Chapter 3

January 23, 2023


  1. Develop and grow a photos service that had an impact on Amazon's success as a business.
  2. Learn to be an intentional operator at Amazon-scale.
  3. Build and foster a team that would be vibrant and durable beyond me being there.


These were my 3 professional objectives when I decided to join Amazon more than 8 years ago.

I've achieved these objectives – Chapter 2 has its beginning, middle, and end – and so Friday, January 20th was my last day at Amazon, and now I'm onto Chapter 3.

freeze frame; rewind

Chapter 1

Most readers of this know me from Chapter 1. Chapter 1's beginning started in my early-20s at the point in my life when I was finding out that there was a place for me. In college, neither I nor my advisors nor my parents nor any friends had any or enough awareness of the tech industry and it's roles, opportunities, and personalities to know that that's where I belonged. Some thought I'd be a TV producer. Some a Teach for America teacher. Some didn't push me anywhere, just wanting me to be happy (you can guess who that was). But through my first year out of college - totally lost and working in the wrong industry - daily GChats with my friend Evan slowly introduced me to the world of tech and startups and the earliest phases of what would become called Web 2.0. I started dipping my toe in the water and then in an overnight that actually lasted 8 years I found myself having started a few startups, building an incubator, learning to code, finding a family in the NY tech community, joining and then leading the NY Tech Meetup, becoming boy wonder, advising VCs, meeting my partner Jackie, and was off to the races in a thrilling and fulfilling career in early stage startups.

I could write more about Chapter 1 but actually I did write more about Chapter 1 – all on this blog. One thing I never wrote about was how Chapter 1 ended:

12 years ago I co-founded a startup called Picturelife with two friends. It was only a few months after I learned to code, and my co-founders were far more accomplished than I was, so I started with the least equity and from Day 1 I was tasked with building the backend.

In 2013 I became Picturelife's CEO and quickly focused the company on a major concern of mine: that as a VC-backed business we needed to scale faster than we were, but as a gross-margin negative business in the cloud-storage and processing space scale would crush our runway if we scaled. My plan was to walk and chew gum at the same time, continuing to build out our service's experience while spending 25% of my time with my friend Chris, our CTO, figuring out how to cut costs.

Meanwhile, our peer startups in the space – nearly all of whom were founded the same year we were but raised less capital than we did – all started dropping (due to the same dynamic of slow growth and shit economics), and soon the customers of Snapjoy, Everpix, and I can't even remember who else were flocking to Picturelife as the last remaining hope in the quest for a cloud-based, photo-focused memory preservation platform (hard to remember, but no Google Photos or Amazon Photos existed yet, and Apple Photos was still iPhoto with a bizarre Photostream feature tacked on).

Having only made a dent in our unit economics the new scale wasn't enough to raise a round on immediately but crushed our runway nevertheless. I had wanted to wait to raise another round after we had a profitable product and after were able to test enough in performance marketing to show that our Series B would pay for the healthy, profitable growth that wasn't happening organically – a typical Series B SaaS narrative in those days – but by Q2'14 I knew it was likely we'd be out of cash by the end of the year without those milestones being met, and it was time to start cutting employees and raising funds regardless. You can see how frustrated I was at needing to balance product and product economics at the same time in this Medium post: Finally, Storage Wars.

But while our economics were improving, and we continued to scale steadily (though not quickly) some other countervailing winds started to blow stronger: In 2013 a Yahoo! Flickr (not a direct competitor, but of considerable interest) announced they could just "give" 1TB away for free. We also started to see Google's interest in buying Picasa so many years earlier, as they tacked a Photos tab into Google+ and started launching some pretty neat tech and a solid free storage option inside it. In July 2014, Amazon launched the Fire Phone with Unlimited Photo Storage for photos taken on the phone. Facebook started "privately" storing photos from your phone for free, though I'm not sure anyone was ever naive enough for that one. Either way, the big companies were making moves and their first move was to take cost out of the customer's equation. Dropbox was also pivoting hard away from consumer and into business around then, having stumbled in personal photo storage themselves.

By late summer and 20+ VC meetings later, it was clear a new round was unlikely to happen and a profitable/self-sustaining Picturelife equally unlikely with the unit economics and runway we had left; and so while I tried to find courage/stomach in our existing investors for a bridge round I also started engaging with corp dev teams, including Amazon. In October of 2014 I flew out to Seattle with one of my co-founders and Chris to meet and pitch the Cloud Drive team. It was clear they wanted to pivot into photos and we were the last, great independent product in this space.

