Why I Joined HeadsUp

Sam Maynard4 min read
Sam Maynard

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!


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