Lessons in Copywriting From a Good Wedding Speech

In the thick of a mildly successful, part-time stand-up career, I was introduced to someone who would change the course of my writing life.

I met Cameron through my friend Steve. Steve and I went to high school together and even roomed together for a year in college. At the time I was doing stand-up, Steve was pursuing his MBA at Cleveland State. One of his classmates, Cameron, was interested in learning a little bit about stand-up, so he reached out to me to ask if I’d look over his jokes.

I went to Cameron’s condo and read what he had. I remember thinking that for his first time writing jokes, this guy was pretty good. I also remember the only thing he had in his fridge were two Red Bulls, which explained his enthusiastic, all-over-the-place nature.

I went to support Cameron at his first open mic, and he did well. He came to a couple of my shows and we kept in touch.

A couple months after we met, he called me with a funny story.

Cameron was at a wedding for one of his friends. The groom approached him with an interesting request before the reception started.

“Hey Cam, listen, I know my best man is going to make an ass out of himself when he gives his speech. I know you’ve been doing some stand-up so can I ask a favor? When he’s done with his toast, can you stand up and say a few words after? I don’t want the room to be in a bad place and figured you might be able to get a few laughs.”

Being the mensch that he is, Cameron agreed to help out. Sure enough, the best man rambled on about god knows what. After, Cameron stood up with a few “impromptu” remarks and got some laughs. The evening proceeded.

Later on during the reception, another one of the groomsmen approached Cameron.

“Hey, saw what you did up there and loved it! I am going to be the best man in another wedding a couple months from now. Would you help me write my speech with a few jokes? I’ll pay you.”

Enter Laugh Staff.

Cameron asked me, in not so many words, “What if we start a company where stand-up comedians write wedding toasts?”

I was intrigued. And I liked the fact that Cameron presented it as a way for comedians to make money during the day while they paid their dues hitting the stages at night.

Cameron and I were full steam ahead. No, really, Cameron’s full-time job was that of tugboat captain! A tugboat captain with an MBA starting a comedic speechwriting business.

Cameron’s enthusiasm was palpable, and he had an entrepreneurial spirit that really got us off the ground. He got a couple of friends to invest in the company and started working on a business plan. He also took it upon himself to work with a web design company to build out an e-commerce site.

My job was to round up comedians. I reached out to a few comics I had worked with and then asked a few other comedians for individuals they thought would enjoy this type of work. Our initial team consisted of 10 or so comedians. The two biggest names we had were Jay Black and Curtis Cook.

I had worked with Jay at Hilarities in Cleveland. He was a former high school English teacher who made the jump to stand-up and never looked back. (In my experience, former teachers always made awesome stand-up comedians, since they had a captive audience: the classroom.) Jay opened frequently for guys like Brad Garretty and Kevin Nealon.

As for Curtis, he and I had done some shows together around town. He was young, having just graduated from College of Wooster, but like Jay, was receptive to the idea of Laugh Staff. He was also responsive and respectful, which were rarities for comedians. Eventually, he went on to be a writer for Comedy Central’s The Jim Jeffries Show and wrote for HBO Max’s Friends reunion.

Before I go any further, I should probably tell you how we settled on the name Laugh Staff. Cameron had started thinking of some names, and he had a web/ marketing company think of names too. I found an old email from 2013 when we were in the naming process. Here it is:

Looking back, it probably would’ve helped a ton if we’d actually had “speech” somewhere in the title (to help with SEO/people actually finding us online). But Laugh Staff conveyed two things we were after: the comedy element and the company element. At the time, we thought “staff” made us sound legit.

From a creative standpoint, Laugh Staff provided me with my unofficial introduction to creative briefs. Every time somebody bought a speech package (there were three speech packages available), an automated questionnaire would be sent to the customer asking for relevant speech information.

In the questionnaire, we’d ask for basic info like:

• Groom/Bride Name
• Age
• Occupation
• Interests/Hobbies
• Siblings’ Names and Ages
• Parents’ Names
• Parents’ Marital Status
• Number of Wedding Guests
• Percentage of People You Know at the Wedding

Then we’d go a little deeper with questions like:

• Why did the bride/groom choose you to be the maid of honor/best man?
• How did the bride and groom meet?
• What’s something you love about the bride/groom?
• Describe the first time you met the bride/groom.
• Tell us about the engagement.
• Can you pull off sarcastic jokes?
• Are you nervous about this speech?
• Do you have an accent or any unique physical characteristics?

