Trip to Chicago – How Kyle, Sunny & I Met

If you follow me on Twitter or Instagram, you know I flew to Chicago last week to visit my two friends Kyle McDonald and Sunny Singh. I’ve mentioned them on this blog and on social media before, but I don’t think I’ve shared the story about how we met online. This trip and other interviews between the three of us have sparked the conversation about how we met and how we’ve stayed in touch for so long.

I’ve started looking back at how we became friends through the internet almost a decade ago. We have stayed in contact over the years, talking practically daily the whole time. Kyle and Sunny helped shape my love for technology, marketing, and sparked my entrepreneurial mindset. They are my two closest friends, even though we’ve lived hundreds of miles away from each other.

Before I talked about Chicago, I wanted to share the short history of how we connected online and how we’ve stayed in contact over the years;

Short History

We first met online through the Freewebs community (now known as when we started building websites through their page builder. This was in late 2009 when we were beginning highschool and getting our first computers. I ventured online and started building my own website when I got my first laptop – a Gateway Laptop. Back then, the communities were small, and we were able to start chatting in the little flash powered chat’s that were offered on every Freewebs website. While we connected through Freewebs, we also took our conversions to IRC chats, where we would go and talk after school. We did this through most of high school and college, moving from IRC to Slack. While we were chatting and texting, we also started to game together at night through online Xbox games such as Rainbow 6 Siege and Rocket Leauge. We did this for years, and this was a big reason we were able to get so close.

We were not only growing our personal relationship during these years, but we were also starting our business partnerships. In the beginning, we were working on independent sites and projects while we were in school. I was building Digital Bounds; Kyle and Sunny were working on Hylus, Codebee, and Ninjality.

Recently, we have teamed up together to start SLK Media and IronMic. These projects and lately, IronMic has helped us grow together professionally and personally while helping us stay connected over the years.

Trip to Chicago

Since we turned 18 (about 8 years ago) we have been making a point to travel and meet up together. The first official time we met was in Las Vegas to attend CES together. Even though this was the first time meeting, we felt like we knew each other, and it was natural hanging out in person. Then we went back again the following year, and haven’t seen each other in person in almost 2 years.

This trip to Chicago was somewhat last minute, and we didn’t have a big reason other than getting together to hang out and work on IronMic a little. We may have wanted to work on IronMic more than we actually did, but exploring a new city was a great bonding experience. Kyle, who lives in Chicago, gave us a great tour, from seeing the Chicago Bean to eating at some of the more hidden gems of the city.

We were also able to record an in-person interview for Kyle’s podcast Git Rest. It’s a development podcast where Kyle talks to developers, designers, and marketers on various topics. His game show format where he asks people if they want to “push, commit, or stash” projects, software, or everyday things, makes his podcast styled slightly different than other tradtional interview podcasts. This sparks conversions with people and has a more casual and playful format that helps make it more entertaining.

Take a listen at!

What’s Next

Chicago was an excellent way for Sunny, Kyle, and I to connect IRL. We were able to talk over dinner, lunch, and play video games together. It was a fantastic time, despite the exhausting walking all over Chicago. We know we want to do these meetups more often to not only connect, but also to talk about new projects and catch up on personal lives.

We’re already talking about our next meet-up. Maybe it’ll be my turn to host the guys here in San Antonio. Or Kyle and I will venture to Charlotte to take over Sunny’s city. Regardless, it’ll be great to catch up in person again.

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