Community//

Charles Edge of Bootstrappers: “Visualize the hallway track”

Visualize the hallway track. The hallway track is hard. I feel like discussing things in hallways at conferences has always been a great way to meet new people (I have lifelong friends I met that way at professional conferences). Being able to discuss sessions in breakout rooms (e.g. in Zoom) has felt forced, but chatting […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

Visualize the hallway track. The hallway track is hard. I feel like discussing things in hallways at conferences has always been a great way to meet new people (I have lifelong friends I met that way at professional conferences). Being able to discuss sessions in breakout rooms (e.g. in Zoom) has felt forced, but chatting in Slack or Discord has been great. There, speakers and organizers have been able to chat with people we might not otherwise have ever met. We’ve seen an increase in those kinds of channels even at live events for years, so it stands to reason that’s a permanent impact.


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 Charles Edge.

Charles Edge is the CTO of bootstrappers.mn and former director at Jamf. He holds 35 years of experience as a developer, administrator, network architect, product manager, entrepreneur, and CTO. He is the author of 20 books and more than 6,000 blog posts on technology, and has served as an editor and author for many publications. Charles also serves on the board of directors for a number of companies and non-profits, and frequently speaks at and helps organize conferences including DefCon, BlackHat, LinuxWorld, the Apple Worldwide Developers Conference, and a number of Apple-focused conferences. Charles is also the author of krypted.com and a cofounder/host of the MacAdmins Podcast and The History Of Computing podcast.


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 a bit about your “childhood backstory”?

Sure! I started in computers in school and studied them while at the University of Georgia. After bouncing around the world consulting, I happened to end up in Los Angeles right when the Mac switched to a Unix-based operating system. Having worked on Unix for a long time, I accidentally ended up being one of the people who knew how to wield the new servers and so was asked to write a few books on the topic. From there, Apple devices started showing up in huge companies and I was lucky enough to end up documenting much of that over the course of a couple dozen books and keynoting and getting involved in dozens of conferences over the years.

Can you tell us the story of what led you to this particular career path?

I always loved computers. And my dad made me read a lot. I was going to be a writer when I started at the University of Georgia, but after learning BASIC and PASCAL in high school, I got exposed to object oriented languages and realized that computers were actually gonna’ be something I might make at least minimum wage at! That is, until I realized I could write about computers. At least it I made minimum wage at it for a little while!

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?

I was giving a presentation on a tool at DefCon one year and some guy was in the audience and corrected me on a point. I was sure I was right but after the session he comes up and we talked and I realized he was a world famous developer who wrote the tool I was talking about. Moral of that story is unless you’re completely sure-sure-sure, don’t say something!

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?

Hackers: Heroes of the Computer Revolution by Steven Levy was a big one for me. I think one of the bigger impacts it had was how I realized that while I was supposed to be pretty knowledgeable about the IT industry, I had a few things just dead wrong. That led me on a path to my next book, which I’m about 80% of the way finished writing, on the history of computers. Every single page I realize how little I knew going into this project. It’s actually been a wonderful experience!

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

“The best way to predict the future is to invent it.” Alan Kay I don’t know I would have been inspired to start writing my own software if I hadn’t of heard this quote. Sometimes I’m asked to write something or help someone someone else build something that I think is better than any ideas I have. But Kay is an inspiration not only for that quote but for many of his contributions in computing overall.

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 would love to! I have been doing smaller events for non-profits since college. And I started working with Macworld conference back when Apple ran it. I’ll never know as much as the organizer of that show (Paul Kent) has forgotten about conferences. He is a real class act. When I started working at Jamf I was asked to get more involved with the Jamf Nation User Conference, which has a couple thousand attendees at this point, and worked with these two guys Dusty and Cam to select speakers and develop a schedule. Over time, I ended up running that until it got turned over to Katie English, who is about the best I’ve ever seen at it. I’ve also helped here and there in much smaller capacities with DefCon, MacSysAdmin, and a few other venues.

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

I’d say it started with attending a few, like Comdex maybe a decade ago. They never turned out that great to be honest, but it was fun to watch the technology evolve. In that time we saw webinar technology and streaming get really good. I am a host or cohost for three podcasts and we routinely live stream one of them. So it wasn’t a huge surprise when most of the conferences I work with or do presentations for announced they were going to try a virtual event when the pandemic started. I was lucky to be involved in a lot of those conversations about how to pivot and I have really enjoyed how the organizers have stepped up to the challenge.

At this point, I’ve been involved in a number of virtual conferences this year as an organizer, paid sponsor, speaker, and keynote speaker. I’d say the best story of the year in virtual conferences would be when I did the keynote for Everyworld in Australia and

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?

