What I learned hosting my first copywriting conference. - The Copywriter Club

What I learned hosting my first copywriting conference.

It was Saturday evening—one day after the last speaker left the stage and our first ever copywriting conference was over—I sat down briefly with Kira to look back on the events of the past couple of days…

  • Two days of incredible presentations about copywriting, persuasion, and freelancing from true A-listers like Parris Lampropolous, Marcella Allison, and Kim Schwalm—and 15 others.
  • Dinner out at a fancy Italian bistro with our Think Tank crew while other conference attendees went to dinner with one of the speakers.
  • A women’s only breakfast for those who could drag themselves out of bed for Eggs Benedict.
  • A killer after party in the rooftop bar where everyone at the conference went to unwind, laugh, share what they had learned—and “drink like Hemingway” as we say. Then there was the after-the-after-party-party.
  • And the optional day-after scavenger hunt that took us to Mafia bars, Chinatown tourist spots, and coffee shops around the lower east side. Nudge… ask Kira who’s team won.

We were exhausted.

“How do you think we did?”, Kira asked.

“I can’t believe I’m going to say this, but I feel like we hit a home run.”

Honestly, I couldn’t believe it had all come together so well.

In less than 8 weeks, The Copywriter Club In Real Life (TCCIRL) went from an idea we thought we would tackle in a few years, to the what we think is the best copywriting conference anywhere. Not that we’re biased.

And we learned a few things along the way…


Lesson #1 If you organize it, they will come.

We’ve worked hard to build a community of smart working copywriters from around the world—all dedicated to doing great work and building successful copywriting careers.

Copywriter ConOver the previous year we had attracted a good-sized audience for The Copywriter Club Podcast and added about 5,000+ members to our free Facebook group. We had successfully filled The Copywriter Accelerator program and the first “class” of our Think Tank mastermind group.

But would a group of introverted wordsmiths attend a conference about copywriting in the middle of winter—over the Valentine’s Day weekend?

Easy answer: Yes.

More than 80 copywriters of all skill levels packed into the conference room at the Hotel 50 Bowery to listen, laugh, and learn.

Even though we had never met the vast majority of people who were there, we immediately knew we were among friends—not the kind of friends you occasionally see post their vacation pics on Instagram—but good friends you want to hang out with again and again.

Jay Rooney, one of the copywriters who came to Manhattan with us, said this about how easily fast friendships were formed…

Best Copywriter Event

These ~100 new “friends” made TCCIRL an amazing experience for all of us.


Lesson #2 Great things happen when you work your a**es off.

Kira at Copywriting EventThere is a massive amount of work that goes on behind the scenes at a copy conference like this.

This won’t surprise you if you’ve been involved with an event before, but the process includes negotiating with the hotel, hiring an AV team, convincing speakers to attend, selling tickets, arranging for coffee breaks, printing signs and books, assembling the swag and name tags and presentation slides, setting up the after party and dinners and activities… and… and… and… <–this list is looooong.

Easily the hardest thing we did was trying to get everyone back into the room after breaks—there was simply too much to talk about, people to meet, friendships to form.

Fortunately Kira had some experience with events. And we connected with a fantastic event coordinator (Elaine Wellman) to help organize everything and keep it moving. It wouldn’t have happened without her.

The lesson here? Great things come to those who work their tails off.


Lesson #3 TCCIRL isn’t the Kira and Rob Show. It takes a team to pull something like this off.

Copywriter EventI already mentioned Elaine who was a big part of putting TCCIRL together. But she wasn’t the only one.

The AV crew was there to help make sure the sound and presentations came off without a hitch (or maybe just one hitch… see below).

Joanna Wiebe gave us permission to print one of her digital-only books to create a valuable, one-of-a-kind gift for attendees.

Brian Kurtz gave everyone a copy of Brilliance Breakthrough by Eugene Schwartz.

Christine Laureano helped find a case of water so our speakers wouldn’t suffer from dry-throat.

We had a photographer ready to catch each Kodak moment. <– do Kodak moments still happen?

Justin Blackman showed up a day early to help put together the swag bags.

Brit McGinnis, our community manager, was there to help with anything else—like handing out badges and chasing down Coke Zeros or lunch when I didn’t have time to get food between sessions.

I know I’m not giving credit to a bunch of other people who promoted the event, hosted groups of attendees for dinner, and supported us in a dozen ways. If I’ve left your name off here, please forgive me.

Without all of these amazing people, this copywriting event never would have happened.


Lesson #4 A successful copywriting conference is all about getting the right people in the room.

Copy ConferenceWe’d love to take credit for how great everything turned out, but the truth is, the copywriters who took the stage as well as those who sat in the horribly uncomfortable chairs in the room made the real difference.

