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Josh Youngblood

@joshyoungblood.bsky.social
280 followers 80 following 142 posts

EA, NTPI, CTRS, CRETS, Tax 💰, Tech🧑🏻‍💻 , Traveling ✈️. joshandtaxes.com | josh.tax | joshyoungblood.eth

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Reposted by Josh Youngblood
Think Outside the Tax Box @tottbnews.bsky.social · 14/04/2026
A client pours everything they have into a business, and the venture doesn’t make it. When that happens, the Internal Revenue Code provides several meaningful tools to ease the tax pain when a business fails. Check out @joshyoungblood.bsky.social's article: bit.ly/4vrEwil #taxes #tax
bit.ly
When Your Client’s Business Fails: Easing the Tax Pain - Think Outside the Tax Box
The Internal Revenue Code provides several meaningful tools to ease the tax pain when a business fails. The problem is that many of these provisions require advance planning, timely action, or both. I...
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Josh Youngblood @joshyoungblood.bsky.social · 28/03/2026
My $500 ViewSonic OLED travel monitor shocked me. Literally. Two weeks in, it popped and died. Found its replacement hiding in HP's commercial division. The Series 5 Pro 514pn. I break it down in my latest Substack Note. #TaxSky #JoshAndTaxes substack.com/@joshyoungbl...
substack.com
Josh Youngblood, EA, CRETS (@joshyoungblood)
I've been on a quest for the perfect portable monitor to sit under my 40-inch ultrawide. Not for travel. For a command center. Facebook Messenger on one side, Google Chat or Slack on the other,…
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Josh Youngblood @joshyoungblood.bsky.social · 28/03/2026
The FBI Director's personal Gmail got breached by Iranian hackers. Not FBI systems. His personal email. If his inbox isn't safe, neither is yours. Lock down your personal accounts, especially if they've ever touched client data. #TaxSky #Cybersecurity
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Josh Youngblood @joshyoungblood.bsky.social · 26/03/2026
The 5th Circuit vacated the FTC's ban on TurboTax advertising as "free." Didn't touch the merits. The ad was deceptive, and everyone knows it. But Intuit gets a procedural off-ramp and zero accountability. #TaxSky Read more - substack.com/profile/6019...
substack.com
Josh Youngblood, EA, CRETS (@joshyoungblood)
The 5th Circuit just vacated the FTC's order banning Intuit from advertising TurboTax as "free." The FTC found Intuit ran a deceptive ad campaign for years. The "free" product was only available to…
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Josh Youngblood @joshyoungblood.bsky.social · 20/03/2026
Quoted in Bloomberg this week. I'm already seeing clients in trouble because AI gave them confidently wrong tax advice. One didn't report a crypto transaction after AI said income under $3K wasn't reportable. (It is.) www.bloomberg.com/news/article...
bloomberg.com
People Are Using Claude to Do Their Taxes (But Maybe They Shouldn’t)
Accountants warn of the potential for costly mistakes using ChatGPT and other AI tools.
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Josh Youngblood @joshyoungblood.bsky.social · 17/03/2026
You know that little thing on your computer you keep working around instead of fixing? It's going to take 10 minutes. You've already wasted more time than that avoiding it. I've spent the last two weeks knocking out little irritations and it makes a huge difference. What's on your list? #TaxSky
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Josh Youngblood @joshyoungblood.bsky.social · 12/03/2026
We need more people in the tax profession. But "more people" and "more qualified people" are not the same thing. I wrote about the service bureau model, what's broken, and what should change. open.substack.com/pub/joshandt...
open.substack.com
The Tax Industry’s Worst-Kept Secret: Service Bureaus, Ghost Preparers, and the Regulation We’re Missing
If you spend any time in tax professional Facebook groups, you’ve seen the posts.
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Josh Youngblood @joshyoungblood.bsky.social · 08/03/2026
Great article by @benappel.bsky.social www.theatlantic.com/ideas/2026/0...
theatlantic.com
In Defense of Effeminate Boys
If anyone had suggested that I might really be a girl, I don’t know how I would have responded.
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Josh Youngblood @joshyoungblood.bsky.social · 05/03/2026
Claude rhymes with Maude. Both showed up and dared you to keep up. AI is the biggest shift in tax practice since e-file, and the question is whether you are ready. New on Josh & Taxes: And Here Comes Claude. open.substack.com/pub/joshandt...
open.substack.com
And Here Comes Claude
For those of you of a certain vintage, Claude rhymes with Maude.
