Bluffery, herd mentality and a sprinkle of due diligence: this is what happens when 18 venture capitalists play their own version of The Traitors.
Speaking to those involved in the two-week trial of treachery, Sifted heard how the game quickly spiralled into thousands of paranoid WhatsApps, a fake investment committee meeting — and one VC feeding the chat logs into ChatGPT to hunt for killers.
For the uninitiated, the Traitors is a reality TV show in which players attempt to root out a hidden murderer in their midst, inevitably turning on one another in the process.
Ryan Procter and Ana Fernandez, who both work for VC firm Nauta, decided it would make for a great networking format and the pair recruited as many VC participants as they could.
“I'm a terrible liar so I thought this would be a great growth opportunity,” says Hannah Skingle, marketing lead at Frontline VC, who signed up to play.
“I went in thinking, ‘These investors are going to be really manipulative and I'll be the unassuming marketing person to steal victory from them,’” Skingle says, which is almost how it turned out.
The game’s afoot
The game started when the 18 players met for a pub dinner. Fernandez donned a wig — giving her more than a passing resemblance to UK Traitors host Claudia Winkelman — and set out the rules.
Before joining, each participant had to tell Nauta whether they wanted to be a faithful or a traitor. Skingle was chosen to be a traitor, as was Michelle Wilk, a principal at Pi Labs, and Thomas Diehl, a senior associate at Notion Capital.
For the next fortnight, the players had to complete challenges, such as setting up fake companies. Then every evening, a brutal round of WhatsApp voting on who they thought the traitor was.
The faithfuls weren’t doing very well and were repeatedly bumped off. But they did catch Diehl. He was voted off after someone suggested his ears and cheeks had seemed suspiciously red during dinner.
Procter would notify the banished player — "Sadly, you've been murdered” — who in short order submitted a voice note, revealing whether they were a traitor or a faithful.
Skingle, who was in a separate group chat with the other traitors, used her knowledge of the TV show to avoid suspicion. “The key tactic is: Don't get noticed too early,” she says. “The people who go the furthest play dumb.”
Not everyone understood this. "Those who know me personally will be surprised to hear I was murdered for being too vocal,” says Gökçe Ceylan, a principal at Oxx. “I was all but banished the moment I opened my mouth,” says David Houghton, a principal at Antler.
Skingle’s gameplan, by contrast, was to be “medium-engaged” in the WhatsApp chat. She kept notes on how players responded to votes, challenges and banishments. She even jotted up a matrix, which helped her to decide who to kill based on whether they were a threat or an asset.
‘I was a hunter’
Skingle had good reason to be worried about one player: Isabella Vahdati, a principal at Brighteye Ventures, who was obsessive.
Vahdati used the software tool Notion to track votes and keep notes on the slightest flicker of treachery. She even fed the history of the group chat into ChatGPT to see if the bot could help her find the traitors (the AI picked the wrong people).
“I was a hunter,” Vahdati says.
Her greatest triumph came when she caught Notion’s Diehl in a lie. He had suspiciously absent from the group one day, which he explained away with reference to an investors meeting — which Vahdati soon rumbled had never taken place.
“I caught him after doing some digging and making a few phone calls,” Vahdati says.
Besides Vahdati, Ada Venture’s Diarra Smith was the most active participant. “He played a very honest and noble game,” says Skingle. “It came back to bite him. The more active you are, the more data you're giving people, the more they can use against you.”
As more players fell away, almost everyone stopped using the main WhatsApp group. The paranoia drove VCs into separate subgroups, where they honed their alliances.
Vahdati was approaching the final with a near-fatal blindspot: her friendship with Wilk, who was doing a good job of convincing everyone she was a faithful.
But Vahdati grew suspicious of her friend after meeting her one evening before the final. “I could tell she was a traitor because she said she was very worried about being featured in this Sifted article.”
Wilk’s attempts to cast herself as a faithful had backfired. “Ironically what led to my downfall was going to support my friend while she was speaking at an International Women’s Day event,” she says.
The finale
It came down to a nail-biting finale at Nauta’s office last week.
The Nauta team had once again added their flourishes. There was a fake fireplace and the defeated players were in a separate room watching the final on video. Fernandez had her Claudia wig back on.
Skingle, whose paranoia had been slowly building, feared a possible confrontation. “I can do this behind a screen but if it's in person I'll crumble.”
It was a 50:50 finish. Vahdati teamed up with Prosus Group’s Luca Ricolfi — the other remaining faithful — and the pair correctly identified Skingle and Wilk as the two traitors. “Luca’s a Traitors maniac,” Vahdati tells Sifted. “He’s even seen the Italian Traitors.”
The final vote being a tie, it was eventually decided by chance. Skingle was instructed to choose between two bags, containing either a red or green apple. Skingle picked the bag containing the red apple. The faithful had won.
“I was disappointed to fall at the last hurdle,” says Skingle, “but a whole lot lighter for being relieved of my traitorous duties.”
Did the experience teach the players anything about the VC world? “It confirmed we’re all very competitive,” says Vahdati.
Smith was reminded of the importance of trust: "Once spent, it’s difficult to earn back."
“Having high conviction about something isn't always good,” was Procter’s lesson, though people jumping on bandwagons — usually considered a bad investor trait — was certainly useful for the traitors, as they sought to whittle the number of faithfuls down.
Ceylan’s takeaway: “Having a strong thesis and sharing it widely will get you killed quickly.”
