Why I’m Hanging Up My Founder Hat for a While & Joining a Growth Stage Company
Update: Looks like the “for a while” was about half a year. Earlier in April I decided to leave Postmates as it just wasn’t the right fit for me. Over the next months I interviewed with some amazing companies that I would have been lucky to take on a role with, certainly still excited to find my next opportunity.
Along the way though I started researching and talking with folks in a space I hadn’t worked in before and fell deep down the rabbit hole. So here I am again…needing to scratch the itch that is this new idea. We’ll see where all this leads next…
In the meantime, I’m leaving the content below as I still believe in its core message — that above all else the journey should be about learning.
I won’t bury the lede here—beginning next year I’m joining the team at Postmates as VP of Product Design and couldn’t be more excited. It may not seem like the typical entrepreneurial path to go down, but after a lot of conversation and consideration I’m confident it’s the right one.
First things first, what happened after Circa shut down?
A lot! It’s been just shy of 18 months and has been quite a journey. I did product design consulting for a handful of companies—including a stint of living in Norway for three months and working on some awesome stuff with Schibsted. There was a lot of travel, a ton of hiking, and I worked hard to establish some good habits, like *finally* adding fitness to my daily routine. All in all it was a perfect reset after the stress of the last few years.
Got it, now why take a reguar job?
To some that may seem like a silly question, but among fellow entrepreneurs and startup folks it’s the first question I get. For me, it’s all about learning.
Over the years I’ve come up with two requirements for how I consider the work that I do: I should be constantly learning, and I should be happy and fulfilled in that role. If one of those things isn’t present, I need to deeply understand why and perhaps take another path—which led me to here.
I’ve co-founded three companies now, the work totaling nearly ten years of my life and almost all of my professional career. All of my blood, sweat, tears, heart, and soul was poured into Socialthing, SimpleGeo, and Circa over those years and I don’t regret them in the least. But as I think about continued learning one thing was obviously missing: doing pretty much anything at meaningful scale—leadership at scale, product and design at scale, everything.
But can’t you just build a great startup and scale it huge?
Yeah. Uh. I tried that. Three times. And while I got close to breaking through a couple of those times ultimately the startup game is really fucking hard and not everything is a rocketship unicorn.
When I looked out to some of the founders I respect the most, a number of them had “done their time” at a large company—some having had jobs early on in their career, but others coming in by way of an acquisition. Aside from the very short-lived time that I spent at AOL following the acquisition of Socialthing, I’ve just never had that opportunity. Running a startup is a massive challenge in and of itself, but there are totally different problemsets seen at larger companies. I knew that to short-circuit my own learning it made sense to take matters into my own hands.
While there are a lot of startups out there that are on their own early rocketship trajectory I focused my search on large companies who have already found their product-market-fit and were pretty well established. That, it felt like, would be the best environment to learn from. The hope is to learn from great leaders, a big team all cranking away at the same goal, and see the innerworkings of interacting with customers at a massive scale.
How did you look for opportunities?
Here’s the thing: as a founder I was practically invisible to recruiters out there so if I was going to find something it was going to be on my own accord. When recruiters are out there looking for leadership candidates, they’re often searching for people that have held similar roles at other companies, or at the very least carry a similar background to others at the company. You can probably imagine how often they might search for “co-founder” or “CEO” to fill their pipelines.
Since the ball was entirely in my court I fired up my contacts app and carefully looked through it to identify folks that may be able to tip me off to some great opportunities—colleagues, former investors, friends, etc. Ultimately I hadn’t been deep in the game for a while so asking around for “who should I be talking to that I may not know?” seemed like the obvious choice. That led to countless conversations—uncovering interesting companies, potential opportunities, and also just great advice. One bit came from Peter Pham who told me to go work for a market leader, whatever role that happened to be, it just needed to be the top in their category. That gave me some great color for who to seek out.
My resume was probably pretty foreign to most—just three co-founder/CEO gigs, no college degree, etc. How in the hell is someone going to use my past as a measure? That’s why whenever I would go in to talk to a company, it always seemed that reaching out to that company’s founder or CEO, or the highest person I could get to, would be best. Essentially I was just trying to find someone who could be my own internal cheerleader through the process.
So why Postmates?
Well first, I’ve been a customer for many years. Second a good friend of mine Noah Lucas joined there earlier this year and has loved it. Turns out I had a few more friends there as well! So, I thought I’d do a bit of research that included checking out Bastian Lehmann’s Twitter…turns out he followed me already so I figured I’d shoot him a note. That went like this:
A short while later I popped by the office and had a great conversation with Bastian. The topics ranged from what I’d been doing the last few months, how Postmates has been growing, the round they just raised, design, etc. He uncovered a lot about the business that wasn’t obvious to me as an outsider, and it just left me intrigued. Not to mention the fact that there aren’t a lot of three-sided market places out there (customer, courier, business) the thought of which opened up some really interesting challenges in my mind.
Over the next few weeks I spent a good amount of time with a handful of folks there and was impressed. Any opportunity that I took was going to involve a lot of time spent with people, and since it wasn’t me doing the hiring this time, I kind of treated it as a thought experiment of “would I also hire these people for my company?” That was a resounding yes—it would be a pleasure to learn from and work with everyone I’d met.
And will you start another company again sometime?
Shhh! I’m not even thinking about that right now! That very well may still happen, but get back to me in a few years.
So that’s it?
Yup! After all of that I was presented with an offer to be VP of Product Design—a role that would see me leading the creative and visual design aspects of the product. It’s an exciting opportunity so without any hesitation I accepted, with my start date just after the turn of the year.
Soon it’ll be time to build. There will be a lot of new challenges, new opportunities, well, new everything. It’s uncharted waters for me and I feel ready, but most of all I feel fortunate and excited to be joining the team!