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the big change at Out-Of-Pocket - This fall will be the last live run for most of our paid courses. So if you’ve been considering taking or sending your team to any of the following courses, you should sign up because it’s probably your last chance to do it live! (link in next tweet to sign up)
Courses have been the largest revenue source for OOP thus far, so this represents a big change. There are a few main reasons we’re doing this:
1) We’re getting more demand for custom courses and workshops - While the courses do a good job of explaining how things work, companies want to understand how it applies to THEIR problems specifically.
So we’re leaning into creating custom courses for companies and workshops around our existing courses.
2) Live courses are getting harder to enroll - This is probably some combination of us not investing in marketing it outside of the newsletter and learning and development budgets being cut. And let me tell you, everyone signing up for a course 5 days before the course starts makes everything incredibly stressful. This is also why we’re focusing on groups - it makes more sense for us to spend time honing the content in for companies than spending time on marketing.
3) We’re focusing on other parts of the business - Because I only send this newsletter once a week (if I’m REALLY feeling divine intervention with ideas), the surface area of what we can advertise is limited. With limited space, it means we have to pick and choose what we’re selling. As we lean more into events and other things, we can only do so many time-sensitive alerts without annoying all of you.
Courses are one of the things I’m really proud of at OOP. People have loved taking them - our average course is rated 8+ out of 10 in our post-course feedback surveys. The instructors get texts all the time from people that the course helped.
We paid out instructors nearly $1M over the life of doing it. Instructors were able to quit their full time jobs to explore startup ideas while this gave them some income. And instructors got to show off their skills they’ve learned over many years and fights with their CEOs. But we have to adapt with the times, and we think this next phase will have even more impact.
You can sign up for the last runs here:

LLMs in Healthcare** (starts 9/8) - We'll dive into core concepts, explore how LLMs are reshaping the healthcare landscape, and guide you building LLM-driven prototypes.
How to Contract with Payers (starts 9/15) - The essentials of contracting with payors, including strategy, presentations, negotiations, and deal closure.
Healthcare 101** (starts 9/22) - I’ll teach you all the main laws, players, money flows, etc. you need to know about US healthcare.
Selling to Health Systems (starts 10/6) - This course will get you ready to confidently knock on hospital doors and sell to every person who has a seat at the decision table.
EHR Data 101 (starts 10/14) - Hands on, practical introduction to working with data from electronic health record (EHR) systems.
**we’ll keep running live versions of these two courses for a bit
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