Taking the Words Out of My Mouth (With AI)

[aminaas1576]

Everyone has a different idea of what they’d do with a time machine. Mine’s pretty simple: Head back to 2012, find myself working on a side project to film a documentary, and grab my younger self by the lapels and shout, “A 1099 IS NOT A REIMBURSEMENT! GET AN ACCOUNTANT!” before whatever energy sending me into the past gave out.

That simple mistake on my part had truly stunning financial consequences. When the tax bills and penalties started hitting my mailbox around 2014, it became a mass of stress. The IRS is undefeated in the award for Most Intense Collection Letters, and they were coming on a regular basis, even as I started directing more and more of my paycheck towards paying the debt.

A few friends generously sent me money to help beat back the interest and costs, but the combination of this and other debts had me backed into a corner, so I decided on a simple plan: Run a phone number database Patreon campaign where I told stories and opinions in short episodes, which were then supported by the audience, with all the proceeds going into debt repayment. The resulting podcast, Jason Scott Talks His Way Out of It, helped dig me out of that hole.


But it had an interesting side effect – coming up with new topics of discussion and consideration, once a week, meant that I had to mine deeper and deeper into my own outlook and relevant stories. After the first fifty episodes, I turned further inward. After one hundred, it became equal parts emotional and technical. And as I’m heading towards three hundred episodes, I’m surprised I have anything left to say at all. But I apparently do, and having now been doing this podcast weekly for six years, its episodes span a truly panoramic spectrum of topics.