Jul 29, 2026 · 16 min · 9 segments
Over $1 million lost, an IRS audit two years after her divorce, and a lawsuit she couldn't afford to fight — Ali Katz gets brutally honest about the belief that cost her the most. In this solo…
Ali KatzHost
After I had built two million dollar businesses, I had lost a Probably close to a million dollars at that point already.

On the other side of all of that, I decided I was bad at business and I should just walk away from everything.

Because I started at a big law firm, I didn't think that any of the legal, insurance, financial and tax parts of business applied to me.

I was like, no, if I'm doing business with people that I trust, I don't need legal agreements.

I was naturally very skeptical of insurance after that because I had been paying for insurance that wasn't the right type.

Then the first year that I made a million dollars in my business, I had an unexpected $116,000 tax bill and I didn't have the money to pay it because I hadn't been planning for that kind of taxes.

And it turns out that had I been planning, I could have paid a $50,000 tax bill instead of $116,000 tax bill.

I started my career working on tax transactions for Warren Buffett at Charlie Munger's law firm.

After I had built two million dollar businesses, I had lost a Probably close to a million dollars at that point already.

On the other side of all of that, I decided I was bad at business and I should just walk away from everything.

Because I started at a big law firm, I didn't think that any of the legal, insurance, financial and tax parts of business applied to me.

I was like, no, if I'm doing business with people that I trust, I don't need legal agreements.

I was naturally very skeptical of insurance after that because I had been paying for insurance that wasn't the right type.

Then the first year that I made a million dollars in my business, I had an unexpected $116,000 tax bill and I didn't have the money to pay it because I hadn't been planning for that kind of taxes.

And it turns out that had I been planning, I could have paid a $50,000 tax bill instead of $116,000 tax bill.

I started my career working on tax transactions for Warren Buffett at Charlie Munger's law firm.
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