This post is 3 parts: A quick personal COVID update blog, a pretty long biography that I’ve been meaning to write, and sharing news of a big milestone. I hope you find it informative, inspiring, or at least entertaining.
The start of January 2020 found my family in a pretty happy position. Me working at a Startup, my wife working a new job at Facebook. Our home in the suburbs of Sunnyvale, CA was being remodeled and we found a nearly identical layout home to rent while the walls were torn down and framed. Our investment property in South Lake Tahoe was staying busy with AirBNB guests, and everything was on track. Hard work, lots of luck and privilege had us in a pretty good spot. I had worked at Facebook as well, but had chosen to try my hand at the small startup world for less up front compensation for the ability to learn up close about entrepreneurship and a longer term chance at building something that would lead to a big “pay day” when the company was acquired or went public, allowing me to pursue entrepreneurial dreams.
COVID-19 came in February, and it changed a lot for many. Our family was better off than most, both my wife and I able to work from home. But the needs of public safety and the travel ban stopped both the renovation construction as well as vacation rental income. For an unknown time then, we would find ourselves paying rent and 2 mortgages off salary alone, and I was worried. So I began to look for work back in the higher salary world of FAANG (Facebook, Apple, Amazon, Netflix, Google) to find a way to be able to deal with the worst-case, months of no income from rental, and extended construction delays.
With 10+ years experience in the tech industry, and some boning up for the interviews, I was able to secure an offer to return to Facebook, an offer from Amazon as well as one surprise offer from a SPG (Special Projects Group) at Apple. I was now left with the kind of hard decision that everyone should be lucky enough to have. Our journey down the trail of life is full of twists and turns, and mine will have one more. But first, a little backstory.
A little bit about the BadPirate
Some of you may have heard parts of this story, but I thought it would be nice to write it all down in one place as the background here was pretty relevant to the choice I made, and even if no one else reads it, having a firm idea of one’s own story is a good way to stay on track with who you are and who you want to be.
From a very early age, I was into technology. I was lucky enough to be around the “latest” gadgets, and had family members and teachers who were early adopters of some of the technology that we know are surrounded with.
Some of my earliest memories involve learning to read from “Sticky Bear” so that I could understand Oregon Trail well enough to beat Dad on his work Apple II/e. By 7 or so I had co-opted that computer into my room. I also had a pile of 5 1/4" floppy disks -with no instructions- containing various utilities and games that Uncle Steve, also a teacher, had given to me. Many hours I spent holed up in my room figuring out, and then playing games, or printing banners and fractals with The Print Shop. But the real inspiration happened around 5th grade, when a teacher at my school began a “Programming Club” and I got my first taste of software engineering through BASIC programming. From there it was the Macintosh Classic, AOL, and ANSI C. I got real satisfaction from creating something that worked in code, but unlike almost every other vocation, the real power was that for just a little extra effort on top of the creation, I could create thousands of copies. I knew tech was for me.
By the time I was 15, I was a full on Apple Fan boy, and had decided that my career would be working at Apple for Steve Jobs. I printed up a plaque for my room to keep me on track, its actual source was debated but was undoubtedly a quote Steve had his hand in. I’ve still got the plaque in my room today.
I knew I needed a degree in CS to get an Apple Job, and I didn’t have money saved up for College, and my high school GPA wasn’t strong enough for scholarships. So I concocted a plan. Dad taught at Front Range Community College, and I had taken a couple of computer courses while in High School already. I would get a discounted Associates Degree from the community college, and then start a CS program at the local state college (CSU) with 60% of my credits already completed. Even with this plan, and a decent night job at a Call Center, it would be tight, but I could get a degree on the cheap, and because CSU only cared about my Associates degree grades, my 2.7 High school GPA wouldn’t be noticed.
For the next year I put my plan into action, attending community college part time while working fulltime. I maintained a 4.0 GPA, but my degree was moving along slowly, as I couldn’t afford full time tuition or to work only part time. And 2002 Silicon Valley was going through a Tech Bubble “correction”, jobs were hard to get.
I wanted to be sure that all this work I was doing was going to pay off. So I concocted another plan. I bought a ticket to Macworld, packed my best and only suit (no tie), printed a stack of faked resumés which listed where I planned to be in the next few years rather than where I was, and hopped on a plane to San Francisco.
I got to see my first glimpse of Steve Jobs as he unveiled the iLamp (iMac G4). And the whole week that I stayed up in SF was a blur.
