Making Your Own Fortune
I am nervously excited to announce that after 15 years of contiguous full-time employment (mostly) at software startups I am taking a break from work. I plan to reflect and recharge at first and then give my own software startup aspirations a go. This post is the first in the series of reflections and talks about the themes in my career so far and extrapolates hopefully transferable guiding principles.
“An entrepreneur is someone who jumps off a cliff and builds a plane on the way down” - Reid Hoffman
My entrepreneurial aspirations and startup ideas largely draw upon my professional experience. My career developed in the intersect of good fortune, serial Zero to One experiences, and building software for more effective, productive, and meaningful work. I hope to make my startup calling within this intersect by applying what I’ve learned about building great teams and recognizing and seizing opportunities.
Learning Optimizations
I’ve been a fortunate recipient of many great people taking their time and money and investing in me. My family invested the most. They always encouraged me to think long-term and to continuously invest into my academic and professional learning opportunities. This long-term learning-optimized view freed me from focusing on any immediate success or following popular more predictable routes. Instead, I opportunistically walked through a series of open doors with ignorant ease. For example, during my second year of highly theoretical studies at University of Toronto, Computer Science students were allowed for the first time to participate in the Professional Experience Year program. I applied but was encouraged to stay back another year and complete more workplace relevant courses. This sounded somewhat absurd and I counted on someone recognizing my eagerness to hands-on learn about the real world software systems. I landed only one interview but I made it count.
Apprenticeship
That internship was a great engineering gig at a fast-growth company where I rode the rising tide through an IPO. Instead of returning to my studies full-time, I decided to continue to take on new projects at work and match my part-time university courses to my work assignments. In addition to engaging my university professors, I sought feedback from my senior colleagues. Starting a debate in class and posing questions at the end of team meetings became my (somewhat annoying) trademark. I soaked it all in. Mentorship from several future VPE’s and CTO’s propelled me to a senior software engineer position a couple of years later and to leading front-end efforts on a CEO’s pet project. The following year we were acquired and I emerged through a massive restructure leading an R&D team – while most of my colleagues were interviewing elsewhere, I used the time to make sure everyone agreed my project was important.
Learning Loop
When I heard some of the company founders were putting together their next venture, I reached out and after several brainstorm sessions I joined them as a founding engineer and the first employee. I applied and further enriched my learnings on building product teams and early products. In parallel, I learned about a whole new world of venture capital raising and startup hustle. We started talking to the social networking phenomenon from Palo Alto later that year about our social performance management platform. After an intense multi-year period of product development and learning loops they rolled out our software following an aspirational team meeting announcement. I was beaming with pride and awe in the audience. Watching our usage that weekend I realized they and our other Bay Area customers would benefit from local tech support and close relationship with our product team. I knew then that I should move to San Francisco to be a part of this software entrepreneurial Mecca. The move was a breeze as my colleagues rooted for me and the founders rallied to use the opportunity to get an SF-based eng team with me at the helm going.
Paying it Forward
The five years since then have been even more incredible. Moving to another country, a successful startup exit, becoming a father, and starting and growing with another great product team made me more aware of how fortunate I’ve been in my career. By seizing unconventional opportunities, I’ve joined great ideas and teams at their inception and stayed on for the learning journey. I am focused on paying that forward by building services that help individuals and companies alike fulfill their long-term aspirations. I will use this blog to share my startup idea evolution and my learnings so far.
“To Whom Much is Given, Much is Required” - Luke 12:48, paraphrased by John F. Kennedy in The City upon a Hill speech.
Making Your Own Fortune
I thought it would be relevant to share some highlights from my career story so far in this post about my next big career step. I also hope this was a useful illustration of the following key career-building principles that worked well for me so far:
- Think long-term
- Create your own opportunities
- Invest into comprehensive learning
- Find mentors for every stage of the journey
- Apply yourself and practice what you’ve learned
R&R
Now, back to my plan for reflecting and recharging. It’s simple. Not having a full-time job commitment will afford me the free unstructured time I cannot remember ever having. I’ll certainly pursue stereotypical goals of spending more time with family and traveling. Yet, at the same time, I’m trying to practice mindfulness and live with purpose - one that I expect will lead me to start or co-found a software startup. I’m starting small. I’ve already significantly cut back on coffee and alcohol in favour of fresh vegetable juices. I additionally plan to recharge through playing basketball. Talking to others lets me think things through and I plan to write for this blog as an additional reflection mechanism. I trust this will all combine for a far less funny and star-studded software startup version of Comedians in Cars Getting Coffee. Please reach out if you’re thrilled by the prospect of a wheatgrass shot after a game of H-O-R-S-E and vigorous debate of startup-building essentials. You just might be featured in the next blog post here.
