Josh Youngblood

National Coming Out Day The Courage to Be Seen

Today is National Coming Out Day. I don’t usually write about topics like this, but this one’s about something bigger than taxes or tech — it’s about being human. Special thanks to Natalie & Tom for their perspective. open.substack.com/pub/joshandt...

Focus, Found in Ink or E-ink

After years of chasing productivity apps, I’ve learned the truth: the yellow legal pad was right all along. #TaxSky #EA #CPA #Productivity open.substack.com/pub/joshandt...

Depreciating Gracefully 44 Truths at 44

I turned 44 and decided to write about it — not taxes or tech this time, just life, coffee, clutter, and the fine art of depreciating gracefully. #TaxSky open.substack.com/pub/joshandt...

Taxing Justice The Fortune-Paladino Case and the Taxation of Settlements

Sympathy ≠ exclusion. In Fortune-Paladino, a harassment settlement was fully taxable. Why the words in a settlement matter, and how to avoid §6662 penalties. #TaxSky #EA #CPA #TaxCourt open.substack.com/pub/joshandt...

Amex Business Platinum Gets a Refresh... and a Price Hike

Yesterday I broke down the Personal Amex Platinum. Today? The Business Platinum just got a refresh: $895 fee, $600 hotel credits, $1,150 Dell perks + more. Worth it for small biz + tax pros? #TaxSky #Travel open.substack.com/pub/joshandt...

Expensive? Yes. Ridiculous? No Here’s Why I Love My American Express Platinum Card

The @americanexpress.bsky.social Platinum Card now costs $895. Sounds ridiculous? It’s not. Here’s why I gladly pay it — and how I turn that fee into $3,000+ of value. 👇 #TaxSky open.substack.com/pub/joshandt...

IRS Modernization All Spend, No Shutdowns

$190M spent. $39M/year burned. 0 legacy systems retired.
TIGTA’s latest report shows the IRS’s modernization effort is stuck in neutral. I explain why this matters for taxpayers + practitioners. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

And the Winner Is… Plus a Quick Snippet on the Best Tech

The results are in! Thank you for the feedback, you want more IRS representation, practical tech, and practice management. Plus, the prize winner and a quick tech snippet. Find out below. #TaxSky #EA #CPA
open.substack.com/pub/joshandt...

Loopholes, Liberty, and Judge Learned Hand If you’ve been around seasoned tax educators, you’ve probably heard them quote Judge Learned Hand.

He never sat on the Supreme Court, but Judge Learned Hand shaped the way we think about tax planning, substance over form, and even liberty itself. His words still matter in 2025. #TaxSky #Taxlaw #EA #CPA open.substack.com/pub/joshandt...

1,000 Subscribers 🎉 Let’s Celebrate With a Giveaway! Today Josh & Taxes crossed the 1,000 subscriber mark — and I couldn’t be more grateful.

Josh & Taxes just hit 1,000 subscribers!
I’m so grateful for everyone who’s read, shared, and encouraged me along the way.
To celebrate, I’m hosting a giveaway. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Blow It Out Your Tubenburbles The Truth About Mortgage Comfort Letters

Tax pros argue about plenty of things — from pancakes vs waffles to obscure corners of the code. But one topic brings us together: we hate mortgage comfort letters. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Empathy with Boundaries The Underrated Skill That Keeps You in the Game

Empathy gets them in the door. Boundaries keep you from walking out.
The people who do this work well? They lead with empathy.
The ones who last? They know when to set a boundary.
I wrote about why empathy matters — and how it can destroy you if you don’t protect yourself. #TaxSky #EA #CPA

The Case for VPNs Privacy, Streaming, and a Little Bit of Stubborn Freedom

Public Wi-Fi = unsafe.
ISPs = selling your data.

Do you still need a VPN in 2025? Yes. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Looking forward to this @incite.bsky.social event tomorrow @ 1PM EST with @emdeeem.bsky.social where we talk about using an @elgato.com Stream Deck in your practice. If you aren't an InCite member, check it out! Incite.Tax #TaxSky #EA #CPA

Thank you. ChatGPT for the win! lol

IRS Transcripts Made Easy My Review of PitBullTax Transcripts

IRS transcripts = clunky. Most software = dated.
I’ve been using @PitBullTax Transcript Delivery and it’s a game changer: fast pulls, clean client reports, and runs right in the browser (yes, even on Mac). #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Password123? We Need To Talk You need a password manager!

