Out-Of-Pocket Slack Application

Hello everyone! For anyone that read the Out-Of-Pocket game plan, the fourth step of the plan was to connect people in healthcare and help them continue learning from each other using structured assignments and discussion.

The Slack is now about a month old and I’ve learned a ton from the first group. Everything from the macro legislation changes to Medicaid, to discussions around strong patient engagement strategies, to understanding the problems around data structuring and challenges AI faces today.

Messages like this make me feel like something is working.


To that end, I’m happy to announce that the application is open once again, and you can fill it out here. APPLICATIONS WILL CLOSE 6/24.

I am currently adding 10 new members to the group each month to maintain the community feeling instead of scaling too quickly. I will be reaching out to accepted participants over the course of the next few months, so if you don’t hear from me it does not mean you were not accepted, and please keep an eye out for an email from me. But also please don’t consistently ping me on the status of your application.

***I’m also trying to actively get more diversity in applicants for this round. I’ll be reaching out to groups and individuals myself, but would love your help in telling people from underrepresented groups about this application. Healthcare impacts us all extremely differently, and having a diversity of perspectives is important in understanding how to make the system better for all of us.

At the moment, this group will be focusing on people building things in healthcare. I will your primary role today is an investor (VC, PE, etc.), you will be added to the waitlist and if the rule changes in the future I will reach back out.

You can see more about the rules of the group below, and if you have any questions please ask!


While there are lots of healthcare Slack groups today, I think there’s room for a channel that: 

  1. Has an increased level of vetting for community members, decided based on criteria including

    • Broad knowledge of healthcare trends

    • Specific technical knowledge in a certain part of the industry

    • Strong opinions with an open mind and willingness to engage in constructive debate 

    • Demonstrate they’ll be an active, contributing member to the community

  2. Has planned small events (both virtual and in-person) to foster a stronger community via face-to-face connection. 

  3. Focuses on making multiple high quality small/medium size groups with a moderator. The goal is not to maximize the total number of people in the channel, but rather to maintain quality discussion and connections. 

  4. Requires participation from its members via occasional short assignments and occasional events.

  5. Is focused on developing stronger, more organic ties between members instead of sporadic asks from strangers

  6. Is more heavily moderated to reduce the amount of self-promotion and encourage thoughtful discussion and sharing of tactics.


The Out-Of-Pocket slack channel will initially be $20/month. This process and pricing is meant to self-select for a high quality group of people and discussion that would find this valuable. It also incentivizes moderators (aka me, for now) to put the work in to make the group high quality by providing structure.  

This will initially prioritize people building companies before potentially allowing people that are currently investors. No offense investors.

You must be a subscriber to Out-Of-Pocket to join. I’ll be using the newsletter frequently as a discussion starter in the group + will use sentiment from the group to inform future newsletters.

Over time, these groups will slowly allow more people, but each group will have a maximum size (to be determined).

Other than the (hopefully) organic conversation that happen, there will be some structure from me. I’ll set up a calendar to see the upcoming events + when your assignments are due. 

Daily - Twice a day there will be something short and hopefully fun/interesting. One will be posting the answers from a given member from the weekly assignment below, and one might be a rotating question of the day for everyone, or trivia, 

Weekly - There will be a slightly longer weekly assignment. Each week, a group of people will be asked to complete their weekly assignment by Sunday. You can expect to do this once every 4-6 weeks, and will know in advance when it’s coming. This is mandatory to complete.

The length of answer here is up to you, but I think the length of a long email feels like a good benchmark.

Some example assignments might look like:

  • Can you walk me through what an average day looks like for you?

  • Can you tell me about a project you’re working on now or completed recently, what’s difficult about it, and what success for the project looks like?

  • What’s a healthcare problem we don’t know about that we should know about, and can you explain why it matters?

  • Etc.

Monthly - There will be monthly virtual gatherings that will involve a few people giving short presentations to help practice public speaking + presentation design. Attendance to one of these events once per quarter will be mandatory.

Homework and prompts are meant to keep members invested, learn about each other beyond a surface level context, and help structure your thoughts. Every good community requires some work + contributions from its members, and this is no different.

Everything above is subject to change, this is an experiment.

Community Rules: 

  • This is a moderated community. Violating any of the rules means you will get kicked out without a refund.

    • To start, I will be the only moderator. As the group size increases, I may ask for help with moderation and will explain the rationale behind making someone a moderator

  • If something doesn’t make sense to you, ask questions. There are no stupid questions. Healthcare has so many moving parts, there’s no way you’re going to understand all of them. The point of this community is to learn.

  • Do not harass/bully anyone. Zero tolerance policy for this, if it happens you will be kicked out.

  • I will encourage some one-on-one an small group meetings, but feel empowered to reach out and organize the larger group yourself as well

  • Everything said in this channel should be assumed to be off the record. If it’s found out you’re spreading information outside of the channel, you will be kicked out. 

  • This channel requires participation. There will be “homework assignments” used as discussion starters and ways to bring the community closer together. If you consistently skip the required assignments, you will be kicked out. 

    • If there are extenuating circumstances (which does not include “work got really busy”), please reach out to me.

    • Missing the assignments will be a three-strike system. If you miss 3 in a given year, I will ask you to re-apply to the group later

  • Do not use the group solely to promote things. Promote things in the appropriate channels if you are a regularly contributing member in the other channels.

  • Be personable! If the goal of Out-Of-Pocket is to informalize healthcare, then this group should be able to joke around, share details about their personal lives, and get to know the people behind the group.

  • Contribute to building the community. I won’t be able to do everything myself, so I’m relying on others to help with different parts of fostering a community, hosting events, etc. If you can step up to help, please do.

  • Things will be constantly changing as I experiment with how to make this group better. I appreciate the patience as we learn how to make this community great.

    • I’m extremely open to constructive feedback (positive and negative) on how to improve the group! I may not make every suggestion a reality, but I can guarantee you that I will listen to every single one.

Once again, if you’d like to apply the form is here. Looking forward to it!