Meet Denise Winkelman | Comedian/Silly Billy Goat

We had the good fortune of connecting with Denise Winkelman and we’ve shared our conversation below.

Hi Denise, is there something that you feel is most responsible for your success?
What is the most important factor behind your success / the success of your brand?

One of the biggest factors behind my success has been learning how to work smarter, more efficiently, and with intention. I’ve had great mentors. I’m not 23 anymore, and I’ve had to figure out how to balance my career, my health, and my goals without burning out. In comedy, there’s a lot of pressure to say yes to everything—driving two hours for a five-minute set in front of three people. But learning how to be selective and politely say no to opportunities that aren’t mutually beneficial has been a game changer.

I always think of that scene in The Pursuit of Happiness. Will Smith’s character was competing with interns right out of college who worked 12-hour days, but he had a son and had to leave early. So he learned how to cut downtime, stay focused, and work smarter and he ended up getting the job.

There are so many comics who work hard and go up all the time, but sometimes it’s without a clear purpose. They’re not fine-tuning their sets, learning structure, applying to festivals, or building relationship. They’re just going up to go up. For me, being organized and intentional with my time has made a huge difference. I’m constantly asking, Why am I doing this and is there a better way?

Let’s talk shop? Tell us more about your career, what can you share with our community?
My comedy blends dynamic storytelling with heart, honesty, and a lot of laughs. What sets me apart is that I don’t just tell jokes—I take the audience on a journey. My debut comedy special, Bougie on a Budget, is a great example of that. It’s high-energy, raw, and real. I talk about being a transgender woman, growing up with conservative parents, surviving professional wrestling, living with fibromyalgia, and ultimately fighting to live an authentic life. The through line is always: be yourself… unless you’re a monster—then maybe be someone else.

I’m incredibly proud of this special. It’s being distributed by Comedy Dynamics and is coming out August 19th. The response so far has been amazing, and I can’t wait for the world to see it. I wanted to create something that was both hilarious and deeply personal, Something that could uplift people while making them laugh so hard their sides hurt. I think we pulled that off.

Getting to where I am now wasn’t easy. I’ve had to navigate the comedy world while managing chronic pain and fatigue, gender transition, a ton of douche nozzles and the reality of not being 22 and carefree anymore. I’ve worked corporate jobs, dealt with burnout, and performed through pain—both emotional and physical. But through it all, I believe comedy was my true calling.

One of the biggest lessons I’ve learned is that authenticity is your superpower. You don’t have to follow the crowd. Comedy is a buffet now: everyone may not love you, but there are a lot of people who will. You don’t have to do what everyone else is doing. You just have to do what works for you. And when you lean into what makes you different, that’s when real connection happens.

I also created Team Hussy-a cool, inclusive community to support the Hussy (that’s me) and just have fun. It’s silly, a bit of a secret, kind of underground, and totally unapologetic. Think the NWO meets Pride month meets a funny ending of a This is us episode (lots of tears and hugs and farts). You can sign up to join at denisewinkelmancomedy.com for exclusives, updates, VIP access to all the fun stuff I’ve got coming up. Bougie on a Budget is just the beginning.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
The best thing about LA is you can find anything you could ever dream of—for the right price. And the beauty of Southern California is that within three hours, you’ve got access to beaches, mountains, casinos, wine country—literally everything. Here’s how I’d plan the ultimate week:

Day 1 – Classic LA Sights + Comedy Night
Start with lunch and shopping in Beverly Hills, then hit the Walk of Fame and snap that classic Hollywood Sign pic. At night, it’s all about The Comedy Store. It’s iconic—you might catch Iliza, Nikki Glaser, Bert Kreisher, Matt Rife, and Jeff Ross all in one show. After that? Maybe a club or a secret party in the Hills. We’re doing LA right.

Day 2 – Beach Day + Dinner in Santa Monica
Head to Malibu, El Matador, or Santa Monica for a chill beach day. Then dinner at Fia in Santa Monica (My favorite restaurant in Los Angeles) followed by a walk on the pier or Venice Beach to people-watch and soak up that ocean breeze.

Day 3 – Studios, Hike, Art & Korean BBQ
We’d hit Universal Studios or do a studio tour for the Hollywood experience, then take a scenic hike at Runyon or Griffith. Afterward, check out an art museum like The Broad or LACMA. And for dinner: Korean BBQ in K-Town—because nothing beats grilling your own meats with soju flowing.

Day 4 – Big Bear Escape
Road trip to Big Bear! Skiing in winter, or hiking, boating, and relaxing in summer. It’s peaceful, beautiful, and the total opposite of LA traffic. The perfect reset.

Day 5 – Wine or Desert Adventure
Depending on the vibe, we’d either sip our way through Paso Robles or Santa Barbara, or head east to Palm Springs for some desert chic poolside downtime. Both are weekend-worthy getaways just a few hours away.

Day 6 – Nightlife & Hidden Gems
Back in LA, we’d grab cocktails in West Hollywood or Silver Lake—maybe find a rooftop bar. Then something different: a secret comedy show, a pop-up immersive art exhibit, or a late-night Korean spa trip. This city lives for late nights and weird adventures.

Day 7 – Sunday Funday Send-Off
We’d wrap it all up with brunch at The Abbey in West Hollywood—great food, strong drinks, and even stronger people-watching. Maybe a flea market, Griffith Park, or one last sunset at Venice Beach.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
So many people. I’ve been really lucky to have incredible mentors and supporters across different stages of my life.

In the business world, I had several professional mentors who taught me how to lead, stay organized, set clear agendas, and focus on both process and outcome. Those lessons have been invaluable, especially as a performer managing my own career.

When I was a professional wrestler, I had the opportunity to learn from amazing veterans like Nikita LeFleur, Roger Ruffin, Chavo Guerrero, Karl Anderson, and Rob Conway. While I wasn’t super close with everyone, just getting to work alongside people like that taught me a lot about how to build a brand, sell merch, and work for yourself in a tough industry.

In comedy, I’ve been fortunate to have mentors like Dat Phan, Chris Clobber, Bobbie Oliver, and Vicki Bauman who’ve helped me avoid a lot of mistakes that take other comics years to figure out. And then there are seasoned headliners like Ralph Porter, Joe Dalo, Sally Mullins, Mike Langworthy, Chuck Roy, and Adam Cayton-Holland who’ve dropped some real gems of wisdom over the years.

I wouldn’t be where I am without all of them—and I’m grateful for every conversation, opportunity, and tough lesson along the way.

Website: https://www.denisewinkelmancomedy.com

Instagram: denisewinkelmancomedy

Twitter: @dwinkscomedy

Facebook: https://facebook.com/denisewinkelmancomedy

Youtube: https://youtube.com/denisewinkelmancomedy.com

Other: Tik Tok, threads and Blue sky @denisewinkelmancomedy