Daniel O'Shea

The difference between ordinary and extraordinary is choosing the right extra.


My first job with computers was in high school. I was part of a team of students that had been recently trained by the Santa Cruz County Office of Education in web design. We built the first website for our high school and were feeling very accomplished until we tried to post updates to our site only to watch them fail. The SCCOE had a few different people take a look but they were not able to solve the issue. One day the head of technology was visiting our school and offered to take a look, I was in the library1 watching the debugging process with curiosity because I had never worked with a unix system before, as I watched over his shoulder at some point I made a comment could this be a permission issue, did we use the same account for the initial upload that we were trying to update the site with? He turned around looked at me, back to the computer, typed some commands, back at me and asked “What are you doing this summer?” I had passed my first technical interview, I was too young for the SCCOE to hire me as a student so we waited a year and from sophomore year to graduation I worked first in the lab teaching teachers how to use technology, to becoming a jr unix sys admin2, to writing my first software used by other people. The position also helped me discover computer engineering which would become my major at the University of California San Diego.

College Years

In college I had two internships the first with a research lab at the Scripps Institute of Oceanography with a group that measured ocean photosynthesis via satellite images. The second with Sun Microsystems3 with the team responsible for the software that managed their top of the line enterprise servers. That job was also my first real world code review, and the System Management Services and Solaris Kernel teams took code reviews very seriously. I was very proud to have my first bug fix accepted into the Solaris ecosystem.


After college I went to work for Accenture, my first client was in San Diego three miles from my house, I never had a second client in three and a half years, they kept giving me new projects.

After three and a half years I was looking for something new, and right before thanksgiving a friend from Google gave me a call about a company he wanted to start to do online appointment booking for doctors visits (this was in 2006). I quit my job, packed up and moved into an apartment in Berkeley and joined my first startup, I was now a real entrepreneur and I was hooked on startups.

That first startup did not ultimately work out for me, but it lead me to another company Sparkart that was a digital agency building websites and web applications for entertainment brands. One of the artists I worked with was Bon Jovi, and at the time we signed the contract they told me that in all the years the band had a web presence no vendor, not even the big ticketing sites had been able to withstand the traffic caused by the announcement of a global tour. They called this phenomena the Bon Jovi Tsunami. For context this was back in the days before AWS, when you had to sign lease agreements to buy servers and pay people to rack and stack them for you, lead time and capacity planning were critical.

I took this as a challenge, I wanted my team4 to be the first to conquer the tsunami. So we dug in, understand what parts of our stack would be bottlenecks, did our capacity planning, got that lease with Dell signed, got deliveries of new hardware, coordinated with ops to get everything online and installed, launched the site and then came the announcement of the world tour. We survived becoming their first vendor to do so!

The Startup Life

At this point I was looking for something beyond web applications, I thought mobile was interesting and wanted to try a venture backed startup. I eventually found Humin a mobile startup that wanted to reimagine the contacts app, to create a knowledge graph of all the people you knew across social, email, calendar, and your local contacts and made them all searchable using natural language. To really make the challenge difficult we wanted to do this in a privacy preserving way all on the phone, with minimal servers. I had just fallen into the immense challenge of distributed systems and I loved it.

Humin eventually was acquired by Tinder, we had built people discovery technology that they wanted, and after demoing it to the CEO, he couldn’t believe that we were able to make it work. He accused me of faking the demo, he sent an associate out to buy a brand new phone, download our app from the store and see if it still worked. I didn’t need to fake anything, our technology worked and when the associate came back, and the application performed as it did in the demo, the deal was sealed.

With the acquisition closed I sought something new, I found my way to BlueOwl and became employee number two. I helped build the engineering team, launch a behavioral auto insurance product and launch an insurance company in 18 months5. What started as a backend engineering individual contributor role, became backend lead after two weeks, director of engineering after two months, and VP of engineering just after two years. Now I am responsible for the technology that powers the HiRoad Assurance company and the engineering organization at BlueOwl where I help enable teams across:

  • Front End
  • iOS
  • Android
  • Backend
  • Data Engineering
  • QA
  • Security & Privacy
  • Platform & Reliability
  • IT Operations

I’ve worked all over the technology stack from the operating system to enterprise applications to browser and mobile. I’ve been an individual contributor, technical lead, leader of people and leader of leaders. From writing a patch for an operating system, mobile application development (cross platform things in C, to Swift, to Kotlin), distributed systems and data pipelines, javascript for global superstar recording artists and clients like Microsoft, to a cloud based platform of services in one of the most regulated and security conscience environments in the US.

My passion is pursuing bold ideas, building disruptive technology, and recruiting/ mentoring/ growing stellar engineering teams.

Photo Credit

  • Title - Me
  • UCSD Geisel Library - Photo by MILAN KOVACEVIC
  • Computer - Photo by Cl√©ment H on Unsplash
  • Startup - Photo by Starta√™ Team on Unsplash

  1. I had persuaded the school to give me class credit in exchange for doing IT in the library computer lab. They were happy to let me do it and the librarian at the time ended up writing me an amazing letter of recommendation, it simply said – I don’t understand much of what Daniel does to keep our computers and networks running but I do know that I can trust him completely. [return]
  2. That website I created freshman year, now it had a team of people working on it, unfortunately one day it got hacked, I was the person who got called to the principles office to fix the site and work with the police on the investigation. The computer crimes officer was new to technology so I ended up explaining to him what IP addresses were and how I was able to tell him where the person who defaced our site had come from. [return]
  3. Sun had bought a division of Cray Supercomputer in San Diego. One of the reasons I got the internship was during the four hour interview (yes they interviewed interns for a half day, this was the kernel after all!) I was asked by one of the kernel engineers Dan, if I knew how the SPARQ assembly instruction for multi-processor memory synchronization worked? I had taken one undergraduate assembly course and that was definitely not covered. I answered truthfully, I did not know. Then I asked Dan how did the instruction work? At this point I figured if that is the level of experience and knowledge you need to get an internship with this group, there was no way I was getting the job, so I might as well learn something. Then Dan told me, he wasn’t sure, he was dealing with a bug in Solaris and thought it might be related to the use of that instruction. He had asked me that question to see if I had the courage to say I don’t know, and he liked that I also had the curiosity to find out. I did get the job and worked and learned a lot from Dan. [return]
  4. I was leading engineering for Sparkart at this time, I had started as an individual contributor, my first task was to rewrite the caching system to speed up all our sites, the second day my feature was live, Criss Angel (the mind freak) started an illusion on his TV show that required you to go to his website to see the reveal, at that moment the account manager for Criss Angel did a full cache purge on the site (prior to my change people didn’t trust the caching system and human behavior is hard to change :-)), this was going to be a great test of my change, could it keep up or would it go down in flames, I watched our internal metrics and as the wave of traffic hit us, things went hot as the cache refilled, stabilized and then kept humming right along. [return]
  5. At the time that HiRoad launched in Nov 2018 no one had built an auto insurance company and product and team from scratch that quickly. [return]