On the weekend of the 17th and 18th of April, I had the pleasure of co-hosting a new virtual conference, which I had spent a good part of the previous months co-organizing with Skelli. The concept was simple: get some rookies to talk about something fun in infosec or osint, or tech in general.

The execution, however, was a lot more chaotic than I had originally foreseen, in equal amounts good and bad. In this post I will try my best to aim for full transparency, talking about what went well, but also exposing some issues we had encountered. This is the main reason why this post took so long to write, because I mulled on it for a long while.

The organization phase

An event like this, virtual or not, requires a certain amount of dedication and of organization. One would usually gather a team of interested individuals to share the load for the entirety of the time relating to the event. My personal first mistake was not involving enough people from the get-go.

Back in December, I floated the idea to Skelli, which got the whole project launched in our minds. We had a wireframe for the event, which we'd host within the constraints of the Digital Overdose Community.

To have a certain platform on which we could promote the conference and other community events, we built a website (from scratch), and that started us off. This took a certain while, but didn't end up encroaching on our timeline. The only thing it did do was solidify my own semi-isolationist mindset ("We don't need help" and other lies we tell ourselves).

The Call for Participants

We then opened up a CFP process, which would last for a few weeks, in which speakers could submit their talk ideas, and then these could be reviewed by an independent group of people.

Not having researched platforms built for that objective, we ended up getting the CFP submissions at our conference email address. This made it extremely complicated to have the CFP's independently reviewed. Because of this, we anonymized the data and copied the titles and descriptions to BusyConf, a conference management and review tool. A week or so later, all the proposals were rated, and we were almost ready.

Fucking up, badly.

Prior to the CFP deadline, I'd personally granted 2 people a deadline extension, because they'd asked ahead of time, one of them citing health reasons and the other having been made aware of the conference only a day or so prior to the deadline.

This turned out to be the most mentally challenging decision I'd make in the entire event, but that story comes up later.

In the meantime, we had our speakers announced, everything was speeding up, and most of the speakers had joined our Discord server. We had made it so that the speakers didn't necessarily need to interact with the community, but still being able to communicate with them in a more efficient manner than email. Not everyone joined, but it was manageable.

Mentoring

One of the main aspects of the conference was that the rookies could be mentored by people already having given talks in the industry, some more prolific, and some recent ex-rookies.

Finding a time for a kick-off session was extremely complicated, because due to the more international scope of the conferene, time zones and availabilities between the mentors and the speakers made the whole thing quite complicated.

Scheduling

3 weeks before the conference, we asked our confirmed speakers to give us their availabilities, and were able to release the conference schedule in time.

This led us onto the final stretch, wherein speakers were prepping their talks, and we were prepping our infrastructure and OBS layouts.

During the final stretch, we had 2 speakers drop out of the running for personal reasons, changes which we adapted in our schedule.

On the day of...

The weekend of the conference arrives, and we are already 2 speakers down.

Not too stressed out, I install the AV setup and test my network conditions. Everything is nominal, and we can get started.

I botch the intro a bit due to my excitement, but everything else is on track!

We move some speakers along to avoid having holes in the middle of the schedule, and all goes according to plan. Day 1 is finished.

Day 2 arrives, and we notice that one of our speakers that was supposed to send us a video file has not responded, and another desisted by tweet.

Thankfully, I'd asked James whether he'd be up for a panel consisting entirely of ex-rookies, and he said yes. I also contacted some ex-rookies and a few of them were up for it (thank you very, very much, by the way).

In the meantime, we had 2 AV issues on the second day: 1 where music superimposed on a talk (and we had to start over the first 2 minutes of it), and the other where the network connection cut and YouTube ended the stream, resulting in me quite stressfully setting another one up.

However, at the end of the day, everything was kind of okay, and everyone enjoyed themselves -- or at least said so. We had a lot of stress, but in the end we coped with it and enjoyed ourselves tremendously, so it felt awesome on our end.

The W. conundrum

Around the time of mentoring, one of our "late submitters" -- let's call them W. -- desisted from speaking at the conference for fear of harassment (which is perfectly valid), but then changed their mind after some reassurances were given. They were also -- quite understandably -- annoyed at the email they hadn't received (because of the Microsoft Exchange outage), on their main and secondary email accounts (both being Outlook accounts).

Later on, W., had closed their DM's on Twitter, which was the channel I was using to inform them that we'd emailed them. So we sent them another email, saying that we hoped they would get the previous one.

Then and there, W. announced that "[they are] happy to announce that [they are] no longer participating in this conference". That should've been the end of it, but this being our first conference, we wanted everyone to have a good time. Skelli responded directly saying that we would remove W. from our schedule, signing with their name and not the default "The Digital Overdose Conference Team".

Suddenly, W. appeared to change their mind (which, in hindsight, should have been at least the 3rd red flag out of all of our exchanges).

Following this, W. made a few requests for changes in their bio and talk description (about 3-4), but only one at a time (therefore making us edit, build and deploy the website multiple times and taking a lot of time).

A day or so later, I personally receive as a DM from W. a link to a Tweet (below), dated from a few months earlier, and provided with absolutely no context.

This somewhat "Cold War"-esque exchange made Skelli and I think that it was commentary on my personal contributions to the conference.

As such, I felt extremely uncomfortable having subsequent exchanges with W., and we attempted to remove them from the conference. That wasn't as effective as we'd anticipated (and I will get into a personal opinion about the situation afterward), and another person recommended we just hear them out.

So Skelli and W. organized a call to "clear the air", which W. delayed multiple times until after the conference. (As of 20/07/2021, this call has not yet happened).

So we were effectively stuck between a rock and a hard place.

On the day of their talk, a tweet by W. announces to their followers they won't be speaking for medical reasons. It would have been nice to know that ahead of time, but it created a situation of load trade-off: I didn't have to feel uncomfortable having them on, but I needed to fill the gaps.

Conclusions

Running a conference is fun, but exhausting. Doing a second run at organizing and hosting this type of event is not a certainty, but if it were to happen, I would tell myself to do it with a greater group of people and to delegate as much as possible.

This also helps if at any point a speaker gets too complicated, we can have a group chat and collectively decide to yeet them because the risk to our sanity is too great.

Asking for help is a skill I'm horrible at. That's a thing I'll need to work on in the future.

My opinion on conference speakers

The few times I've spoken at a conference, I've always tried my best to be as helpful and straightforward as possible, to avoid wasting other people's time. I've gone from the approach that it was a privilege to have been selected to share some of my insights at events, and that I should treat it as such.

I'm deathly aware that being selected for an event does not mean we are entitled to it, as actions have consequences.

So if I were to be rude and passive-aggressive with conference staff, I would half expect to be yeeted off of the roster.

That approach is the one I explained and that we tried to take with W., and is probably an approach we will have to make more explicit in a potential future iteration.