Sometimes the best opportunities come from the most unexpected places.
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I wasn’t looking to take on a $5+ million tax case that day. I was just looking for a panel truck.
It was early in my tax resolution career, and I’d found what seemed like the perfect truck on Craigslist. I drove out to meet the seller – let’s call him Bill – expecting a quick transaction. Buy truck, drive home, done.
But then Bill asked the question that changed everything: “So, what do you do for work?”
The Conversation That Started It All
“I help people with tax problems,” I told him.
Bill’s face changed. “Tax problems? Man, do I have tax problems.”
What started as small talk quickly became something much bigger. Bill and his sister had inherited their father’s vending machine business – mainly pool tables, dart machines, and an incredible collection of vintage arcade games. Two giant warehouses packed with everything from Pac-Man to Galaga to games I’d forgotten existed.
The problem? They knew how to run arcade machines, but bookkeeping? Not so much.
Bill hadn’t filed a tax return in over 10 years. The IRS and Iowa were claiming he owed more than $5 million.
The Moment of Truth
I’ll be honest – I was terrified. This was my first major tax resolution case, and the numbers were staggering. But I’d learned something important in the Marines: when faced with an overwhelming problem, you break it down systematically.
Step one: Diagnose everything that’s wrong. Step two: Get the client current (file all missing returns). Step three: Attack each problem methodically.
So that’s exactly what we did.
Walking Through Gaming History
The best part of this case? I got to tour those warehouses. Room after room of arcade history. Bill even had a special room for the “good stuff” – pristine machines that belonged in a museum.
(Side note: I bought a dart machine from him that day. It’s at home and we use it every week.)
The Result That Changed Everything
After months of systematic work – filing returns, organizing records, negotiating with both the IRS and Iowa – we got Bill’s tax liability down from over $5 million to under $30,000.
Let me repeat that: From $5+ million to under $30K.
Bill was stunned. His sister cried. I realized I’d found my calling.
What I Learned About Tax Resolution
That case taught me everything I needed to know about helping people with overwhelming tax problems:
1. The IRS isn’t the enemy. They’re actually quite reasonable when you know how to work with them and have your facts straight.
2. Most people aren’t trying to cheat the system. They’re just overwhelmed. Bill and his sister weren’t tax evaders – they were small business owners who got in over their heads.
3. Systems matter. Once we got Bill caught up, we implemented simple bookkeeping systems so this would never happen again.
4. Every problem has a solution. Even $5 million problems.
The Clients I Love Most
Today, 25+ years later, my favorite clients are still people like Bill – self-employed small business owners who started a company to follow their passion, not to become tax experts. They’re craftspeople, service providers, restaurant owners, consultants who are great at what they do but feel completely lost when it comes to taxes.
If you’re reading this and thinking “that’s me,” here’s what I want you to know:
Your tax problem isn’t as scary as you think it is.
I don’t care if you haven’t filed in years. I don’t care if the IRS is sending you letters that make your heart race. I don’t care if you’ve been losing sleep over this for months.
There’s always a solution. Always.
My One Piece of Advice
Just start. Don’t wait until next week, next month, or next year. The sooner you address your tax situation, the sooner it can be resolved.
Bill waited 10+ years, and while we got an amazing result, those were 10+ years of stress he didn’t need to carry.
The Power of Unexpected Connections
I never did buy that truck from Bill, by the way. But that Craigslist conversation led to the case that defined my career and taught me that sometimes the best opportunities come from the most unexpected places.
Whether you find me through a Craigslist conversation, word of mouth, or this LinkedIn article, I’m here to help turn your tax nightmare into a success story.
Because if we can take someone from owing $5+ million to under $30K, imagine what we can do for you.
Ready to Turn Your Tax Nightmare Into a Success Story?
If you’re a small business owner who’s been losing sleep over tax problems, let’s talk. Whether you haven’t filed in years, owe money you can’t pay, or just feel completely overwhelmed by the whole process – there’s a solution.
Here’s what I’m offering: A completely free, no-obligation consultation where we’ll:
✓ Review your specific tax situation
✓ Identify exactly what problems need to be solved
✓ Map out a clear, step-by-step plan to get you current and compliant
✓ Show you how we can potentially reduce what you owe
✓ Answer all your questions about the process
No pressure. No sales pitch. Just straight answers about your options.
During our call, I’ll give you the same systematic approach that turned Bill’s $5+ million problem into a $30K solution. You’ll walk away knowing exactly where you stand and what your next steps should be – whether you work with us or handle it yourself.
Ready to stop worrying and start solving?
Call now (641) 753-4905 or Schedule Your Free Consultation Today
Don’t wait another day carrying this stress. The sooner we start, the sooner you can get back to focusing on what you love about your business.
Hamilton Tax Solutions – Where IRS nightmares become “how did you do that?” success stories.
