In short, I worked for a corporation and got laid off. At that point in my life, I’d never made more than $47,000/year but had accumulated a significant 401k and done okay with some investments including the company stock options which I was able to cash in with the layoff for $38k. I had credit card debt from college but lots of room on the cards. So instead of clearing my debt and joining another corporation, I over extended my credit, cashing in my 401k and all investments, and started my own business which crashed hard within 3 years. I skipped mortgage payments to pay staff and in the end the business went under, my first marriage dissolved, and I had a little bit of a nervous breakdown..you know

…breakdowns come
And breakdowns go
So what are you going to do about it
That’s what I’d like to know …

I quit opening mail. Didn’t file taxes. It took about a year for me to pull myself together and by that time the fees, interest and penalties on everything was ridiculous. Of course I didn’t earn a reportable dime that year but the IRS kindly did my taxes for me and billed $11k. They did that for another year then pointed out that while I was skipping mortgage payments to pay the employees that I had failed to pay the employee taxes (so I really do owe them $8k where I screwed up the employee taxes. Of course $8k + penalties + interest gets absurd). The business I ran basically cost me everything and profited nothing. The IRS has me on the hook for more money than that business ever brought in.

And it gets worse. This year I paid the IRS $5300 and they turned around and billed me $8200 beyond the $5300.

The lesson that business taught me? 1) first hire a really good accountant, 2) second hire a really good attorney, 3) hire a really good sales person, 4) if there’s any money left, run the business.
The way I did it was 1) advertise 2) advertise 3) advertise 4) do everything else myself. Tough lesson.