One of the major reasons why Facebook, Dropbox and other hyper-growth startups grew exponentially was incredible product market fit coupled with amazing timing. There are obviously exceptions, however in most cases their initial product carried the company through the majority of its growth. This will come across harsh, but what most of the mid-stage (and a lot of the early) team had to do was simply hang on to the rocket ship.

This isn’t to say they didn’t work enormously hard and did whatever they thought was best for the company - but there was simply very little an average employee could do to meaningfully accelerate the growth and almost nothing they could do to derail a company like Facebook in its earliest days. Performance management simply wasn’t a priority given their growth (very understandably). Many of these types of employees can easily fall into a confirmation-bias fallacy where they assume what they were doing was correct because the company was growing.  Maybe it was...but there’s an equally large chance they what they were doing wasn’t working and was simply incorrect. There was simply no positive or negative feedback cycle given the company was growing organically so quickly.

At the next company these ‘learnings’ will be viewed as accurate, verified and will likely not be questioned given their background - however, they have little or no grounding in reality.

I’m not sitting on a soap box saying that people at hyper-growth companies are bad or you shouldn’t hire them - I’m simply warning my future self that just because someone was ‘successful’ at a hyper growth company or ‘early’ at a unicorn it’s no barometer or signal for how effective they’ll be at your company - and be beware the trap that they can confidently believe the wrong thing is right.

Early on this was fine - I channeled my energy until building. Coding, creating, breaking, just building things was what mattered most to me. Earlier in life I didn’t think you needed to write to create - however, I was entirely wrong. I could be forgiven to think that with the advent of the internet writing would become less crucial. Engineering seemed on the cusp to overtake liberal arts. However, the opposite happened.

It became so easy to communicate we became more governed by good writing. Internal documentation, emails, product plans govern any technical company. As an engineer we spend more time writing up product plans and documentation than we do coding - as a manager this multiplies, as a founder even more. I have confidence in my ability to build products but I don’t have confidence in my ability to tell their story, to build that narrative on paper.

So why am I writing? I’m writing to get over this fear. Julia Cameron talks about it well in the Artist’s Way.

[Quote]

I’m writing to write - I’m writing because I hope with enough repetition the fear will go away or be numb enough not to notice it. This isn’t my way to pontificate on the internet or write down some novel philosophy - its not for you, its for me.

A recently wrote a small application that uses Whatsapp to keep me accountable to to recurring tasks each day. I call it Drill Sergeant and I've recently open-sourced here. It’s incredibly basic (<200 lines of code) but its been very successful in keeping me accountable each day.

There are daily recurring tasks that I want to check off everyday (todo lists are the secret to everything). For me they’re super benign such as stretch for 15m, workout for 30m, etc. However, having a daily list to hold me accountable and get that green check at the end of the day is extremely rewarding. I didn’t want to introduce another app in my life so I wanted to integrate it into something I’m using constantly anyways.

I picked Whatsapp. I’m already using Whatsapp each day to talk with my wife, family, friends and colleagues. I'm a Android loyalist, but most of my close friends and family are on iPhones. Its one of the best cross-platform messaging applications, everyone has it, and its great on both mobile and desktop. Unfortunantly, Whatsapp isn’t great on the developer side and not built for bots. However, Twilio does offer a decent option by making a developer account on Twilio and running it yourself.

It uses Typescript to interact and listen to events from a Whatsapp Twilio developer account number (you have to be a verified business to distribute it for public consumption). It's backed by redis to keep track of the users and their history. It has five basic commands.

• add - ie: add [30m] stretch
• remove - ie: remove [30m] stretch
• complete - ie: complete [30m] stretch
• list - will list out the daily tasks for today and what you've completed
• history - will display a rough calendar of the past 30 days and when you've accomplished all of your goals.

It tries its best to match inputs to commands. You can use shorthand and only use the first couple letters. ie co stre will match complete [30m] stretch. The only exception is remove, which needs to be exact. A new day starts at midnight PST and a reminder message is sent at 8am PST.

