Engineer by Day, Venture Capitalist by Night

For the past three years, I have had two jobs. I work full-time as an engineer at Google and part-time as an investor at Bessemer Venture Partners. Many people have asked why I do this, how it happened, and how it works. I hope this post addresses all of these questions.

WHY I DO IT

I value learning above all else, and I have organized my life around this value. This might change in the future if I ever have a family of my own or amass enough knowledge where I feel I should spend more time “influencing” the world, but right now, my life is about attaining knowledge.

Growing up, I was always encouraged to explore my interests, so I found myself chasing my curiosities from a very young age. From the beginning, I was fascinated with two things: humans and the world we have created. These fascinations never subsided and have motivated me to become an eternal student, which has led me to where I am today.

Having two jobs is the most effective way to learn about the topics that interest me. I’m currently learning about machine learning, distributed systems, technology investing and critical thinking.

HOW IT HAPPENED

In 2017, I decided Google would be the optimal place to work next for two primary reasons:

(1) I would learn how to build systems at scale. Having worked at only startups, I was very curious about how large distributed systems were architected.

(2) I would have access to the most incredible datasets in the world. I am always trying to learn about people and let’s be honest, Google knows more about us then we do at this point.

With these reasons in mind, I applied to Google and landed a job working on core Search.

Within my first week, something became hyper apparent: Google really does value work-life balance. Previous companies I worked for boasted a balanced lifestyle, but employees would still stay late and work on weekends. This was not the case at Google. By 7pm, I would be alone in the office, bored and antsy. I decided I would fill the extra time with learning how to angel invest, which was at the top of my “to learn” list.

I made a few investments and quickly realized I had no idea what I was doing. I had no clue what made a company “interesting”, what “good metrics” looked like, or even how to properly analyze an income statement. While I could do grade-A technical diligence, complete with a full code review, my investing process had gaping holes. After some brainstorming, I decided I would try to join a venture capital fund to learn the ropes of the industry. Having a deep understanding of software engineering, cryptocurrency, and machine learning, I figured this skill set could be valuable to venture funds and started informally pitching venture capitalists on taking me on part-time. Thankfully my pitch of offering technical diligence worked, and I started contracting with venture capital funds in the valley by the summer of 2018. Eventually, Bessemer and I met and it was the perfect long-term match. I knew a lot about crypto, an industry they were looking for an expert in, and they were masters at technology investing, the skill set I was looking to improve. So in December of 2018, I signed to work with Bessemer.

HOW IT WORKS, TACTICALLY SPEAKING

I work at Google from 9am to 5pm and I work for Bessemer early in the morning, late at night and a bit during the weekend. There are a few cardinal tactics I employ to make this manageable.

Being Bi-Coastal

In order to participate in Google engineering sprints, get face time with particular Bessemer partners, and be a part of Silicon Valley culture (mainly networking “happy hours” where no one drinks #keto), I need to be on the West Coast.

In order to see my family, interface with other key Bessemer colleagues and have a social life, I need to be on the East Coast.

When I first took on this second job, I would travel back and forth every few weeks and stay with friends or in hotels. This got exhausting. Deciding to have two apartments has been a complete game-changer. It has been critical to doing both jobs well, having a full social life, and maintaining my sanity.

Many people wonder how this makes sense financially. I rent small rooms and I like plain walls.

To-do Lists

Having a to-do list is one of the fundamental habits that enables me to be productive and manage my time.

I write to-do lists every day. Normally I write them in the morning but I add to the list and often rewrite the list many times throughout the day. I have tried countless digital apps and they do not work well for me. I do use Microsoft To-dos and a series of Google sheets / docs / Evernote for longer-term goals but for daily goals this notebook is my savior.

(pink=personal, blue=Bessemer, green=Google)

Detailed to-do lists may seem like a waste of time but I believe that planning is 90% of the battle to getting things done.

“Give me six hours to chop down a tree and I’ll spend the first four sharpening the axe.” — Abe Lincoln

My calendar

If it isn’t on my calendar, it doesn’t happen. Although, I have learned my limits with this. Scheduling a first date by sending a calendar invite doesn’t seem to go over so well.

In general, everything goes on the calendar, even coding blocks. I follow the same color scheme as my to-do list so I can glance at my calendar and get a quick digest of what the day is going to look like. Engineering is a super focused and solitary activity while investing is a lot of meetings and developing ideas. It takes a lot of energy to switch between the two work modes, so I craft my calendar to avoid the switching cost. In other words, my social skills are non-existent after an afternoon of coding, so I wouldn’t schedule an important meeting that evening. Anyone who programs will get what I mean here. Talking to people casually becomes nearly impossible after staring at your terminal for 6+ hours.

Reflections

I do monthly, quarterly, and yearly reflections with close friends. Every month, we first read last month’s reflection and then answer the same questions for the current month.

I have been doing these monthly reflections for seven years now and they help me stay centered, focused, and honest with myself. I am an avid believer that in addition to planning, reflecting often maximizes your chances of accomplishing goals. There is also ample research behind this. One recent study came from psychology professor Dr. Gail Matthews. Her research shows that participants who wrote down their goals, defined their action plan, and provided weekly progress updates to a friend were 33 percent more likely to achieve their goals than those who did not take these actions. Aside from the obvious benefits, it’s also hilarious to look back in time.

