From Private Dinners to Epic Conferences: A Guide to Throwing an Event for Your Newsletter Readers

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We talk a lot here about our newsletter communities — has yours ever had the chance to meet other members face-to-face?

There are lots of different ways to produce an event connected to your newsletter. They can be as simple as a Zoom meetup, like the kind W. Kamau Bell hosts for his subscribers, built around an Ask Me Anything format. They could be in-person conversations with an author at a local bookstore, like the one I attended earlier this year in Chicago hosted by the team from Joanna Goddard’s Big Salad. They could be happy hours at a local tavern — that’s what Dan Oshinsky did with the first Inbox Collective meet-up, which he hosted in 2019 at the Online News Association conference in New Orleans. He spent about $500 on a bar tab, with hopes that it might lead to a new client. It worked — Inbox Collective landed four new clients from the event. 

Events can also operate on a much larger scale. In 2023, Jacob Donnelly used his media newsletter to launch a $1,000-per-ticket conference called the AMO Summit for B2B media operators. He brought out 130 attendees for the first summit — this fall, he’s moved to a larger venue, The Times Center in New York, with aims to sell over 300 tickets. Or take a look at how the team at Bulletpitch — a newsletter that aims to connect start-ups with investors — has used their newsletter to get readers out to events in New York and Austin. Some events have involved up to 1,500 attendees, and the team has more events planned for Boston, Los Angeles, and Miami this fall.

Why might an event be a good idea for your newsletter? There are a few reasons you might want to consider one:

• It gives you a chance to build a community around your newsletter — Writing a newsletter can be a lonely practice. But when you host an event, even if it’s just for a handful of readers, you get the chance to actually meet your readers, ask them questions, and give them an experience that goes far beyond what you can do in the inbox. A really good event allows you to build loyalty with a reader in a unique way. A great newsletter might convince a reader to come back and open your newsletter again next week; a great event might make them a loyal follower for years to come.
• You can host conversations you can’t have anywhere else — One of the best things about email is that readers can write back to you after you send a newsletter. But there’s a catch: you might be having a lot of 1-to-1 conversations with readers, but other readers can’t participate in those conversations. By building an event, you can put many of your readers in the same room and facilitate conversations that might be difficult to hold anywhere else. And as a bonus, these conversations tend to be more human than what you’d see on social media. Readers show up excited to listen, learn, network, and have fun.
• Events might help you expand your newsletter’s reach — Most writers ask readers to share their newsletter with a friend, and word-of-mouth sharing can be a powerful engine for growth. But with an event, you might be able to pull in even more of those second-degree connections. A reader might invite a friend or a few along to the event, giving you a chance to bring new folks onto your newsletter list.
• Events can open up new revenue opportunities for your newsletter — Some newsletters with a paid membership or subscription will offer exclusive events to those members, and events can be used as a tactic to convert readers from free to paid. Other events monetize through sponsorships or ticket sales. Some newsletters even lean into all three opportunities — with the AMO Summit, Donnelly is selling tickets, offering discount codes to paying members, and has also lined up several sponsors.

Of course, there are plenty of reasons why an event might not make sense for your newsletter. Hosting something — even on Zoom — requires significant coordination and promotion. Ask anyone who’s put on a large event, like a conference, and they’ll probably tell you about pre-event stress dreams. (What if we booked the wrong date for the venue? What if we forgot to book a caterer? What if no one shows up?) Events can also be costly — anywhere from a few thousand dollars (to host a private dinner) to hundreds of thousands of dollars (to rent out a venue big enough for a conference), not to mention the cost of hiring additional vendors and planning all the little details that make a good event great. Putting on a big event comes with the risk that you might end up losing money if ticket sales are soft and sponsors don’t sign on.

I’ve attended and put on events myself, so I know some of the risks and rewards firsthand. In 2004, author John Green and I started a humorous reading series in Chicago called Funny Ha-Ha. It started after we noticed that at literary readings, the short, funny pieces were much more enjoyable than the longer, more serious performances, and in comedy-rich Chicago, there was an opportunity to showcase humor writers who were not necessarily standup or improv artists. Many of our shows were standing-room only and raised hundreds of dollars each for a local children’s literary non-profit. More importantly, it was just a good time and introduced audiences to some of the city’s finest storytellers. 

So, what does it take to put on a successful event? Whether you’re renting out a bar’s back room or a gigantic conference center, I’ve found, through my own experiences and through talking with other newsletter creators/event producers, there are a few essentials to figure out first. Here’s what you should consider if you put on a live event for your readers.

