In today’s newsletter:

• Opportunities & Updates

• Semafor & Other New Media Companies Going ‘Events-First’

• Should Events Be Focused On Revenue or Driving Subscriptions?

• The Social & Demographic Forces Driving the Festivalization of B2B Events

• 2 Causes Of Crappy Speakers

• Using Subtext to Live-Report from Cannes

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Opportunities & Updates

• The DOJ approved Amex GBT’s $540 million acquisition of CWT. The deal, originally announced in March of 2024, had been held up by a Dept. of Justice antitrust lawsuit filed in the closing days of the Biden administration, which was just dismissed. Good news that it was finally approved, but you have to wonder about the impact of losing momentum for over a year.

• Skift announced 2 acquisitions this week: the membership and event community Women Leading Travel & Hospitality, and podcasting platform Hospitality.fm. I like both of these moves, which lean into the trends toward niche communities and more engaging and targeted content, respectively.

• On October 7th I’ll be leading a session on M&A at the SITE (Society of Incentive Travel Excellence) C-Suite Agency Summit during IMEX America. This is a closed-door, invite-only event for 25 agency leaders to discuss strategic challenges and opportunities, exchange ideas, and build peer relationships. If you’re interested in one of the few spots remaining, email SITE CEO Annette Gregg.

• On September 15th I’ll be speaking at the Skift Meetings Forum in NYC in a session (tentatively) titled Event Entrepreneurship: Big Ideas Require Bold Moves. Heather Mason and Robyn Duda will talk about their journeys in launching their own events (The Impact Lounge and RacquetX respectively), and I’ll provide insights on how buyers value event businesses, and the state of M&A in general.

• Skift is trotting out an interesting concept at their Meetings Forum: Keynote Listeners, a curated group who will observe the sessions and then presumably report their takeaways at the end. I love the idea of helping the audience recap key insights, which is helpful for organizers to see what resonated (and what didn’t). I did something like this at PCMA’s Educon in 2023, and found it especially impactful after a multi-day event.

• I’m advising an event production company (creative, scenic, staging, lighting, sound, etc.) on a roll-up. We’re looking for companies with around $1M in EBITDA. To learn more, email me here.

The Rebooting's Brian Morrissey on Event Economics for Content & Media Brands

In last week’s article, The Canceling of Colbert and the Rise of the Creator Economy - Events Ecosystem, I wrote about how the changing economics of media creation and delivery offered a huge opportunity for events, as vehicles to bring niche audiences together to build community, and as ‘AI No-Fly Zones’ to serve as a bulwark against AI summaries eroding creator web traffic.

To get an insider perspective on this, I sat down with Brian Morrissey, founder of The Rebooting, an insightful newsletter and podcast about the changing media business, which is increasingly relying on events. Previously Brian was CEO of Digiday, where he drove strategy for their various brands, and saw firsthand the confluence of content, subscription, and events. Some notable articles include The Unbundling of Events (March 2021), The Pivot to Events (July 2023), The B2B Events Reset (October 2023), and Meetings People (May 2025).

In addition to writing about and interviewing business leaders in media and events, Brian hosts his own event series for The Rebooting. Here he shares insightful perspectives on event sponsorship, pricing models, leveraging AI, and what’s next in this space.

The Evolution of Events & Media

You experimented with SMS platform Subtext to share live reports from Cannes Lions this year. I found the updates - and the new format - super interesting. What was your experience with it?

Throughout the week, I sent off short messages to a couple hundred people who opted in to get them. They could respond to me but not a reply all. I found it very effective for an event like Cannes, but also a qualitative difference to an email. Text is more personal than email. People get far more aggravated about spam texts than spam email. Many people mentioned getting the texts where I ran into them, which is one of my core success metrics for anything new. It’s easy to overdo texting and become annoying, but done right, it’s a promising way to build a personal connection.