Coaches

Another core belief of mine is that we don’t share enough of the knowledge we obtain throughout our lives. Given this belief, I try to learn from others and teach often. If someone has dedicated years to understanding a subject, why would I try to learn it myself and start at ground zero? We should all be leveraging one another in an authentic way.

Kat, my holistic health coach, helps ensure I fuel my body and brain well.

Logan, my relationship coach, helps me navigate relationships and love.

Monica, my career coach, helps me think through big career moves.

Mia, my assistant, helps me make sure my time is well spent.

P.S. If you are looking for referrals on any of the above, ping me! I LOVE all my coaches.

So those are the tactical habits that make the system work: two apartments, to-do lists, an organized calendar, frequent reflections, and harnessing experts.

WHY KEEP DOING IT

Even after I explain all of this, I still get asked what it is really like to have two jobs and why I continue doing it. Why stress yourself out, and put so much pressure on yourself?

My first rebuttal to this line of inquiry is that every parent undoubtedly has two jobs. Having two professional jobs may be rare but having two jobs generally speaking is very common. Being a girlfriend is a job, being a mom or dad is a job, and being a caregiver is a job. I am privileged to have extra time on my hands. I am young and only responsible for myself and chose to take on another more traditional job to fill my spare hours. I can thankfully do this without neglecting my family or friends.

I also don’t think about my jobs as work. I think of them as structured ways to explore my interests. I learn about machine learning and software systems at Google and I learn about investing and developing world views at Bessemer.

A lot of people then ask, if the goal is learning, why not just take online courses? Why do you need jobs to learn? I actually love classroom learning and may be going back to school in the near future, but I have found jobs to be an incredibly effective way to learn.

Tell me and I forget, teach me and I may remember, involve me and I learn.” — Benjamin Franklin

Jobs are the best way to ensure I am involved and truly absorbing knowledge.

When it comes down to it, I am driven by learning and having two jobs is my way of ensuring I am maximizing my hours and keeping me stimulated. I love getting to use my brain in various ways every day.

With a finite number of years on this planet, I think it’s crucial to be intentional with your time and for me, I feel most fulfilled with these two commitments.

With all this said, this is just my approach to living a life that energizes me.

You have your way. I have my way. As for the right way, the correct way, and the only way, it does not exist. — Friedrich Nietzsche

Q&A

Q: Do you ever see your friends?

A: Yes. I intentionally live with friends so I see those people every day. I also take one day a week completely off from work — usually Sunday. On that day, I see friends and family. While I am a terrible texter, I call my closest friends very often and my family daily.

Q: Where do you find the time?

A: Something that saves me a fair amount of time, and mindshare, is not being active on social media. As more research is conducted on the long-term effects of social media, I am more convinced now than ever that this one decision has made a massive impact on me. In a recent issue of the American Economic Review, a paper titled “The Welfare Effects of Social Media”1 was published. Two significant findings in this study of nearly 3000 people include that deactivating social media site Facebook freed up on average 60 minutes per day and caused a small but significant improvement in self-reported happiness and life satisfaction.

I also eat all meals at Google so food is another big thing I don’t have to worry about or dedicate time towards. Lastly, despite my strong desire to have a bulldog named Ubud, I don’t, so I spend no time on dog walks. One day, though.

Q: What percent of your day is spent working?

A: This is a tough question because a lot of activities I partake in straddle the line between work and play. For example, is a happy hour with other friends in venture “work”? Is a brainstorm session with friends about the lasting effects of COVID on the economy “work”? Is reading a book on neural nets, closely related to my latest project at Google, “work”?

I would say 90% of the things I do are loosely related to one of my two jobs but I don’t experience any of these activities as drudgery. Since my jobs are rooted in my greatest interests, work involves tasks that I am happy to do and this prevents me from getting “burnt out.” I guess my jobs are less like jobs and more of a lifestyle. I think most investors will get this. There is no real “off” switch for that job. You are always kind of working because every conversation or event may lead to a deal down the road.

Q: How much do you sleep?

A: I sleep eight hours every night and sometimes nine on the weekends. I need high-quality sleep.

Q: What do you do for fun?

A: Truly, my jobs are fun. Even if I didn’t have to make money, I would still split my time like I do — oscillating between coding and investing. I feel so honored to interface with the people I do at both Google and Bessemer. But that’s not all I do for fun. I go to bars with friends on the weekends. I attend amazing events throughout the year like Burning Man and meditation retreats. I also travel a ton with friends.

Q: What’s the hardest part?

A: The hardest part is managing my schedule and that’s why the tactical techniques are so important. In the beginning of this arrangement, I missed many meetings because I would forget to wake up early. I also missed many dinners with friends because I let meetings run over. Over the course of my first year, through trial-and-error, I have found that the tactics described above work wonders for me.

If you have any other questions. Ping me! I check Twitter 3–4x a week!

1a: https://pubs.aeaweb.org/doi/pdfplus/10.1257/aer.20190658

1b: https://www.calnewport.com/blog/2020/02/29/top-economists-study-what-happens-when-you-stop-using-facebook/

Engineer @Google | Investor at @BVP | Twitter: @caseykcaruso

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store