How I Prepared for Being on WGN Radio

Do you know the best way to prepare for being on the radio for the first time? Not just the radio, but WGN in The Chicago Tribune Tower. The answer is a tequila party.

Thursday, August 17, 2017, Amanda Elliott, founder of Windy City Cosmo was part of a special radio show – Pretty Late with Patti Vasquez Birthday Edition. We were celebrating Patti’s birthday and talking about dating in Chicago.

Since this was my first radio show – I had a few questions – like how long I was going to be on air, what topics they wanted to discuss, and most importantly – how would I sound on air.

So, I thought the best option to prepare for a late night radio show was to:

1) ask my friends who runs a podcast how I should prepare (check out Deena McKay from Black Tech Unplugged: A Tech Podcast here)

2) figure out the meaning of life – and read this blog post 

3) go to a Codigo Tequila tasting event before the show

4) make friends

5) invite a friend

6) take the PR girls’ advice and take the last bottle of tequila left at the party and bring it to the show

7) go to the Chicago Riverwalk and have a moment  (aka cry)

8) eat a Wonder Woman cookie

While this thought process may sound like a bad idea – it was actually the best thing that I’ve ever done. And not only that, being on the radio is by far the coolest experience I’ve ever had.

So, I know you want to know how this night unfolded. I’m going to say yes I made it to my interview.

I’m Going to be on The Radio:

It was finally the day – the day I was going to be on the radio. I had met Patti Vasquez at a Lollapalooza after party. I was talking to Ken Smith and pitching him to be on his show, The Mancow Show. We had met at brunch and after about a year or two of pitching, he finally said that he was doing me a favor by not putting me on his show. I later found out that it was the truth because I had dinner with Chris Bukowski, former Bachelor contestant, who was on The Mancow Show and he backed up what Patti described as being a pretty raunchy show.

Back to the story – so Ken told me to talk with Patti Vasquez at this Lollapalooza after party. I was in a sparkly dress from Akira – 3 fake tattoos in, with a donut hole from the donut wall in one hand and my second Jack and coke in the other. It was about 1 am. It was there that Patti and I talked about how I shouldn’t be on The Mancow Show, but should be on her show. Less than two weeks later – it was happening. I was going to be on Patti’s show!

The night actually started in the late afternoon when I got into a huge fight with the guy I’m dating. This is how all good stories start – with a fight. I walked away and he went on his guy’s trip.

About two hours later, I left work late and decided to go to a Codigo tequila launch party. I show up, unattached. After a few crab legs and a tequila drink, we made it to introductions. I had a fellow blogger from Chicagogrammers, a Chicago Instagram Influencer community,  meet me at the party.

There were a few notable people at the Codigo launch party including the Chicago Food Dude, Adam Soko,  who was there with Victoria Kent, Founder of the restaurant, hospitality and lifestyle company, Victoria Kent PR. Victoria immediately knew the show, Pretty Late with Patti Vasquez, because a couple of her clients were on the show. She advised to be calm and bring a bottle of alcohol to the show.

Later into the night I met the Account Director of Lion & Lamb PR, Amanda Watenberg, and Chief Strategy Officer at The Worth Agency, Shaena Flangan.  They helped me further prep by asking me questions about Tinder dates and what it’s like dating in Chicago. You know it’s bad when you start quoting 90’s country songs about a broken heart, John Anderson’s “Straight Tequila Night.”

Getting to the WGN Studio:

Around 11:30 pm it was time to walk the mile to The Chicago Tribune. Tequila bottle in hand, we were off.

This part of the night was the saddest. It was time to switch tequila for some fresh air. Me and my blogger friend, Lee from It’s In Chicago, took a walk on the river walk to The Chicago Tribune. It was here where I started to realize I’m about to be on air -where I thought about what I had to say. I thought about why meeting in person was important, but then how despite how much I wanted a career, I still wanted a man and that there’s no guarantee. No matter how many jokes you remember or dates that you go on, you can still end up swiping for the fifth year in a row to find your soulmate.

I heard my phone vibrate and two guys were texting me. It wasn’t the time for “why didn’t we work” texts. I sat on the river and put my hands to my face crying about my ex’s, about the fight I had with the guy I’m dating, and about being worthy enough to be on the radio. My friend, Lee just stood there – he let me cry. And then he nudged me – assuring me to dry my eyes because I had a job to do.

The Green Room:

We made it to The Chicago Tribune and checked in. I’m not going to lie, it was an incredible experience. I literally had so many strangers help me prepare for this moment. We went to the green room and we took all the back stage photos we could. It was a special night because there were Wonder Woman cookies. I felt that extra boost of confidence  – that women were supporting women.  And, also bloggers were helping bloggers.