Figure out what type of event you want to run

If you operate a newsletter, there are a lot of events you could spin off for your readers:

• You could host a webinar where you teach readers about a particular topic.
• You could host a Q&A with an expert or an AMA where you answer questions.
• You could organize a book reading or a book club.
• You could hold a dinner, happy hour, or networking event for your community.
• You could host a conference or in-person talk.

Any of these could be interesting events to run — or you could put your own spin on things and host something totally different. It’s up to you to decide which fits with what your audience needs. Just make sure that it makes sense for your publication, your audience, and yourself.

Set a clear goal for your event

Once you’ve picked the type of event, you need to figure out your goal for it. Do you want this to be a profit driver for your newsletter? Do you hope to convert free readers into paying supporters? Do you want to boost sales for a local shop or restaurant? Is it a fundraiser for a non-profit? Do you want to give your readers the chance to exchange ideas? Do you want attendees to learn something? These decisions will help guide your logistical, budgetary, and messaging decisions.

Agnes Varnum, who runs an event consulting agency called Power the Press and writes a newsletter about events, said that too many producers kick off without any type of plan. “You’ve got to understand your audience strategy, your revenue strategy, your audience, your communications before, during, and after,” she said. “You can still get by if you fly by the seat of your pants, but you’re not going to get as much benefit, and you will have used up a lot of your energy if you don’t have an ROI,” or plan for your return on investment.

Your event goal doesn’t have to be lofty. Wesley Verhoeve, a photographer and newsletter writer based in Amsterdam, organizes regular photo walk events for his newsletter, Process, to let his readers meet each other. “Photography is quite a solitary profession,” he said. “The opportunity to get together with like-minded people who are pretty nerdy for this topic is very fun. It’s something that I would want to attend if I didn’t organize it.” Donnelly told me he had a straightforward goal when putting together the first AMO Summit. “I wanted to talk to smart people on stage,” he said. “I wanted people to have an opportunity to meet each other. I wanted to make sure that it was profitable. Nothing revolutionary.”

Pick a date and figure out your invite list

You’re going to need a date and time for the event. That part is fairly self-explanatory, right? You want enough time to plan sufficiently. You might want to make sure it’s not a time of year when many people will be on vacation. But you’ll also want to think carefully about who is welcome.

Is your event open to all your readers, or do you want to focus on a specific segment of your audience? Or is it a perk for just your paying supporters? If parents are invited, can they bring kids? Your venue’s capacity and restrictions will likely dictate a lot here, as will the way you monetize. If you’ve brought in a sponsor, they may be hoping that you’ll focus on a specific type of reader — one who overlaps with their target customer.

Think through your budget and consider sponsorships

It’s easy to plan a low/no-cost event (BYOB meet-up at the park from 5-6:30!), but if you intend to pull off something bigger, how will you pay for catering or promotion? Donnelly’s budgetary philosophy for the AMO Summit was to find sponsors to cover the event costs and have ticket sales serve as the profit margin. “The hope was to have four sponsors. I missed it a little bit,” he said. “There were some printing costs that were a little bit more than I expected, but it wasn’t too big of a deal.” He found his sponsors by reaching out to current sponsors and sending out — and receiving — cold calls. “You know, it’s sales.”

If you’re selling sponsorships, you’ll also want to think about what sponsors get for their money. Is it just being associated with the event? Will they get the chance to present content— and if so, how much time do they get? Trying to find the balance between the editorial content and the sponsored piece is a tricky balance. Do too little, and the sponsor may not feel like they got value from the sponsorship. Too much, and attendees may feel like they’re constantly being pitched.

Pick the right venue

Would this event be better as a digital event or in-person? Digital events are generally a bit easier to plan. It’s one thing to try to get dozens (or hundreds) of people together in the same space, but it’s quite another for someone to be able to join from their desk or their couch. The stakes are often a lot lower for digital events, and you can host them from wherever you work. (It’s also worth noting that there are plenty of digital events that are huge productions — just in the email world, events like Email Camp and Litmus Live involve dozens of speakers and feel more like conferences than webinars.)

If you’re doing something digital, you’ll want to explore different tools that can help you host these events. A small Q&A with a few dozen subscribers might work just fine on a Zoom Pro plan (about $160 per year). A full-day event with 1,000 attendees that requires a virtual backstage for speakers and chatrooms for attendees could cost $1,500 with a Zoom Sessions plan. And, of course, there are plenty of non-Zoom platforms that can host events, like BigMarker, Hopin, and Venue.

If Zoom still gives you pandemic vibes and you want to host something in person, you’ll have some bigger questions to ask. Sure, you could throw an event meetup at your home, but you probably want your newsletter event to occur offsite. 

