Heather Mason of Caspian Agency: 5 Things You Need To Know To Successfully Run a Live Virtual Event

Tyler Gallagher
Jan 19 · 15 min read

The number one thing to understand if you’re going to successfully produce a virtual event is that you aren’t going to be able to replicate the in-person experience. Simply putting events online is a fool’s errand, so don’t even bother trying. And once you’ve adopted that mindset, you’ll quickly realize just how liberating this can be. You can’t replicate exactly the in-person experience online, but you absolutely can create something new and exciting that people will remember. That should be your barometer for success, so don’t start with the wrong goal in mind.

As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Heather Mason of Caspian Agency.

Heather Mason founded Caspian Agency in 2005, intent on bringing a scientifically-based strategic discipline to white-glove event planning. Her expertise in the innovation and social good business space has led to successful projects around the globe for the Skoll World Forum, Rockefeller Foundation, Kew Foundation, Code for America, Participant Media, among many others. Prior to launching Caspian, she managed events for Charles Schwab, producing conferences across the country, and worked in Hollywood and the early Internet boom.

Early on, Heather recognized that there was no codified method for creating and executing strategic events at scale. In response, she created the Caspian 10 Essentials. This methodology has been taught internationally, and it is featured curricula for the San Diego State University Masters in Meetings and Events degree program where she is a Senior Fellow and also an instructor.

Heather is a board member of Social Venture Circle (SVC), American Sustainable Business Council (ASBC), Utah State University Alumni Board, and a strategic advisor to Women Founders Foundation and Purposewerx. She is a consultant on convening design for The Rockefeller Foundation, and a frequent keynote speaker, MC, and moderator. Heather is also the creator and founder of SUREFIRE Girls and CEO-U.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us the story of what led you to this particular career path?

I have always wanted a life of adventure. My favorite movie as a child was Indiana Jones, and I wanted to be Indy. Or at least, I wanted to make movies like those movies. In fact, when I ran for office in high school, I roped my father into helping me make an 8-foot tall boulder, my best friend into hanging up a sign that read “Let the Adventure begin!” that would fall to the gym floor with the pull of a string, and a group of friends into dressing up as ninjas. My friend pushed the button on the stereo to the famous Indy theme, the sign rolled down, and I ran out and fought off the ninjas. The boulder then rolled in, and as it chased me out the door I shouted, “Vote for Heather!” I’m proud to say that I won. That position led to me getting a leadership scholarship at Utah State, where I was in charge of all the Broadway shows and speakers coming to campus. In essence, what I do today is what I did at college. I then did stints in Hollywood development and production, the Cannes Film Festival, marketing in the first dot-com boom, and produced the largest non-officially sponsored event at the Sundance Film Festival before starting my own business. And it all has absolutely been an adventure. Still is!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

That’s easy. When I first started my company, we were producing an event at a boutique hotel in San Francisco. It’s a gorgeous old hotel, and the guests were very excited when they arrived. My mother was working for me on the registration desk (as happens when you’re just starting out), and she pulled me aside to tell me that people were coming back after checking into their rooms and saying that they didn’t get a single King, but had a single Queen instead. I went to speak to the GM, pretty upset that they’d made this mistake with so many of our guests. He told me, “This is an old hotel and the rooms are small, we don’t have any King beds. Everything in this hotel is a single or double Queen.”

Oops. So I went back to my mother and the other women at the registration desk, called them over, and told them, “Tell everyone that as they are experienced cosmopolitan travelers, surely they are familiar with a EUROPEAN King bed, which are smaller than American sizes, and of course that’s what this high end boutique offers.” They went to everyone and it worked. Phew!

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I loved The Chronicles of Narnia so much as a child that I named my company after Prince Caspian. But another more recent example is David and Goliath by Malcolm Gladwell. I love everything he writes, and this book was almost like a ‘Wicked’ style retelling of a story that I’d heard and read a million times. It’s a lot like the lesson the film industry continues to remind me of — everything we tell ourselves about our lives, about our past, what is happening to us, and/or what could be, is something we have the power to craft. We own the narrative of our own life. That is a powerful lesson, and it’s one that I think needs to be repeated often.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite is from Archimedes: “Give me a lever and a place to stand and I will move the world.” In other words, everything is actually possible. It really could be possible to move the earth. Never limit yourself based on what is surrounding you right now. I grew up in Idaho Falls, Idaho on the numbered streets. We didn’t have a shower, so I washed my hair in the sink. Now I have two showers in my house! Figure out what you want and how long the path, or lever, is to get there. If it’s truly impossible, pick something else that you want to go after and then just do it!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

I’ve worked in the arena of producing events for over 20 years. I’ve produced events at Sundance, Cannes, the Olympics, at the UN, for The Rockefeller Foundation in Bellagio Italy, in multiple cities around the world for Participant Media, and many others around the US (New York, San Francisco, LA), including ones on ocean-going vessels with helicopters, submarines, and billionaire CEOs. For the past 15 years, Caspian has produced the Skoll World Forum in Oxford, England.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

Caspian has produced several virtual events, especially in the past year. Last spring, we helped in the design and production of the Eat Forum for The Rockefeller Foundation, which drew over 4,000 attendees. This was notable because we began the project with a typical event online model, and ended up changing it into a broadcast news model instead. We later hosted an online discussion for the Beijing+25 Initiative, and helped to produce a multimedia report that can now be found on the Rockefeller website.

