The Out-Of-Pocket Game plan

How to build the on-boarding system for healthcare

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Out-Of-Pocket has gone through several iterations as an idea. It actually started as building “The Daily Show for healthcare” and creating a healthcare media/comedy empire.

But it’s morphed over time, and here’s where the idea is today.

Out-Of-Pocket’s goal is to be the on-boarding system for people that aren’t in healthcare, want to go deeper into it, and continue to level up as they learn more. It is meant to be very accessible for people at the top of the funnel, and then create steps that self-select for people willing to put the work in and result in high quality companies, community, and builders in healthcare.

This is a 5 step plan.

Step 1: You are not in healthcare, but are interested in understanding trends in the space and learn more.

This is where the Out-Of-Pocket newsletter comes into play. The newsletter is meant to be accessible, digestible, funny, and informative about what’s happening in healthcare.

You can sign up here.

Step 2: Your interest in healthcare is piqued and you want to learn more about a specific part of healthcare that you want to get involved in.

I’ll be building paid, 3-day intensives in conjunction with experts to talk through a specific part of healthcare. How do clinical trials work? What is the health insurance claims submission process? etc.

You can think of these as mini-bootcamps to learn how healthcare works. This will be for people trying to crack into healthcare, as well as employees at companies that are either being on-boarded or building new product lines that they’re unfamiliar with (what up, education stipends).

Step 3: You now know about healthcare and would like to find a job in healthcare that suits you.

There’s a better talent matching system to be built. To people searching for jobs in healthcare, Out-Of-Pocket will help you find companies that you might be interested based on what you’re looking for, help you interview prep since you may not know what kinds of questions to ask companies if you’re new to healthcare, and will help you negotiate your offer.

However, to be considered for this, you’ll need to either complete one of the courses or fill out an application and be selected. This is designed so people who self-select are ones that are willing to work and have a baseline level of knowledge before entering the job search, showing they’re serious about working at a healthcare company.

For companies looking for talent, Out-Of-Pocket will be working with that self-selecting high quality group I described above. If a candidate is chosen, the company will pay Out-Of-Pocket their internal referral bonus for that role + X% of the salary on top if they stay for 6 months. The salary amount is a bonus, not detracted from the hired candidate’s salary.

Step 4: You are now working in healthcare, but want to learn from other people building companies in different parts of the industry, learn best practices, and continue to level up your knowledge.

The Out-Of-Pocket private Slack channel is a paid channel for people in healthcare that includes assignments, talks, and required participation. This Slack includes members from every part of healthcare (policy, payers, front-line providers, etc.) and a diversity of perspectives.

You can read more about it here.

Step 5: You are deep in healthcare and want to build a company in healthcare

Out-of-Pocket will (hopefully) raise a fund to invest in companies that come through members of the Out-of-Pocket slack community. This may look like a venture studio model with the group starting several companies at once, or may look like a traditional early stage fund. This is way down the line, but in the back of my mind.


Why don’t you do a paid newsletter? You could probably make a decent living off that.

Yes, I could probably do a paid newsletter. But that sort of defeats the point here. I want to get more people into healthcare that aren’t currently in it. By making the newsletter paid, it’s going to exclude the people that are tangentially interested, and those are the people I most want to attract.

That being said, in the future there’s a possibility I’ll be launching an ADDITIONAL paid newsletter for people that do already know about healthcare. Still TBD on what this looks like, but I have some thoughts.

I will additionally likely be adding paid job placements or advertisements on the free Out-Of-Pocket. This is still TBD as well.

How do I get into the Slack group? Do you need to be an experienced healthcare person?

Please read this. If you’re on the Out-Of-Pocket newsletter, you’ll also get a note when applications re-open.

You do not need to have deep experience in healthcare, but you need to be currently working in the space, have a baseline level of knowledge, and can think about parts of healthcare critically and with a unique perspective. The application is designed to filter for that.

Note: If your primary job is an investor, right now you will not be allowed into the Slack. This might change in the future, but right now this is focused on people who are at companies building stuff.

Are you raising right now?

No. At the moment I don’t intend for this to be a venture-scale business, I intend for this to focus on working with a smaller, high quality group of people and projects. IMO venture funding (especially too early) ruins communities because they focus on scaling vs. getting the community down. This is going to take years to build, and I don’t want to rush it.

Who’s going to teach these classes?

I plan on working closely with experts both within the Out-Of-Pocket Slack community and outside to co-develop curriculums. I will be putting out a call for experts to do this in the Out-Of-Pocket newsletter in the future.

Have you considered starting a podcast?

I don’t think the world needs another 30 min healthcare podcast where someone interviews a founder or VC. However, I’d consider doing it further down the line if there was a unique angle to the format or content. One I’ve thought about doing is basically getting really hammered and talking about one specific thing with someone for 5 minutes.

Are you funny?


Why are you making this game plan public? Couldn’t someone steal your idea?

First of all, if this is super easy to replicate then I don’t think this would be worth building in the first place. I think doing this is really hard, and I’m confident in myself to be able to execute against this. Plus if more people copying this idea gets more people into healthcare, I consider that a societal win.

Second, I’m a believer that if you make your plans public there’s a much greater chance someone will reach out to help you build it vs. someone who’s going to stop everything they’re doing to copy your idea.

If I have some thoughts about this or think I can help, how should I let you know?

DM me on Twitter @nikillinit or respond to the Out-Of-Pocket emails.

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