Introducing How’s Work? with Esther Perel

November 11, 2019·55 min·4 clips

The moment two Navy fighter pilot co-founders realize their business split is emotionally identical to a romantic breakup.

Alex Bloomberg steps in quietly. Without Fail is off for the week, so he points listeners toward How's Work?, Esther Perel's new Gimlet show about workplace relationships. The pitch is plain enough: Esther talks with co-workers, co-founders, and colleagues about the feelings people try to keep outside the office, even when those feelings are already running the room. This episode follows two founders facing a split. They have been basically inseparable since flying fighter jets together in the Navy, and after a decade of building together, separate ventures are suddenly real. Alex calls it a breakup, and that framing fits. The men are not only asking what happens to the company. They are asking what work becomes when the other person is no longer beside them. Esther listens past the business language, especially for what Mike and Jay have left unsaid. Mike is carrying blame like it belongs only to him. Esther catches the trap in that thinking: if he made everything alone, then every failure has to be his alone too. Letting go of that burden also means letting go of the cleaner story that all the success came from him. That lands hard. Mike describes sitting there, trying to force the next idea out while feeling completely blocked. Esther widens the frame without making it neat. The block is not just a shortage of ideas. It is the weight of believing one person has to keep feeding everyone connected to the business, including two of his brothers. The episode stays close to two partners trying to say what separation would mean after years of depending on each other. Calm, intimate, and uncomfortable in the right way.

As heard by us

A founder breakup framed through responsibility, failure, and the hard work of leaving a defining partnership.

A workplace breakup becomes a founder story about responsibility, dependence, and the emotional cost of building with someone you have long trusted.

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Why you'd press play

When your co-founder story turns into a breakup.

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