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Josh Youngblood @joshyoungblood.bsky.social · 03/03/2026
The secrecy around pricing in this profession isn't protecting you. It's costing you. New practitioners undercharge because they have no benchmarks, and experienced practitioners hesitate to raise rates because they lack context. open.substack.com/pub/joshandt...
open.substack.com
Let’s Talk About Pricing. Yes, We Can Do That.
It’s March.
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Josh Youngblood @joshyoungblood.bsky.social · 28/02/2026
substack.com/@joshyoungbl...
substack.com
Josh Youngblood, EA, CRETS (@joshyoungblood)
Cyber Vigilance in Times of Conflict: What Business Owners Need to Do Right Now With U.S. military strikes on Iran underway, CISA and the FBI have warned of heightened cyber threat activity targeting...
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Josh Youngblood @joshyoungblood.bsky.social · 24/02/2026
I've worked from home. I've had six different offices. I work with clients entirely remotely and wouldn't change that for the world. Here's what I've figured out: where you work matters, but the answer isn't the same for everyone. open.substack.com/pub/joshandt...
open.substack.com
Home, Office, or Somewhere in Between
I worked from home off and on for years.
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Josh Youngblood @joshyoungblood.bsky.social · 17/02/2026
Your client has a newborn. There's a $1,000 government contribution sitting on the table. Are you going to tell them about it, or are you going to let your feelings about the name on the account make that decision for them? open.substack.com/pub/joshandt...
open.substack.com
The Tax Code Doesn't Care About Your Politics
I have strong political opinions.
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Josh Youngblood @joshyoungblood.bsky.social · 10/02/2026
A Tax Court judge just compared a lawyer's brief to something "cooked up by AI." Three fabricated case citations. A collapsed soufflé metaphor. A DOGE defense. And a one-word warning from Judge Holmes: "Yet." I break down Clinco v. Commissioner. open.substack.com/pub/joshandt...
open.substack.com
When AI Cooks Up Fake Case Law: Clinco v. Commissioner
Want to listen to this instead of reading it?
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Josh Youngblood @joshyoungblood.bsky.social · 03/02/2026
Transcripts cost nothing but time. They save enormous amounts of it later. If you do tax representation work, they're not optional. They're foundational open.substack.com/pub/joshandt...
open.substack.com
The First Step in Any Tax Problem: Pull the Transcripts
When a new client comes to me with a tax problem, they usually start with a story.
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Reposted by Josh Youngblood
Think Outside the Tax Box @tottbnews.bsky.social · 21/01/2026
Every tax season, well-intentioned taxpayers get lured by false tax advice on social media, only to end up in trouble. As tax professionals, you will encounter clients who need you to untangle the mess. Check out @joshyoungblood.bsky.social's article! bit.ly/4sOlphj #tiktok #taxhacks #tax
thinkoutsidethetaxbox.com
When TikTok Tax Hacks Backfire: Helping Clients Misled by Social Media Scams - Think Outside the Tax Box
Jessica, a self-employed consultant, was thrilled when she found a viral TikTok video promising a “little-known” tax trick. The video claimed she could get a huge refund by claiming a special Fuel Tax Credit and even writing off her family's beach vacat...
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Josh Youngblood @joshyoungblood.bsky.social · 26/01/2026
“Big Brother is watching you.” —1984 TikTok’s new privacy policy exposes mental health, GPS, & immigration data to U.S. agencies—with fewer safeguards. Here’s how to opt out, protect yourself, and take back your privacy. open.substack.com/pub/joshandt...
open.substack.com
The TikTok Trade-Off
Staying Safe
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Josh Youngblood @joshyoungblood.bsky.social · 21/01/2026
New guest piece on Josh & Taxes Aaron Dickerson breaks down why he ditched the MSP model and rebuilt his firm’s tech stack to actually comply with the FTC Safeguards Rule. Practical, candid, and a must-read for firm owners. open.substack.com/pub/joshandt...
open.substack.com
The Dangerous Comfort of Outsourced IT
I’m excited to welcome Aaron Dickerson, CPA, CVA, CFE, to Josh & Taxes.
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Josh Youngblood @joshyoungblood.bsky.social · 19/01/2026
Passkeys are the future of logging in, and that future is already here. Apple, Google, Microsoft, Amazon, GitHub, and a growing list of sites already support them. open.substack.com/pub/joshandt...
open.substack.com
Passkeys Explained
What They Are and Why They Matter
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Josh Youngblood @joshyoungblood.bsky.social · 08/01/2026
Translating tax law into something clients actually understand is half the battle. Google’s latest NotebookLM updates can turn research, memos, and spreadsheets into slide decks and infographics in minutes. I wrote about how tax professionals can use this for client education and internal training.
