What I’ve been doing at Oscar.

These past few months, I have been helping a couple of startups I like.

Sometimes, I have been investing in them. (Well, I’m trying to: I am basically making it up and learning as I go along, but it could be argued that’s what all angel investing really is about.)

Sometimes, I have been spending time hanging out at a company and helping more directly.

But regardless of whether I invest or help a team more directly, I think the way I’ve been thinking about it is to only get involved in projects that I wish I myself had started. (Max Levchin said it best: “One of the best heuristics I found when deciding to invest [in] a startup is whether I would seriously consider joining it, if asked.”).

The company that I’ve spent the most time with recently is Oscar Health: I’ve been here for the last five months.

If you know me, you already know I’ve been curious about and playing around in the health space. My hacking around in the quantified self space brought me to personal health, which is basically the idea of using tools (either built by the community or by health & fitness companies) to take charge of our own health. This personal health movement can be thought of one model where care is proactive rather than reactive. All this got me closer to learning about where the healthcare system is really broken and needs technology’s help the most.

That, of course, brought me to Oscar. I had already known the guys before they got started and I was always excited about the possibilities anytime we got together to talk about the idea of starting an insurance company. If you want, think of my exploration as a see-saw: “things that we do for ourselves” on the left and “things a care provider does for us” on the right. I started on the left and I slowly started learning and moving right. And then I figured I should skip ahead and jump all the way to the right and see the world from Oscar’s perspective.

I’ve been helping Oscar in various roles: with recruiting for different parts of the team (mainly on the product and engineering sides); with general company “things” (helping with PR/marketing, with process, organizing engineering and recruiting meets, &c.).

I also spent a lot of time helping build different parts of the product:

The mobile experience – of course, this one was easy. Many of our members are young and tech-savvy and almost always on their mobile phones. They order food, their cabs, buy movie tickets, read the news, see train times, search for things exclusively on mobile. So why shouldn’t they have a great experience where their healthcare questions and delivery also happens on mobile? I made this a big priority for the team for the January 1st launch: we worked nights and days with a very tiny team. And, in something like eight weeks, we put together a great Oscar Member app for iOS. (Yes, Android at some point very soon!).

The care finder – this tool can be thought of as your first point of contact when you look to solve an issue in health for yourself or a family member. Instead of blindly Googling for an answer, we imagine that Oscar itself can be your first point of contact. You could even think of it like foursquare’s “Explore”: before you go somewhere, use the search and allow it to pass you to the right spot. The mechanics of how this works are hidden behind the scenes in order to keep the interface simple, but the idea is that it will use basic information about each provider to point you to the right place. Over time, we imagine this system can get better as more data points and views from your friends are added in. “Show me only doctors that can speak Spanish.” – “Go here because many people your age go here.” – “Show me only providers that have many years of experience and happen to be tech-savvy, too.” Why should a health insurance company only step in at the very end of care? (That is: at the point where care has already been delivered and the insurer only steps in to pay your bill for you.) The idea instead is that when you need help, you ask us and we point you to an appropriate place of care that not only solves your needs but also does it transparently.

The “Doctor on Call” – this one is something we are really proud of and excited about. Some of us were lucky enough to grow up with a family doctor who would be able to answer simple questions over the phone: helping you get care and saving you time from having to drive out to the doctor’s office and taking a couple of hours out of your work day. Whatever happened to those days? Oscar’s "Doctor on Call” does exactly this. We’ve partnered with Teladoc and their physician network to provide this service. So, at any time, no matter where you are (in the U.S.), you’ll be able to ring up a doctor and talk to them about a problem you have. The doctor will be able to recommend a solution, prescribe you medicine or, in cases where a further in-person visit is needed, send you to a specialist to get care. And the best part: all this is free for members. We could have pointed members to independent applications out there now that seem to do this, but we wanted to embed this experience natively into Oscar itself. This way, you never have to leave this ecosystem and use yet another login to use such a system. And by seamlessly integrating this, we could also hide the costs and make it free for you in a much easier way.

All-in-all, this is just the start of even deeper products and issues Oscar can solve.

The appeal in Oscar is not only that we get to see through 2014 eyes and solve all the things that incumbents have trouble solving. Or the fact that we can bring a tech-focused approach and solutions to the health care space. To me, the most exciting is that by starting over from scratch, we have the ability to write a new playbook on how a health insurance company should work. We have a chance to provide additional features and services that customers have not expected before. We have the ability to start your care and our relationship with you not after you get hurt and after you’ve been fixed up by the doctor, but rather by being the first point of contact when you do need care. And perhaps, someday, so easy we will even get one step ahead of you and actively alert you to offer you services before you come to realize you need them.