The Startup Journey: Lessons from the Trenches
Like many others, I found myself captivated by the world of startups during my formative years. As a college student in India in 2006, I first heard about a new and upcoming company that was quickly making waves—Twitter. At first glance, it seemed like a simple concept, even a scaled-back idea, yet it was capturing the attention of people all around the world.
This sparked my curiosity. I wondered what life was like for the engineers working at such a company. How did they decide what code to write? Who were these individuals chosen to shape the future of this innovative platform? And with private equity involved, was the risk truly worth the reward?
However, after spending about five minutes pondering these questions, I moved on, not paying much attention to Twitter again—at least not until Elon Musk bought the company to replace the toilets.
Despite my brief engagement, the experience planted a seed of curiosity and fascination with startups. It ignited a dream within me—the dream of one day building something of my own or working at a startup.
From Amazon to the Startup World
After spending around six years at Amazon, where processes were well-defined and the company operated like a well-oiled machine, I decided to venture into the chaotic yet exhilarating world of startups. My first foray was with Porch.com, a hot Seattle startup at the time.
Porch was full of energy, with tight spaces, loud voices, and a palpable sense of enthusiasm. But what surprised me was the lack of seemingly obvious processes and tools that I had taken for granted at Amazon. Moving from a large, established company to a startup was a shock to the system. Porch was willing to move fast and discover the right processes on the go, a stark contrast to Amazon’s meticulously planned operations.
For example, pipelines—ubiquitous with any development team—were sort of present at Porch but stitched together with Jenkins, Team City, and some manual processes. I realized that for us to move fast and succeed, we needed to address both the process and tech debt. Over the next year, we adopted some stable and some not-so-stable technologies. We moved to GitLab, built the CI/CD infrastructure, and adopted Kubernetes. The transition was fraught with issues. For the first few months, we struggled with a Sev-2 incident almost every day. However, the engineering leadership was steadfast in the vision. We eventually overcame that hurdle, and honestly, I thoroughly enjoyed the chaos and the learnings that came with it.
The Challenges and Rewards of Building Something New
After Porch, I went to USAFacts.org as their Head of Engineering. This startup, initiated by Steve Ballmer and led by Poppy MacDonald, had a unique mission to provide the public with transparent data about the U.S. government. My charter was to build the engineering and data organization and assist in achieving product-market fit.
Within a few months, we had a solid roadmap, strong engineering teams, and a well-oiled recruiting pipeline. But then Covid-19 struck, and we had to go back to the drawing board. Being nimble allowed us to pivot quickly, enabling us to help the world access the right data during a critical time.
Following my time at USAFacts, I joined Pandion, another pre-product startup, in 2021. My learnings from previous startups helped me invest in the right areas and avoid overinvesting in others. This strategic approach allowed us to move fast and save money upfront, which is critical for any startup.
Key Lessons from Startup Leadership
After multiple stints in startup leadership, I’ve learned some invaluable lessons that I carry with me:
Join the Mission, Not the Title: In the early stages, everyone is an operator. Titles are secondary to the work that needs to be done.
Hard Things Are Hard: Challenges are inevitable, and you can’t control everything. Don’t be too hard on yourself; there will be more down days than ups.
Time to Market Is Critical: It’s okay to under-engineer and add tech debt if it means moving faster. The key is to deliver value quickly.
Document Your Decisions: In a fast-paced environment, it’s easy to forget the reasoning behind decisions. Writing things down helps maintain clarity.
Own Problems: If you see an issue, don’t leave it to others to solve. Take ownership and drive the solution.
Seek Guidance: You don’t have to figure out everything on your own. Seeking advice from others can provide new perspectives and save time.
Conclusion
The journey through the startup world is challenging but immensely rewarding. From the excitement of building something new to the chaos of rapid growth, every step offers lessons that shape your perspective and approach. For those considering a move to a startup, my advice is simple: be ready for the ride of your life, embrace the chaos, and always keep learning.