Having written a year in review last year, I found the practice of reflection rewarding. So I decided to do another one this year. 2018 felt like play. 2019 felt like playful work.
I learned a bunch of lessons about doing startups. I’m sharing some of them here, in writing, but I cannot fully share how they feel. And I think unless felt and internalized deeply, these lessons are hard or impossible to apply. Each of them took me months, and by writing this review my main goal is to capture them for my future self. They might resonate with you, if you’re building a startup or something comparable, and we might have a swell time diving into a discussion.
Startup lessons from Sleek and Swift
I started the year building a startup called Sleek, which later got renamed Swift. The goal was to eliminate waiting in line, by providing a super fast and convenient way to order through a phone. Within months, myself and a cofounder were able to build and iterate on the idea, pivoting away from our initial plan to use a chatbot. We found a pilot customer (Bonito Poke - their fish is fresh AF), and every few days I’ll go there, deploy our system, see what didn’t work well, and go back home and build a solution around it. Over a couple months, the system become decent - it was able to move people off the line faster than the kitchen can handle it and processed thousands of dollars of orders.
But ultimately, me and my cofounder split ways. Which lead me to one of the main learnings from this year:
“Unless you’re certain there’s a great fit between cofounders, don’t start a startup”
The focus is on the words “great fit”, and I find it relevant to most important decisions in life. Armed with “great fit” as a decision boundary, I was able to find a path through the rest of the year, and ended up joining another team, which I think is a great fit. But more on that later.
I also found saying “I don’t think it’s a great fit”, plus some specific reasons, to be an honest and less stressful way to reject opportunities and people. In the months after splitting with my cofounder, I talked to a whole lot of people about building a company. Most of them were amazing and great and are now doing awesome stuff. If someone is not a “great fit” to my situation doesn’t mean they aren’t great things in their own right.
I do not know of a great litmus test for a great cofounder fit, but I know it needs to include at least:
Another corollary of the “great fit” criterion, is that there has to be a great fit between the founder and the startup. I realized that while I cared about Swift’s mission - to save people time, and eliminate waiting in line, it wasn’t that important to me that I would jeopardize my health by staying regularly up until 5am coding/preparing for the next day. Yes, time is one of the things I care about most, and I’ll chose inferior product with less wait. And my blood boils quickly when someone wastes my time. But saving time ordering lunch from food trucks didn’t feel like it would be that powerful in reclaiming valuable time. I wasn’t willing to dedicate my time to it. Which leads me to my other startup takeaway from 2019.
“To start a company, find a problem in the world that is a great fit for you - that you are able to suffer for.”
And because I didn’t find a cofounder to share the load, I considered putting Swift on hold and considered joining another team. I talked to multiple excellent startups, and interviewed. My intent was to only join startups that I feel are great fit.
I felt that joining Slapdash as the first non-founder would be a great fit to further my journey to build a company. I also really clicked with the team. Ivan, the CEO, gained my respect from the first email he sent me. In it, he asked a direct question which set the tone for a candid, high signal conversation. Soon I met the rest and my intuition told me we’d make a cohesive team. The mission also appealed to me. At the time I interviewed, I understood it as the ability to quickly search across all your cloud applications, saving time. My vision with Swift was to save people time, and on that front Slapdash resonated - and it even felt like it might be saving a more valuable piece of time than food ordering.
After I joined Slapdash, our vision crystalized to “Work at the speed of thought” - and I think that’s something I can put more skin behind. I’ve experienced how hard it sometimes to get in a state of flow, and how easy it is to get disrupted. When I was an engineer at Twitter, I wrote a simple script to notify me when my unit tests finish running so that I can interrupt whatever distraction lodged itself in my head while I was waiting for the tests to pass, all in order to keep my state of flow.
