But really, why Stir?

Annie Cheng
Feb 16
10 min

Hey folks – Annie here 👋

I recently joined Stir as a product engineer. This career move was 5 months in the making, with a lot of soul searching during the process. Today, I want to rewind and share that journey with you.

📖 The Backstory

Although I'm an engineer by trade, I always felt like a creative at heart. Raised by an artist mom and drafter dad, I spent my childhood taking oil pastel classes, making origami & crafts, and designing puzzle boxes in my free time. Engineering was a career I accidentally fell into (through an unexpected series of events). I'm grateful for it — I really do enjoy coding and building things — but over time, I realized that I also need a creative outlet.

For the last few years, I had been feeding this creative need through hobbies outside of work. I had been doing a series of monthly creative challenges, including learning photography & photo/video editing, travel sketch booking, playing the ukulele, and even turning my closet into a vocal booth to record voiceovers:

This “engineer by day, creative by night” life worked well for the most part. But, at the back of my mind, I couldn’t help but wonder if I could bridge the gap between the two.

🎯 The Goal (early July 2021)

At the end of H2 2021, while re-evaluating my career goals and interests, one thought immediately came to mind: I want to lean more into the creative direction.

But what did that really mean? And how could I do this in a way that complemented my tech skills? With these nebulous thoughts and a strong desire for change, I jotted down a goal that would guide my job search for the next 5 months:

📚 The Research (early-mid July 2021)

Over the next few weeks, I spoke with engineers from companies of all different sizes and industries.

Initially, I had imagined joining a 1000 person company (tiny, right? at least compared to my then-employer Airbnb). But as I chatted with more and more people, I couldn't shake the impression that I'd just be reliving the same experience I already had at a larger company. One week went by, and I was set on a company size of 500 people max. Then 250. Then less than 100.

Before I knew it, I was only talking with folks who had either started a company or had joined one as an early employee. Through these conversations, I picked up on some common themes around joining an early-stage startup: a high sense of agency & ownership, freedom & flexibility to expand responsibility, and exponential growth & learning.

It became clear to me that being at an early-stage startup could be a major career accelerator, and I knew that was exactly what I wanted.

🎨 The Creator Economy (mid-late July 2021)

During my research, I had been casually browsing through companies in creative industries (e.g. entertainment, media, animation, music, audio, social) until one night, I stumbled on this list:

... which led me to Li Jin and her Passion Economy thesis, and to me joining the Means of Creation Discord. That night, I barely slept. Something had clicked, and a whole new world of possibility had opened up to me.

How so? As I mentioned before, I had been pursuing creative hobbies outside of work. One of these was designing my own enamel pins & stickers. Back in 2019, I had run a Kickstarter for some of these products and started my own little Etsy shop:

Unfortunately, my Etsy shop days were short-lived (thanks covid...). My original intention was never to turn this into a steady income but to at least break even and have a fun, creative outlet. Even so, the experience provided a glimpse of how hard it was to make a living as a creator.

In reality, I spent more time handling the manufacturing, tracking the finances, and marketing the products than making new designs. This wasn't just about creating content anymore; it was about running a business... and frankly, a business that would barely scrape by.

It was no wonder that my parents, who initially pursued creative careers, had always discouraged me from taking that same path. "It's a rough life," they would tell me (from experience). And now, I clearly understood why.

But why did it have to be this way? It didn't feel fair. Here I was, making a cushy tech salary while some of my favorite creators, who brought me so much joy and helped me get to where I am today, were struggling to make a living through their passion.

To say that the creator economy resonated with me would be an understatement. This was it. The creator economy was that perfect intersection of my creative and tech interests, and I desperately wanted to help change the current narrative.

🤔 The Whim (late July 2021)

In my spiral down the creator economy rabbit hole, I had seen one particular company come up multiple times: Stir. Initially, I passed them over because I wasn't quite sure what they did. Back-office tools? I had been targeting consumer-facing products at the time. It didn't seem like a fit.

But one Saturday morning, while casually browsing through LinkedIn, I stumbled upon Stir once again. As luck would have it, I sent this message (on a whim) to Hari, an Airbnb alum who also happened to be an engineering lead at Stir:

By that point, I had spoken with over 30+ engineers from different companies. I had a whole script of questions that felt like second nature to go through. So, I was taken aback when Hari said, "Let's not chat about Stir first. I want to get to know you. What are you looking for?"

What was supposed to be a quick chat turned into a 1.5-hour long conversation about our journey into tech, our experience at Airbnb, our career aspirations, etc. I remember feeling so excited to meet someone who shared a similar mission-driven mindset, product engineering perspective, and career approach as I did. Hari talked about the journey that led him to Stir and how much he had grown as an engineer in the past 6 months there.

Out of all the conversations that I had, this was the first one where I felt immediately afterwards: wow, I want to work here.

↪️ The Detour (early August - October 2021)

At this point, I was excited about Stir but I also knew the timing wasn’t right for me to commit. I was still traveling, there was an important project I wanted to see through at Airbnb, and I needed more time to get into a settled place before diving into the hectic startup life.

