The internet is known for anonymity, which is often used to protect people with nefarious intentions, but hidden identities can also be used for more positive, impactful actions. Such is the case with successful retail investor Sir Jack, an online personality who has gained notoriety and respect from the WallStreetBets community by winning millions of dollars and sharing his strategies.
For those unfamiliar with WallStreetBets, the online communities, which include 14 million members on Reddit and over 500,000 on Facebook, have grown in popularity over the past few years with growing interest in “meme stocks” (stocks that gain popularity through social media) such as Gamestop and AMC. The community that Sir Jack describes in the MSNBC documentary Diamond Hands: The Legend of WallStreetBets as “a very large group of idiots who are fed up with the world … fed up with being told ‘just go to college … be get a job…make a living, honestly, that’s just not realistic for our generation.” WallStreetBets members take pride in sharing successes, failures, memes and tips to offer everyone the opportunity to make money in the stock market.
Meme stocks and WallStreetBets helped users learn about investing and share information about stocks, which led to some investors quickly generating huge amounts of money – including Sir Jack, who turned $35,000 into over $8 million in 21 months – while others suffered significant losses, including the Melvin Capital Hedge Fund, which lost $6.8 billion betting against Gamestop. Sir Jack has become idolized among this community, generating over 50,000 followers across various social media platforms.
On Wednesday, June 7, 2023, Stonks and Andreessen Horowitz hosted a GoogleGOOG Gaming Demo Day in Venice Beach, California as part of LATechWeek. Panelist Andrew Chen of Andreessen singled out one particular audience member, asking, “We’re going to have the man in the big hat, right? I just want to make sure.”
The hat belonged to the CEO of AfterHour, one of the companies chosen to present. During the presentation, CEO and founder Kevin Xu, a former Googler (“Xoogler”) and Stripe engineer, revealed himself to be Sir Jack. The announcement caused a stir in the room, with many in the capacity audience picking up their phones to share messages and social posts.
After the presentation in which Xu described building AfterHour as a platform to take on his mission to help others find success in stock trading, and the rest of the presentations concluded, Xu was crowded with many entrepreneurs, investors and fans in general to they congratulate him and thank him for the revelation.
Brian Penick: This reveal was a big deal, why did you decide to do it and why now?
Kevin Sue: We just launched the app last month and the community is really taking off. I think in order to grow, I have to mix the two worlds. It was becoming increasingly difficult to talk about just Sir Jack or Kevin Sue individually. I believe the community appreciates getting to know who I really am. Knowing my background lends legitimacy to what I’m doing—people wonder if some kid who works at Wendy’s is giving them advice, but instead it’s someone who worked at Google, is an engineer, and wants to build a great place for people , to learn and discuss the stock.
Penny: Did anyone know your identity before this week?
Sue: About 12 people knew, from family and friends to my employees and investors. One of my best friends found out on his own and freaked out, which was funny.
Penny: Do you think this will make changes to your online presence?
Sue: Oh yeah. So I think about it in two parts: this is probably going to change my life a lot. Now that my ex-colleagues and other co-workers and friends know that I’m such a freak online, a part of me that I’ve been hiding for a few years. But it’s also liberating because I can finally talk about it more openly because finances and money are sensitive topics. It’s taboo and we won’t go into specifics, but I and many others want let’s get into the specifics, shall we? It’s just like this weird cultural taboo and I’m finally at the stage where I’m ready to share everything like I used to share as Sir Jack, but now I can finally share it as Kevin Suh. This opens up a lot of new connections and the ability to do videos, interviews, TikToks and cool stuff like that. So I’m looking forward to the next stage now that I can be free and open about what I’m doing as Sir Jack, what I’m doing with AfterHour and just the money thing in general. I am very passionate about money and helping others and now I can talk more openly about it.
Penny: will this change your relationship with online communities like WallStreetBets?
Sue: Well, WallStreetBets, unfortunately, went under after GameStop. I look at it more like an Instagram meme thread to be honest because you can’t scale a SubReddit. It’s just full of memes now. But the spirit, the desire to learn more about the markets, the discussions are still there, spread across the internet. I see this all the time. There are a few offshoots, like SubReddits, offshoots of WallStreetBets that have really good discussions and the occasional Twitter, but it’s just impossible for people to find that high quality of a session, especially because the internet is full of scammers and liars trying to sell a course or something. That’s why we created AfterHour, which has vetted stock positions and people who put their money where their mouth is. So far the discussions have been excellent and people can also enjoy themselves on our platform.
Penny: What’s next for you?
Sue: For me, it continues to evolve our platform in my vision. I want to build the social Bloomberg for Gen Z. The next generation of investors values transparency, social communication, fun and reliability. We have the right DNA and the right primitives to foster a great platform for all kinds of discussions about personal finance, from stocks to crypto, whatever.
More generally, with the revelation, I look forward to continuing to help others on their financial journey. People came into my life that I was able to give advice to, and now I can speak with more authority to a larger audience. Who knows, maybe I’ll become a YouTuber.
A big trend is the rise of financial influencers like Graham Stephan and Meet Kevin, and I see that increasing because people want someone they can relate to, less like TV talking heads like Jim Cramer. Many of us can relate more to these people on YouTube and they also have really good tips and examples; I can only see this trend increasing. Finance is not something people in school want to learn from a textbook, but more so to be exposed to the right community, which is why resources like WallStreetBets and YouTubers are amazing.
Penny: I always ask investors about their market predictions: where do you think we’re headed?
Sue: This is the most confusing market I have ever seen. We feel like we’ve gone from a crazy bull market to a bear recession, then a bull market again; thank you AI! The data I see are the top seven major tech stocks driving this rally. It seems to have a proxy effect for the rest of the market, so it’s all good. Consumer demand is still strong, so the economy feels healthy. I just hope we don’t accidentally fall into another bubble and it grows healthily for the next few years.
Thanks to Kevin Sue, aka Sir Jack, for your time and perspective. For more information on investing and entrepreneurship, I encourage you to read my ongoing series, “Navigating the VC Landscape 2023.” and follow me on Forbes.com.
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