A few questions you may want to ask:

• What’s the maximum capacity — and will it be big enough to support our event?
• Does this venue charge for its use? Are there food or drink minimums? And what taxes or fees will be added on top of those minimums?
• Is it easy to get transportation to the venue?
• Is the venue accessible to all attendees?
• Does the venue offer its own staff for the event, or will you need to bring in outside vendors to handle things like the audio/visual elements of the event?

All of this can get complicated quickly. You may want to start smaller with an event before moving to something more ambitious, like the event Bulletpitch hosted this year at South by Southwest, where participating founders had to find a way to incorporate their pitches into carnival-type games. Take Dine & Deliver, a series of private dinners for newsletter operators that Inbox Collective co-hosts with the team at Email Revenue Solutions. The get-togethers are kept small — about 20-25 people — and held at restaurants with their own staff to handle food and service. There’s still lots of planning involved, but the actual night-of event is straightforward — just dinner and conversation. After seeing the success of Dine & Deliver, Email Revenue Solutions launched The Newsletter Conference, a 350+ person event in New York that featured multiple events and dozens of speakers set across two days. But they started with the smaller event series first to prove the concept — and then moved up to a bigger event.

You should also think about how you’ll handle tickets for the event. Maybe the event is small enough that basic tools, like Google Forms or Paperless Post, will work just fine. If it’s larger, you look at platforms like Eventbrite or Ticket Tailor. (Another fun wrinkle: For large conferences, it’s common for platforms to hold a percentage of revenue until the event is complete, which means you may not get your money for a while — even if vendors or venues want cash up front.)

Figure out what additional help you can get

Who will be in charge of selling tickets, managing returns, keeping track of RSVPs, and, if needed, handling audiovisuals for this event? If you’re asking people to travel, are you going to answer questions about accommodations and transportation, or is that something you can hand off to someone else?

It’s good to know ahead of time where you need backup and what you can delegate. Istanbul-based food newsletter writer Vidar Bergham uses a travel agent to help get guests to the culinary adventures he hosts. “I can’t organize all this stuff [alone],” he told me. For his photo walks, Verhoeve utilizes an RSVP software that allows guests to indicate if they can no longer come, and the software automatically moves people off the waitlist.

My advice? While many low-key meetups don’t require more than one person to plan, it’s always good to have someone to run things by, worry out loud to, and help you stay on top of the list of things that need to get done. Plus, hearing how other producers run their events can give you some great ideas for folks to include or programming angles to try for your own get-together. 

Put together the programming

It will be harder for your guests to pull the trigger on buying a ticket until they know what they’re leaving the house for. This doesn’t have to be complicated. The Big Salad event I mentioned earlier consisted of Goddard and culture writer Hunter Harris in conversation onstage, followed by an audience Q&A. I hosted a meetup for readers of my newsletter, Evil Witches, at a local indie bookstore over the holidays, where the program was super simple: Cocktails and mingling, a book recommendation chat, and then more cocktails, mingling, and shopping. I had two goals for the event: that readers engage IRL at a fun night out and that we move merchandise for the store. I was happy to have achieved both.

If your event is on a larger scale, like the ones put on by Bulletpitch, the programming may require more strategy. “It’s easy to just say, “All right, we’re going to go rent the back room of a restaurant. Three-course meal; you got to talk to the person next to you,’” said Brett Perlmutter, Bulletpitch’s founder. But dinner might not be enough if the goal is, as Bulletpitch intended, to create networking opportunities for their community, said Perlmutter. “Never do a dinner without a cocktail thing before, so people can engage, meet the right people, and then sit down next to the people that they want to.” 

A conference like the AMO Summit required months of planning to make sure attendees got value from the event. Last year’s event consisted of eight panel discussions — 25 minutes each — and four sponsored sessions that lasted 15 minutes each. “You basically got 50 minutes of editorial content for every 15 minutes of sponsored content,” Donnelly said. He kept the sessions tight on purpose. “You would be floored how exhausting it is to sit in the audience and listen for a long time, even if it’s interesting content.” He packed in networking opportunities in between panels and lunch to make sure nobody was left hungry or sitting for too long.

An experienced moderator can help keep discussions valuable and concise. “To some extent, you have to cut [speakers] off sometimes,” Donnelly said, in order to keep the panels on time. “It is a subtle form. In those 25 minutes, it’s your job to guide them towards information that matters.” Too many panels, he said, are moderated by people reading questions off note cards. “If you ask a question, the person doesn’t answer it, reframe it,” he said. “Get them to go at it a different way. You have to. Otherwise, you’re going to get bad content.”

