Today is a big day filled with a lot of different feelings. It marks the end of an epoch in my life, spanning the entirety of my adult life. But it also is the footing from which I take the leap into new challenges. Specifically, I’m gonna do my first solo startup named jswzl.

Looking back 

After dropping out of high school in 2010 to pursue a career in Iceland, I would eventually join Syndis in 2014. Little did I know just how far and wide that would take me, or have any inkling that I would go on to write a training solution which we used to train a lot of developers in Iceland in security and then co-found adversary.io. To suggest luck played a role is an understatement, but here we are!

From 2015 to 2019, I would be involved with both Syndis and Adversary until I went full-time on Adversary. This culminated in 2020 when Adversary was acquired by Secure Code Warrior. The theory was that our technology for missions, deep security knowledge in the team, and SCW being the front-runner in the relatively young market would combine to be a once-in-a-lifetime situation with far more opportunities and have a far more significant impact on the world. And I’m thrilled to say that I genuinely think we pulled it off. 

While we were busy integrating our challenges into the SCW platform, we went on to sell Syndis to Origo, setting the stage for the team of brilliant hackers to scale and put a dent in the mountain that is security debt in Iceland. Origo’s support was critical in my mind to allow the business to grow, rather than just being a 5-10 person team who did a good job but had the opportunity to do something much bigger. And it sure did, doubling the size of the team very quickly! 

Reorienting

But going through an exit of multiple businesses that have been at the core of one’s personality for such a long time is not easy, as it turns out. The Yale School of Management did an excellent publication about this in What’s Next? Search Fund Entrepreneurs Reflect on Life After Exit, which I highly recommend. 

I had the luxury of sinking myself into new challenges at SCW while processing the experience and discovering who I am without defining myself by what I do for work. It took me about two years, but after a lot of soul searching, it became clear that I had options in front of me that, while scary, would lead to a far more fulfilling journey.

Looking forward

While taking an extended Christmas vacation in 2021, I worked a lot on my bug bounty tooling. One problem I set out to tackle was: How can I integrate a javascript link finder into my tooling or make something that’s better? What would a reimagined version of it look like, done from first principles?

Over the following months, I’d implement a better but naive version in my tooling. Realizing there was a solvable problem with an excellent ROI, I decided to do a few iterations through to April/May 2022. Up until that point, I thought maybe this was a fun side-project. 

But as I worked on it more and found a lot of enjoyment, I wondered if there was any way to spend more/full time on it. More discussions with people who have been excellent sounding boards for me led me to realize that I could pursue this full-time if I commercialized the solution. 

Even then, it took me weeks from thinking it was just a side project to deciding that this was the right path for me. At the same time, I wanted to spend more time on my weightlifting training and doing more leisure things (Something that you don’t have time for as a founder). 

The first steps

As I take my first steps on this new journey, I can’t help but feel somewhat scared. The global economy is in shambles. The war in Ukraine is still raging. It’s normal and healthy to feel scared when entering times of uncertainty. But I’ve learned from my journey that success largely comes from taking chances. Letting yourself be comfortable shunts growth. 

But I’ve been lucky recently to start a daily Ashtanga Yoga practice, which has helped me cut through the noise of my worries and give me that stability the mind seeks. I would not be excited about a future if I did not see a path that provided me with challenges that would help me grow as a human being. By that same token, it has risks. But stagnating as a person would be a far worse destiny. 

Next week, I’ll be in Vegas for DEFCON. I’m excited to see old and new faces for the first time in a while. Afterward, I will probably need some time to unwind. But I can’t wait to get rolling with jswzl, seeing how better RE(con) tooling can help security engineers be more effective and efficient at testing web applications.