At the end of 2005, I was interviewing with Craig Walker at a company called Grand Central. They didn’t have funding at the time, so I ended up taking a different position at Intuit. Two weeks later, Craig calls me up and here is the conversation:
Craig: We got our funding, we can give you lots of stock. Please join us!
Me: I feel guilty. I just joined Intuit 2 weeks ago.
Craig: Wow. Ok, but I think you might live to regret this decision.
Me: Yeah, you might be right.
Well, 18 months later, GrandCentral sells to Google and becomes Google Voice. Yes, I lived to regret that decision. (Although, it did lead me down a different path with Marketo.)
Then almost 10 years later in 2015, I left Marketo to join Engagio. I left alot of money on the table and made the decision because “I was unhappy”. 12 months later, Marketo sells to a private equity firm and fast forwards all stock grants. I would have made millions that year alone. I lived to regret that decision too.
At that moment, I thought about the advice I would give my younger self. I imagined that I could only give a short message, like a tweet, without company specifics. This was what I settled on:
Don’t make decisions based on happiness or guilt. Make decisions based on financials.
As I’ve previously posted, I took a position 2 months ago at Sitetracker. Good people, good product. I learned first hand that Salesforce really is a viable platform for specific types of new companies. I thought then and think now that Sitetracker has a bright future.
Rewind back to May, I met with this company, Treasure Data, that I liked very much. I liked the position and the people. Unfortunately, they couldn’t reach my salary requirements at the time. It turns out that they were getting acquired by Arm (the chip designer) who had previously been acquired by SoftBank (the mega investor). Thus, they had their hands tied.
Fast forward to last month, they got back in touch with me and said that the acquisition was done and (after some process) made me a very, very generous offer. An offer that reminded me of Craig Walker in 2006. Immediately, my short advice popped into my head. This was a similar situation. I felt guilty, but the numbers made sense.
My advice is not for everyone, but it makes sense for me.
So long story short, today is my first day at ARM Treasure Data. I am the Director of Design and lead a team of 2. I will likely grow that team in 2019. For now, they need a full design system.
Oh, one wrinkle. They are a Mac-ONLY shop. So after 26 years of Windows and every beta of the OS Microsoft ever made available, I am now a Mac user. It’s scary, but WordPress and Figma seem to work so I think I will survive. I did sign up for the beta of MacOS Mojave, which will make me feel better.
Also, now that I have a Mac, I can try out some Mac only design tools. Upwards and onwards.