Connecting the Dots
How My Unconventional Journey Led Me to Angel Investing
The journey to becoming a startup founder and angel investor is seldom a straight path; instead, it is a winding road filled with pivots, adaptations, and hard-earned lessons. My path up to this point can be roughly divided into three distinct phases:
Early exposure (2007-2012): During this period, I primarily worked in blue-collar jobs while putting myself through school and learning about Silicon Valley from the sidelines.
First non-blue-collar work experience post-Berkeley graduation (2012-2018): This phase involved working in finance and three startups at various stages and with different outcomes.
Transformational experience at NEAR (2018-2023): My time at NEAR significantly shaped my professional growth and understanding of the industry.
In 2024, I am embarking on a new chapter as I begin my journey as an angel investor. Let's briefly explore each of these phases, focusing on the highlights and lessons learned during these periods.
When I arrived in San Francisco in 2007, there were no startups in the city itself. However, I started to learn more about technology companies by hanging out with some Stanford students in South Bay. They introduced me to the unique and special nature of this place and its significance to the world. As I spent more time there, I delved into the history of the area and realized that I wanted to be a part of it somehow. During this period, I worked various blue-collar jobs, including modeling, construction, moving, working as a busboy in a restaurant, a security officer, and a "jack-of-all-trades" at a small startup.
After graduating from Cal in 2012, I worked on technology mergers and acquisitions. One trip to Silicon Valley significantly altered my perspective. We drove to meet with the senior leadership team at Palo Alto Networks. Upon returning to my desk, I found myself questioning why I was staring at spreadsheets while others were doing truly fascinating work at a company that was actively being built and developed.
In 2013, I made the decision to quit my job in finance and start my own startup called Nibbol. The experience was short-lived but taught me valuable lessons. One of the biggest challenges I faced was the additional stress that bootstrapping placed on our team. Instead of seeking angel or venture capital investment, we relied on my personal savings, which quickly depleted. As a result, I found myself sleeping on friends' couches and floors, unable to afford rent. Another key learning was the difficulty of building a two-sided marketplace. Lastly, I realized that having too many decision-makers involved in the startup can lead to premature failure. Despite losing all my savings from my finance job, the experience provided me with important insights into the realities of entrepreneurship.
After my startup experience, I decided to join more established technology companies. I started with MuleSoft, which had around 600 employees at the time and was on a steady trajectory of increasing revenues every year, rapidly marching towards its IPO in 2017. The company had strong leadership, particularly on the sales side, which is the function I joined. At this stage, I spent most of my time with my peers, who were incredibly hardworking and focused on driving the company's fast growth. Although I thoroughly enjoyed my time at MuleSoft and it provided me with a much-needed confidence boost after my startup failure, I ultimately decided to follow the recruiter who had brought me there to his next venture, MemSQL (now known as SingleStore).
Joining MemSQL was a significant change, as the company was ten times smaller than MuleSoft. I was aware that I was trading the stability of MuleSoft for the chaos of a startup, but I believed that this move would provide me with valuable learning opportunities. Due to MemSQL's small size, I found myself working closely with various cross-functional teams, including product, engineering, marketing, and operations. This exposure was in stark contrast to my experience at MuleSoft. Notably, MemSQL's engineering team, responsible for building the database, was highly regarded in Silicon Valley for its expertise. Although my own function underwent numerous challenging changes during this time, I had the opportunity to collaborate with many brilliant individuals. As a result, my decision to prioritize learning paid off, and I gained a wealth of knowledge during my time at MemSQL.
When I joined MemSQL, its first employee Alex Skidanov, who later became a good friend of mine, was considering his next career move. He had a deep passion for Artificial Intelligence and was thinking of leaving the company. After his departure, he explored two ideas in the AI space: one focused on consumers and the other on general research. During this time, I took a two-week "vacation" from MemSQL to help him with his second idea, which involved teaching machines how to code. I tried my best to encourage him and his new co-founder, Illia Polosukhin, to build a practical, enterprise-focused startup rather than a research-oriented one.
Despite my efforts, Alex and Illia decided to pursue research-oriented approaches. I followed their progress from the sidelines. Six months later, they realized that their model was not performing as well as they had hoped, and they were losing a talent war to Google. As a result, Alex and Illia pivoted into the blockchain space and renamed near.ai to NEAR Protocol.