On Air:

It was finally the moment I was waiting for – being on air. We were escorted to the iconic WGN radio studio, where I learned it was Patti’s birthday. We all took a group photo.

This special edition included Dan Kotowski (Child Serv), Scott Stantis (Chicago Tribune Cartoonist), Rep. Anderson, and Rep.  Ann Moller, Amanda Elliott from from Windy City Cosmo and Comedian Paul Farahvar, host of the Podcast “Singles Only”.

I had the pleasure of being on air with the host, Patti Vasquez, Dan Kotowski (Child Serv), and Comedian, Paul Farahvar.

Once we went on, it was like having a normal conversation. We literally talked about dating faux pas like using a Groupon on a date, and about where we find men. Then we went on to talk about ghosting and how to get out of a bad date.

It was a perfect evening. We closed the show at 2 am, when we all got a moment to share our gratitude. I felt so encouraged to do this segment and supported by friends and party goers alike.

In the segment I said, “I’m just thankful for the Chicago community. There’s really great people who are actually supportive of your goals and dreams. The bloggers – I mean I’m part of Chicagogrammers and the person who is here tonight is part of Chicagogrammers and they’re all very supportive of helping you reach your goals so that’s huge that we actually care about each other.”

I feel like Chicago is a special city with a great sense of community and support not only in business and blogging, but in life. Lucky to be Windy City Cosmo and live here and date here and write another chapter of my life here.

What I learned from being on the radio:

There’s a few things I learned from this experience.

1) You never know who you are going to meet at brunch.

2) Be persistent – even if you don’t get the job or the opportunity you were pitching, it might lead to a better pitch.

3) Build a support network – tell people about what you’re doing and help one another.

4) Take lots of photos.

5) Bring a gift – even if it is a bottle of tequila.

You can listen to the full show here. My segment starts an hour into the show. Let me know what you think about dating in the city and about preparing for a big presentation or event in your career. Cheers!




Simply Stylist Annual Fashion and Beauty Blogger Conference

For every Girl Boss in Chicago and actually the midwest for that matter, there is one conference that you want to attend – the Simply Stylist annual conference.

We checked into the Dana Hotel and Spa in Chicago on Saturday, July 16, 2016 for the day long conference.Beauty bloggers and stylists were treated to a day of doing what we love – hearing from the successful business woman and bloggers, drinking cucumber water, getting our hair and makeup (my favorite makeup) done, and oh, of course jumping into a ball pit for charity.

The Chicago event was hosted by my second favorite voice from E!, Catt Sadler.

And the line-up of speakers included everyone from YouTube blogger, Belinda Selene, (one of my favorite videos) to stylist, Lindsay Albanese, to the founder of one of the most iconic blogs, The Everygirl, and even the costume designer and stylist from the hit show, Empire, Paolo Nieddu.

While there were main speakers in the morning and breakout sessions in the afternoon, the real beauty of the day was that it was a gorgeous day in Chicago and we were on a rooftop.

When I got off the elevator, I wanted to look down. The shoe game was strong. Everyone was dressed in summer prints and  florals that even Kentucky Derby style only won because we weren’t wearing hats.

In between sessions about being self-confident, how to balance your life, and tips on public relations, the bloggers and business woman enjoyed champagne gummy bears and sips of cucumber water in between pampering sessions from the latest beauty app.

The Glam App

The Glam App, described by People magazine as being Oscar’s glam on demand, is available in 27 international cities including Chicago. It’s known for bringing a glam squad right to your business or home at an affordable price. The founder, Cara Santana, was there to talk about her success. The Glam App is about a year and a half old, and Santana told Windy City Cosmo that apps are a lot like businesses, it usually takes 2-3 years to break even. The app is currently funded by venture capitalists.

Midwest bloggers had their hair styled, got a touch up on their lids or lips, and had a quick nail touch-up from the Glam App. Honestly, I was most impressed with the stylists and nail technicians. The glam squad had over 5 years of experience and everyone was really excited to be doing what they love (P.S. that is Simply Stylist’s motto).

Across the room, there were balloons spelled out “Girl Boss” for you to pose with your new look. Which, by the way, was sketched by a talented artist. In one hour she would have a sketch of you based on a single photo.

H2O Beauty:

And despite the stilettos or your attire, we all had to jump into the ball pit from H2O + beauty to benefit  charities to help women. One of Chicago’s fashionista’s from the Frock Shop was there volunteering, Jennifer Burrell.

Midwest Bloggers:

Overall, when I met some inspiring Chicago bloggers like Anneke Knot of Knot Couture Blog and Lan Ho of the blog, Scholar in Stilettos. Even midwest bloggers like Katrina of Inspoandco traveled from Wisconsin and stayed in Rosemont for the weekend.



Amanda Elliott is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.