Tax meetings are stressful to plan for. As advisors, we only have a few deliverables each year and planning / strategy meetings are a big one.

So early in my career when the client told me during one of these meetings that, "this was the biggest waste of time I've had in a while" - it's one I took home and really thought about.

Why It Sucked

For starters, I didn't appreciate where I fit in as a tax advisor in the finance team - and I think most CPAs still don't. 🔄

But let me lay the background of what was happening:

• New client - we had just finished their returns and were reviewing them and talking about taxes due + estimated taxes
• Bad accounting - we had to post a lot of adjustments to get their books in order to prepare the tax returns 🫨
• Inherited tax problems - a majority of our time on top of the tax returns was spent replying to IRS notices
• Dropped balls on promises - the initial call was strategy-focused and we dropped some balls since then 🏀

It was the perfect storm and set-up for a disappointing meeting - but we went in with our boxes to check and were on a mission to check them.

We went over the returns we had prepared and told them how much they owed for last year based on the returns.

> One box checked. ✅

We then went over how much they should pay now to safe harbor in their current year tax due.

> Two boxes checked. ✅✅

The client then slid over the current balance sheet - asking if we had any idea on how the hell he is supposed to pay those taxes and where all the money we were going to save him with those ideas was.

> Sh*t. We had the wrong boxes the whole time. 🤷‍♂️

What I Screwed Up

Back to my first point - it's hard to keep perspective as a CPA on where you fit in.

The primary deliverable wasn't a tax return - it was a cash outflow. And that outflow was some 7-8 months in arrears. I whiffed on the client's need for predictable cash flows that aren't negotiable (taxes). 📆

The next SNAFU was scope creep - something that happens all the time in SMB tax world. The client's books are a mess, but you need to clean them up before you can prepare the tax return. It doesn't matter if it's 1 or 25 journal entries. And it's a battle to go bill for that time.

To boot, the IRS notices that we didn't initially plan for were a time suck - providing no real value. And because we were distracted with notices, we weren't delivering on the promises we had made, 💣 it felt hard as a young partner to charge for those notices.

Where It All Ended

The client fired us and went back to their old CPA. And I lost one of my first clients as a young partner. It was brutal having to sit down with the managing partner and list out all the reasons it wasn't my fault - and why we had a huge write off to boot.

This was the genesis of designing what I wanted tax relationships to feel like. I wanted one source of truth ☝️ for:

• Tax strategies we're pursuing and timelines 🗓️
• Tax payments due in the next 18 months 🏦
• Returns and compliance matter updates 📄

This was the bones of the "Gameplan" we now include in our highest tier of Tax services - but the most important takeaway that developed over time was the need for a holistic view of tax and how it can drive a better SMB finance function. That's the point of this newsletter.

How It's Shaping My Frameworks

Better Accounting > Better Tax Planning > Better Forecasts > Better Decisions

That's where I see CPAs fitting in now. A core component of SMB decision making.

I am currently obsessed with codifying foundational frameworks for these core areas that drive better decisions (accounting, tax, forecasting). And with CPAs and experienced accounting professionals dwindling by day, I feel the urgency to open source as much of the finance function as I can.

Some of the frameworks and methodologies I've developed along the way and will continue to share:

A core mission of this letter's content, and my future endeavors, will be to educate and support small business founders, owners, operators by open sourcing the finance function in plain English. Thanks for following along as I build.

🫡

If you don't already, check this channel out on YouTube - I appreciate all the feedback if you have any.

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