First we asked two of our mentors, Joanna Wiebe and Brian Kurtz to come. Both were enthusiastic early supporters. Then we started reaching out to the other copywriters we wanted on stage—Marcella Allison, Hillary Weiss, Kevin Rogers, Laura Belgray, Sam Woods, Ry Schwartz, Kim Krause Schwalm

We thought most of them would be too busy so we invited even more.

When they all said yes, we suddenly had 18 people to fit into our two-day agenda. And when Parris reached out to ask why we had invited all his friends but not him, well, who’s going to pass up the opportunity to have Parris speak?

Parris Copywriting

Somehow we made it work.

And it wasn’t just the people on stage.

Margo Aaron came and wrote about TCCIRL for Inc.

Marcella Allison brought her laugh. 

Others brought small gifts.

Kirsty Fanton and Ami Williamson flew in from Australia. Per Andreason came from Denmark. Sharon Mann flew in from France. Sorcha MacKenzie came in from London. Tepsii came from South Africa. And Prerna Malik came all the way from India—she spent an entire day in airports just to spend time with us at TCCIRL.

Are you kidding me? We were thinking a few people might fly in from around the United States or Canada (and they did) but so many from around the world? From Australia? South Africa? India?

And now—several attendees from last year already have their tickets to join us on stage for this year’s copy conference.

We met them, learned about their work and businesses at the first TCCIRL. It just makes sense to have them come back and share what they’ve done over the past year. And just like last year, I’m guessing we’ll find a few of next year’s speakers in the seats this year.


Lesson #5 There are much better ways to make money than hosting a copywriting event.

When we told people that we were producing our own event, several of them warned us that no one makes money on their first event. “You lose money on the first, break even on the second, and hope to make a little on your third,” they said.

We don’t know about the second and third parts of that advice, but the first part was true.

We didn’t make any money by holding an event. Fortunately, we didn’t lose too much either. And we probably won’t quite break even on our second go.

So why do it again, if we’re not making money from TCCIRL?

Because the real ROI isn’t the money spent or earned. Attending an event is rewarding in so many other ways.

Copy ConGetting copywriters together in real life is what The Copywriter Club does. We’re not solely interested in creating online relationships via Facebook and Zoom. Seeing friends from the FB group in real life is a difference maker. We want to keep building lifelong friendships, partnerships, and collaborations—and those kinds of relationships only happen IRL.

Hanging out (dining, drinking, dancing) with other writers is freaking awesome. And the lessons learned and information shared is so worth it.

Last year’s presenters shared business secrets that they don’t talk about anywhere else. The ONLY way to learn this stuff is to get into the room with them. That’s why it’s worth it to us—even when we don’t make money in the process.

And let’s be honest, this event helped attract even more members to The Copywriter Club. It was a big brand builder for us… so it definitely pays off in other ways.


Lesson #6 Glitches happen. You’ve just got to roll with them.

Copy Conference Hillary WeissAt one point on the second day, I had the wrong version of Hillary’s slides loaded on the laptop we used to run the show.

No problem. She started talking as I started downloading the correct slide deck. But hotel conference wifi is slooooooooow. <– this number of o’s dramatically understates the slowness of the wifi.

It took almost 12 minutes to get the right slides up on screen. 12 minutes! Hillary is a total pro. She jumped into her presentation without the slides and didn’t miss a beat.

And then there were the chairs. So uncomfortable. Sorry about that. We won’t make that mistake again.

Stuff happens. That’s part of life. Fortunately people are forgiving and made due. Again, we are so grateful for their generosity.


Lesson #7 Every quantum leap requires an actual LEAP.

A year ago, if you had asked “are you ready to produce your own copywriting event?” we would have said, “no way.”

We absolutely were not ready.

And then the opportunity presented itself and we jumped at it.

If not now, when?

We did a hundred things we’d never done before.

In 8 short weeks TCCIRL went from an idea we might get to “when we’re ready” to a successful conference that no one wanted to end. And it was 100% worth it.

TCCIRL isn’t the first copywriting conference (in fact, it’s the newest).

It’s not the largest copywriting conference (it’s probably the smallest and most intimate).

And it’s definitely not the most well-known event for copywriters. But it IS different from any other copywriting conference you’ll attend.

Of course, we’re biased, but we were blown away by the positive feedback we received post-event.

Great Copywriter Conference Best Copywriting Conference Best Copywriter Event

The best value. The best learning. The best community. That’s what we tried to deliver with TCCIRL last year. And this year? Well, we’re going all in to make sure our event March 13-15 is better than ever. (If you still need your ticket, get it now.)

Note: There are two ways to get the recordings of all the presentations from last year’s TCCIRL. You can buy them here. Or, you can get them free when you join The Copywriter Underground for a full year. #worthit


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