In order to run this yourself you'll need to setup a (free) Twilio developer account. If I have more free-time someday I'll try to register it as a business and make it publicly available, but that's for a different day. However, if you’re up for the challenge you can check it out on Github here!

Email, Gmail on my android and Superhuman on my laptop, along with messaging, WhatsApp consume a disproportionate amount of my digital life.  For my own efficiency I try to orient a majority of my work inside or around these applications.

In this regard I've created a couple specific routines and pieces of software around this workflow. I thought it could be interesting to open source and write a bit about them. Here I'll attempt to give an overview of an android and ios app I've written to handle tasks in email - Paper Plane.

Tasks and notes.

A couple years ago I went about thinking how I could make some common workflows more efficient. I identified basic note taking and task management as an area that I was not efficient in.

There was, and is, a proliferation of notes and reminders applications - each with its own set of power features. However, my note taking and reminder flow is pretty basic - I write down some copy, maybe attach an image and want that plastered in front of me until I finish it or have it remind me at a certain time. If I can label it - all the better. After having tried all of them - from Google Keep, Notion, Evernote, Wunderlist (RIP), etc. they all felt like I was getting a semi when I just wanted a scooter. So I fell back to the simple solution of just sending myself a simple email.

Email has everything I need - I can title my note to myself (subject line), have it plastered in front of me all day (sitting unread in my inbox), remind myself at a later date (gmail, superhuman, boomerang all support this), and the best part - it fits into my normal workflow. I don't need to check this specific todo app and my email everyday to figure out what I need to do. I can just open up my email to see all of my outstanding tasks!

After working in this flow for a couple years I hit a snag - as email applications got more fully featured they got slower to load and operate. The workflow started to take a while to just send myself a quick reminder.

Open email app →️ hit compose → subject →️ type note → click send

While maybe that 20 seconds seems short - it adds up and I'd rather have that time to think about something else - not staring at my device. Equally important when I'm in meetings and with other people - staring at my phone for 20s while I write down a note based on our conversation can seem pretty rude.

After playing around with a couple solutions I started to think I maybe needed some bespoke app to send myself an email....🤦. So goes my great theory of less apps the better. But I internally justified it to myself as simply just an extension of the existing app - just a more targeted and faster compose window. 🤷‍♂️

After a bit of research I found a couple of applications on iOS that do something very similar - the most popular one being Captio (Squarespace Notes was close - but they killed it in 2018). I used Captio (along with a decent amount of people I knew) for a while, but it had a couple limiting features and the dealbreaker - it was iOS only. Ever since I started my love affair with Android years ago I've been out of luck. I guess it was time dig in and write my own.

Enter Paper Plane

It's very basic - like very very basic. Imagine it as a dedicated email compose window - with your own email filled in and the subject dynamically generated. Its built to be extremely fast and work in offline and online environments. 20s -> 5s to get a note to yourself.

Available on iOS and Android. Quick list of features:

• Does one thing extremely fast and efficiently. Sends your email an email to yourself.
• Dynamic subject generation with prefixes (helps with labeling in gmail).
• Attachments.
• Allows you to send at a later date and cc another person.
• History of emails: queued & sent.
• Email can be sent from an application email, IMAP (your email) or you can host your own server and do it all yourself!
• All open source.
  

Apart from being an extremely useful app that I now use a dozen times a day it was also actually my first foray into mobile programming. Historically I’ve spend most of my time on the infrastructure and backend side so it was a fun way to move to mobile for a bit. I used React Native - which was a bit of a mixed bag, but overall positive. If you're interested in seeing the innards or downloading for Android or iOS check it out here!

note: I originally published this on Medium

A couple of weeks ago I shared the following message (with some internal logistics redacted) to our team at Plaid:

Plaids,

As most of you heard today during our team meeting, I announced that I’ll be transitioning from my day-to-day role at Plaid to a solely board position.