More recently, Caspian worked with a confidential client on a full day event (10 hours), wherein screenwriters were gathered together to share and showcase clips of their work. This was an incredible experience, because it proved that with the right model, it is possible to create a highly engaging full day program without fatiguing attendees. Most recently, Caspian produced an event that brought together experts from around the world on Artificial Intelligence to debate and discuss their views, policies, and ethics around AI. Similar to the screenwriting event, this was a lengthy program, but we took a chance of letting attendees break off for a lengthy 90 minute one on one session in the afternoon for deeper discussion. We were worried that people wouldn’t come back, but instead, they all came back reinvigorated and refreshed.

In general, Caspian consults with a wide variety of clients about how to reimagine their events for the virtual realm, and every client has an interesting and unique story behind them. For example, we’re currently working with one client to help them reimagine their exhibit hall as Superbowl commercials. It’s a different medium online, so we’re helping them to find new ways to showcase their products.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

In my opinion, TEDWomen last fall completely knocked it out of the park. Now, it’s true that they created their own bespoke technology, and not everyone has the resources to do that. But they basically took the best of the web and combined it with the features they needed, which is what you need to do if you want to create an interesting and engaging day of content. For TEDWomen, that basically meant creating YouTube+. They had a typical speaker screen, but surrounded it with features that helped attendees engage and interact with each other, including matching attendees with others who have similar interests. And it was all done fantastically well and seamlessly. If you want to replicate this success, you have to look at what people get addicted to online, and then find ways to replicate that experience within your own event. TEDTalks flourish on YouTube, so TEDWomen didn’t just put their event online. They created such an inspiring and exciting YouTube+ experience, I personally couldn’t tear my eyes away.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

The number one mistake people make when trying to produce virtual events is trying to directly copy over an in-person experience online. You can’t just put events online. Your title has now changed. You are no longer an event producer. You’re now a TV producer and YouTube creator. That’s your new hat, so put it on and own it.

I believe that we will see much more sophistication in the virtual realm going forward. 2020 saw a lot of people throwing spaghetti against the wall. But I think in 2021 and beyond we will see a revolution in virtual events. We will see a higher level of production value and narrative. We will also see more clarity in the language as we evolve, meaning it won’t just be “virtual events”. Instead, we’ll start to divide into various titles, such as shows (broadcast level production with in-studio hosts), discussions (Zoom), and work groups (Muro/Mural type tools). In a sense, in 2020 we were Friendster, but now we’re gravitating towards MySpace. I think some folks will get to Facebook by the middle of the year because things are moving quickly.

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

My personal favorite at the moment is Glisser. It’s a platform that replicates the YouTube experience, but with robust add-ons such as chat rooms, polling, and extensive metrics data. But what I like the most about it is that it has a TV show interface, and in general, I like technology that does that. Online events are all about having a screen that is surrounded by other features that attendees can use to interact with the content. In short, a super-interactive TV. That’s what virtual events are all about.

Are there any essential tools or software that you think an event organizer needs to know about?

This may sound silly, but at a really fundamental level, event producers simply have to understand how the Internet works. This will help you to understand the terminology and how the technology works. “I don’t understand technology” is no longer an option. You have a responsibility to learn about the technology of the Internet and what is out there. And by that, I really do mean understanding bit rate, transfer protocols, and how the various bits bounce around the world to get to your screens. If you do this, you’ll not only be more knowledgeable, but you’ll also be more confident and nuanced in your discussions with services providers.

When it comes to products, Hopin is certainly one of the industry leaders in conference platforms. They just acquired Streamyard, so it’s going to be an interesting platform to watch. And of course, you need to know Zoom. They’re proceeding with their Zapps store, which is mimicking the apps store in Apple. This means that they’re allowing technologies to be built from their foundation, and it’s going to be fascinating to see how this develops. It has the potential to become the focal point of where the industry goes for event technology.

