200 – Mistress Carrie – Cocktails in the War Room

200 – Mistress Carrie – Cocktails in the War Room

“Don’t lick anything Weird and Wash your Damn Hands!” that is what the shirt says, but it means so much more.

Mistress Carrie was on #62 and #100 for Oscar Mike Radio. Mistress Carrie had worked at 107.3 WAAF in Boston for almost 30 years when the station was sold in early 2020. Combine that with COVID-19 and she realized she needed to adjust to a new reality fast.

Mistress started doing cellphone livestreams over Facebook Live called “Cocktails in the War Room” in March of 2020. It caught on and before you know it people like me who had listened to Mistress Carrie on the radio were tuning in to get connected. There were jokes, serious talk, Wednesday the Goth Pug doing her thing, and Mail Call. Before I knew it, it was the place to be during a time when there was no place to go.

Then one day Mistress had this idea. What if she had T-Shirts made and the sales of those T-Shirts went to help a Veterans Cause? The images below were made into T-Shirts. Mistress thought that she would sell maybe 300…… She sold almost 1000! The money went to the Massachusetts Military Support Foundation Food 4 Vets Program. This program provides food for Veterans in need. It was a great moment that showed how good can come out of anything.

That wasn’t all Mistress Carrie was doing from March when Cocktails in the War Room started till now. She has been working on putting together a company and get her podcast off the ground. You can catch her podcast on https://mistresscarriepodcast.simplecast.com/.

We spent time talking about the transition from WAAF DJ and Radio Personality to having to re-invent herself in today’s world where nothing is stable right now. In many ways her journey is like many of us transitioning out of the military. You have to make a plan, coordinate resources and network with other people who can help you achieve your goal. It doesn’t happen by itself.

As of this writing, her 7th podcast will have dropped. Even now Mistress Carrie’s podcast has been heard in almost every country on the planet. The Mistress is truly in flight.

It was an honor to have Mistress Carrie on for #200. I learn something each time and take a minute to think about how far I have come. I can’t wait to see what is next for her and hope to see you during Cocktails in the War Room! Thank you again Mistress.

Mistress Carrie’s Social Media Feeds

Thanks to my sponsors Joyce Asack, Mark Holmes and Shaun Schubert for supporting Veterans!

Asack Real Estate


Reaper Detailing and Powerwashing

Red Seal Martial Arts

  • Red Seal Martial Arts 155 Millennium Cir Lakeville, Massachusetts
  • (774) 259-9258
  • www.redsealma.com
Episode 100 – Mistress Carrie

Episode 100 – Mistress Carrie

Episode 100 – Mistress Carrie

100. 100 Episodes equals about 60 hours of content that have been produced in the last two years. I first want to thanks family, friends, co-workers and those unknown who have taken time to listen to me work on this. What is this? What is Oscar Mike Radio? Oscar Mike Radio is my way raising awareness for Veteran and Military by giving a voice to stories that would otherwise not be told. 94 episodes ago I met Kip Clark, host of the podcast Stride and Saunter (https://www.strideandsaunter.com/) and he told me I could do this.

Before the first episode was even created, Keith Hayes and Anthony Arnold got behind me to get this idea off the ground. I am happy and proud to be part of the Whoobazoo Network (https://whoobazoo.com/). This team continues to move me in the right direction, and the podcast has only gotten better.

So Episode 100 it seemed fitting to ask Mistress Carrie to come back on the show. Her first time on Oscar Mike Radio was Episode 62 – Click link here for entire show –  Mistress Carrie – Episode 62 This episode was eye opener for me. I thought I was getting good at interviewing people and talking about Veterans’ Issues. Mistress Carrie was gracious and engaging and I learned a lot about content production. She is a total pro with decades of experience and I had a blast talking with her.

I worked to get better. We met up again for Episode 84 – Mistress Carrie Part 1 and she talked about working to be embedded with an unnamed Special Forces Unit. To hear how she had to prepare and what happened around that was a great story. This kind of story doesn’t happen that often, and it was cool getting the behind the scenes info.

Having Mistress Carrie back on for 100 seemed fitting. Yes she is a public figure and celebrity, but no one can argue that she walks that the talk when it comes to Veterans. I enjoyed talking with her about Richard Fitts Jr.’s documentary, 21 Years a Folded Flag. Both us of have interviewed and talked with Richard Fitts Jr. and are looking forward to seeing the finished film.

If you look at the picture below, the story behind this image made the entire experience for episode 100 worth it. I am not going to spoil it here. I will end by saying that I hope to see what is going in with 22 Kill Boston at Jump Town, and I am looking forward to seeing what Mistress Carrie is going to do next. Thanks for celebrating 100 with me Mistress, Semper Fidelis.


American AF – Great Story behind this picture




Episode 84 – Mistress Carrie Update Pt.1

Episode 84 – Mistress Carrie Update Pt.1

Mistress Carrie – WAAF DJ – Update Part One

Mistress Carrie is a DJ for WAAF in Boston, MA. She came on Oscar Mike Radio for Episode 62. Click here for (OMR Episode 62 Link) for the podcast. We had talked about all the trolls who blew up over a picture of her and Senator Elizabeth Warren. The whole thing went way out of proportion and people were talking all kinds of crazy stuff about how Mistress Carrie didn’t care for Veterans. Well, suffice to say she went scorched earth on that idea!  At the end of the podcast she told me she was working on the top secret mission would update me later.

Fast forward to March, and we setup a time to talk again. Suffice to say she got a big welcome to life in the military! Hurry up and wait to go nowhere fast!!!

All kidding aside, when you understand what was required to get ready to go on this mission, to get the no go order at the last minute was a big let down to say the least. Listening her talk about what it took to go, much less execute, you can see that this wasn’t a publicity stunt. She genuinely cares about those who are in the military and veterans.

My question is I wonder what will be next for her?

The reason I am doing this as two parts is once we got done talking about her latest mission, the conversation kept going and, I didn’t want to cut it. So I will do the second part of the conversation in a couple weeks.


Rolling Heavy with her new SideKick