Plaid has been the central guiding force for what has now been the entirety of my adult life. I was immensely lucky to start Plaid with one of my best friends (👋Zach), write its first lines of code my senior year of college, learn how to maintain conviction and keep pushing despite seemingly infinite challenges, and even meet my wife through friends at a Plaid party!

As Plaid has grown I, too, have had the immense privilege of growing and maturing as an adult, manager, and leader. With this growth has come introspection — introspection as to what brings me joy, and where I believe I can create the most value and ultimately have the most significant impact. I am now at a place where I have a personal desire to take a step back and breathe, taking comfort in the fact that we have hired leaders at Plaid that can and are currently doing that which I’ve historically been responsible for, just now in a more scalable way!

This conclusion was neither a rash nor a recent decision. Over the past couple of years I have known that there would come a point at which I would choose to move to a purely strategic and advisorial role. And during the past year, I have started to work towards this goal. As many of you may have noticed, I have been working up to my transition by slowly removing myself from day to day projects and teams where I was the responsible party, seeing how it fared, and stepping in when necessary to guide and level up. I’ve decided to announce my transition to a new role now because I finally feel that this passage is complete. At the end of the quarter I will officially transition to a solely board role. However, if I’ve done my job well, the following weeks, months, and quarters shouldn’t feel any different for anyone.

Seven years ago I was lucky enough to be able to start Plaid with one of my best and smartest friends. Since then its been inspiring to see Zach evolve as a leader and CEO. His product sense is unparalleled and I trust his guidance more than anyone else’s. I have nothing but the utmost confidence that he will continue to effectively help guide the product and engineering teams — just now in a more direct way.

With Eric now up and running as COO, Zach will take over the Engineering and Product reports. JDG will be focused on our builder teams by managing Engineering and Design and Baker will begin managing the Product and Product Support teams.

I am regularly asked what has been my proudest moment at Plaid. My new answer is Now. It is a testament to what we’ve all built together that I’m able to transition out of direct management without doubting for a moment the certainty of Plaid’s future. I believe it is every leader’s job to constantly focus on hiring people better than his or herself, empowering them to constantly push above their current role. I have the opportunity to do so now.

The team at Plaid is unparalleled; I doubt that I’ll ever again have the opportunity to work so closely with such humble and brilliant friends. For the rest of your careers, I promise to always make time for you. That may be a lunch to bounce around ideas, a quick meeting when you need another perspective, or perhaps a trail run to discuss how we really came up with the name Plaid… I will never be a stranger and I truly hope none of you will be as well.

Seven years ago we set out to change financial services — with a platform that puts the consumer and builder first, one that empowers the smallest of developers or the largest of companies to build a better financial future for all people. We have made more of an impact on this mission than I ever could have imagined — and it’s incredible to think that all we’ve done will only be a small chapter in the long story of Plaid.

Plaid out,

William

So, what does this mean…? In reality it changes and means very little.

In tech, it has historically been taboo to talk about founders or executives transitioning to different roles inside companies. Leadership transitions need to become a bedrock of any company that desires to endure across decades. I’ve simply decided to be more public about my own transition than perhaps other founders have in the past, and in doing so I hope to set a precedent that leaders too should have the space to evolve in the ways in which they deliver the most impact.

As a founder, I believe it is my job to empower everyone who works at the company — sometimes this means holding multiple roles throughout the lifecycle of one’s company. For the first seven years of Plaid, I found the most effective way to add value was as a hands on builder and manager. Today, I think Plaid is mature enough that I’ll be most effective providing strategic guidance and mentorship vis-a-vis a board role.

At Plaid, we have maintained a pragmatic yet inspirational culture that emphasizes the importance of allowing each person to evolve into their best selves. I have never been more confident in the future at Plaid, and the ability of our team to conquer what have always been our radically ambitious goals.

-William