1,000 Days of Climbing
In January 2019, I founded a startup with two friends. By April 2020, the startup had failed, and the team disbanded.
In summary, we made a thousand mistakes. The first thing we did after incorporating was to take team photographs. We then spent months writing pitch decks and over-engineering design: Kubernetes, micro-service architecture, both SQL and NoSQL databases, and GraphQL — but avoiding writing the code. We focused on endless iterations of all aspects like branding, styling, and UI. We even fought over the font sizes in our pitch deck. We watched endless videos on how to create the best pitch decks and practiced the pitching 10s of times.
I must admit that a lot of it was my fault. I didn’t read enough, I didn’t ask others what to prioritize. We just did what we thought we were supposed to be doing. We were in Seattle at Amazon. Had we been in Silicon Valley, had any friends in YC or other, and had some source of consultation to model or follow, maybe things would’ve been different.
After seven months of not writing a single line of code and pitching to several VCs, we met Byron, the former CEO of Heroku, who properly chewed us out. I'll never forget how he said to us at dinner, "Why are you showing me a pitch deck?" It was only after we dropped the pitch deck that he gave us some man-to-man advice: focus on the product and drop all the other nonsense. He told us that he would write the pitch deck for Heroku the night before pitching; in essence product and traction may be more important than pitching.
This was a shock to our systems. It took us at least a week of quiet embarrassment to process.
Gradually, things began to improve. I read The Lean Startup. We started cutting back on technical scope. I called a family friend who was a VP at a prime customer for us, and they took a chance on us to do a proof of concept (POC).
We cut scope and abandoned the micro-service nonsense. We stopped learning kube-ctl, and switch to a single NodeJS Lambda. We stopped using Step Functions, Airflow workflows or any scheduling crap. Then as our deadline approached, we took a look at the DynamoDB schemas we were iterating; renaming;re-organizing and thought - "Jesus Christ, let’s just get trash all of this."
Then... the universe dropped us a gift: Y Combinator’s Startup School (YC SUS). Somehow those lecture videos snuck into our periphery. We watched in cold shock as these people laid out every mistake we could make (and that we already had made). We eagerly absorbed information and were accepted into their winter Startup School batch. [YC's SUS is a free program that's about teaching and educating, and funnels into the Y Combinator application if you are successful]
As the deadline for our POC neared, I had a tough conversation with the team about the "Wizard of Oz" approach. We all agreed to drop the tech entirely and run our MVP off Google Sheets and Instagram DM's.
It was a success.
We learned so much about our market and discovered that our novel method of self-sourcing products and using micro-influencers offered a fivefold reduction in advertising costs for the same impact. (5x reduction in Cost-per-engagment).
We iterated based on these learnings, realized we needed to build a marketplace, and shifted our sites to the supply side. We launched two more MVPs in two months. Finally, we were operating as an early-stage team should.
But in March 2020, financial strains and a failure to fundraise led to the team's breakup. A large part of the internal tension was my fault. I received some of the hardest feedback I've ever faced regarding my anger and its impact on my team. I was devastated. It's difficult to face reality and know that you are negatively affecting your team.
It took a while to piece things together. The day after receiving that feedback from my co-founder Ryan, I committed to meditating. I kept a calendar and marked a big "M" on it for every day I meditated for at least 20 minutes. As of today, April 2023, I have accumulated around 700 "M"s. I've even switched my meditation style from interceptive to exteroceptive. Back then, I needed it.
A few months later, I had the strength to take a hard look at myself and my failure. I conducted a retrospective analysis of what I had personally done wrong and identified six gaping weaknesses that jeopardized everything.
These were the critical fragilities I discovered in myself.
- I needed someone else to build it (coding).
- I had no fundamental stability in my personal life: habits, fitness, mental, social, sleep - my foundation for health was fucked up.
- I lacked options in what market problems to solve - (the industry we picked wouldn’t be my first choice today; I want to help people, not advertise)
- I did not manage risk properly. I had no strategy to limit my downside.
- I wasn’t focused on the building but on all the other surface things.
- I did NOT have the confidence to go at it alone even if no one followed me.
These 6 critical fragilities separated me from realizing my potential.
The last three years, from August 2020 to today, have been dedicated to strategically eliminating all SIX of those fragilities.
I created a plan for each of those categories and then put in the grueling, painful, shitty work.
As CT Fletcher says, it's been a magnificent obsession for these last three years. I have thought of nothing else. Every action I've taken, every piece of travel, every seemingly callous or random move has been primarily motivated by fixing these six fragilities.
It's important to note that my fragilities are INTERNAL. I haven't created an EXTERNAL goal like "make X $'s" or "build a Y." That is the OUTPUT of the system.
My every thought has been to apply pressure internally, to metamorphosis the system (ME), so it operates how I intend for it to operate.
The last three years have been incredibly painful as I've discovered, step by step, through sacrifices that I had to make. Almost every time I sacrificed something of the old me, I learned I had to sacrifice even more.
Today, the sacrifices are less and less frequent. Perhaps a sign that I'm approaching the correct system? The correct inputs into my life?
My life today is extreme by common standards, but to me, it's better than I ever thought possible. I remember reading Jocko's words, "Discipline = freedom," and frantically underlining it, but truly understanding it. It was aspirational underlining, a desperate move on my part to internalize that sentence and transform my life.
I eventually arrived at that understanding, but not through books or underlining. Instead, it came through intense pain and discomfort, through 1,000 days of stepping beyond my comfort zone.
There is no other way. And I'm better for it.