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Josh Youngblood @joshyoungblood.bsky.social · 23/12/2025
As the year winds down, I’ve been thinking less about resolutions and more about intentionality. I shared 10 things I’m doing heading into the new year to protect my energy, my practice, and my sanity, without treating tax season like a monster to survive. #TaxSky open.substack.com/pub/joshandt...
open.substack.com
10 Things I’m Doing to Start the New Year Strong
The end of the year always feels a little strange for tax professionals.
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Josh Youngblood @joshyoungblood.bsky.social · 23/12/2025
🔐 Ready to demystify data security for your tax practice? Join me for #NATP Creating Your Firm’s WISP with Confidence, an on-demand workshop designed to help tax pros build a practical and compliant Written Information Security Plan (WISP). Real-world guidance and 4 CE/CPE.👇 #WISP #TaxSky
natptax.com
2025 Creating Your Firms WISP with Confidence On-Demand Online Workshop
Learn how to quickly create a practical, compliant WISP for your tax practice – without the fear, confusion or tech jargon.
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Josh Youngblood @joshyoungblood.bsky.social · 12/12/2025
IRC §7216 isn’t just a technical rule. It has criminal penalties. Sharing tax returns with other professionals, lenders, or through outside systems can trigger disclosure requirements many firms overlook. #TaxSky #EA #CPA #Taxes
open.substack.com
The Overlooked Risk in Tax Collaboration
Why Section 7216 Disclosures Matter
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Josh Youngblood @joshyoungblood.bsky.social · 02/12/2025
Giving Tuesday tip for tax pros: teach clients how to vet a charity before they give. I break it down in my new post: verifying 501(c)(3)s, spotting red flags, and reading Form 990s. #TaxSky #EA #CPA open.substack.com/pub/joshandt...
open.substack.com
Vetting a Charity Before You Donate
A Giving Tuesday guide for tax pros and the clients who trust us
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Josh Youngblood @joshyoungblood.bsky.social · 29/11/2025
Updated @ignitionapp.bsky.social review. What’s new, what still works, and how it fits into my workflows. Black Friday – Cyber Monday offer included. #TaxSky
joshandtaxes.com
Ignition: My Updated Review and an Offer Worth Grabbing
Early last year, I wrote a full review of Ignition and how it transformed my proposals, onboarding, and billing.
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Josh Youngblood @joshyoungblood.bsky.social · 27/11/2025
Happy Thanksgiving everyone! I want to take a moment to thank all of you who have subscribed and shared my posts, I really appreciate it. What started off as an experiment to do something fun has turned into more than I ever imagined. Enjoy your day! #TaxSky #EA #CPA #cybersecurity #JoshAndTaxes
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Josh Youngblood @joshyoungblood.bsky.social · 26/11/2025
I kept my Black Friday and Cyber Monday list simple this year and shared what I’m actually buying and why. If you’re sorting through deals or trying to decide on tech or gear, feel free to join the subscriber chat and ask anything. open.substack.com/pub/joshandt... #TaxSky
open.substack.com
My Black Friday and Cyber Monday Short List
I’m keeping my Black Friday and Cyber Monday shopping focused this year.
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Josh Youngblood @joshyoungblood.bsky.social · 25/11/2025
I wrote about the pressure to always be “on,” the blur between work and life, and what I’m learning about rest, guilt, and remote work. If you have ever struggled to step away from your business, this one is for you. #TaxSky #EA #CPA open.substack.com/pub/joshandt...
open.substack.com
There’s Always Something To Do
But That Doesn’t Mean You Should Do It
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Josh Youngblood @joshyoungblood.bsky.social · 20/11/2025
TRMNL might be the first device I’ve used that actually respects your attention. Excited to be joined by @emdeeem.bsky.social and his thoughts on it. Quiet tech is underrated. open.substack.com/pub/joshandt... #TaxSky
open.substack.com
Meet TRMNL
The Anti-Notification Device That Actually Helps You Work
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Josh Youngblood @joshyoungblood.bsky.social · 13/11/2025
Apple just added digital passports to Wallet. No, you can’t use it for international travel yet. Yes, Android folks, we know you had it first. Still a win for TSA, hotels, and ID checks. Took me 5 minutes to set up. Huge fan of carrying less stuff. ✈️ open.substack.com/pub/joshandt... #TaxSky
open.substack.com
Your Passport Is Now on Your iPhone
But Here’s What It Actually Does
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Josh Youngblood @joshyoungblood.bsky.social · 12/11/2025
New AskJosh: “Is Grammarly safe to use?” 🤔 After acquiring Superhuman + Coda, Grammarly is now Superhuman Platform Inc. and your data may touch more systems than you realize. (I am a user of Grammarly and Superhuman) joshandtaxes.com/p/ask-josh-i... #TaxSky #cybersecurity #EA #CPA
joshandtaxes.com
Ask Josh: Is Grammarly Safe to Use?
