My Friend Tom Castiglia

It all started in Los Angeles for TechEd 2010.

After moving from Seattle with a big friend base, we found ourselves starting all over again. It didn’t take us long, but eventually we found intelligence gold! A very knowledgeable individual was doing a deep dive presentation on Windows Workflow Foundation. I was quite impressed and made it a point to strike up a conversation. Little did I know would this person, Zoiner Tejada, would eventually end up being one of my best friends, but also introducing me to his boss at the time, Tom Castiglia, co-owner of Hershey Technologies.

Hershey had a competitive product to SharePoint and Zoiner thought it a good idea to do a review of features between the two. I ended up meeting Tom and chatting for a few hours about the feature gaps between the two and if they should continue development. I was impressed with Tom’s quick acumen to pick up what I was saying…in typical Tom fashion:


Being that I had just left an incredible user group in Seattle (Puget Sound User Group) I was looking for something similar in San Diego. We had one, but it wasn’t doing what I felt it needed to do at the time, so I created I was lucky enough to have my friend Kevin Landry offer his facilities at New Horizons Miramar and after the first couple of meetings, Tom started attending. He offered up to be a sponsor and eventually became my founding member and vice president. As it started to grow, Galen and Tony came into the picture and joined our board.

Tom Castiglia and our first year of

Little did I know that these friendships would evolve into something magical. SharePoint Saturday’s were still in there beginnings back then and were on the upswing. I decided to pursue our first SPSSAN and we went big. I was able to call in a lot of personal favors and we had an amazing budget that allowed us to host it at the San Diego convention center.

If you run a user group or a SPS, you know how much work it is. After the first couple and $20K of my own money into it I decided to pass on the reins and Tom gladly accepted the role as President. He did an amazing job with the group and eventually convinced Microsoft to host us at the La Jolla office. And that’s where the lovely Sal Rosales came into the picture. He has been our sponsor and biggest fan. Through the years we were able to create incredible presentations and invite speakers from all over the world. Our user group and our events are, in my opinion, second to none. I believe that to be true due to the incredible bond we all have with each other.

It was always nice to go out afterwards and have a beer…that was definitely Tom’s favorite. He loved to go to Brewski’s Bar & Arcade. We’d all meet and talk about our month and what we were working on, do a little gossip of the what’s happening around town, they were insightful chats. In many cases, raw, unfiltered and full of trust.

As we worked more and more with the user group, I came to appreciate Tom’s hard work and dedication. It was at this time I was approached by eBay/PayPal to look at performing their SharePoint migration. I knew that it would be a big project and I’d need help. I approached Tom and he gladly accepted the challenge and trusted my estimate of the work. Hershey and I was able to complete the project successfully and within $5K of my original estimate.

It was quite the project and Tom and I talked almost every day for 4 months and we had a blast running around San Jose and San Francisco together. After we finished the project, we continued our user group activities and then Tom and his wife would join me on all my SharePoint conference adventures. eBay was featured that year as a reference customer and we had the Microsoft video crew out to eBay to film all our hard work.

As the years went by, Tom made a global name for himself and took advantage of every opportunity. I watched him from a far and we talked about a lot of stuff (selling Hershey, hiring Joel, leaving Konica and doing his own thing….). We trusted each other and he was a good friend that had his opinions on things but always accepted my crazy odd-ballness over the years. He was a true friend in every sense.

I’d have parties at my house, he and Martha was at every one. He had parties and we would go over and we had a blast!

Just last year I made it a point to get out of the country more. I was able to join Joel and Paul for China; Sheila and I went to Singapore. But more importantly, we also were able to make it down to Cuba. Running around Havana with Tom and Martha was a once in a lifetime experience and I’m happy that we got to have it with them.

Since the original crew started (Tom, Galen, Tony, etc), we have only grown our family here in San Diego. We now have Joel and David, and Ryan. Ryan has been generous enough to step in to take over the San Diego user group reins. With Tom no longer here, Ryan’s help is even more needed to keep things going as we all have so many things going on.

It’s hard to come to terms with the fact I won’t get to see him again. It’s also tough to know that he had such a exponential curve going for him; business, career and life-wise. He had big plans, and although the road was slow going, he kept at it. Everyday.

Knowing that this didn’t have to happen and could have been prevented is one of the tougher parts to deal with. We can only focus on the “butterfly flaps its wings” purpose of it happening and how we’ll change ourselves to honor his memory. I’m by no means the person Tom was, but he gave me a template and something to work towards. It’s the best way I can honor his memory till it’s my time one day.

It’s inevitable that people will come and go in your life, some will be more influential than others. For Tom, he leaves a hole in our local and global community that can’t be filled by any one person. It will take a little bit of everyone to help fill that gap. Tom represented Satya’s and Microsoft’s vision of empathy and caring. The world could use more Tom’s, not less. I encourage you (and even more-so myself), to try to be like Tom.

Miss you brother. Love.

If you have a story or pictures that you’d like to share about Tom, please post them to the memorial site we setup in his honor:

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