The majority of the time, I never actually talked with the customers; I can remember maybe two or three phone calls. But I think this is how we (the customer and myself) preferred it. It was just email, the preferred communication method of millennials worldwide, next to texting.

The answers they provided gave me a peek into their personalities. How the customer answered the questions revealed how much they were willing to push the envelope. If someone included some f-bombs and inappropriate stories in their answers, I knew I could straddle the line of a PG-13 or R-rated speech. If the answers were more concise and hinted at a religious or conservative personality, I knew to keep things PG.

My curiosity into these people’s lives helped make Laugh Staff more human. If I got a questionnaire back that was bare bones, I’d email the customer directly, putting a real person behind this crazy, little-known company they’ve entrusted to capture their words.

My emails always went something like this:

Taking an interest in the speech givers was almost as important as the speech content itself. Why? Because we were asking people to talk about their favorite subject: themselves.

I tried to dig deep into the younger/adolescent years of the best man or maid of honor. Nostalgia, I thought, was a good way to get the maid of honor or best man comfortable telling stories. It also went over well with crowds, as most of us can smile as we look back on what we thought was cool or trendy.

Like I said, the majority of these speech exchanges were through email. My goal with every speech was to have the customer at least smile or smirk a couple times when they first read it. (If they snorted, even better.)

Here is an excerpt of a maid of honor speech where, based on how she answered the questionnaire, I knew I could push things a little:

As you can see, the maid of honor was comfortable in her abilities and didn’t mind being a bit brash with her words. Remember how I said every copywriter comes to the table with their own, unique past? “Hips, lips, and fingertips” is something a buddy of mine used to say in middle school about girls he wanted to go out with. Always stuck with me. Can you think of any fun, memorable lines your friends said growing up? If so, jot them down. They might just find a place in a future headline or body copy.

With wedding speeches, attention spans can be tough. Most people just want to get to dancing and free drinks. Numbering a series of events can slow the speech down so the audience can follow along. This also works when writing emails or direct mail when listing the benefits of the product.

Obviously, nobody is going to confuse the above with the Gettysburg Address. Some of the lines might even seem corny. But for the person reading it, they could roll with it or just take out parts that they didn’t feel were “them.” Sometimes it’s better to give too much rather than not enough, and you can use that same approach in copywriting.

Below is a maid of honor example that skews a little more heartfelt:

A letter is so personal. You can imagine someone unfolding it, and stopping to read it, and maybe reading it again. It also gets the audience wanting to know what was in the letter. And it sounds better than, “When she asked me to be her maid of honor, she sent me a text.” You can use this personalized approach in your copywriting as well. What’s going to make your end user feel special?

In her questionnaire, the maid of honor did an awesome job of conveying the simplicity of the relationship between the bride and groom, much like you should keep things simple within your headlines and body copy. For them, there weren’t any extravagant proposals or near-death experiences, just an appreciation for the day-to-day interactions. “Elevating every moment/When words aren’t necessary.”

In this final part, she was able to inject a little personality despite this speech being a more sincere one. Even when you’re writing more serious copy, make sure you don’t make it stuffy.

In the span of seven years, I wrote about 200 speeches. Stand-up introduced me to creative writing, and Laugh Staff helped me tell stories with structure. Cameron and I believed that a best man or maid of honor speech might be the closest opportunity one has to stand-up in their lifetime (if they decided to go the humorous route). Therefore, we wanted to write the best “set” or speech we could.

Maybe the toast gave the best man the confidence to dance with the bride’s cousin. And maybe they went out on a date. And maybe they got married and started a family. Who knows?!

Needless to say, Laugh Staff was exciting and experimental. And it was the biggest feather in my cap, having not had agency or traditional copywriting experience.

Stephen King would scold me for using too many adverbs in my speeches, but for a best man or maid of honor, I could get away with it. No way I would still be a copywriter without Laugh Staff. So thanks, Cameron.