I had no luck sending applications to the Apple career site, without the right background it was a black hole. I wanted to try and make connections with Apple employees to see if I could find the back door. Plan time again. I found out about an invite only Apple party, dressed in my suit at the hotel that Apple had reserved for their own employees and offered to “share a limo to the party” with some obvious badge wearers. The wife of a C-level got in the rented limo and figured out my ruse half way through the drive to the party, she promised not to tell and snuck me in. I got to meet Steve Jobs (briefly), and watch the CEO of Aladdin (of Stuff-it fame) sing Karaoke. It was an exciting time. I made friends, shook hands (pre-covid) and handed out resumes wherever I went. But it wasn’t all good news. Everyone I talked to wouldn’t hire future me. He didn’t have any work experience, and they had just let go of some people that had a thicker resume. My degree plan seemed on a road to failure. The tech job market needed time to recover, and I needed a degree AND experience. It was time to concoct another plan.
A few months prior a friend of mine had taken the ASVAB (Military entrance test) and aced it (99) and in a competitive spurt I told him I could do that while hungover. A week later I was getting ushered out of the Denver MEPS, with a headache and a slip of paper certifying me as being a part of the top 1% of folks to take the ASVAB. While I hadn’t intended to join the Navy at the time, my experience in San Francisco gave me an idea for a new plan.
I signed up for 6 years as a Navy Electronic Technician about a week later. I was working at the call center awaiting my ship date when two planes ran into the WTC, but decided I had already said I’d join so went through with it. I served a year in Iraq, a year or two traveling the world (as they’d promised), a year on a little island in the Indian Ocean, and the rest in beautiful Hawaii. But despite being in the Navy for 6 years, I never set foot on a ship once. The “BadPirate” was born.
What the Navy left me with in 2008 was a degree from Hawaii Pacific University, a two bedroom condo in Mililani that I had purchased with my VA Loan, 6 years work experience, a top secret clearance, and no debt to speak of.
It also had dropped me into a recovered economy. I made a number of calls, and another flight to San Fran (this time from Hawaii) dropped off some resumes and sent another hundred or so applications into various job sites
/dev/null — Turns out that while being a veteran helped, I would need real industry experience to get noticed by any of the companies I wanted to work for. So another plan? This time I setup an S-Corp and started writing applications for the newly released iPhone platform. Specifically by taking up contracts from local Hawaiian businesses and individuals who wanted to pay me a few thousand bucks for a chance to get rich on this new marketplace. I made apps for learning the ‘ukulele, a Hawaiian word of the day, and for the now defunct local news paper the “Honolulu Advertiser”, probably a dozen or so all told. I also started an S-Corp and learned a bit about the joys of running your own business from paradise. But it wasn’t changing the world. When I got a call from TATA Consultancy services to do contract software work for “a big company in Cupertino”, I packed it all up and moved to Cupertino, CA.
For a year I worked as a contractor at Apple, and it was interesting, building on a product called “iLog” which Apple customer service used for taking calls. My paychecks came from TCS (Largest employer in India), I was a little jealous of my Apple Employee co-workers. I wanted to get into the interesting work, and my manager at the time let me know that if I worked somewhere else for a while, they would hire me back.
I then spent 8 years building my experience, at Good Technology, I grew from Junior dev to “Architect”, rebuilding their Email, Contact and Calendar product into something good enough to be purchased by Blackberry as the flagship iOS product in their “pivot” from being a hardware. company to a software one.
*** Contact your IT administrator for any help with setting up BlackBerry Work *** Take care of business simply…
I spent 2 years working at Facebook on News Feed, Stories, and Messaging. For a number of months I sat about 100 feet from Mark Zuckerberg’s “Fishbowl” meeting room, and the work felt interesting and important, it was wild writing code used by over a Billion users.
But I still grew restless, I wanted to put my signature on something new and revolutionary, and while I had a chance at Facebook of finding the right moment to get on a 0–1 project, there wasn’t a clear path to my goals. I had some ideas, but I would need more business experience, and a big enough pile of cash to keep feeding the family and paying a mortgage while I pursued them. The plan came with a job offer to UnifyID, a startup with around 25 employees, and an interesting product in the security space. So I traded in the comfort of the Facebook job for the chance to work closely with a small business CEO, and over a longer time period, perhaps find my big win in the way of stock option buyout. Half way through my first year at UnifyID, COVID struck. And that takes us to today, and the decison to make.
Back to Facebook to try and change the world there, continue on at UnifyID and hope it could launch me into individual success, explore a new big company and vision with Bezos’s Amazon, or finally see what it’s like to do big things at Apple.
Here’s to the Crazy Ones
I think I always knew. I accepted the offer to go work for Apple Special Projects Group. Like most things at Apple, I don’t actually know yet what that means exactly, and once I do, I won’t be able to say. It was the door that I couldn’t close. Lots of things have changed since I set out to become a big time Apple Engineer and/or change the world, and I know that there is a chance that this turns out not to live up to the dream I’ve been pursuing for the better part of 3 decades. But I have to know what’s behind the curtain.