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My first PM job at Intuit was making desktop Quickbooks accessible through regional ASPs (Application Service Providers). We spent hours at small, regional hosting companies trying to make desktop software accessible in the cloud. It was a project that seemed impossible and that wouldn't scale. And it was.
Yet I wouldn't have traded it for success. It taught me that product management isn't just about success - I'm blessed my first project was a failure because I learned that even with a failed project, I still loved the job of product management.
The project was a failure because the economics didn't make a lot of sense. Who was going to pay almost double the price for a hosted version of Quickbooks when they could buy the boxed software. Looking back, I think we were ahead of our time, since that's the core model now.
The most valuable learning was that a failure can help your career. Despite the project not making it, I presented at a very young age to many executives who remembered me and respected the work I put in and who would find me projects and jobs later in life.
I'm grateful to the managers I had at the time, Dan Beck, Marc Canabou, and Adrian Fung. As a sign of how crazy a project it was, I had 3 managers in 6 months. Despite the fact I was young and a complete PITA, it forced me to learn resilience.
I still remember Marc Canabou sitting me down in one of the most mature conversations of my early career and leveling with me that we weren't seeing eye to eye and then using that to create shared understanding. He probably doesn't remember the conversation, but it was formative for me.
It provided an example of how to communicate with a younger employee who thought he knew it all and needed a straight forward discussion to get aligned with his manager. It was a lesson I carried for a long time.
The biggest lessons were 1. You can learn a lot from a manager, even if they only manage you for a short tenure. Each manager was my boss for 1-3 months max (the project was only 6 months).
Dan Beck taught me the value of speed and challenged me to move faster. Even though I wasn't sure if I was doing things correctly, Dan pushed for quick thinking and rapid delivery, which is something I value highly today from my teams.
Marc showed me it was possible to have compassion while also pushing someone.
Adrian Fung showed me that I could take on as much responsibility as possible and pushed me to really own the project. He enabled a young PM to have a lot of autonomy, and that served me well throughout my early career.
It was also a great learning about timing. The ability to access SMB accounting software in the cloud mattered and would later become absolutely table stakes. But in 2005/2006, the technology had not evolved to the point where the economics worked.