Why I Joined HeadsUp

Sam Maynard
, Momo Ong
June 4, 2021

I've loved building products and watching them come to life since the first time I alerted "Hello $name!" using Javascript in fifth grade.

I've spent my time since then chasing that feeling, through internships and side projects in college, an internship at Microsoft Research Asia post-college, solo-founding ankidecks.com, and now working as the third engineer at HeadsUp.

In college I decided I wanted to be an indie hacker, which is a term for bootstrapped one or two person online ventures. I wasn't sure what the product was going to be, but I was confident I could do it. So I turned down the offer I had from a mid-sized Silicon Valley software company and set out on my own journey, which actually started in China.

I graduated college with a minor in Mandarin, and post-grad I knew I had to move to China and really learn the language or else I'd slowly forget it. I found an internship with Microsoft Research in Beijing for a half year, where I worked on building an experimental database. I also worked hard on my Mandarin, made friends, and explored the city. After my internship was done I spent another half year or so traveling, which you can read about on my travel blog if you are so interested!

After returning home from my travels, I started my indie hacking in earnest, working full time on Anki Decks, a marketplace for flashcard packs for the spaced repetition app Anki. This being my first time building something that people would actually used I learned a lot about things like data privacy, handling money, handling email, marketing, legal, and all the other hats you have to wear as a solo founder. The site made its first dollar about six months after I started work on it, which counts as a success in my book!

I was still bumping along as an indie hacker when Justin, a friend of a friend, reached out to me about joining the team at HeadsUp.

I was initially hesitant, but as I thought about it, I realized that working as the third engineer at a small startup like HeadsUp would be like leveling up my work. At HeadsUp, I'd experience more interesting challenges, larger scope of work, more customers, more data, and I don't have to handle my own legal work!

I accepted a work trial, and from day one, everyone was receptive to my questions and feedback – I was trusted as if I'd been on the team from the beginning.

After ramping up quickly I dived into product work and was amazed at how much faster things seemed to move when working with a team rather than as a solo founder. I was having much more fun at HeadsUp than I was previously and ended up deciding to join the team!

I've really enjoyed my first few months here – the product team is highly communicative and focused, and the engineering team is built on a culture of autonomy and openness. I enjoy wearing many hats and being cross-functional; as a solo founder, I felt I never had enough time to code after dealing with everything else, but at a startup, I've found a good balance where I get to focus on my strengths in engineering while also being able to pitch in on sales, product, strategy, and even hiring.

Since we're a small startup, I have the founders' ears, and the whole team is very open to feedback about anything and everything – we are constantly working to improve our processes and communication habits.

I feel like HeadsUp is as growth-oriented and ever-evolving as much as I strive to be personally, and I'm excited for the future!

Latest Posts

Make the most of the data you have

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.