The beginning of March for Jon Colston, like for many, was looking grim. The 44-year-old entrepreneur had to close down the mortgage startup he was developing as the economy took a beating from the coronavirus pandemic.

Fortunately, he had a side gig that was about to earn him a six-figure payday. Colston, who has a background in data analytics, taught himself the ins and outs of cybersecurity through videos and other online resources, and since late 2018, he had been moonlighting as an ethical hacker, helping companies find bugs in their code.

With other distractions gone, he quickly found himself doing freelance cybersecurity work at all hours of the day, up from about 10% of his time before the coronavirus outbreak began.

"My ritual for the last few weeks has been: wake up, roll out of bed and onto the computer, hack until I can't stay awake anymore, go to bed and repeat," Colston told Protocol last week. As a hacker he goes by nickname @mayonaise, and he lives in Las Vegas with his wife.

In early April, his dedication was rewarded. Verizon Media, which for the last several years has focused on building relationships with the ethical hacker community, held its live hacking event in partnership with bug bounty platform HackerOne. It was the first such virtual event for both organizations who decided to experiment with the new format due to the coronavirus pandemic. Verizon gave 50 hand-picked hackers from 13 countries access to some of its closely guarded code and paid them generously for any bugs they found.

"It was a playground," said Colston, who earned more than $200,000 from the event after reporting about 30 bugs. In total, Verizon Media paid out $673,988 in bounties. Colston credits about half of his success to a single, critical issue that he found on several servers. He declined to elaborate on the bug's details, but he said he's seen it affect several organizations since last May.

"I call it the MOAB, the mother of all bugs. It's everywhere, it's high in critical impact, it's across technologies," he said.

The weeklong virtual event was an "incredible success," said Luke Tucker, senior director of community at HackerOne.

And it almost didn't happen.

The event was originally scheduled to be in-person based around the Black Hat Asia cybersecurity conference at the beginning of April. Fifty of the top security researchers on HackerOne's platform would be flown to Singapore, where they would meet with Verizon Media's security team and prod part of its Yahoo product line. Verizon acquired most of Yahoo's internet business in 2017.

But by late February, with the RSA cybersecurity conference barely going off as planned, organizers from Verizon Media and HackerOne decided to pull the plug on an in-person event in Singapore.

"I remember we were on the curb at RSA, and we were talking about the current situation, where the virus was going, and we decided we didn't want to put any of the researchers or our employees at risk," said Sean Poris, director of product security at Verizon Media. "So we agreed at that moment we were going to have a zero-travel policy on our event."

"It was obviously the right decision to cancel the Singapore event," Tucker said. "And the second good decision was to make it virtual."

Making virtual lemonade

HackerOne has put together 20 in-person hacking events over the last five years with more than a dozen organizations, including Dropbox, Shopify and the U.S. Air Force. Live bug-hunting events have become an important way for companies to entice independent security researchers to help find problems in systems before criminal hackers do. Like many other organizations with in-person gatherings planned for this year, HackerOne was forced to completely rethink its playbook. Tucker said that HackerOne had brainstormed what adding a virtual element to its events would look like, partly inspired by esport competitions, but it didn't have plans to try it out anytime soon.

"We were trying to crack that nut and figure out the right way to roll out a live event experience that would be really dynamic and interesting, and then COVID-19 happened, and we were able to take the lemons of not going to Singapore and make lemonade," he said.

Pulling off a virtual hacking event poses unique technical challenges, unlike other virtual conferences or events. Organizers used a wide range of tools to make sure that the security researchers were able to collaborate with each other, share bugs with Verizon Media, and do everything in a way that would keep all the information confidential and out-of-reach from criminal hackers.

Verizon Media declined to provide details on the scope of the event, citing confidentiality, but the company informed the hackers of the specific products they would probe about two weeks before the event took place. During that gap, the hackers were encouraged to perform reconnaissance and testing in the same way that a criminal group might extensively surveil a network before trying to breach it.

"I was so excited about the targets we were given; it was a very rare opportunity that was provided to us, and I wanted to make the most of it," Colston said.

Hackers communicate on Zoom during Verizon Media's virtual hacking event.Screenshot: Courtesy of HackerOne

For the event itself, organizers made use of a smorgasbord of remote work tools. Hackers used Slack, Zoom and Google Hangouts to communicate with each other and Verizon Media's security team. Organizers used Discord and Twitter to broadcast leaderboard positions and answer spectator questions about how to start a career in cybersecurity. At one point, hackers used the drawing website skribbl.io to take a break and play a mass game of Pictionary.

Although the event wasn't originally planned to be virtual, Verizon Media would consider doing similar competitions in the future, according to Poris. "It built a foundation we can launch from for future events," he said.

Another HackerOne customer has already signed up to hold a virtual live-hacking event in June, Tucker said, though he declined to name the company due to customer confidentiality agreements.

Pros: More participation, more concentration

Thanks to going virtual, organizers were also able to open the event up to many more people. Thousands of spectators — many of them students stuck at home — were able to watch the hackers and ask them questions through Twitch livestreams and YouTube videos. In-person events typically have educational workshops, Tucker said, but they're generally reserved to about 20 to 50 people invited from nearby schools.

"Where we really spent a lot of time was asking how do we open up the opportunity and provide a social experience to as many people as possible," he said.

Verizon Media was also interested in expanding the event's reach, in part to attract new employees, Poris said, adding that he's hired ethical hackers in the past. "There are way more openings in the security field than we have people. The more we can mentor and educate and get people pumped into the field to reduce that pressure overtime, [the better]," he said. He also wanted to "share our brand to researchers and have folks understand how important security is to us."

From the hackers' perspective, participating in a virtual event likely makes it easier to find bugs, Colston said. He was able to work from the comfort of his home, on his own workstation, and didn't have to deal with travel hassles or distractions.

"I'm one of those people that needs complete focus," he said. "I say I'm going into my hacker hole — time slips away, and I'm completely focused on what I want to achieve. That definitely helped out in submitting more reports."

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Cons: Outages, time zones and canceled karaoke

The event would end up having some unique challenges: A bug show-and-tell during the closing ceremony livestream, for example, was briefly knocked offline because the person hosting it from her home in Indiana had her power knocked out by a nearby tornado. Time zones were also difficult; participants came from 13 countries, including Argentina, Germany, Russia and New Zealand, so some hackers had to keep odd hours to take part in question-and-answer sessions and daily updates.

"One thing you lose in a virtual event is that there's something special about the concentration of security researchers, the HackerOne folks, and us all coming together physically and being able to break bread, chat, and argue about the merits of a given finding. That's just facilitated so much more in person. We really spent a lot of time thinking about how to create as close as possible that community feeling," Poris said.

Not everything could be re-created: Poris said he especially missed not being able to go out to karaoke with the hackers at the end of the event.

"It's become a tradition, and we missed that this year," he said. "But the closing ceremonies were really strong, and we recorded the show-and-tell sessions, which will help us understand what's going on in the minds of security researchers."