With The Band | Alexandra Dempsey

Behind almost every musician, at least if they are lucky, is someone or some people, at home keeping things running. We thought it would be interesting to speak to these women and men who help the musicians we love keep their thing going on the road. 

Some of these people are doing projects and creating, and are just as fascinating as their significant others. Two sparks of light can attract each other. I find these stories priceless and worth telling. The perspective of a lover or a wife or a partner is so different than what we as the fans experience. Oftentimes the stories behind the love story are so special and magical, a simple twist of fate or chance encounter. 

Alexandra Dempsey (wife of Twiddle keyboardist Ryan Dempsey) has been growing her brand @TourWifeTourLife since before she met Ryan or listened to Twiddle.  A deep and loyal dive into Phish in college lead her to tour and then to the lot selling her wares to fund being on tour, a story I’m sure some of us can relate to. Her blog, which originally started as a Phish and music-oriented blog, evolved into a Travel/Fashion/Lifestyle blog that encapsulates the wife of a touring musician. With over 20K followers, @TourWifeTourLife has taken on a fan-base of its own. 

We asked Alexandra to talk to us about her Instagram following, the evolution of her brand, and of course her Tour Stories! 

An Interview with Alexandra Dempsey

Tour Stories: Where are you from originally?

Alexandra: Queens, New York.

Tour Stories: I grew up on Long Island! Do you visit often?

Alexandra: It is such a small world, Do I visit Queens often?

Tour Stories: Laughing… Yes, well you’re in Vermont, you’re kind of close to Queens, right?

Alexandra: Yes, My dad still lives there so I’ll go visit him occasionally. Especially if there’s Phish show by his house, or whenever there’s a concert at The Garden that we want to see.

Tour Stories: That’s the thing I miss the most about being on the East Coast. There is such a closeness to each of the venues. You can go see music state to state. It’s different out here.

Alexandra: It really makes a big difference. Well, actually I guess the West coast is like that if I think about it. I’ll usually go out for Twiddle’s West coast runs and we go from Washington all the way down the state of California. It’s not that hard to do, but it is way easier here.

Tour Stories: You are right. That trip and to Colorado is doable. How often do you go on their bus for these trips?

Alexandra: I’ve only been on the bus twice and both times were pretty random and unplanned. Once was on a winter tour on the West coast – it wasn’t safe for me to drive on my own. The other time I accidentally fell asleep in Ryan’s bunk and then woke up the next morning and we were in another city! To be honest, it’s kind of hard living on a bus with that many boys.

Tour Stories:  Too many people packed into a tight space. Laughing

Alexandra: Yeah. The one time that I went for an extended period of time, I think it was for like five or six days. It was actually very pleasant because they are all so nice. It’s like family.

Tour Stories: When you are meeting Ryan out on the road how do you decide where to stop. We see via your blog and Instagram you’re very good at picking interesting places to visit along the way.

Alexandra: Well it depends if Ryan has time or not, because sometimes he’ll be busy during the day doing meet and greets and stuff. In that case, I’ll cater things more to what my interests are. But if I know he’s going to have time, I’ll usually look on Pinterest to be honest. I look for the best places to eat in the towns of each venue. At this point it was probably a year ago when I did the West coast tour on the bus with them. We went all over, we walked every single town, we got up early and got off the bus and we went into shops or out to eat because I wanted to give the other band members their space too. In Spokane, Washington, they have the biggest radio flyer wagon. It was really cool and I am glad that I saw it but I don’t think I probably would have ever gone if it wasn’t for tour.

Tour Stories: Wow, we will need to check that out.  I was reading through your blog and is it safe to say that Phish is probably your favorite band?

Alexandra: Yes!

Tour Stories: When did you first start listening to Phish and how did seeing Phish lead into what you’re doing now?

Alexandra: Well, I started listening to them when I went to Binghamton (University). I stayed an extra year and extended my studies to pre-med cause I went to school for film.  I could have graduated when I was a sophomore, but I didn’t want to. So, with that I was pre-med and I stayed an extra year and the new friends that I had not been friends with before, they got me into Phish.  That was in 2009 and my first show was at Jones beach. From there I would see them maybe just like once or twice or three times a year until 2013. In 2013, I decided to do every single show that year.

Tour Stories: Wow, that’s dedication. I’ve never made it through a full tour.

Alexandra: That’s how I created my business. My brand initially, was to fund my concert going. I would sell merch on the lot and then I eventually turned it into an Etsy shop and then into an actual website. It was called The Shakedown Shop. Then I started the blog, Tour Wife Tour Life, but I didn’t start that until after I met Ryan. For a certain period of time, I had my blog, but it also linked to my store. At that point in time, my blog was more music oriented. Now I’ve branched off into our home life, fashion and beauty, travel tips and tricks… kind of just me but as a blog, I share just about everything about my life

Tour Stories: Transitioning from a store to a blog did it just evolve? How did you end up changing the name? 

Alexandra: I think it just kind of evolved because my domain was The Shakedown Shop .com and then I started Tour Wife Tour Life and just redirected it. Both had my blog page and then my shop page attached to the same link. If they went to The Shakedown Shop, they would be able to see both my blog and the store. Then eventually I shut the store down just because it was so much work and I wasn’t able to really tour as much with Phish anymore because of Twiddle. I actually just reopened my Etsy, the original Etsy from seven years ago when quarantine happened, because I was cleaning out closets and I found so much old merchandise, so I put it on like super sale on Etsy.

