3 Lessons Learned By An Accidental Entrepreneur

Every entrepreneur starts with a dream of building a world-class product, creating a business, living by their own rules, changing the world and making millions–if not billions–in the process. Right?

Not me. I never dreamed of being a founder. I just ended up becoming one on some random day back in 2013.

My journey as an accidental entrepreneur began after I graduated from MIT. I worked at Oracle but was restless and thinking about what I wanted to do at the next stage of my career. I had a friend who was working on a thesis project. He was trying to combine information from email communications with contextual data from the college’s student directory, which sounds simple. Or boring. But it was so complicated from a developer standpoint that I couldn’t resist. I had to give it a shot. So, we built our prototype and started sharing our solution with our network of developers. Before I knew it, I found myself wearing the title co-founder and CTO of a company some fancy marketing agency named Nylas. 

Seven years and $55 million in venture capital later, and here I am, an ‘accidental entrepreneur.’ In the process, I’ve learned a lot about building a company: How to invest in employees, how to make tough decisions with imperfect information, and how to keep pace with changing rules as we grow. 

If I could travel back in time, here are the three leadership lessons I would share with a younger me.


Lesson 1: Define the problem first; the product second

Take the time to identify a big problem versus rushing to build the solution. Business objectives do not equally value propositions, and many companies learn this the hard way when they try to establish a product/market fit. So do your research. What problem are you trying to solve for your users? Who is the competition, and how will you be better and different from them? What is going to be your unfair advantage? Or be even more confrontational: What is your right to exist? 

These are hard questions. Asking them of yourself and your co-founders can be confrontational, but it’s worth the time spent to understand the problem space and the needs of your customers. 

Once you have a thesis, start testing with your users and never stop. Getting feedback from developers was critical for developing Nylas’ early products and is a practice we still use every day. You have to move fast and iterate continuously once you’re in-market. And–every successful entrepreneur knows this–you must be clear on your core mission before inviting in users and asking for their feedback.


Lesson 2: Navigate growing pains by narrowing your focus 

Three years ago, we found ourselves in a conundrum. We had developed an email client that had a lot of users, and we were getting positive feedback from users and media alike. We also had developed an API for email communications that developers could use to build productivity features into their software. The former product was in a more mature state; the latter was nascent. 

However, it was clear from the business metrics that the API product would be more successful if we focused our resources on it. And it was also apparent that we couldn’t afford to scale both products. So we dropped the email client and refocused our company. It wasn’t easy. We lost all those users and quite a few employees as well. 

In retrospect, it seems obvious that a team of 15 would struggle to build, scale and support two wildly different product lines. Many entrepreneurs chase too many opportunities and end up not raising the right amount of money, developing the most valuable features, or hiring the right people. As a result, 90 percent of them fail. Thankfully this wasn’t the case with Nylas, but that’s because we decided to build a company in which choosing to focus in times of ambiguity is our default.


Lesson 3: Don’t conflate perks with culture

Prioritizing company culture is a must for the 10 percent of startups that succeed. Ask yourself every day how to build a winning culture that goes beyond having a keg of kombucha in the office. 

Perks are great, but winning cultures begin with people feeling empowered to make decisions independently and execute without managers breathing down their necks. I’m always here for advice and feedback, but I always encourage my team members to try something by themselves at first—even if they fail. 

Company culture today looks much different than it did in February 2020. But the same principles remain, even in a remote-work environment. Maintaining a remote culture doesn’t have to include Zoom happy hours or video chats, which I know we’re all tired of. Demonstrating appreciation for your employees is still key, and even a quick Slack message goes a long way to making sure people know they are valued.

Another essential aspect of leading a strong culture is prioritizing work-life balance, and I don’t mean working fewer hours in the day. Ensure you give your team the freedom outside of work hours to do something meaningful. From Day One, I told myself I wasn’t going to compromise my mental or physical health to lead a successful company. I try to lead by example and instill this same mindset in my employees.

Finally, it’s essential to carve out the time to discuss your mission as a team. If employees don’t understand the ‘why’ behind what they are doing, performance will suffer. Giving people snacks and gift cards is a nice gesture, but nothing beats having a stake in the company’s long-term vision.

Christine Spang is CTO and co-founder of Nylas, a pioneer and leading provider of universal communications APIs that allow developers to quickly connect their applications to every email, calendar, or contact provider in the world. She studied engineering at MIT and enjoys rock climbing and exploring the outdoors in her free time.

  • Originally published January 12, 2021