I love the authenticity of seeing speakers, executives, and planners in their homes. Some have seemed staged, others have just felt really prepared. There’s a difference. CEOs from Okta, Jamf, and other conferences streamed out of their living room, occasionally with a child or dog hopping in screen. Those moments are fun and authentic. Jamf also sent halo lights and other tools to speakers to help get really quality recordings or streaming. Being prepared to make great content is important. I have seen a few really contrived moments, which is fun when done to be funny but comes across weird otherwise. For example, a popular UX Research conference had a puppeteer MC a conference. It was funny. Her guidance throughout the show helped keep the sessions flowing, fill gaps with technical difficulties, and no one took the skits too seriously.

As speakers, I’m finding a lot of us are a little more prepared and a few are way less prepared. I’ve spoken at one conference in Sweden (macsysadmin.se) for 10 straight years and I usually have my slides done before I embark on the flight there, but get the opportunity to rehearse it in my head plenty during the travel. This year, with kids at home needing help with schoolwork and no time on airplanes I didn’t have that. However, since it was recorded I was able to do a few takes to get it a little better. Of course I had to find a time when the kids weren’t home so there wasn’t a bunch of background noise! That conference used static pages and just posted the movie files for all the sessions at the beginning of the day. There was a Slack channel we could then all discuss the sessions during the day.

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 one aspect I haven’t loved is sponsoring. At a live event, people stop by a booth and we talk about products and capture leads. We can run what amounts to webinars during events but the conversion rates to qualified leads have been pretty poor. This is an area that needs a bit more innovative thinking about how to actually engage with people looking for solutions in meaningful ways. One organization at a conference did a trivia night. They used a little web tool that cost them about ten bucks for the night and it took a lot of work to put the questions in the system but the people playing along had fun showing off their industry knowledge. One even got a new job out of it! I guess the moral of the story is that as with a lot of things during the pandemic, a little more intentionality goes a long way.

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

It comes down to the amount of planning. I have done a few where the organization running the event paid a bunch of money for platforms and some went great and others didn’t. I don’t think you need to spend a lot of money. Some of the corporate conference had great platforms but less energy than others that did things on the cheap. It’s about how much work goes into testing and making sure attendees don’t have to hunt for links to join sessions. As an example, I did the keynote for Everyworld in Australia ( https://auc.edu.au/everyworld/about/ ) and the organizers sent us a recording guide that was made just for the conference. It was a work of art. They streamed sessions but also setup a Discord server so the speakers could chat with attendees during the streaming of recorded sessions. That level of planning and intention was refreshing and it was a blast to get to discuss the session while people were watching it rather than wait for them to come up afterwards and ask questions!

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

There’s the platforms that connect conference and big packages and the live streaming software. But the two tools I’d definitely look at are instant messaging during sessions (the main tools there would be Slack and Discord) and using tools like the OBS project ( https://obsproject.com ) to get quality video embedded in a cutout. To me though, it’s less about technology and more about being really intentional about the experience and putting on a quality show.

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. Visualize the hallway track. The hallway track is hard. I feel like discussing things in hallways at conferences has always been a great way to meet new people (I have lifelong friends I met that way at professional conferences). Being able to discuss sessions in breakout rooms (e.g. in Zoom) has felt forced, but chatting in Slack or Discord has been great. There, speakers and organizers have been able to chat with people we might not otherwise have ever met. We’ve seen an increase in those kinds of channels even at live events for years, so it stands to reason that’s a permanent impact.
  2. Dry run everything. None of us want to have the attention of our attendees wander of during tech fails.
  3. Queue speakers that you can hear them. Next time I hear “can you hear me?” I’m gonna’ pop.
  4. Expect a fail. Anticipate a speaker can’t get online or they cut out in the middle and have a contingency plan.
  5. Have fun with it! Life is to short to run conferences if doing so isn’t a blast.

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?

Ask people who might attend the conference what they want. What people in my industry want and need and their access to various types of technology is different than some others might find. It’s best to start with the people we’re doing these things for and then reverse engineer a solution to meet their needs.

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.

Virtual conferences are a great example of technology reacting to the changing needs of organizations and people at home. I hear pitches from businesses seeking funding all the time and have seen a boatload to fill the gaps for conferences. But they’re just an example. Look around and anywhere you see a gap, that’s an opportunity for an innovative new product, open source project, or company to support people who just want to do awesome things. If there’s one thing I have felt great about these past months, it’s the incredible innovation that’s happening, and that anyone can make the next big thing happen.

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.

Vint Cerf. Because TCP/IP!

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

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

The Hallway Principle

by Rebecca Barnes-Hogg
Julien Christian Lutz, professionally known as Director X for Operation Prefrontal Cortex, Design Exchange, Toronto, Ontario, Canada, 2019, Photographer: Ajani Charles
Community//

Professionally Known As Director X, Julien Christian Lutz Is Saving Lives In Toronto Through Meditation

by Ajani Charles (E-mail: [email protected], Instagram: @ajaniphoto)
Community//

Leadership Edge with Matt Garratt, Managing Partner of Salesforce Ventures

by Christina D. Warner, MBA
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.