Passwords on sticky notes?
Saved in Chrome?
Still using the same login everywhere?
You’re one breach away from disaster. #TaxSky #EA #CPA

53 says. . Liz Truss served the UK 50 days.

From the IRS to Iceland Billy Long's Unexpected Career Pivot

Billy Long shares what he loved most about leading the IRS and what his next chapter in his career will be. #TaxSky #EA #CPA #Taxes open.substack.com/pub/joshandt...

From Code to Courtroom Why Tax Pros Should Read Court Cases

Why read court cases? Because tax is law, and we work in it every day. Court opinions show how rules get applied, where taxpayers go wrong, and how to sharpen your advice. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Useful, Thoughtful, Creepy? Real Talk on AI Meeting Tools

Useful, Thoughtful, Creepy? I tried 3 AI meeting tools—Krisp, Plaud Note & Zoom’s AI Companion. What’s helpful, what’s overkill, and what’s just creepy. Plus $50 Amazon gift card giveaway! #TaxSky #EA #CPA #TaxTech open.substack.com/pub/joshandt...

To Charge or Not to Charge That Is the Question

To charge or not to charge? That’s the question for business owners when it comes to credit card fees. I break down the pros, cons, and how I personally handle it in my latest article. #TaxSky #EA #CPA open.substack.com/pub/joshandt...

NotebookLM AI That Cites Its Sources? Yes, Please.

NotebookLM - How are you using this? #TaxSky #EA #CPA open.substack.com/pub/joshandt...

Add to Cart My Favorite Prime Day Picks (and Why)

Amazon Prime Day = 96 hours this year 😳
Here’s my short list of stuff actually worth buying—AirPods, Anker gear, protein hacks & one espresso tip you didn’t know you needed ☕💻 open.substack.com/pub/joshandt...

You Can Do Anything - But Not Everything A reflection on time, focus, and the danger of trying to do everything. Plus: a crucial update on the OB3 and why you need good CE.

A reflection on time, focus, and the danger of trying to do everything. Plus: a crucial update on the OB3 and why you need good CE. open.substack.com/pub/joshandt... #TaxSky #EA #CPA

BOOX Note Air 4C Review A Colorful Leap for E Ink Tablets

I reviewed the BOOX Note Air 4C — a color e-ink tablet perfect for tax pros, students, and serious PDF users. If you’re tired of eye strain and want more power than a reMarkable, this might be the one. #TaxSky #EA #CPA #EINK #tech

Beyond Doomsday: The IRS Has a Plan—And It Survives the Apocalypse

“Nothing is certain except death… and taxes—even after nuclear war.”
I explored the IRS’s Continuity Operations Plan, Cold War bunkers, and what tax collection looks like in a worst-case scenario. open.substack.com/pub/joshandt... #taxsky #taxes #WW3

What is an EA? Understanding the role, authority, and value of America’s lesser known tax professional, the enrolled agent

open.substack.com/pub/joshandt... #TaxSky #EA

Part 3: Post-Tax Season Upgrades Pro-Level Accessories

Still using those free earbuds from a 2019 conference? Time for a post–tax season upgrade. I put together my favorite pro-level accessories for tax pros—headphones, mics, lighting, and more. These are the tools I actually use. #TaxSky #EA #CPA #TechTax open.substack.com/pub/joshandt...

Freelancer Deductions: What You Might Be Missing and What You Need to Remember - Think Outside the Tax Box Even savvy freelancers often miss deductions that could significantly reduce tax liability. The IRS offers legitimate ways for freelancers to deduct business-related costs, but it’s not always obvious...

Even savvy freelancers miss legit tax deductions. Confused about what qualifies? You're not alone—bad advice online doesn't help

@joshyoungblood.bsky.social breaks it down in his latest article: common missed write-offs, real examples & tips for pros. Don’t miss it!
#taxes #deduction
bit.ly/3FnRsAO