Tour Stories: How did you and Ryan meet?

Alexandra: We met… it’s kind of hard to explain. I say that we met through Facebook because I went to my first Twiddle show I believe on April 4th, 2015. It was at Irving Plaza in New York city. And then I was obsessed after that first show. The next week they were playing in Baltimore and I was with a bunch of friends. We road tripped to that show and Ryan had made a post on Facebook that said that Barbara Walters had died, and I commented on it. I was so mad because he just created this rumor as a social experiment, and I love Barbara Walters! So, I commented on it. He messaged me after the show, and he said that he had saw me in the crowd and that he wanted to fly me out to the next show. I said, “No!”.

Tour Stories: laughing, That is an amazing first encounter.

Alexandra: Yes, and then he kind of just kept texting me. We texted all the time. He asked me to be his girlfriend before we had ever even met in person. We ended up meeting in person, at Rock N Roll resort, it was our first date.  

Tour Stories: What a whirlwind. And then how long after that, did you guys, did he propose to you?

Alexandra: He proposed to me in 2017. He proposed to me at LOCKN’. In front of Trey. Laughing…

Tour Stories: What!

AlexandraLaughing, Trey was standing there, and he asked Trey if he could ask me to marry him and then he got down on his knee.

Tour Stories: I live off these stories. I think it’s funny. You start out as someone who just really appreciated the music and then you have the opportunity to experience all of these things. I mean firsthand, it can really blow you away.

Alexandra: And I think it is cool to see just how much the fanbase has grown in total. When we first met the ballrooms were much smaller and now they have like thousands of people. It makes me cry to think of it because I am so proud of them.

Tour Stories: It is, it’s a very cool journey to watch.

Alexandra: I used to only cry at Phish shows, but now I cry at twiddle too.

Tour Stories: As a New Yorker it must’ve been pretty cool to see them play at The Cap. What was that like?

Alexandra: The Cap is amazing. Pete Shapiro is just such an incredible human being. When we got engaged a LOCKN’, as a congratulations gift he gave us backstage passes for Phish.  We were able to stand on the side of the stage. The only other people there besides me and Ryan were Phil Lesh and Johnny Miller. I don’t know if you know Johnny Miller. He is a huge Phish fan.  But going to The Cap, it’s an amazing experience. The staff there is so nice and there’s just this crazy energy in that room, especially when they light up the ceiling.

Tour Stories: Lot’s of history in that room. Well, the first time I saw Twiddle was when they played City Bisco very early on, it could have been the first one but I remember it was nice to get to see a new band and my friend really liked them.

Alexandra: Laughing, That’s great. I don’t know what’s going to happen now. I don’t know how new bands are going to get that exposure.

Tour Stories: I know, it is a very difficult time for musicians and the industry. I am not sure there will ever be “normal” again. We will see how it all pans out.

ALEXANDRA: Yeah. And I think it’s cool that bands are being innovative, like that drive in idea could be really cool. We will adapt. The music industry is not going anywhere. No way, we need music because people need music to get through so many life struggles. You can use it to celebrate and to express sorrow. It’s just really amazing.

Tour Stories: Can you recall your favorite music experience?

Alexandra: Oh, that’s hard! My favorite was probably when Page (Phish) played with Ryan at Tumbledown because that was just, I mean, it was like both of my worlds colliding. Like I could cry right now, just even remembering it. It was basically everything that I love, all at once. They played when it rains, it pours, which is just like the classic Twiddle song. And just seeing Ryan so happy. It was amazing. I ugly cried for sure.

Tour Stories: Tell us a tour story.

Alexandra: I would say the whole entire year of 2013. I made a promise to myself that I was going to see every single Phish show that year. I ended up going to Toronto. They had canceled the show because it was flooding or something. It was the first Phish show that they had canceled in a really long time. And I was on the runway and I still had to go all the way to Toronto and then all the way back.

Tour Stories: Brutal. Laughing

Alexandra: So, I say I saw 42 shows and technically 43, because one didn’t happen, and I ended up even going back and seeing the makeup date. They played “up” in Toronto. I think it was the Molson Amphitheater.  I think that tour kind of solidified for me, how important music is, because I honestly was not that big into music growing up. I liked rap music and pop music, but it wasn’t until college that I found Phish and then Phish changed my whole life. I think it changed who I am as a person. I became a kinder person and I liked having a place in a community like that. I feel like a lot of people don’t have anything that’s comparable to something like the Phish community or the Twiddle community.

Tour Stories: I agree with you. I think that’s why it’s such a tight knit experience especially in those groups. I notice a lot of empowering each other.

Alexandra: Yes, I mean look at the group Phish Chicks, it’s amazing to see women empowering each other so much and just being there for each other. Some things that I read on there, of women finally opening up about either a bad home situation, or if they have a health issue, and everyone is just so kind and supportive. I don’t see that anywhere else.

Tour Stories: It’s so true.

Alexandra: It’s a common bond. Everyone supports each other and then everyone supports each other’s businesses too which is just so cool to see. It really is like a living thing.


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Sep 17, 2021