Get your readers out to the event

You’ll need a promotional plan for the event. Maybe your newsletter audience is loyal enough that you can promote the event once and fill whatever venue you choose. More than likely, you’ll need to send a sequence of emails and reminders dedicated to promoting the event. Plus, you’ll probably need to include a few more nudges within your regular newsletter and do some heavy promotion on social media. You may consider setting up partnerships with other newsletters to promote the event and make sure you hit your sales goals. 

Identify what is due when 

Every live event involves a to-do list of tasks that can only be accomplished at certain intervals. When I ran Funny Ha-Ha, my to-do schedule included alerting the press (which required at least a month’s notice), getting bios from the readers, sending emails out telling them where to be and when, getting a babysitter for my kids, printing out copies of the running order and “reserved” signs for seats the day of, and sending thank-you emails to everyone who performed.

If you run a dinner-centric event, like Dine and Deliver, you’ll need to plan out the flow of the meal — When should the entrees come out? Should it be a pre-set meal, or will guests order it at the table? — and make sure to collect your guests’ dietary restrictions. You may have a deadline by which to place orders for signage and, before that, by when to acquire hi-res logos from sponsors. At Bulletpitch, Perlmutter said, “Each founder that comes to the event can submit their logo to be featured on a massive billboard in the middle of the room,” which he said is both an advertising and networking strategy. “You happen to be talking to someone. You’re going to be like, ’I’m so sorry, I’ve got to take this picture because that’s our logo.’ ’Oh, what does your company do?’ It changes the dynamic.”

Varnum recommends including some form of signage at the event, even if it’s just a slide with the name of your newsletter that’s projected in front of guests. “Let them know, ’Here’s how I can follow along and continue the conversation,’ the same way you would in your newsletter,” she said. “You’re going to have a blurb at the top about how you subscribe and why supporting is important.”

Have a backup plan

Stuff happens. Technical difficulties. Canceled flights. Weather events. Speakers might cancel or get sick at the last minute. One memorable time, Samantha Irby was due to perform at my show, but a dog bit her at her veterinary clinic job, and she had to go to the hospital for a preventive rabies shot instead. Even venues cancel — one Dine & Deliver dinner had to be shifted to a different restaurant when the original venue informed organizers that the health inspector was shutting down the restaurant for the day for an inspection.

It’s great to have a backup plan when possible, but sometimes that’s just not feasible (like the live events I’ve had to cancel due to COVID and then COVID variant surges.) At the very least, figure out the most expedient way to communicate changed plans with your guests, and if feasible, inquire with your venue or ticketing service about how to handle refunds or rescheduling. 

Follow up after the event

Producing your event will involve effort. Once it’s done, you may be ready to go home and flop down on the couch.

But make sure to take notes on what you might do differently if you plan on hosting another event. You can survey your guests to hear what they thought of the event, Varnum said. “You need to know if they encountered problems that you weren’t aware of.” A survey is your chance to learn more about what else you can do for them. “It’s an opportunity to ask them what kind of events they might like to see in the future.” Not everyone sends a survey, though — Perlmutter prioritizes other messages in a follow-up email. “We will typically send something afterward that says, ’Thanks so much for coming, and thank you to our sponsors,’” he said. “I have this thing as a creator that I hate spamming people’s inboxes.” Instead of surveying, you can simply celebrate the fact that you held an event by sharing photos and recaps of the way Big Salad did after a recent event, which keeps the afterglow going and builds anticipation for the next party.

At the very least, you’ll want to reflect on what you have learned. Donnelly said he had some unexpected takeaways from the first AMO Summit that he’ll apply in the future. “When I get the badges made again, it needs to have the person’s name on the front and the back,” he told me after he observed how often name badges got turned around and were rendered ineffective. He will also not wear an Oxford blue shirt next time. “I was so anxious the day of the event, by the time I got on stage, it looked like a royal blue shirt because I had completely sweat through it,” he said.

Embrace the lessons you learn, any faux pas made or forgotten details, as opportunities for the future. “Something will go wrong in an event, inevitably,” Perlmutter said, recalling the time his team had to send out 100 guests who had already entered because they needed to be re-checked along with their IDs. “Everyone left, everyone came back in. But they weren’t mad enough where they were like, ’Oh, I’m leaving.’” Mistakes might get made, but you can also use those to improve your pre-event checklist for the next event.

If you have a sneaking suspicion that your newsletter readers would have a good time together and you have most, if not all, of the event essentials listed above, why not go for it? “The question is, if you’re putting the right people in the room and you have the right intentions, will people enjoy it and embrace whatever you’re giving them?” said Perlmutter. “The answer is overwhelmingly, ’Yes.’”

Looking for additional resources to help you plan your event? The American Press Institute released this workbook to help you build, monetize, and promote an event.

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