The Check You Almost Wrote
From Decision State with Joe Steele by Joe Steele
May 12, 2026 · 25 min · Episode 59
About this episode
Eric Hoffman discusses his journey from attorney to legal tech entrepreneur and the challenges of self-reflection in business.
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…
People in this episode
Host: Joe Steele
Guest: Eric Hoffman
Topics covered
- legal tech
- entrepreneurship
- AI
- cold calling
- startup pressure
Keywords
- legal tech
- entrepreneurship
- AI
- cold calling
- Reddit post
- coaching decision
- self-reflection
Mentioned in this episode
Organizations: aiesquire.io, Amazon, Reddit
Books & works: The Runway Is Behind You
More episodes of Decision State with Joe Steele
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- The Call Nobody Wanted to Make · May 26, 2026 · 34 min
- You Thought You Could Fix It Later · May 19, 2026 · 32 min
- The Fix That Made It Worse · May 5, 2026 · 30 min
- When the Room Knows and Nobody Says It · April 28, 2026 · 25 min
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