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

  1. The number one thing to understand if you’re going to successfully produce a virtual event is that you aren’t going to be able to replicate the in-person experience. Simply putting events online is a fool’s errand, so don’t even bother trying. And once you’ve adopted that mindset, you’ll quickly realize just how liberating this can be. You can’t replicate exactly the in-person experience online, but you absolutely can create something new and exciting that people will remember. That should be your barometer for success, so don’t start with the wrong goal in mind.
  2. Say goodbye to the concept of time when envisioning your online event. Think critically about whether or not an event truly has to be live. In-person gatherings are exciting and electric, but they are also incredibly stressful for event producers due to what I refer to as the ‘Tyranny of Minutes”, namely, that we never have enough time to produce the event that we want. With virtual events, all of this stress goes away, as we now have the opportunity to pre-produce and pre-record the content. Speakers going off-script and derailing a panel? Now you can fix them in post. Pacing starting to drag? Time for some edits. When you get right down to it, it is not necessary for the majority of events to be live when they are happening in virtual spaces, so use that to your advantage.
  3. It is not necessary to completely reinvent the wheel when it comes to virtual events. This is because the switch to virtual spaces is not in-person to online. It’s in-person to broadcast, and thankfully, we have decades of broadcast history to draw from when making this transition. The key thing to remember is that virtual spaces reach your attendees through a screen, so create all of your content with that in mind. Curate it in a way that encourages attendees to surf within your event’s ecosystem. Develop it with longevity in mind, as you can keep content online long after the event is “over”, thereby reaching ever-increasingly larger audiences. When it comes to producing virtual events, always think like a broadcaster.
  4. In the past year, one of the biggest challenges I’ve heard people talk about with regards to virtual events is the issue of interactivity. How do we make these virtual events interactive? It’s a valid question, but I want to challenge the idea that more interactivity leads to more value. Or more specifically, what exactly do we mean by interactivity? How are we defining it? It doesn’t have to be all chat boxes and polls. Instead, imagine you create an entire ecosystem of content that attendees can bounce around and explore as they wish. That agency to define their experience of the event on their own terms can be the interactivity, and a pretty engaging one at that.
  5. In-person events were often a series of smaller events brought together by the constraints of physical space. With virtual events, these constraints no longer exist, so when it comes time to create your event’s content, the first thing you have to do is deconstruct the event down to its core content blocks. Once you’ve done that, you can focus on each one individually to ensure that they are all being made fit for purpose. As an added bonus, attendees can then access these blocks in whatever order they choose, thereby allowing them to create their own event horizon that is tailored to their specific needs and wants.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

The number one step for producing a virtual event is to reimagine and deconstruct. What I mean by this is reimagine what events are capable of. Virtual spaces liberate event producers from so many constraints, so take the time to think outside the box of what these new spaces can achieve. Deconstruct the event down to its smallest pieces and determine the specific goal of each one. As I’ve said before, this will require a significant change in your mindset, but once you do, the possibilities are endless. You’re not limited by the screen in front of you. If you take the time to really think about what your audience wants and what gets them excited, you’ll find not just the right answers, but creative and unique ones as well.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

One of the things that I find most frustrating about the business world is the hyper-focus on VC funding and finding the next billion dollar company. Sure, those stories are sexy and exciting, but they also only account for a tiny fraction of the overall businesses that exist. Especially when it comes to businesses that are owned by women. There are approximately 13 million women-owned businesses in the US, and their average revenue is 143K. A lot of these businesses are not fancy or flashy, but they have the potential to provide stable and comfortable financial security for their owners.

Now, if we could give these business owners the resources to increase their revenues by just 20%, we could change the financial trajectory of women in the United States. Studies show that women invest up to 90% of their income back into their families and communities, so just imagine what could happen if 13 million women-owned businesses had the proper resources to significantly increase their revenues.

I started Caspian back in 2005, and I don’t even want to know how much money I wasted because of things I simply didn’t know or understand. There are so many lessons that I learned the hard way, and I don’t want others to repeat my costly mistakes. That’s why I founded an organization called CEO-U, with the goal of teaching small and micro-size business owners how to properly manage and scale their business. Giving them the resources to properly understand the tax code, contract law, and insurance policies. Most very small businesses don’t need or want large venture capital. But they do want and need knowledge, and the right knowledge could potentially double their revenue. No, these women aren’t going to be the next Jeff Bezos, and that is fine! They don’t want to be. I don’t want to be. We need to normalize that. It is fine to start a business that just makes you comfortable and happy. And our economy and communities will be better off for it if they do.

I actually self-funded the very first CEO-U conference out of pocket because I am that passionate about this issue. The best part is that I know the collective impact model of CEO-U works, because I’ve since used it with my SUREFIRE Girls Conference in LA and Salt Lake City. My hope is to scale CEO-U across the country, because it has the potential to really change the financial situation of these businesses for the better and in a hurry. It drives me crazy that everyone is constantly focusing on the unicorns of business, but no one is talking about the microbusinesses. That’s where the potential for real change is.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Oprah. No question. I would give anything to have breakfast with Oprah. She is an inspiration, she is tough love, she is business, but above all else, she is authentic. Helping others understand their true purpose seems to be her highest mission. And I think just spending time with her to tell her ideas, hear her perspective, and probably get tough love as well would be life changing.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Authority Magazine

Leadership Lessons from Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

Tyler Gallagher

Written by

CEO and Founder of Regal Assets

Authority Magazine

Leadership Lessons from Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.