OOP's 3 year anniversary

some thoughts/reflections

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Reflecting on things

It’s officially been 3 years doing Out-Of-Pocket, which is honestly crazy actually writing that out.

I could be humble about it, but one of the things about being solo is you never really celebrate much. So I’m going to take a second to be proud of how much happened in the last 3 years and then some lessons I’ve taken building this.

The 1 person empire has grown pretty vast and broadly falls into 2 buckets.

  • How do I make it easier for people to understand how healthcare works?
  • How do I make it easier for people to start a healthcare company?

A mish mash of things I’ve learned since I’ve started. This is basically a note to myself 3 years ago, so it probably won’t all be relevant to you.

Only fixate on things that are unchangeable

I remember how much time I spent trying to figure out what kind of incorporation I should pick for the business and how much that plagued me. Turns out that kind of stuff doesn’t really matter and you can always change. Certain decisions though you can’t change, and really should spend time thinking about (e.g. taking external funding or bringing people onto the team).

Your peers and the people you want respect from will inevitably shape your business

I don’t think people want to admit this to themselves, but everyone is pretty externally motivated. It’s sort of inevitable that you want people to think you're successful, but the dimensions of “success” are different from person to person. If you hang out with a bunch of people that think having sequoia on your cap table or being on panels means you’re successful, you’re probably going to optimize for that even if that’s not the best decision for your business. There are a handful of people I really care about what they think, and every decision I make I think about how those people would look at me if they knew I made X decision. And they care about quality, thoroughness, and if it’s true to me more than anything else.

There’s an ideal mix of outsourcing and doing yourself

I tried doing 100% of things in the business and suffered some weird psychosomatic issues as a result of the stress (no joke, mostly because of trying to figure out taxes). Those are so energy draining that it made sense for me to outsource it. But simultaneously I think people are way too quick to just hand everything about their business to virtual assistants, third-parties, etc. I still like to be pretty in the weeds of everything because each piece is reflective of the brand. There’s a balance to strike here that I’m still figuring out, but if you outsource too quickly you start losing control + being detached from subtle signals your customers give you IMO.

Develop a strong gut feel instead of relying on data or systems

When I started a lot of the advice I got was around using SEO keywords, cross collaboration strategies to grow your audience, etc. Not only did that feel kinda scammy to me, I also knew that if everyone else was getting this advice there’d be competition. I think people like to rely on data because it gives them justification to make a decision, but developing a strong intuition and gut feel helps to stick out. I use virtually no data to guide my business other than money in/money out. I have always listened to my gut on whether I think something is a good idea and I have confidence in myself to execute even without data or an organizing system.

There’s a lot of benefit to diversifying revenue streams

Having multiple streams of revenue is very useful. You can negotiate from a stronger place for any individual revenue stream (e.g. if I don’t want to write a sponsored post, I don’t need to feel obligated to because the courses are doing well). And you can start bundling those different revenue streams together to make more valuable packages (e.g. I can sell seats to the healthcare 101 course, which is 0 marginal cost for me, as a part of the sponsored post package). 

Not everyone is going to like you, focus on the people that fuck with you

If you want everyone to like you then no one is going to remember you. One of the reasons I curse and have memes in the newsletter is because it annoys people who take themselves too seriously, and I frankly don’t care what those people think. And because that group you’re specifically targeting fucks with you heavy, they’re really invested in your success. Almost every one of my best ideas for the business has come from someone on the newsletter suggesting it because they wanted OOP to succeed.

2 meetings a day

Clearing my calendar of meetings when I left my last job was sexually gratifying. I now only take 2 meetings a day, and my productivity has never been higher. You’re brainwashed into thinking meetings = progress, and I promise you that’s not the case. I also push almost everything into emails or DMs, and bang them out between 11pm and 1230am. 

Becoming accustomed to unpredictable income

One of the hardest parts of starting the business was navigating a very complicated relationship with money. You see the savings go down and you feel like you’re going backward. You take shitty consulting projects to make up for it, but that’s not scalable. The biweekly paycheck doesn’t come anymore so you’re not sure how to plan your expenses/vacations. It took me a VERY long time to become comfortable with making money on an unpredictable basis, but now I realize how much upside you’re giving up in exchange for that predictability.