At the end of our pitch it was my time to ask questions: "With the Prime membership and your recent addition of other benefits, why isn't storage just free?" The team's GM ran out of the room and came back with a mockup that had been posted in the hallway: "Well you can't tell anyone, but we're launching Unlimited Storage for Prime members in two weeks."

Picturelife had a staggeringly amazing product and product development team, just around $1MM ARR, and a decent freemium customer-base; but with no IP ultimately we were not large enough to get Amazon corp dev beyond a short bout of diligence. "We can't buy you but do you all want to work on this here?" After some long conversations with our lead VCs (the bridge round was a "no"), I circled up the team in New York and told them it was time to accept the fact that this would not be a storybook ending, but we had a shot of still working on this great product - or some version of it - together at a company we all admired. Everyone took the interview, 6 of us got offers, and 4 of us wanted to make the move. We adored Amazon but 6 of us also interviewed at Facebook for good measure. I bombed that one but at least one of the guys who didn't get an Amazon offer found a soft landing with a NYC office at FB. Meanwhile, I had one startup still in the pipeline interested in acquiring the company in its present state - product, tech, customers, liabilities, and all – and while I packed my things in New Jersey, wound-down my NY Tech life, and started researching places to live in Seattle, I closed a deal for for $99 that found Picturelife its next home. Maybe this would have a bittersweet ending after all? Nope. Picturelife's ending had no sweetness at all; a story for another day.

Chapter 2

Chapter 2 is also a story for another day but here's the TL;DR: 8 incredible years at Amazon. In that time we launched Amazon Photos and – in a world where Google and Apple own mobile and leveraged both their privileged position on those devices and their 15-20 year head start with photo software – we made something that *matters* and continues to scale impressively. When I say "matters" of course I mean to our customers but recall personal objective #1 for me: I wanted to make something that mattered to Amazon's business at Amazon's scale, and we have. In that time I also "grew up" as an operator. Chapter 1's subtitle was "fake it 'til you make it." I didn't want to fake it anymore – the most prevailing motivation for trying corporate life – and at Amazon I couldn't. I had a brutal start, almost flunked out, but then found my groove. Ultimately I got good. I felt effective. I wasn't faking it (as much) anymore. I learned how to be a deliberate operator while staying true to who I was. I climbed the ranks and I grew my scope. I met my objective #2. The most important part of being a deliberate operator is building a durable organization and key to that is growing and recruiting the leaders who are so good they make you irrelevant. This was the hardest part of it all - and I have plenty of ink to spill another time - but by April 2022 I knew everything was in place and I told my leadership it was time to take these hard-won lessons back into the startup world I loved and missed: 2022 would be my final year.


And what a year. In April I had no idea how the market would shape up, but at every turn my calculus for leaving was proven out: economic headwinds, hiring freezes, and reductions in force hit the tech sector and even close to home at Amazon, and yet this incredible team operated through it relatively unscathed and seemingly stronger. We beat our most critical goal for 2022 despite unplanned roadblocks. While tough and unfortunate it was incredibly validating: this team can do anything, the future is bright for Amazon Photos, and I can leave.


Chapter 3

This post is titled Chapter 3 and yet there's not much to write about what's next for me. There are three things that scare the shit out of me right now and I'd like to do something about at least one of them:


  1. The global climate emergency
  2. The global health emergency
  3. The US political and civic emergency


I don't know what I'll end up doing and I know that after a 12 year, non-stop marathon - 4 with Picturelife, and 8 with Amazon – I'm going to take this next phase super slowly.

I do know which way I'm leaning: Outside of work, my last 4+ years has been focused on my own health and the health of loved ones. The global COVID pandemic has and continues to shine a light and magnifying glass where I was already looking. More than any other topic, I've found myself reading and listening to as much as I can get my hands on about chronic diseases and what people can do to help themselves in a system rigged against truly helping them. Health inequity is bad and getting worse. So, I do put a slight weight on me doing something in or around personal health and population-scale health solutions. And yet I've also spent some of my recent free time tinkering with ActivityPub, have tinkered with helping fellow operators on Product strategy and operations, and I'll always love building little consumer-y things for myself and friends, so who the heck knows where this ship could land.

Starting today my plan is to prioritize catching up with folks I've lost touch with in my last 8 years (being inside a big company can really insulate you!), and to meet new people of course. I also want to learn to swim, have challenged myself to learn to bake croissants, and have a list of house projects that won't fix themselves. I have the privilege of some near-term flexibility and I plan on taking advantage of it.

During this time I also plan on writing more. So here's the opening to Chapter 3. We'll all need to wait and see what comes of it.