Eric Hoffman spent years as an attorney before building a legal tech company on his own. What started as a conversation about cold calling and startup pressure turned into something more specific: what happens when nobody is around to interrupt your thinking while you're carrying too much.

In this episode, Eric talks about the Reddit post that made him question whether he was really building a company or just hiding inside one, the $35,000 coaching decision he almost made, and the moment where AI recognized a pattern in his behavior before he fully did himself.

This conversation isn't about entrepreneurship advice. It's about what judgment starts to feel like when there's no co-pilot in the room.

Eric Hoffman: aiesquire.ioLinkedIn: Eric Hoffman, Esq.Book: The Runway Is Behind You — available on Amazon

If you recognized something in this episode — joesteele.com.

Follow Decision State on Spotify, Apple Podcasts, and YouTube.

Chapters

00:00 — The pricing build

02:45 — No one catches it but you

04:16 — What AI Esquire actually is

06:41 — Following the rule book

10:35 — The Reddit post

12:34 — Checkbook in hand

15:00 — Cold calling for a company nobody knows

16:15 — Claude as co-pilot

19:03 — What hasn't worked

21:07 — Razor sharp at 10 AM, gone by 7 PM

23:22 — Where to find Eric