Chicago, Cougars, the Bulls, and the Wind!

By Ian Fernando

Past couple days I went and visited my buddy Jason Rubacky from Shareasale. I promised I would visit him back in the summer months but I just been so busy I ended up going this past week. Plus I went ahead and spoke at his local affiliate meetup in Chicago.

The first couple days was def a bit chilly but then the rest of the days were actually nice prob in the 50s to the 60s. Jason showed me around the city and I went shopping as well, which I really didn't want to but I saw some nice clothing. Chicago is actually a nice city and I wouldn't mind moving out there. The only factor is the fall/winter season wonder how cold it really can be in Chicago.

The best part about Chicago I can say is the city is clean and the food is amazing. I watch the travel channel or food channel and there is always a mention about Chicago something. I tried out their beef and deep dish and they were both filling and good. We went around and toured the park and most of the city highlights.

One day we took the time to head out of the city and head out to do some go kart racing. Now that is a rush in itself. There were professional go kart racers there with their own suites and boots taking the race real series. One interesting part is we bumped into Ian from LFM Network and he was surprise to see Jason and I at the track. What a coincidence.

There were 2 tracks and we did 3 races and by the second time I got use to the handling and came in 2nd in one of the tracks. One of the more complicated one I didn't do so well, but it was def fun. The complicated track had mad sharp turns and s curves in it, didn't do too well, but I didn't crash. 🙂

That same day we headed out into the city and hit up a bar because I was starving and had a burger with an egg on it. Never really had an egg on a burger but it was an interesting combination flavor wise. We met up with other local affiliates and headed into town.

Howl at the Moon is where we headed into and there was a huge line. I assume it was 1 out 1 in type of deal. I was not going to wait in line, so I went to the front door and if any of my friends know me, they know the line I say to the door man. I wasn't drunk enough so I just asked what will it take to skip and I simply paid the dude and walked in. I wave to the line with a smile and walked in with Rubacky and Chris.

The scene was interesting I have never been to a cougar hangout spot before. Granted I have seen older women in clubs but at Howl a the Moon there were quite a few. Since it was my first time to walk into a place filled with cougars, I just hung out at the sideline and drank the bucket we got, yes BUCKETs!

During the night, I ended up on the dance floor and I was being grabbed by all these older women, it was an awkward moment. These women are mad aggressive and know what they want. I literally was the only guy on the floor getting stripped of my clothing gear by at least 3 women at the same time. I tried to call for wingman support but I guess I was on my own.

off topic... I haven't promoted a dating cougar offer and I know there are some out there, it is interesting to see how I can take my weird experience and put it in a marketing perspective. hmmmm

After 2 more buckets, we headed out to an other bar and met up with 2 more affiliates. We had a conversation with some females about jobs and marketing, I didn't pay attention because they weren't really meant to be paid attention to. By the end of the night me and Rubacky just headed back and called it a night.

.. the next day was just a day of relaxation and recovery.

The day next day after recovery it was more tourist ish for me. I wanted to head out to the Sears tower and up to the Sky Deck. I really just wanted to walk on the glass ledge and that I did.

It was damn serious but I got on the glass panel while many other tourist were skiddish to get on. I was doing flips, laying on my back, etc - it was fun and entertaining being that high. I think we had to turn our cell phones off being so high...

After I had my first deep dish pizza and that is filling after just one slice. I manage to finish 2 and it is an 'eat and sleep' type of meal, I think. Luckily after the deep dish I had some Effen Vodka and it got me up and ready for the Bulls game later. Jason and I relaxed for the day before headed out to the Chicago game.

It was the Chicago Bulls vs Denver Nuggets and we were in the theater box courtesy of ShareaSale. The food was amazing and I was sippin on Ciroc all night. We went out to the game with 2 other affiliates and just talk big business. We talked about the industry and where it is going and about these 'Clickbank' guys who apparently knows alot about marketing....

Good conversation, it is always great to talk to people with like minded ideas and thoughts about marketing in general.

The game overall was good, I actually enjoyed y time at the game and it was a close game! The night ended and I had to get ready for my leave out of Chicago the next day. It was def a great city I wouldn't mind moving to. Almost New York but isn't - I feel Chicago is much more cleaner and less more compact. I wonder how it is in the spring/summer time.

Overall video:


Want to thank Jason Rubacky and ShareaSale for the Chicago experience and showing me around an amazing city.

Ian Fernando
Involved in the internet space since 2002 and have been through the ups and downs of this online industry. I am a traveling digital nomad, media buyer, online strategist, and many more online titles.

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