Much has been written about the ‘Festivalization’ of events. Last year Informa paid $1.5b for Ascential (producers of Cannes Lions and Money 20/20) to create Informa Festivals. In less than 3 years, Future Proof Festival and Citywide events, targeting the financial advisor world, has grown to $30m in revenue. Is this where business events are headed, or is there still a place for traditional formats?

I’m not a big fan of traditional B2B formats. Trade shows seem out of a time capsule. Hosted buyer meetings are painfully cheesy. Three-dudes-in-blazers-on-stools should have been retired long ago. I assume the festivalization of events is one response to the reality that many events formats are as outdated today as the typical inverted pyramid 700-word news article. People want connectivity and fun with some useful insights mixed in. I think overall this is part of a couple trends.

1. One is the casualization of everything.

2. The other is how work and social have blurred together. The expectations people have for work events, like business-related content, is just as high as what they choose to do in their personal lives.

It feels like events have become increasingly central to the business models of media companies over the past few years. A case in point is Semafor’s founder Justin Smith said “When we started Semafor (in Oct, 2022), we knew events would be very central, especially for a new company looking to find profit quickly.” What do you attribute this to?

It’s due to the weaknesses of the old models of producing content for webpages, getting traffic to it from search and social, and monetizing it through programmatic. Events are an off ramp. It’s hard for legacy publishers to fully pivot to events because they need to operate the old businesses while building the new. Justin doesn’t have to do that with Semafor, so he doesn’t have to worry about pageviews and programmatic yield. The downside is that events involve a lot of work and different skillsets to be done well.

The proliferation of tools for launching newsletters and podcasts has powered the Creator Economy, making it easier than ever for someone with a voice to build a dedicated audience. Many creators then turn to in-person events to bring their followers together, turning those audiences into communities. How much of this is about generating revenue vs. deepening relationships with subscribers? Or is there value in the content captured from events as well?

I think done well, events can solve a lot of purposes, but first and foremost, in most models the purpose is margin. I did a podcast with Blockworks CEO Jason Yanowitz not long ago. I made some kind of airy statement about “community” and events, and I appreciate that Jason corrected me to say that the job events do is high-margin revenue. It can be different in different models, but I think for many publishing businesses that’s Job 1. The rest is additive. I would never recommend holding an event for the purpose of capturing content, unless it’s a little live podcast.

These tools have led to the rise of new “narrow but deep” niche media brands, like The Ankler and The Information, that can create content around specific topics and bring a curated group of people to their events. How are traditional / larger media brands competing with this?

Larger media brands can be comprehensive and simply bigger: Bigger brands, bigger reputations, bigger reach. I’m unsure if that will be as enduring a competitive advantage, but that’s certainly one. The Information is great, but it’s hardly a comprehensive source of the entire tech industry. Same for The Ankler. I just did a podcast with Variety’s co-editors-in-chief. They went out of their way to talk about the big stars on covers and all the different offshoots of the brand. Bigger publishers have many disadvantages in this world, but one they have and should emphasize: They often have bigger brands. And you can make money off a brand in lots of ways that don’t involve putting ads on webpages.

2 Causes Of Crappy Speakers

Conference organizers increasingly sell sponsorships to individual sessions. Sometimes that simply means their logos are on that section in the agenda and they get either a shout out from the podium or their rep gets to speak for 2-3 minutes. Other times, however, they let the sponsor supply the speaker(s) and the content, which is always a red flag to me. What’s your take on this?

Conferences have never been a bastion of church and state, so my realist reaction is: Whatever the market will bear. I always found with events your incentives as an organizer was to see how far you could push the envelope before people revolted. Usually, when push comes to shove, margin wins. I don’t see a ton of long-term thinking when it comes to events, which I believe is why events franchises tend to have shorter lives. 

Many writers are terrible speakers, and even worse moderators. How important is it for a media brand’s writers and editors to be moderating every session of their events?

