Jake vs Boss

My friend Jake has a difficult boss. Well, kind-of-boss. They're technically co-founders, but the equity split, titles (CEO vs COO), and age/seniority difference put Jake in the junior position. It's been three years of grinding together on the startup, and this year-end, Jake's boss told him "Look, we've got a money problem. 2026 is going to be a challenging year financially and we need to buckle down. But also, I've worked really hard this year and after running this startup at way below what I think I should be earning for a few years, I'm going to give myself a raise."

"Okay, fine," thought Jake, "seems not great when we need to be frugal, but whatever."

But the next week, Jake saw the actual 2026 budget and his boss' raise, and his heart sank. Jake's boss had allocated himself 75% of the $100,000 reserved for raises. Jake would be getting nothing, and be responsible for allocating pennies to the rest of the team (Jake manages almost the entire headcount).

I was talking with Jake about this, and he said "I need to tell my boss how financially irresponsible this is, and how its a risk to [...]

---

Outline:

(00:09) Jake vs Boss

(01:33) Thinking vs Unfolding

(03:34) Jake vs Boss 2

(09:00) Jenns Misanthropy

(12:55) Holding Love and Comparison

(18:51) A Few Implications

The original text contained 3 footnotes which were omitted from this narration.

---

First published:

Source:

---

Narrated by TYPE III AUDIO.