I just had the most complicated tax year of my life. What surprised me is that I walked out of it understanding how money moves in this country better than I ever have.
After more than six years as Managing Director at Techstars, I left and started something new. Add prior businesses, K-1s from investing, retirement accounts, and a property, and the filing had more moving pieces than any year before.
Last year, the same kind of work took me an evening. This year, thirty minutes.
I went from bracing to owe Uncle Sam five figures to landing a decent refund instead. Every i dotted, every t crossed. Or so I hope.
People keep asking if AI is coming for their jobs. The usual framing is that these tools let you outsource more of your thinking. For me it worked the other way. A tax situation like mine used to mean handing the whole thing to a CPA and trusting the output. This time I sat down with Claude and a private fork of Brian Lovin's tax-ui I'd customized for my setup, and talked through my situation the way you'd talk to a genius accountant sitting next to you. TurboTax still filed the return. A CPA would still have earned their fee. The difference is that the thinking was mine, and the understanding stayed with me.
The shape of my finances had always been opaque. My taxes didn't just get easier this year. I could finally see the whole of them. Once you can see the whole of something, you move through it differently.
After more than six years as Managing Director at Techstars, I left and started something new. Add prior businesses, K-1s from investing, retirement accounts, and a property, and the filing had more moving pieces than any year before.
Last year, the same kind of work took me an evening. This year, thirty minutes.
I went from bracing to owe Uncle Sam five figures to landing a decent refund instead. Every i dotted, every t crossed. Or so I hope.
People keep asking if AI is coming for their jobs. The usual framing is that these tools let you outsource more of your thinking. For me it worked the other way. A tax situation like mine used to mean handing the whole thing to a CPA and trusting the output. This time I sat down with Claude and a private fork of Brian Lovin's tax-ui I'd customized for my setup, and talked through my situation the way you'd talk to a genius accountant sitting next to you. TurboTax still filed the return. A CPA would still have earned their fee. The difference is that the thinking was mine, and the understanding stayed with me.
The shape of my finances had always been opaque. My taxes didn't just get easier this year. I could finally see the whole of them. Once you can see the whole of something, you move through it differently.