This is true. I’m always surprised when someone is a good writer but not very articulate. That happens. The reality is that it’s a massive liability today if you cannot “perform” in a live setting. Just the self-preservation instinct alone should make writers lead a new skill. And it is a skill like any other, which requires reps and a focus on improvement.

I had a realization a few years into my career that this industry is designed to commoditize you and replace you with someone younger and cheaper. I hated public speaking, but I just said yes to any moderating invitation bc it was a way to differentiate. Now it’s a requirement. 

Event Economics

From your experience at Digiday, what % of a media brand’s revenue should come from events, and what kind of profit margins do you look for from events?

There’s no set percentage. Depends on the brand and the space. In a market like Digiday’s, events are going to be a much bigger percentage of revenue because your entire purpose is matching a buy and a sell side. That’s very different than a local newspaper. 

What % of event attendees were paid subscribers?

I found there wasn’t much overlap between the two groups. That’s because the customers of our events were typically sales people. Subscriptions were sold to people seeking insights, and that was often a different group of people. That can be a good thing because you need to monetize the entire audience.

Talk about how sponsors view events vs. advertising (on websites, in newsletters, podcasts, etc.)

I’m in B2B, so my sponsors almost always view events as a sales development tool. The thought leadership and image stuff is great, but they’re focused on their sales pipelines and how the event/gathering helped build or metabolize it.

I know The Rebooting’s events are sponsor-supported. Do attendees also pay to come to your dinners?

In events – I think of ours as “gatherings,” probably a difference without much distinction – you’re inevitably going to be sponsor-or ticket-driven. Both have their advantages and drawbacks. Mine are mostly sponsor-driven, in that the revenue is derived from sponsors. I offer preferred access to gatherings to TRB Pro members.

How many subscribers did The Rebooting have before you launched your first dinner/event?

It depends on what you consider an event. We did our first at CES in 2023, so maybe like 10,000.

Other Random Stuff . . .

To what extent do you curate your guest list based on who the sponsor wants in the room, or is that not a factor?

It’s very driven by who my sponsor wants in the room. It’s a matter of matching their ICP with my own audience segments. I do all these as collaborations, so it’s a mixture of their prospects and those who are like them as well as those who will make the gathering interesting and successful. I don’t want to be purely a front for sales meetings. 

How, if at all, do you use AI when writing articles, or in any other capacity?

I use AI as a “thought partner” and to mine transcripts for quotes. It basically makes my writing more efficient and effective. I’m not a fan of ChatGPT’s writing, even trained on all of my newsletters. I find it has this annoying tic of always writing it’s-not-this-it’s-that, not to mention the overuse of the em dash. It also tries to call everything “high signal.”

What’s your take on the canceling of Stephen Colbert?

The late-night format long ago entered media’s uncanny valley. This show can exist on YouTube without the band or most of the 200 staffers. Otherwise it will not be able to compete in an Information Space where Colbert’s rivals aren’t Jimmy Fallon and Jimmy Kimmel but YouTubers, TikTokers and whatever else is in a feed that operate with a fraction of the cost base.

Here’s to taking your event business to the next level!

Howard Givner
Senior Advisor | Oaklins: DeSilva & Phillips (M&A) email me
CEO | Heathcote Advisory Group (Consulting) email me

Thanks for reading! Please give me feedback by hitting reply.

Catch up on recent articles:

• Tailwinds

• The View From Private Equity

• Preparing Your Event Business For Sale

• 15 Agency CEOs Walk Into A Bar . . .

• The Silver Bullet to Doubling Your Profit Margins

• A Tale of 2 Acquisitions: Opus Group CEO Shares M&A Insights

If and when you’re ready, here are ways I work with event business owners:

• Business Coaching & Owner Accountability

• Business Diagnostic & Company Valuation

• Growth Consulting

• Exit Planning

• M&A (Buy Side & Sell Side)

Wanna chat? Email me, or schedule an intro call.

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