I joined them right after the pivot, and it turned out to be the most transformative working experience of my life. Our founding team consisted of nine people, seven of whom were engineers. Erik and I were the only ones focusing on business aspects. While Erik set up operations for the nascent startup, I focused on going to market and learning from our future “customers”, who were developers building on top of web3 protocols.
From a learning perspective, my time at NEAR Protocol was the most valuable experience I have ever had. It taught me two crucial lessons:
The importance of having generalists on early teams: In the initial stages of a startup, versatile team members who can adapt and take on various roles are essential. Specialized roles become more critical as the company grows and scales.
The significance of obtaining early market feedback: Engaging with potential customers and gathering their insights from the very beginning is crucial for shaping the product and ensuring its success.
As a generalist on the early NEAR team, I took on a wide range of responsibilities:
Content creation: I published blogs exploring various industries we could tackle, although I am only proud of one specific piece of writing from this period.
Event management: I organized events worldwide to promote NEAR and engage with the community.
Founder engagement: I scheduled numerous web3 founders for our whiteboard series, providing a platform for them to share their insights and experiences.
Fundraising: I actively participated in three fundraising rounds in Silicon Valley alongside the founders, helping to secure the necessary capital for growth.
Accelerator setup: I contributed to the establishment of an accelerator program to support and nurture promising projects in the NEAR ecosystem.
Team building & management: I played a role in building a cross-functional team to support the various aspects of the project.
Market research and validation: Most importantly, I engaged with the market to determine whether our product was in demand and worked on converting web3 developers to the NEAR platform.
By taking on these diverse roles, I gained invaluable insights into the early stages of building a successful startup in the web3 space.
Regarding market feedback, we were fortunate to have excellent timing. It took us 2.5 years to launch NEAR into the mainnet, but during that period, I collected valuable insights from hundreds of developers in the space. At the time, the entire web3 ecosystem consisted of approximately 500 founders and developers, and I managed to engage with most of them.
The most crucial learnings came from early 2019 when I had discussions with numerous blockchain gaming studios. When I pitched the concept of a scalable blockchain to them, it fell on deaf ears as they showed little interest in what we were building. Upon further investigation, I discovered that these studios were losing 199 out of every 200 end users at the MetaMask step alone. This realization led me to conclude that the web3 space would greatly benefit from a user-friendly blockchain solution.
Alex published an article about this issue during this time frame, and it became the third pillar of NEAR's product focus, alongside scalability and developer-friendliness. By incorporating user-friendliness into our product vision, we aimed to address a significant pain point in the web3 ecosystem and differentiate ourselves from other blockchain platforms.
Following the launch of NEAR, I dedicated the next few years to supporting the growth of its nascent ecosystem as a member of the Human Guild DAO. Our efforts focused on providing grants to approximately 75 projects, primarily in the gaming, music, and virtual world spaces.
This experience provided me with valuable insights into the process of building early ecosystems and the key factors that contribute to their success. One of the most crucial elements I observed was the mental resilience and determination of the individuals involved. Building in the web3 space, especially during the challenging period of 2022-2023, required an unwavering commitment to the vision and a refusal to give up in the face of adversity.
Through my work with the Human Guild DAO, I gained a deep appreciation for the importance of fostering a supportive community and providing the necessary resources to help projects navigate the complexities of the web3 landscape. By offering grants and guidance, we aimed to empower developers and entrepreneurs to bring their innovative ideas to life and contribute to the growth of the NEAR ecosystem.
As I embark on this new chapter of my career as an angel investor, I'm reminded that success is rarely a linear journey. It is the twists and turns, the failures and triumphs, that shape our perspectives and equip us with the wisdom to navigate the complexities of the startup world. I am committed to sharing my learnings and experiences through writing. My goal is to provide valuable insights and guidance to those who may be contemplating their own career paths and seeking to learn from others' journeys.
If you find yourself at a crossroads in your career or simply want to discuss your experiences, I encourage you to reach out to me. You can connect with me on Twitter or via email, and I would be more than happy to chat and offer any advice or support I can.
Furthermore, if you are currently building a startup and considering fundraising, I invite you to apply for funding by following this link. As an angel investor, I am actively seeking to support promising startups and help them navigate the challenges of early-stage growth.
By sharing my knowledge and offering support to others, I hope to contribute to the growth and success of the entrepreneurial community. I believe that by fostering a culture of collaboration and mentorship, we can collectively drive innovation and create meaningful impact in the world.