Roast Testimonial
Retirement Man



There are a few ways to celebrate a big birthday. A mid-life crisis hairpiece, sports car, or a comedy roast by your closest friends and family. So…why not all three? We’ll write bring-down-the-house Comedy Central-style roasts for your folks to deliver, and then a rebuttal so you can return the favor in kind!


Congrats on a great career! Now it’s time to send you off the right way, with a Dean Martin-style roast that will be delivered by your friends, family and former colleagues. We’ll help them honor you in the way you deserve, with a night of side-splitting comedy!


Looking for a fun, unique idea for your holiday party and/or annual conference? The professional comedians at Winning Wit will help you have fun with your industry and create an amazing night of laughs! And we promise that all the humor will be tactful and appropriate, so everyone will keep their jobs the next morning…


Fundraisers are a tricky business. People want to donate to the cause, but they also want to be entertained in the process. No worries, that’s where we come in. With a night of customized humor, you’ll ensure that people are lining up to fill those $200/plate tables. We’ll write all the content, and help your folks deliver them like pros on the big night!

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Remember watching the Dean Martin and Comedy Central roasts and thinking…”Did THEY write all that stuff?” Nope. Not even the comedians did it all on their own. They had a team of writers make sure they lit the room on fire, and now it’s time for you to have that same kind of team at your disposal.

Here’s how it all works:
  • Contact us for a free consultation so we can learn all about your honoree/industry/company and the event you had in mind
  • You’ll give us the list of roasters
  • We send questionnaires to each of them
  • We write first drafts for everyone within 3 business days
  • Each roaster will learn how to deliver their roast like pros!
  • You deliver the roasts and give your team the night of their life!



Are you a Maid of Honor, Best Man, Father of the Bride/Groom or party-crashing uncle who wants to make a splash?

The award-winning comedians at Winning Wit will learn all about the speech you’d like to give, and write you a minute toast that will bring down the house!

We’ll help you:

– Conquer Stagefright

– Get a speech quickly before the wedding date

– Be funny, sincere and confident

– Create a YouTube-worthy memory that your friends and family will rave about for years


No woodworking skills necessary

Turn your team into masterful storytellers!

Is your organization struggling with communication? Having a hard time getting your sales team to connect with prospects? Is your training team having a hard time making boring content stick? Time for stand-up comedy to ride in for the rescue.

Geoff Woliner, longtime comedian and facilitator of hundreds of workshops for corporate groups, associations, political groups and volunteer organizations, will help your team make any content, no matter how dry, POP! In a half-day or full day setting, your team will learn stand-up techniques to make training and sales fun, engaging, and relatable to anyone!



Geoff Woliner

When Winning Wit founder Geoff Woliner was 11 years old, he was asked to give a speech for his grandfather’s 80th birthday. Not knowing what to say, he decided to start roasting him. “Papa, you have a bad stomach and love to play cards. You always have the ace of farts!”. Yes, comedic gold. For an 11 year old. But seeing his family, and most importantly, his grandfather, laughing hysterically, he developed a taste for honoring people through comedy.

And after 13 years as a stand-up comedian, he founded Winning Wit in 2011 to help others have this gift of humor at their own events.

As avid fans of the Friars Club, Dean Martin and Comedy Central Roasts, Geoff and his team of award-winning comedians at Winning Wit have one simple philosophy: If celebrities can have fun roasting each other, so can you.




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Comedy roast, birthday roast, anniversary roast, retirement roast