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AI Auditing: the most important coffee break I've ever done.
Today's coffee break livestream was a bit different than what I had planned. I had a whole different show prepared, and then last night, as I was lying in bed, this thought struck me. AI systems are going to be issuing audit notices in the very near future. And we have to build our own AI defense systems starting now. It's way too much for a skool post so go and check out the blog post on the TaxSherpa.com site. Forewarned is forearmed. https://taxsherpa.com/post/audit-by-ai-the-future
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Welcome to The Tax Strategy Network!
You’re in the right place if you want to legally reduce taxes, keep more of what you earn, and have ongoing support as you actually implement strategies in real life.​ How the community is structured We keep things simple with three levels so you always know what you have access to and where to go next.​ - Free Forever (everyone starts here) – This is the open community where you can join discussions, see updates, and get a feel for how we think about tax strategy for business owners.​ - Navigators (labeled “Premium” in Skool) – This is for people who want access to all of the tools, trainings, and resources I’ve created (and will create) to help you design and implement tax strategies on your own.​ - VIP Tax Plans (labeled “VIP” in Skool) – These are clients who have purchased a custom tax plan; they get everything in the lower levels plus classroom resources built specifically to help operate the strategies in their plan throughout the year.​ What Navigators get If you’re in the Navigators level, you unlock the full Classroom, all current and future trainings, and our weekly live call.​ - Weekly Navigators Call: Thursdays at 3 p.m. Eastern (already on the Skool calendar).​ - Deep-dive trainings on specific strategies, tools walkthroughs, and implementation guidance so you can confidently apply what you’re learning.​ What VIP Tax Plan clients get If you’re in the VIP level, you have a personalized tax plan that lays out the math, what to do, and how to do it.​ - The Classroom includes step-by-step resources tailored to operating the strategies in your plan—things like accountable reimbursement workflows and other “how do I actually do this?” guides.​ - As life and business happen during the year, you can refer back to these resources to make sure each strategy is set up and executed correctly.​ Your first action: Coffee Break with Neal No matter what level you’re in, the best way to plug in is to add our weekly Coffee Break with Neal to your calendar.​
Where do you actually stand? New tool, live now (beta).
Most business owners can tell me their revenue. Almost none can tell me which stage they're actually in — Basecamp, Ascent, or Summit — without me pulling their P&L apart by hand. That's what ClearPath Mapper does now, on your own. Upload a P&L export (CSV or PDF). It maps every line into the ClearPath framework — Revenue, COGS, Fulfillment, Systems, People — and hands you back a stoplight scorecard: what's solid, what's bleeding, and which Basecamp benchmark you're missing. It's live, but it's beta. Expect rough edges. If you hit one, tell me — that's exactly the feedback that turns this into something I hand to the whole list with confidence. On cost: this becomes a paid tool eventually — running your data through it costs real money on my end, it won't stay free forever. Right now, in beta, it's free. And once pricing lands, Navigators and VIPs get it included, same as everything else I build. Try it: clearpathmap.taxsherpa.com — or read how it works first at clearpath.taxsherpa.com Drop your results, questions, or bugs in the comments. That's the fastest way to get this ready for everyone else.
Is health insurance deductible? Which door are you? (live today)
Everybody asks if health insurance is deductible. It's the wrong question. The same premium lands in a different place on your return depending on who pays it and how you earn a living. I was live at 3pm Eastern today. What this episode covers: - W-2 with an employer plan: pre-tax in payroll, no second deduction - Self-employed: the above-the-line deduction and the two limits that catch people - S-corp owners: why the W-2 step matters - Businesses that reimburse: QSEHRA, ICHRA and Section 105 plans, and why entity type decides - Marketplace plans and the 2026 subsidy changes - HDHP and HSA: 2026 limits and what's new - Itemizing: the 7.5% of AGI floor - Five traps, and a checklist for before open enrollment Who should watch this: - Self-employed people and S-corp owners paying premiums themselves - Anyone on a marketplace plan or an HSA-eligible plan - Tax pros and bookkeepers who want a clean way to explain the doors to clients Come with questions. Describe your situation in general terms, and please don't post personal documents or ID numbers in the group. Grab your coffee. https://www.skool.com/tax-strategy-network/classroom/9d72b0b3?md=2935422363194ff8a2325f5af19ede01
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Is health insurance deductible? Which door are you? (live today)
Tax resolution ads: what they leave out (live today)
Those "settle your tax debt for pennies on the dollar" ads keep showing up in my feed, and they keep making me furious. So today's Coffee Break is a teardown. Live at 3pm Eastern today. The pitch sells an outcome. The IRS runs a process. Nobody can quote you a solution before they know where you actually stand, and any company that prices you on the first call is selling, not diagnosing. What this episode covers: - What "Fresh Start" really means (there's no application, it's shorthand for four ordinary tools) - Step 1: Where are you? Transcripts, notices, and what was actually filed - Step 2: Get compliant. Why missing returns come before every option - Step 3: The options ladder. Pay in full, partial payment, installment agreement, offer in compromise, currently not collectible - What the offer in compromise numbers actually say (spoiler: "pennies on the dollar" isn't a base rate) - What pauses the IRS's 10-year collection clock, and why waiting it out is a bad trade - Step 4: Check as you go - A quick checklist for spotting a bad resolution firm Who should watch this: - Anyone with IRS debt, unfiled returns, or a notice they haven't dealt with - Anyone who has seen one of these ads and wondered if it's real - Tax pros and bookkeepers who want a clean way to explain the options ladder to clients Come with questions. If you have a notice in hand, bring it to the chat. Please don't post transcripts or personal details in the group. Describe the situation in general terms. Also: I'm building a tool that reads the IRS account transcript you download and explains the codes in plain English. Everyone who joins the waitlist gets notified the day it's ready. Link is in the video description and I'll show the QR code on screen. Watch on YouTube Grab your coffee.
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The Tax Strategy Network
skool.com/tax-strategy-network
Discover and implement proven tax strategies used by smart owners to legally reduce taxes and keep more of what you earn
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