One of my favorite aspects of writing this Substack is when readers send me questions.
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Josh Youngblood @joshyoungblood.bsky.social · 10/11/2025
If you work with real estate clients, the CRETS certification is a game changer. I took it when Natalie first launched it. The fall session starts today, don’t miss it. open.substack.com/pub/joshandt... #TaxSky #EA #CPA
open.substack.com
Why You Should Sign Up For The CRETS Certification
and Why I Loved It
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Josh Youngblood @joshyoungblood.bsky.social · 07/11/2025
Let’s be honest: our field has a credential fragility problem. Too many people use their letters to divide instead of elevate. The best professionals, know that competence, humility, and collaboration matter far more than titles. #TaxSky #EA #CPA #tax open.substack.com/pub/joshandt...
open.substack.com
Credential Fragility
EA, CPA, WTF — Enough Already
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Josh Youngblood @joshyoungblood.bsky.social · 31/10/2025
It’s Halloween, and while most scares tonight will be make-believe, one thing gave me a chill this morning. The US may ban TP-Link equipment. Here’s what you should know. #TaxSky #EA #CPA #Cybersecurity open.substack.com/pub/joshandt...
open.substack.com
A Scary Story for Halloween
The TP-Link Problem
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Josh Youngblood @joshyoungblood.bsky.social · 29/10/2025
Tired of unreliable hotel Wi-Fi or rural dead zones? I tested the Starlink Mini — a backpack-sized satellite dish that promises fast, portable internet anywhere. Here’s what works, what doesn’t, and who it’s really for. open.substack.com/pub/joshandt... #TaxSky #Starlink #EA #CPA
open.substack.com
Starlink Mini
A Lifeline for Remote Work or Just an Expensive Backup
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Josh Youngblood @joshyoungblood.bsky.social · 16/10/2025
You made it through tax season. The final deadline is behind you. Now’s the time to rest, reflect, and be honest about what’s not working. Some clients probably need to go. No one’s coming to save you; it is up to you. open.substack.com/pub/joshandt... #TaxSky #EA #CPA
open.substack.com
You Survived Tax Season
Now Fix What Broke You
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Josh Youngblood @joshyoungblood.bsky.social · 11/10/2025
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...
open.substack.com
National Coming Out Day
The Courage to Be Seen
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Josh Youngblood @joshyoungblood.bsky.social · 10/10/2025
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...
open.substack.com
Focus, Found in Ink
or E-ink
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Josh Youngblood @joshyoungblood.bsky.social · 05/10/2025
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...
open.substack.com
Depreciating Gracefully
44 Truths at 44
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Josh Youngblood @joshyoungblood.bsky.social · 03/10/2025
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...
open.substack.com
Taxing Justice
The Fortune-Paladino Case and the Taxation of Settlements
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Josh Youngblood @joshyoungblood.bsky.social · 25/09/2025
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...
open.substack.com
Amex Business Platinum Gets a Refresh...
and a Price Hike
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Josh Youngblood @joshyoungblood.bsky.social · 24/09/2025
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...
open.substack.com
Expensive? Yes. Ridiculous? No
Here’s Why I Love My American Express Platinum Card
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Josh Youngblood @joshyoungblood.bsky.social · 17/09/2025
$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...
open.substack.com
IRS Modernization
All Spend, No Shutdowns
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Josh Youngblood @joshyoungblood.bsky.social · 10/09/2025
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...
open.substack.com
And the Winner Is…
Plus a Quick Snippet on the Best Tech
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Josh Youngblood @joshyoungblood.bsky.social · 09/09/2025
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...
open.substack.com
Loopholes, Liberty, and Judge Learned Hand
If you’ve been around seasoned tax educators, you’ve probably heard them quote Judge Learned Hand.
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Josh Youngblood @joshyoungblood.bsky.social · 05/09/2025
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...
open.substack.com
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.
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Josh Youngblood @joshyoungblood.bsky.social · 02/09/2025
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...
open.substack.com
Blow It Out Your Tubenburbles
The Truth About Mortgage Comfort Letters
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Josh Youngblood @joshyoungblood.bsky.social · 28/08/2025
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
open.substack.com
Empathy with Boundaries
The Underrated Skill That Keeps You in the Game
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Josh Youngblood @joshyoungblood.bsky.social · 26/08/2025
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...
open.substack.com
The Case for VPNs
Privacy, Streaming, and a Little Bit of Stubborn Freedom
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Josh Youngblood @joshyoungblood.bsky.social · 26/08/2025
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
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