by Alex Dou
A limited series podcast by Out-of-Pocket, hosted by Alex Dou. Each episode is a post-mortem on a product or feature that didn't work the way it was supposed to. The goal: an encyclopedia of known failures so the next generation of builders can skip the mistakes we've already made and fail at something new.
Language
🇺🇲
Publishing Since
11/20/2023
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May 15, 2026
Strap in, young product manager or engineer (or vibe coder!). You have been tasked with the provider directory project. You have scoped it with your engineers, and you think you can get this done in a quarter. And so dutifully you make it your OKR. I'm here to tell you that this is going to be your next year. Certainly not your next quarter. And you should probably listen to this episode so that you know all the things that we have learned the hard way and can sidestep it. Provider directory is a bunch of data and feature and product raccoons all in a trench coat. What makes building one so hard is that you get trapped trying to build each raccoon. The way out is to be clear-eyed about all the different components that get lumped under the provider directory umbrella, be specific and choosy about which ones you actually need to serve your members, and be ruthless about not building any of the others.
April 29, 2026
Shay has been working in healthcare AI since high school, when a cold-email to a Houston lab professor accidentally landed him in an ML research group in 2016. He went on to ClosedLoop, a seed-stage healthcare ML platform out of Austin, where he spent years training models from scratch on claims and EHR (Electronic Health Record) data, embedding them into clinical workflows, and training nurses to use the outputs. More recently, he works in AI governance: advising health systems on which tools to deploy, how to evaluate vendors, and what due diligence on healthcare AI actually looks like. This episode covers risk stratification end to end: what it is, how it gets built, where it tends to fall apart, and what transformer-based clinical event models might mean for the whole field.
April 15, 2026
Emme started as (and still is!) a smart pill case. Beautiful, award-winning, Apple-level-designed, beloved. It was so well-designed that nobody needed to buy a second one and they’ve only had 5 returns in 3 years The CAC (Customer Acquisition Cost) was $400 and the case retailed for $100. I think you can see where I’m going with this Erynn Peterson, CEO of Emme, walks through what it took to flip those economics and what every hardware founder learns too late: your margin isn't 80%. It's 5%, if you're lucky, and that's before you've spent a dollar on marketing. Also you should know that it’s really expensive and fraught to market in women’s health, much less women’s reproductive health The conversation covers the full stack of hardware reality: minimum order quantities before any supplier will take your call, ad channels that shadow ban women's reproductive health products, the shift from SEO to GEO that reshuffled the deck just as Emme had figured out content strategy, and the firmware versioning nightmare that AI has (only recently) made tractable.
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A limited series podcast by Out-of-Pocket, hosted by Alex Dou.
Each episode is a post-mortem on a product or feature that didn't work the way it was supposed to. The goal: an encyclopedia of known failures so the next generation of builders can skip the mistakes we've already made and fail at something new.
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