GiftSpot - Joining the e-commerce dot-com stampede
Back in Seattle, at the height of the first dot-com boom, GiftSpot was building a business selling gift certificates for the burgeoning e-commerce sector. It seemed plausible: Get folks to spend real money on certificates that may or may not be spent, and make interest on the float. Then, funnel them toward affiliate merchants when the money is spent.
GiftSpot involved a consumer-facing web site and back-end services incorporating payments, integrated with other e-commerce sites. This sounded like it could work, at least at scale. Capital expenses for such a business were pretty low, and logistics for electronic gift certificates were simpler than shipping sock puppets out of a warehouse. Selling virtual money seemed more like a running a bank.
A technical PM role
A good friend from Microsoft was their VP of Engineering, and hiring. After informally doing Program Management at Microsoft and then teaching Program Management (among other things) at Yale, I came on board as a Program Manager for GiftSpot, a welcome change after all the years as a developer. At the start of my career I could have joined Microsoft as a PM, but I chose the software design engineer track because I loved writing code and developers were in shorter supply. But I had always wondered - what if I had chosen the other path? The prospect of being a PM in this hot space in a cool office with nice people overlooking Lake Union, a short commute on my e-bike, was too hard to resist.
The PM job involved deep dives into transaction logs and site monitoring and fraud detection and similar fare, and diagnosing front-end web issues. It was actually not quite challenging enough, and I missed writing code. When we launched the service, it worked but was not a runaway success, and with funding uncertain, I made the call to gracefully move on, and they ended up getting gracefully acquired by GiftCertificates.com.
Roads not taken, again
Another local startup that was hiring in the e-commerce space was Amazon. A friend worked there as an engineer, and was unimpressed with their technology in 1999. He said it wasn’t a real tech company, and they tended to just throw more hardware at architectural problems, which turned me off from working there. The customer experience, though, was awesome, and I did feel inspired to buy a good chunk of the stock, which I ended up liquidating at literally 1% of its current value, in order to pay a big tax bill on some profits that vaporized in the dot-com crash at the perfectly wrong time. Oops! It would have been profoundly satisfying to start my own foundation.
Perhaps more wisely I decided not to pursue an opportunity at a startup called BlockBuy that was basically trying to do Groupon, 8 years before Groupon, which I thought was actually a great idea, if a little early, but I didn’t have sufficient faith in the leadership. It seemed to me that a business model that only works in volume would be a challenge to catalyze, which proved correct. After any sale would be a nontrivial fulfillment problem requiring labor that someone would have to pay for, and there was a lot of handwaving about that half of the problem. Some friends did join the effort, and my younger brother scored a job there that jump started his own tech career.