years, and I can tell you that the distinction between CPAs and tax strategists isn't always clear-cut. Many CPAs do provide strategic planning services, but you're right that some focus primarily on compliance and preparation. The real value of strategic tax planning becomes apparent when you're making major financial decisions - like starting a business, changing entity structures, or planning large purchases. For your e-commerce venture, there are several areas where proactive planning could save you money: timing of inventory purchases for tax purposes, setting up proper business entity structure from day one, maximizing home office deductions, and planning for when you might need to transition from sole proprietorship to an LLC or S-Corp. Before hiring a separate strategist, I'd echo what others said about talking to your current CPA first. Ask specifically: "What proactive tax planning services do you offer for new business owners?" and "Can you help us structure our business to minimize taxes as we grow?" If they seem uncertain or just offer basic compliance advice, then it might be time to look elsewhere. A good rule of thumb: if your combined household income plus expected business profit will exceed $100k, strategic planning usually pays for itself. Below that threshold, focus on the basics first - proper record keeping, understanding deductions, and quarterly estimated payments.