In the fall of 2016, I shut down my first company and joined Oscar. Oscar’s mission is to bring health insurance into the 21st century. My task was to carry out a redesign of our mobile properties, built from scratch, in react native.

The whole process took a ton of exploration, prototyping, testing, and development. In the end, we came up with a solution that we feel makes health care easier to understand, more accessible, and convenient.

Here’s what it took to make it happen.

Auditing and taking inventory

When I got to Oscar I quickly began scheduling 1 on 1’s with all our…


What I know now that I wish I would’ve known from day 1

August 2015: Jakub, Kervins, Luc and I shopping for furniture at IKEA for the first time 😭

It’s been about 16 months since Luc and I quit our jobs and started building Often full-time. Since then, we’ve managed to raise a round, have it fall apart, almost get sued by Drake, work out of Luc’s apartment, eat Così everyday for 0.79 cents and somehow raise again. Now we sit at the top of 1 State St in FIDI where we have an office, desks, FIFA, and are building apps for people like us.

Tomorrow I’ll be 24. Even though I feel exhausted, I’ve never been more excited to wake up in the morning and come to work…


For those of you who missed the latest WWDC Keynote, you should check it out.

Here at Often we’ve been working on 3rd party keyboards for over 18 months. At this point we’ve seen just about everything. Keyboards have become these essential marketing tools for publishers and even though their average life span is only 2–4 months, they’re amazing for sharing content.

The problem is, I don’t think Apple expected them to be used this way. Here are a few things we’ve learned:

  • There are two different types of keyboards: Content & Utility.
  • Content “keyboards” should have never been keyboards…


Ever since Kim Kardashian dropped KIMOJI and Google introduced Gboard, keyboards have become the hottest thing since Myspace pages. Everyone wants one. Justin Bieber and Steph Curry literally just dropped their own keyboards this week. The problem is, Apple never designed for 3rd Party Keyboards. They just kinda… threw them in there. Here are 5 changes that could improve the keyboard experience for iOS.

Disclaimer: I’m currently working on Often

1. Installing a Keyboard Without Leaving the App

Installing a keyboard could be exactly like allowing Location Services

Instead of going through 7 different steps, imagine if you could install a keyboard from the app as soon as it opens. Maybe developers would start using the app for…

Regy Perlera

Product, strategy & art direction. Currently Design at Nike. Previously Oscar, StockX, Square. Almost got sued by Drake. 🇸🇻

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