Be at the edges of the industry

If a lot of people are talking about something, find literally anything else to talk about. All the cool shit is happening at the edge of the industry - this is why I invest in really early stage startups, why I’m on reddit all the time, and why I spend a lot of time with people outside of healthcare to learn what I can bring back to healthcare. Venturing into these areas that aren’t the current topic du jour will almost always be interesting to other people + it’ll make you less cynical about progress.

People crave peer learning and benchmarking

When we hosted the first conference, someone told me “wow I really thought our company was a shitshow, but it seems like basically every company even the bigger ones are just as bad”. I think we’re very used to trying to solve problems only with others in our organization, when the reality is that getting perspectives from outside of your organization would actually be more helpful. OOP has taken advantage of this by being single company agnostic and instead grouping people into cohorts (the slack, the courses, the conferences) where you can get info from peers on what normal looks like for your situation/question and get answers quickly from people that have been there, done that. Even the posts are meant to give a sense of “here’s what a lot of companies do/have gone through” which I think others appreciate.

Doing thoughtful stuff in-person is hugely underappreciated

I’m surprised how few good events there are. People default to “I’m throwing a happy hour” or something where they think getting people into a room is the goal. No one leaves an event like that and think “that was one of the best things I’ve been to”. Throw some structure in there and magic happens. Breakouts, a small amount of required pre-work, some interesting presentation formats, etc. People appreciate even a small amount of creativity in the event style and are more invested in the success of the event if they have to do some work for it. 

Give people under the radar their shine

People trying to build their own audience always try to latch onto other people that already have an audience and hope that they can use them for distribution. That’s the selfish route. My favorite part of running OOP is being able to give shine and a platform to people that I know are ballers and don’t self-market. Not only is it more fulfilling personally, it’s also a great way to create evangelists to your own brand as those people grow themselves. I’ve also met a lot of these large following people and trust me they’re less impressive than the person that sends you a really good cold DM.

Where you choose to monetize/shill is important

I always want to be giving way more value than I’m extracting by a large margin. This is one of the reasons the newsletter is free, this is why I don’t charge extra for the annual retreat for the Slack group, etc. I know people that turn everything into a paid expert network call, pimped out NFTs when they were a thing knowing they’d crash, create multiple newsletters to be able to advertise more, etc. But I try to only monetize the things that I think are really highly valuable + companies will pay for, and then give everything else away for free. My general ratio is 4:1 for value to shilling. 4 good tweets per 1 that shills something. 4 newsletters before a paid sponsored post. It’s not always perfectly mapped, but helps guide my decision making. 

People crave novelty

Everything is so algorithmically optimized and predictable that people absolutely love novelty. Who could have seen a children’s book about clinical trials coming? Or a totally weird application based conference? The best part about novel stuff is that weirdos and risk-takers are typically first adopters of them, and that’s who I like to hang out with and spend time with anyway. Honestly something I’m grappling with is how do I keep attracting the weird but curious people since the second run of something always attracts more normies who “heard it was good”. 

Playing a very long game

This might seem like it’s been a 3 year journey but I’ve been writing and slowly trying to grow my brand and knowledge base in healthcare for the last 8 years. And it has been a constant grind, and is still a constant grind. People starting newsletters etc. nowadays ask me about all these hacks to grow but there’s no secret sauce here. ESPECIALLY considering most newsletters are a top of funnel to something else, so what you actually want is people who respect you/your brand enough to convert to whatever the other products are. Building a reputation takes a very long time, and it’s very easy to throw away by not thinking about the long game.

Parting thoughts

Year 1 of Out-Of-Pocket was survival.

Year 2 was experimentation.

Year 3 is all about bringing partners in to run their own things.

I’ve got a bunch of things coming this year that I”m excited to share with you all, and hope this journey takes me many more years.


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