Have you ever had a job that feels so fun that it doesn’t seem very much like a job? I currently do. However, that feeling is not consistent. There are many ups and downs when it comes to how I feel about my work in the startup world. I have devoted eight years of my life to working in this space.
When I imagine a “startup person” I imagine a couple of personas. Maybe a millionaire who was an early employee at some now-public company and is an angel investor of many other successful startups. Or maybe one of those people on tech twitter who post regularly about their productive and ultra optimized lifestyle. I am not either of those people and many times, I do feel like an imposter here. I have been meaningfully involved with exactly two startups. First, with my own startup. Secondly, as the first employee of a real estate technology startup company where I am currently employed today.
I spent the first few years of my career trying my best to enjoy a marketing job. Marketing seemed like a natural fit for my tech savviness and my creative nature. At one job, I was a “Marketing Analyst” – which means I was in charge of sending spam email. Our company bought lists of emails and I would see how many people clicked on the spam emails, and then adjust the subject line and images so that more people would click on weight loss, life insurance, and whatever other clients we had.
Other tasks and jobs I tried included creating ads on Google, creating those full screen ads you see when you play “free” games on your phone, running weekly reports for brand clients, maintaining social media accounts for an independent theatre.
After a few years of this, I realized it was fun to learn about new parts of the world, but then what? I didn’t want to get better at optimizing ads. I thought it would be ideal if I could find a way to combine my tech savviness and creativity AND my desire to contribute more of myself to the world. Tech startups started to look appealing.
My first foray into startups was my own, Croissant. We named the company Croissant because my cofounders and I used to meet in coffee shops to work on projects and ideas, and we’d buy multiple coffees and baked goods to not feel bad about staying there for hours. NYC living rooms were not the best places for working together and we didn’t know where else to meet. What started out as an idea to book seats at the coffee shop for the price of a baked good became a marketplace for shared workspaces.
We bootstrapped it to start and I spent 4 years building Croissant. I learned a lot. I learned:
- How to design an app
- How to create a business model
- How to “put myself out there”
- How to go from having no customers to having a few customers
- How to go from having a few customers to having a lot of customers
- How to deal with a customer who was using our app to hide cocaine at workspaces
- How to hire someone
- How to make a pitch deck
- How to automate processes
- … and many many more
Croissant took me to San Francisco, where our team moved to for 4 months to join a startup accelerator. It also took me to Germany, Croatia, Thailand, and more as I was able to work remotely and travel the world.
I gathered these learnings and then, I was ready to work on something new.
I became the first full-time employee at ility. The founder came from a background in flexible workspace. He had previously developed a platform that automated services and amenities, leading to highly profitable products for the business. He recognized a broader opportunity in repurposing this technology for property owners. The name ‘ility’ was chosen to encapsulate the capabILITY, profitabILITY, and overall ‘ility’ our technology would offer them.
He had already raised a Friends and Family round of capital and I liked the idea of being able to take a steady salary and have a budget to build a visionary technology platform. I was hired as the Head of Product, the CTO joined soon afterwards, and we were off to the races.
Here, I’ve learned
- How to work with an engineering team
- How real estate works
- What Agile is
- What NOI is
- How to be around wealthy people
- How to manage someone located halfway around the world
- How to fire someone located halfway around the world
- How technologically behind the real estate world is
- How to work with a founder who has a strong vision of how he thinks an industry will be in the future, but leaves the execution details up to his team
I’m still at ility today. I’ve been here now for 4.5 years. My life has changed a lot in these 4.5 years.
When I joined ility, I wasn’t sure what I was looking for. I remember one conversation we had over a team holiday dinner in Manhattan a few years ago. The topic had turned to what we wanted out of ility.
We had had a few drinks and I was enjoying my evening with this little group of people that I spend so much time with, but that I realized I knew so little about. One person said, “I am here to get rich.” Another person agreed, saying “I am here to make a lot of money.” There is an interesting distinction there, but the sentiment is similar. A more junior person on the team said, “I want to learn a lot.” Another person said, “I’m here to have fun. I don’t care if the team remains small like this – I just love working with you guys.” I didn’t have a reason that came to my mind. I felt like I saw a part of myself in each of their goals.
If someone were to ask me today what I want out of ility, or what I want out of startups in general, I’d have a more considered answer for them, although its taken me a long time to get here. Here I go:
I want to work with smart people to positively change one tiny part of our massive, shared world. I want to learn about the people I work with and world in which we live, and apply that perceptive understanding to making my equity worth enough that I can have the freedom to do whatever I want. I want to be able to take a few years off working to travel or hike or just for the hell of it. I never got there with Croissant. I really want to get there with ility.
I’ve discovered startups to be a part of the world where hard work, learning, and collaboration can be richly rewarded. I’m eager to work with others who believe in this reality too.
So, this is what brought me to startups and what anchors me here eight years later. I remain hopeful that I’ve found my place. Have you found yours?