Product Engineer by Day, Venture Capitalist by Night - balancing two worlds for the past four months

My journey balancing internships in software and venture

Over the past 4 months, I've been wearing multiple hats in the startup ecosystem: doing product/engineering work at CommandBar, interning at Cowboy Ventures, and supporting diverse founders through the Envision Accelerator. 

This is the story of how and why I did it. I’ll be talking about how I structured my schedule, why doing this made sense to me, connecting both the venture and engineering roles, and what I learned. 

Why I did it

I had been wanting to break into venture for a long time, and when I finally came across a part-time venture internship working for a principal I really admired, I couldn’t pass up the opportunity. I also wanted to potentially be a founder someday, so I also wanted the experience to work at an early-stage start-up. 

Getting to work at a 15-person start-up, while being exposed to investing at the seed stage at Cowboy, as well as helping my founder friends at Envision through their own fundraising process put me in a really unique position to learn about the startup ecosystem from all sides of the table. 

I’m at a stage in my life right now where this makes sense. Learning and curiosity are my biggest values, and I’m still figuring out what I want to do long term.

I only have a few years left to graduate, and I want to spend these special years working with people I admire and can learn from, exploring new industries, and building communities.

Moving to a new city for the first time, my venture and product work have helped me also meet so many people in a short amount of time because of the work I do, from attending writing clubs, co-working sessions, and organizing founder socials to bring people together.  

How I made it work

I’ve been able to juggle these roles by adhering to a few key principles: thinking in systems, seeing how my different roles complement each other, structuring my week consistently, building trust within my team, and strong communication. 

Thinking in systems

Growing up, I got used to juggling many things at once, from balancing clubs with school to studying engineering at Waterloo with recruiting. Juggling all that I’ve had going on the past 4 months felt like second nature. I’ve also never viewed work as something I did as a “9-5”. I love spending my time on things that contribute to missions I’m passionate about, and I view all activities as small puzzle pieces that fit into a bigger picture. 

Nothing ever lives in isolation. I was only able to make this work because all the things I did talked to each other. For example… 

• My principal, Amanda Robson, at Cowboy gave some really great feedback on the blog posts I was writing on CommandBar’s product. 

• James Evans, CommandBar’s co-founder, and CEO, knew about my interest in venture and spent one of our weekly 1:1s exposing me to their term sheet negotiations, data requests, and their own seed deck for my own personal growth. This really helped me see things from both sides. I wouldn’t have gotten this exposure at a larger company. 

• From the founder community at Envision and beyond, I was able to connect to Cowboy for potential deal flow and apply their product learnings to my work at CommandBar. I got to conduct some user interviews with the SaaS founders I knew which was incredibly valuable for the project I was working on at CommandBar. 

The people I worked with are amazing and really supportive of me making the most of all these opportunities and are also generally curious people.

Structuring my time

I tried to structure my time intentionally to make everything work. I usually spent Monday - Wednesday staying in to finish up my venture + Envision work in the evenings so I’d have the rest of the weekday evenings + weekend for social time and exploring my new city - San Francisco . I spent many weekends outdoors, trying to complete a new hike or exploration off my bucket list. I Google Calendared the hell out of my life. I used todoist to manage all my to-dos across all of my work.  I also didn’t cook much - CommandBar provided food at the office, and doing the part-time work at Cowboy also gave me a bit more flexibility in my spending. 

What was also helpful was getting to work in person frequently at CommandBar -  social interaction while working with a new team was fantastic. It was also nice co-working with other friends too! I felt a lot more productive getting to work at an office without any distractions.

However, time management didn’t come without its challenges. San Francisco can be a distracting place. You can find yourself going to “founder” happy hours 4 - 5 times a week and struggling to say no to the constant dinners and hangouts. The city is full of energy, potential, curious minds, and people that are open to connecting. And since I’m new, it was often hard to say no. 

After some time, I started to realize that these events aren’t meaningful when you haven’t had enough experience to share with others. Spending too much time at these social events could cause you to spend more time talking, instead of doing. 

Now I’m more than three months in, I’m finally starting to get comfortable with time alone and just hanging out when I feel like it. I’m grateful for the experiences that saying yes gave me, but like anything, they need to be in moderation.

Build trust early

One of the most important things when being early in your career is building trust with your team. This comes from putting in the work to prove yourself and getting sh!t done. 

What helped for me was getting to spend time over winter break, as well as part of the school year, ramping up on work for CommandBar and Cowboy. Omicron levels were high, so I didn’t mind spending my Winter break working. Because of the time I spent ramping up in advance, I had the opportunity to help build and ship a special project for Commandbar just weeks after my internship officially started in January. I was able to prove myself early and gain trust from the team. 

This ended up playing a huge role in a recruitment process I went through during the past 4 months at a company called Replit. Near the end of the Winter break, I tweeted about getting my dream role at Replit, a collaborative and accessible browser-based IDE that helps anyone build something in seconds. I created a website and pitched myself on twitter. What was so special was that both the people I worked with at CommandBar and Cowboy advocated for my work because of the trust I built. 

A key learning that carried me through the past 4 months was: do good work and everything else will follow.

Key takeaways

A lot of people asked me - now that I’ve tried venture and start-ups- which one am I leaning towards?

At this point, my ideal position would be a bit of both. I’d love to be a founder someday, and hopefully get the financial freedom to angel invest on the side, empowering start-ups that are solving problems I’m passionate about. After spending some time at a startup, I have a stronger idea of how small teams approach building and what problem spaces are exciting in the venture space. 

I’ve switched to the start-up world from big tech and it’s been an amazing learning experience. I love how everything works together at a systems level, and I’ve always loved talking to people and thinking about new problems to solve. 

In venture, I learned how to analyze industries, conduct market research, diligence, and recognize strong storytelling skills. In start-up, I’ve learned how to build fast, make product decisions, foster culture, and how to sell things. And I’m so grateful for what I’ve learned and what’s next!

I feel like I’ve almost experienced living like a founder, and I wouldn’t trade it for anything.  

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Special mentions

This blog was inspired by a post written by Casey who wrote a story ~1 year ago on her experience working full-time as a Software Engineer at Google and part-time as an investor at Bessemer. Check it out here. 

I was really inspired by her strong desire to learn and her discipline of balancing her two lives. Her drive was great and I loved her mindset of using work to explore both of her interests. 

Her story is what told me it’s possible to be in engineering and in venture, and why I sought to apply her tips and embark on my own internship journey of it.