Madison Nicole aka “Gigglypuff” is as multifaceted as they come. A former Harvard cheerleader, Madison turned in her Crimson pom poms upon graduating the prestigious Ivy League institution, earning a bachelor’s degree in Psychology and Computer Science.

Presently, Gigglypuff is a software engineer in the burgeoning field of artificial intelligence. When the time for leisure rolls around, Madison joyfully morphs into a fabulous cosplayer and streamer with a Pokémon spin. Her various wardrobes and content are equally charming and authentic.

Amidst a hectic schedule in California’s hyper-competitive tech industry, Giggly connected with Playboy’s Gabriel Santiago for an encompassing conversation.

Playboy: Let’s start at the beginning—where are you from?

Gigglypuff: I grew up in rural Appalachia. It was a really small town with a country-southern setup. It’s very different from some of the places that I lived later in life, but I love going back. When I’m able to work remotely, I spend a lot of time back there. I still very much love my hometown and miss it, but it’s not really the best place for tech jobs.

Playboy: Tell me about your experience studying at Harvard.

Gigglypuff: It was culture shock at the beginning. It was also my first ever plane ride. I did not know where I was going and I just wandered around Boston until I found Harvard’s campus. It took some time to adapt, but I loved it. I was a cheerleader for my last three years and I made a lot of friends. I loved my roommates. Harvard is also where I was introduced to computer science. I always loved video games, and making a video game was one of my initial assignments. I spent days-straight on it, which was completely unnecessary, but I was so entertained by it. I made a game with Colonel Sanders as the main character with a fried chicken theme. He catches chicken in his bucket and dodges vegetables!

Playboy: As a Harvard cheerleader, did you more enjoy the Crimson football games or basketball games?

Gigglypuff: I’m going to say basketball and here’s why. Football games at Harvard are played outdoors. I was out there in a cheerleading uniform during the very cold and very long New England winters. When the weather was nicer, I loved the football games. However, at a certain point in the year, Boston gets tough outside.

Playboy: That makes perfect sense. So, how did you first get into cosplay?

Gigglypuff: I’ve always loved Halloween and playing dress up. Honestly, I didn’t know that cosplay existed until I was in college. Once I started streaming on Twitch, and it became more and more mainstream during the pandemic, I started getting pretty into it. I didn’t know that it was a dedicated hobby. It’s really fun, so that’s why I started. I brought cosplay onto my streams and then I eventually started finding groups of friends to go to travel to conventions.

Playboy: What was your favorite fandom convention that you attended in 2024?

Gigglypuff: I loved Anime Expo in Los Angeles. I think it’s the biggest anime con in the U.S. There’s so many people, so you get to see a lot of your online friends from around the country and other parts of the world. I love seeing the cosplays, too. I also really like TwitchCon because then I get to see all my streaming friends. Both conventions are nearby in Southern California and they’re both around the same time of year, so it’s kind of perfect. I get a reunion with everybody.

Playboy: You’re an aspiring Pokémon trainer from Pallet Town—are you starting your journey with Charmander, Squirtle, Bulbasaur or Pikachu?

Gigglypuff: I always go with Bulbasaur. I know Charmander is a great pick, but he gets a little too much love. I also love Squirtle. I used to pick Squirtle as a kid, but I’ve converted to Bulba. I recently had a Bulbasaur that was very dear to me. His name was ‘Baby Onion’ and he survived till near the very end and then passed away. RIP to Baby Onion. Please never forget him. He was a hero!

Playboy: Wow, he sounds great. So, if you were a Pokémon gym leader, describe to me what your facility would look like.

Gigglypuff: I would have a fairy-type gym. I’d want it to be fantasycore because it would blend my interests. I love fantasy books and games like Zelda and the Lord of the Rings universe, but I also love Pokémon. I think my gym would have those elements to it with fairy-wilderness themed challenges. There would also be some dragon Pokémon in there. That’d be awesome. It would definitely have Jigglypuff because that’s my signature! Also, Wigglytuff.

Playboy: Brilliant. As a livestreamer, what sort of content do you love to create the most?

Gigglypuff: I love streaming. I really love getting to have cool conversations with people. I’ll play video games, or sometimes I react to things, sometimes I’m doing programming. The main focus is that I really love talking to my community. I’ve cultivated a very cool community online from different social media spheres that have nerdy interests but also are passionate about these things. Also, respecting others is so important.

There’s some cool topics to talk about. I get to have great conversations around literature, gaming, related controversies and more. I really enjoy having a community of smart and interesting people from different backgrounds that have some overlapping interests—that’s the best part.

Playboy: Not only are you an influencer, but you are accomplished in tech. What’s it like being a female thriving in a male-dominated space?

Gigglypuff: It feels like my norm at this point. I’ve been in many male-dominated spaces. I was in Harvard’s computer science department. Every tech company I’ve been in was majority male, especially in the engineering department. Twitch is 80% male. The U.S. gaming and anime communities aren’t far behind, so it’s definitely something I’m used to.

When I was younger, it was a bit more of a struggle. It wasn’t harder, necessarily, just less comfortable. There were many inconvenient scenarios, getting questions like, ‘Wait, are you really an engineer? Are you not a project manager? Do you know how to do this extremely basic concept?’ It was hindering my productivity when trying to accomplish tasks. Nowadays, I instantly shut it down. I’m like, ‘I know how to do that. Can we get this done?’ It gets better with time, but it is something I’m extremely used to.

Playboy: Upcoming, what should Playboy readers be on the lookout for from you?

Gigglypuff: I’m very excited to start streaming more consistently. My community is a conglomerate of people who are serial hobbyists and love learning new things. There will be several random video games. There’ll be a ton of discussions about books, news, game development, programming and anything going on in pop culture. If you love jumping from thing to thing, then my community is the one for you.

Playboy: Finally, walk me through “a day in the life of Gigglypuff.”

Gigglypuff: I normally get up, get ready and run straight out the door. I’m chronically a last-minute person. I put on my sunscreen, brush my teeth, brush my hair, get dressed and run out the door with a bagel or a corn dog. I eat it on my way to work because I walk to work. There’s also a real problem of too many leaf blowers on my street around this time. I’m always dodging leaves and trying to not get them in my bagel.

I work pretty late, usually somewhere in the range of 7:30 to 10 p.m. Then, I run home, cook dinner, do a little unpacking, and if it’s the weekend, I like to stream! I haven’t been able to do that on week nights yet, but other than that, I exercise, shower and hop into bed with a book. I’m currently reading a book on Japanese inventions and pop culture which is really cool. Finally, I go to sleep and do it all again. On the weekends, I get to play games and have a little fun.

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