This Gets CPAs Fired More Than Anything Else ๐Ÿ—‘๏ธ



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. ๐Ÿ”„

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 ๐Ÿซจ
  • 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 ๐Ÿ€

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. โœ…

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

> Two boxes checked. โœ…โœ…

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. ๐Ÿคทโ€โ™‚๏ธ

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). ๐Ÿ“†

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, ๐Ÿ’ฃ 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 โ˜๏ธ for:

  • Tax strategies we're pursuing and timelines ๐Ÿ—“๏ธ
  • Tax payments due in the next 18 months ๐Ÿฆ
  • Returns and compliance matter updates ๐Ÿ“„

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:

Better Accounting ๐Ÿงฎ
โ€ข Fortune 500 Finance for SMB
โ€ข DIY SMB Financial Analysis
โ€ข 13 Week Finance Turnaround for SMB
โ€‹
Better Tax Planning ๐Ÿ“„
โ€ข Tax Life Plan
โ€ข 7 Foundations of Tax Strategy
โ€ข SET Core Tax Objectives
โ€‹
Better Forecasting ๐Ÿ”ญ
โ€ข Maslow's Hierarchy of Finance Needs
โ€ข Statement of Cash Flow Model for Cash Diagnostics and Forecasting

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.

๐Ÿซก

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

video previewโ€‹

โ€‹


๐Ÿ”ฅ Hottest Finance Posts This Week ๐Ÿ”ฅ

twitter profile avatar
Roger Ledbetter
Twitter Logo
@rledbetterCPA
8:32 AM โ€ข Sep 10, 2025
1
Retweets
12
Likes
โ€‹
twitter profile avatar
Boring_Business
Twitter Logo
@BoringBiz_
7:58 AM โ€ข Sep 10, 2025
2
Retweets
82
Likes
โ€‹
twitter profile avatar
Boring_Business
Twitter Logo
@BoringBiz_
6:23 PM โ€ข Sep 11, 2025
23
Retweets
451
Likes
โ€‹

โ€‹


Enjoying The Plug?

Help it grow ๐Ÿ‘‰

๐Ÿ”Œ Forward this on to a friend, colleague, or client

๐Ÿ”Œ Check out more purely tax alpha on my podcast - Today in Tax Court - and follow me on X @rledbettercpa

๐Ÿ”Œ Reply to this email to set-up a paid consultation re: tax, accounting, or firm management

๐Ÿ”Œ Reply to the poll below, or email me and let me know what you thought ๐Ÿ‘‡

โ€‹

Want to read previous issues? Click here.โ€‹

The Plug [Newsletter]

For business owners, investors, and advisors looking to lower their cost of capital. Subscribe for delivery straight to your inbox ๐Ÿ‘‡

Read more from The Plug [Newsletter]

Saving small business and real estate owners on tax is one the best ways I fulfill my personal mission - which is lowering the cost of capital for decision makers. Today, we're going back to school ๐ŸŽ’ with the 5 biggest tools SMB and RE owners should be using to do just that ๐Ÿ‘‡ An S-Corp Somewhere ยง469 Aggregation Cost Segregation 199A QBI Optimization Operating Agreement Planning But first... ๐Ÿšจ The Plug is now on YouTube! ๐Ÿšจ I'd appreciate a like, comment, and follow over there if you're into...

Ask your accountant, and they'll tell you "It depends." Ask your attorney, and you'll get a novel of an email and a $1,000 invoice. But all you really want is someone to tell you how to set up your business to get started without stepping on a landmine. ๐Ÿ’ฅ If you feel this, today is your day. We're going into the structure I advise in a lot of entity structuring and planning calls I have (if you want one customized, just reply to this email to get set-up). This design includes the best parts...

More unnecessary tax is paid from bad accounting than bad tax planning. ๐Ÿซณ๐ŸŽค Bad structures or missed elections can cost a few percentage points on the tax paid on the income. But bad accounting can create phantom income or missed deductions that become unrecoverable - it's something no level of tax planning can help you with. ๐Ÿคท To illustrate - today we're digging into a few real life examples I've seen over the years: Losing Money on Real Estate Owned When you build or improve assets yourself,...