The Leap of Faith: How Regret Minimization Led Me to Leave My Tech Job in California for a Toronto Startup

Date: Apr 25, 2023

Hello there! Today, I'd like to share a personal story about how I left my comfortable tech job in California for a startup in Toronto. So grab a coffee, and let's dive right in.

Living the California Dream at Autodesk

Once upon a time, I lived in a beautiful home in San Rafael, California, and worked at Autodesk for almost five years. It was an incredible privilege. I played a lead role in a flagship product, and my commute to work was the stuff of dreams - a luxury Wi-Fi-enabled bus or a scenic ferry ride across the bay.

Working at Autodesk was fantastic, with talented and experienced colleagues who had been there for decades. For example, almost daily, I was fortunate to discuss 2D and 3D graphics with a world-leading expert. I learned so much from them and am grateful for that experience.

Yet, I started to feel like the product I was on was entering a more predictable phase. The itch to build something new from scratch grew, but I had bills to pay, and California was costly. So I was cautious about my next steps.

The Itch to Build Something New

Enter my friend Andrew, who stayed at my place while in town for a Y Combinator interview. He and his partner, Cliff, were working on a startup. Their pitch was intriguing: "Predictive analytics backed by psychographic data." They wanted me to join as a Technical Co-Founder.

A Startup Opportunity and Self-Doubt

I wanted a change, but I was anxious. I wasn't sure if I had the necessary skills and experience. For example, I knew very little about machine learning or social science. Could I do this? A part of me was afraid I wasn't good enough. After several conversations, I decided to pass. The timing and risks felt wrong.

Fast forward six months. I was instrumental in delivering a high-profile demo at Google I/O. It was public recognition of my work. The timing couldn't be better to consider a next step.

As for Delphia, it pivoted after completing YCombinator and raising a seed round.

Delphia's Pivot

The Cambridge Analytica scandal prompted the pivot. Delphia's "Predictive analytics backed by psychographic data" concept now seemed manipulative. So, in a brilliant move, Andrew repositioned by putting data control into users' hands. And, despite the controversy, he closed a seed round for Delphia, showcasing his exceptional sales abilities.

The Delphia team approached me again while my family was traveling in Canada. After a lunch meeting with Andrew and Cliff, I felt intrigued yet still unsettled.

Then, I came across the concept of "regret minimization."

Discovering Regret Minimization

I had heard Jeff Bezos used this strategy when making tough decisions, so I decided to try it. Regret minimization involves envisioning yourself in the future. You imagine how you would feel about a decision based on different possible outcomes. With Delphia, I surprised myself when I discovered that I would have minimal regrets in any scenario. Even if the startup crashed and burned after 18 months (their current runway post-fundraising).

Deciding to Take the Leap of Faith

Taking such a leap of faith still made me uncomfortable, but I couldn't shake the feeling that this was an opportunity I couldn't pass up. In the past, I had missed out on joining Shopify. Although my reasons were valid, watching their impact from the sidelines was hard, knowing I had a chance to be a part of it. While thinking things through, I remembered some advice from one of Shopify's senior leaders. They encouraged me to work on big, challenging projects, make a positive impact, and avoid focusing on corporate bottom lines.

So I leaped. I moved my family to Toronto and left sunny California behind.

The Painful Transition and Personal Growth

It was tough - I sold my house in a lousy market and moved away from my best friend, who lived a 2-minute walk away. My decision harmed my marriage (imagine trying to move your home and two young children in six weeks). It took years of hard work to recover.

In hindsight, even considering the pain, the regret minimization tactic worked.

The Power of Regret Minimization and Embracing Change

I built the best team I've ever been a part of, and we iterated like mad to make Delphia a success.

Embracing change and taking calculated risks changed my life. The startup experience had its ups and downs, but it aligned with my core values of curiosity and growth. It's not perfect, but I've grown more as a person than I ever would have at Autodesk.

I hope my story inspires you to take risks, embrace the journey, and use regret minimization in your decision-making process.
Remember, it's often about the journey, not the destination. It feels cliche to say it, but it's true.

Taking calculated risks can lead to incredible growth, even if the outcome is uncertain. So, trust in yourself, learn from your experiences, and strive to consider future regrets.

P.S. On a related note, no longer at Delphia. I'm working on a new startup called FForward, which aims to improve communication and decision-making in an innovative way.

Introducing FForward: A Startup for Better Communication

If you believe in continuous improvement and have faced communication challenges at work, I'd love for you to join our waitlist. We're learning and growing daily, and we'd love to have you as part of our journey to help teams with effective communication.

Thank you!