Also, I still wanted to explore my options. With the hope of learning more about the creator economy and startups in general, I joined the YC Women Eng in Startups Series program in late September. Over the next few weeks, I got to meet some incredible women founders, early employees, engineers, and managers at YC startups.

During this process, something interesting started to happen. As I talked with more people and searched for creator economy startups, it somehow always came back to:

Have you checked out Stir? I feel like you'd like it.

Once. Twice. Three times. I was starting to see a pattern:

I took it as a sign and reached out to Hari once again:

🎦 The Updates (mid October - early November 2021)

Hari quickly connected me with Joe, Stir’s founder and CEO. I had heard great things about Joe and saw some video interviews he'd been in, so I had high expectations. Joe did not disappoint. In our 1.5 hour conversation (no surprise here), it was clear how much passion and determination he had for creating a world "where people can make a living off of their creativity together".

Joe showed me several demos of what the Stir team had been jamming on, and I left the conversation feeling so energized about their work (fyi, it's not just back-office tools). Before we ended, Joe said, "I'm sending you progress updates." I thought he was joking. I was wrong:

🤓 The Final Stretch (November 2021)

In early November, my team finally launched our end-of-the-year project. This had been a huge cross-functional, company-wide effort that was 4 months in the making. And looking back, time really did fly by.

Exactly 3 months after my decision to stay for the launch, I told my manager that I was officially leaving, and we drafted a transition plan. I was ready now, and the timing was right. I was fortunate to be in a situation where I didn’t need something directly lined up.

I took 1.5 weeks off before Thanksgiving break, crammed all my interviews into that time frame, and honestly, just hoped for the best. All I could do now was give it my all and see how things played out. And, with Stir, it played out really fast:

  • On Monday, I announced my departure to my team.
  • On Tuesday, I interviewed with Stir onsite.
  • On Wednesday, I had the Stir offer in hand.

✅ The Decision (late November 2021)

To be honest, it wasn't much of a decision. When I got the Stir offer, I knew I was going to take it. In fact, in my gut, I knew 4 months ago. Back in August 2021, in my second conversation with Hari, I had said:

You don't need to convince me. I'm sold on Stir.

And I really meant it.

🤨 But really, why Stir?

I know what you might be thinking: nice story and all but really, why Stir? To be honest, this was a very practical decision (all risks considered) and one that I didn't take lightly. Here’s the gist:

1. Learning & Growth

I left a stable job and took a pay cut to join Stir. But this move was about prioritizing my learning and growth as an investment in my long-term career. I want to dive deep into the product challenges of the zero-to-one phase, build a software system from the ground up, and experience first-hand everything it takes to build a successful business. I’ve found Stir to be a great place to do all that (and more).

Stir is tackling unsolved problems at the intersection of many different industries. Yet, the team remains creative, experiments relentlessly, and ships solutions quickly (e.g. Drops). At the speed Stir moves, wearing many different hats is not an option; it’s a necessity. Having worked with them for over a month now, I can also say that honesty, reflection, and open feedback are core to how Stir operates day-to-day. This is a supportive team that learns together and grows together, and this is the ideal environment for the type of exponential learning and growth that I was looking for.

2. Team & Culture

Trust. Authenticity. Empathy. Not only is every team member a genuinely good person who cares about one another, but everyone on the team is also amazing at what they do (sometimes to a point where I’m intimidated). Work can be intense, but even so, wellness isn’t an afterthought.

There’s also an equally strong engineering and design culture at Stir, and it’s a place where I’m constantly technically challenged and creatively inspired at the same time (my happy place!).  With all that said, if I could sum up the culture in 3 words? It’s good vibes.

Oh, one more thing  – the flexibility. At Stir, you’re trusted to do your best work. Where, when, and how you do it... that’s for you to decide.

3. Diversity & Inclusion

Creators are unique. They come from diverse backgrounds and bring different perspectives to produce content that resonates with their audience. A team that builds for them should be no different. But creating a diverse & inclusive environment, especially at an early-stage startup, takes clear intention and consistent effort.

This is a core value I don’t compromise on, and neither does Stir:

4. Opportunity

We’re at an inflection point. The line between tech and creativity is starting to blur, and the pandemic has only accelerated it. There’s an immense opportunity to re-define the future of work and creative collaboration. For Stir, this means empowering anyone to make a living off their creativity.

That’s hard. I know. But with a strong desire to put creators first, a talented and growth-minded team, and the support of respected investors & creators, Stir is in just the right position to take on this challenge. It’s hard to say what Stir will look like 1 year, 5 years, 10 years down the line... but one thing’s for sure:

I’m beyond stoked to be working with a rockstar crew of thinkers, designers, and builders to push the boundaries of the creator economy. I know it's not going to be easy but at least it'll be one hell of a fun ride.

🙌 That's it!

If you’re interested in joining me on this exciting adventure, check out the open roles here. Or if you just want to chat and learn more, you can reach me via email at or on LinkedIn. My door’s open. Come say hi 👋

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