At Slapdash, I had the privilege to join early. So early, that the we-have-always-done-it-this-way fallacy does not apply. What do I mean? It can be common when joining an already established company to accept its ways as the way it works. Even if you think there’s a better way, it’s a conflict of one person versus the machine with its massive inertia. But in a small startup, the machine is small, and is furthermore actively looking to improve itself. There’s no “this is the way” at startups. Which brings me to the third learning about startups from 2019:
“In a startup, if you think there’s a better way to do something, then you’re almost certainly right, and it behooves you to make it happen.”
To put it another way - in a startup most things are up for grabs - trust your intuition on what could be better, and do it. You will be wrong at times, but the times you are right will more than make for it.
I’m glad to say we were able to launch Slapdash.com so y’all can try it out - and if you think anything can be better - rest assured you’re right! And let us know :)
Self improvement in 2019
The rest of this post is not about startups but rather about how 2019 affected me personally.
During the first half of 2019 I had gained some fat around the abdomen, and was feeling stressed, so I decided to make changes. So in September, I set my New Years resolution and started working on it. That’s a resolution from Sep 2019 until Dec 2020, as I realized that important changes take time. I set some measurable goals for 2020 and my plan of achieving them is to have one thing each month that I’m working on, and build on top of it. So far, I’ve worked on the following:
I also maintained no caffeine throughout 2019 and did 3 continuous months of no alcohol (first one month, then two months). In 2020 I plan to at least match these.
I wrote and published less in 2019 than in 2018. But it wasn’t bad. A post of mine, Giving a name to my sales anxiety, made it to front page of Hacker News. In 2020, I aim to publish more than in 2019.
I also made my own limited edition hot sauce - with labels, shrink wrap, etc.
I was sad and disappointed by how HBO’s producers botched Season 8 of Game of Thrones. I really loved the show’s previous seasons, and had read the books, was reading analyses online and had really high expectations. For me, SHTF with season 8 and after it I didn’t want to see much about GoT/ASoIaF. I felt really dejected from the whole story after that. I wanted something to help me restore my appreciation for fiction and story. Then I found a recommendation about Joe Abercromie’s series “The First Law” and once I picked the first book “The Blade Itself” I was hooked. These books have characters as interesting, or even more interesting than GoT, and they’re a pleasure to read. I’ve since recommended these to friends.
Other notable books I enjoyed and remember are Michael Pollan’s “You can change your mind” which discussed psychedelics. I also enjoyed the first half of “The Dream Machine” which talked about the history of how computers developed. “Bad Blood” and “Born A Crime” were also worth listening to.
I’m grateful for all the travel I was able to afford through the year.
In the beginning, I participated in a Ski house in north Tahoe, ride snowboard in the morning for ~2 hours, and work in the afternoon/evening. I had a total of 13 days such riding. In terms of productivity it was surprizingly good as I was able to find a good focus in the afternoons.
I also fulfilled a dream to visited Patagonia and hike. While in Argentina I also saw Iguazu falls - amazing places. One of the days in Patagonia, we spent nearly 10 hours to go between two huts, with a lot of ups and downs, only to arrive at the modest Refugio Laguna Negra around sunset and find it fully packed. Regardless, the hosts found a spot for us on the table and fed us a tasty lentil & sausage soup. Hospitality I’ll never forget. Later, that dining room turned into a bedroom and all extra guests found some spots on the floor to put their sleeping bags & mats. In Patagonia, I also got to go on a glacier for the first time - woot! Patagonia was super beautiful - I’m happy I went there. Yet, as amazed as I was, I realized “a mountain is a mountain” and there are a lot of similarities between it and other mountains of similar height around the world. Today, I am looking forward to doing more hiking and backpacking in the amazing mountains that are close by the Bay Area - the Sierras!
I was able to feast in the beauty of California. I did short trips to Lost Coast, Mount Shasta, Yosemite and Big Sur. And this year I started backpacking overnight. I am also glad that I had the chance to spend time with friends and family in Bulgaria, China and Morocco.
Last but not least. I started new friendships and kept some older ones.
And I loved and felt loved - the most meaningful parts of life.