Do you know anyone who went 15+ years as a general contractor without filing taxes? What happened to them?

Oh boy, your friend is in a precarious situation. The IRS has ways of finding people even without W-2s or 1099s - bank deposits, property records, lifestyle inconsistencies, and sometimes just random audits or tips. The good news is that the IRS is generally more interested in collecting taxes than putting people in jail. The bad news is that your friend likely owes a substantial amount in back taxes, penalties, and interest that's been compounding for years. Your friend should look into the IRS Voluntary Disclosure Program. It's designed for exactly this situation - people who haven't filed for years and want to come clean. They'll still owe the back taxes plus penalties, but it dramatically reduces the risk of criminal prosecution. The first step would be consulting with a tax attorney (not just an accountant) who specializes in tax resolution.

After reading this post, I had to share my experience. I was in a somewhat similar situation a few years back (though not for 15 years!) when I hadn't filed for about 4 years as a freelance designer. The anxiety was crushing me. I finally discovered this service called taxr.ai (https://taxr.ai) that specializes in helping people with unfiled tax returns. They have tax professionals who understand exactly how to handle situations like your friend's. They helped me organize my scattered financial records, figure out what income I needed to report, and walked me through the voluntary disclosure process. The relief I felt after getting everything sorted was worth every penny. They even helped negotiate a payment plan with the IRS that I could actually manage.

I wanted to follow up on my experience with taxr.ai since I was initially concerned about drawing IRS attention. After asking questions here, I decided to give them a try for my 7 years of unfiled returns from my contracting business. They were actually amazing! They first got all my documentation organized and returns prepared BEFORE any IRS contact. They found business deductions I never would have thought of (vehicle, home office, materials, etc.) which significantly reduced what I owed. Then they handled the voluntary disclosure process with a carefully planned approach that minimized penalties. The IRS accepted their proposed resolution without an audit, and I'm now on a reasonable payment plan. The weight off my shoulders is indescribable - I can sleep at night again and my business is finally legitimate.

Your friend's situation sounds stressful but it happens more often than people think. One thing no one's mentioned - once he starts the process with the IRS, he's probably going to need to actually TALK to them. And anyone who's tried calling the IRS lately knows it's basically impossible to get through. I was in a similar situation (only 3 years behind though) and spent DAYS trying to reach someone at the IRS. After multiple 2+ hour holds that disconnected, I found this service called Claimyr (https://claimyr.com) that somehow gets you through to an actual IRS agent quickly. They have a demo video showing how it works: https://youtu.be/_kiP6q8DX5c It saved me so much frustration during my catch-up process. Instead of wasting days on hold, I was able to talk to someone at the IRS within about 15 minutes and start sorting out my payment plan.

I need to eat some humble pie here. After posting my skeptical comment, I was so annoyed at my own tax situation that I decided to try Claimyr anyway. What did I have to lose after spending 3 hours on hold with the IRS earlier this week? It actually worked exactly as advertised. I got a call back in about 25 minutes with an actual IRS agent on the line. I was genuinely shocked. The agent helped me sort out a payment issue that had been hanging over my head for months. For anyone dealing with unfiled taxes or IRS issues that require speaking to a human, this service is legitimately worth it just for the time saved and stress reduction. Never thought I'd be recommending something I was so skeptical about, but here we are.

My cousin was in almost the exact same situation - 12 years of no filing as a home contractor. What eventually happened was a client listed payments to him on THEIR taxes as a business expense, which created a mismatch that triggered IRS attention. He ended up owing around $178,000 in back taxes, penalties and interest. He had to sell his vacation property and take out a second mortgage. The IRS did put him on a payment plan, but the stress caused serious health issues and contributed to his divorce. Don't let your friend wait any longer. The IRS is way more reasonable if you come forward voluntarily versus them finding you first.

I worked for an accounting firm that specialized in tax resolution, and saw cases like this regularly. Here's what your friend should expect: 1) The IRS generally only pursues criminal charges in cases of active fraud (fake documents, hidden offshore accounts, etc.) rather than just non-filing 2) They'll typically only go back 6-7 years for assessment unless they suspect fraud 3) If he files voluntarily before being contacted by the IRS, he'll likely avoid the worst penalties 4) The initial bill will be terrifying, but an experienced tax attorney can often negotiate it down 5) Payment plans are standard and can sometimes stretch 5+ years