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David Siegel

Co-founder and Co-Chairman of Two Sigma, the New York-headquartered quantitative investment firm applying machine learning to finance; computer scientist with a PhD from MIT who established the firm in 2001

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Overview

David Siegel is Co-Founder and Co-Chairman of Two Sigma [1][2]. Siegel holds the professional designations of computer scientist, entrepreneur, and philanthropist [3].

Career history

  1. Co-Founder & Co-Chairman2001 to PresentTwo Sigma
  2. Chairman2011 to PresentSiegel Family Endowment

Education

  1. PhD, Computer ScienceSep 1983 - Jun 1991Massachusetts Institute of Technology
  2. BSE, EECSSep 1979 - Jun 1983Princeton University

Insights & ideas

The through-line

Across everything, Siegel argues the same thing from different angles: artificial intelligence is an unfinished scientific problem, not a finished engineering one, and the greatest risk is that the field convinces itself otherwise. He traces his interest back to being ten or eleven years old with punch cards on NYU's computers, and says that decades of thinking about what it takes to make something intelligent have left him convinced that "we've scratched the surface" [1][12]. The corollary he cares about most is institutional rather than technical: keep the research ecosystem broad, keep the money flowing to people working on ideas other than the fashionable one, and keep the environment curious enough that people are willing to push on boundaries [1].

The second, quieter thread is that technology is a lever on society rather than an end in itself. He describes his own agenda as having no agenda beyond wanting the world not to fall apart, and says his foundation work is aimed at nudging people to think about the role of technology in society in a positive way and to consider doing things differently, whether in a business or more broadly [1]. Through the Siegel Family Endowment he has backed organisations working to prepare society for the impact of technology [12].

On why AI is not a solved problem

His central disagreement with the way AI is discussed today is with the claim that the science is done. "One of the big disagreements I have sort of with the way AI is characterized today is that uh a lot of people are basically calling it a solved problem and we just have to you know scale it up and we're done," he says, and his answer is "maybe, but I think unlikely" [1]. The reason is empirical: intelligence is "a diverse set of capabilities," and what you actually observe in current systems is "remarkable achievement in one dimension but maybe less remarkable in another" [1]. That asymmetry is why the deepest question for him remains "how does the brain do it" [1]. He is clear that he is not a pessimist about the current wave, and he discusses AI advances and the use of algorithms to analyse data as genuine capability [4]; the objection is to certainty, not to progress.

On transformers, elegance, and warning signs

Presented with the Silicon Valley view that you should change everything except the transformer, Siegel takes the opposite position. He grants that it is a very focused architecture for processing tokens and predicting the next one, that it is clever, effective and "has a lot of mileage," and that it was in a real sense stumbled upon [1]. His question is probabilistic: what are the chances that the thing we stumbled upon is the solution? It is possible, but "there are endless other ways that you could look at how do you build reasoning into a system," and the ordinary history of technology is that you stumble on something good, discover its limits, and then something related or entirely unrelated turns out to be better [1].

He offers a specific diagnostic for where the field stands. The architecture "started out as a very elegant design" and "it's no longer elegant"; it is "turning into hackery in a sense where people are layering all kinds of things onto it to make up for shortcomings that they've observed" [1]. The original hope was that scaling the elegant design alone would keep making it more intelligent, and the shift toward overlays, especially the agent layer, is evidence that hope has quietly been abandoned [1]. None of this means the current line stops working soon. It means the field should read it as a warning sign rather than a victory lap.

On not starving out the alternatives

The practical stake in all of this is funding and attention. He is emphatic that people excited by the current architecture should work to make it better, and that this is a good thing, but "we shouldn't starve out people working on other ideas. That's actually what I care about" [1]. The danger he names is the field talking itself into a frenzy that this is the solution [1].

The same logic drives his defence of academic research. He argues there is a misunderstanding at the heart of reducing research funding, which is the assumption that the point of a lab like MIT's AI lab is to make discoveries, start companies and create economic value. In his view the primary purpose is different: "the purpose of academic research is to build this kind of vibrant community of young people who are well equipped to conquer problems throughout society," and he notes that fewer than half of PhD graduates stay in academia at all [1]. Consistent with that, he is involved with Open Athena, a nonprofit that places AI engineers with university research teams to strengthen their research infrastructure [1].

On curiosity as an operating culture

Siegel says the culture he built at Two Sigma was modelled on 545 Technology Square, where he spent roughly eight years on his PhD [1]. What he took from it was not a research agenda but a set of conditions: the place made him extremely curious, expanded his mind in ways that served him well, broadened his horizons, changed his expectations of the world and taught him discipline [1]. He argues that environment transfers to a corporate setting, because "to get the most out of a group of people you got to make them curious. You want to make them feel that they can push on the boundaries and they shouldn't be afraid to do so," which is what an academic research environment does at its best [1].

He credits a similar insight to David Shaw, who as a computer science PhD and former Columbia faculty member believed in the power of computing at a time when computer scientists were treated as second fiddle, as the technicians who put things together [1]. Siegel says that belief was the reason he took the job, and that Shaw was well ahead of his time in creating an environment now common across the tech industry [1]. In 1991 computers were still primarily a back office function and were not considered a key part of decision making; the transition has been gradual and AI has accelerated it [1].

On how culture teaches us to fear AI

He makes a straightforward observation about the stories societies tell themselves. In the US, films have essentially been made about how AI and robots are dangerous, from 2001: A Space Odyssey onwards, while in Japan robots are portrayed as helpful and kind, and "AI just has never been portrayed as a good thing in culture" in the West [1]. He traces a good deal of today's fear back to Hollywood. Asked whether that is good because it makes people cautious or bad, he refuses the frame: "it's just inserting a bias. That's all. I mean, it's neither good nor bad" [1]. The ask is only that people recognise they have watched a lifetime of evil AI movies and that the stereotype may be overblown [1]. He is also careful to say that 2001 did not make him want to pursue AI; that came from being fascinated with computers as a small child, and anyone involved with computers in the 1950s and 1960s wondered when a machine would be more intelligent than a human [1].

On confidence levels and what "two sigma" means

Asked what the firm's name means, he first gives the honest answer that the domain name was available [1]. The substantive answer is about the epistemics of investing. If you demand six sigma confidence, which might be the right bar for manufacturing quality, "you'll never make an investment" because you can never get that much confidence about the future [1]. At the other end, half a sigma means "you're just kind of going to the casino" [1]. Investing therefore requires deliberately choosing a level of confidence you will act on, and two sigma is that choice.

On getting to children early

He treats his own childhood access to NYU's computers, punch cards and all, as the accident that set the trajectory of his whole life, and generalises from it: something that happens to you at ten or twelve can actually change your life [1][12]. That is why he has focused on Scratch pretty much since its inception, as a way of inspiring young kids [1]. He is blunt about the gap: "I think we in our society don't do a particularly great job of inspiring young people to want to achieve" [1].

On technology, society and the shape of online life

His interest in technology's social effects extends past AI. He has held up the mass shift online during the pandemic as an unplanned large-scale experiment in remote work, education and shopping, one that revealed both things that worked well and things that did not [12]. He has also been critical of the format of internet communication itself, arguing that social media has reduced information to short snippets stripped of context, and that persuading society to spend more time digesting what is happening around it would be a significant improvement [12]. Underlying it all is the claim he makes about his own life: he has devoted it to solving hard problems with technology, and he believes that better harnessing technology in general, with AI as one part of that, would make society substantially better [1].

Takeaways

  • Treating AI as solved and merely needing scale is the view he most disputes; intelligence is "a diverse set of capabilities" and today's systems are strong in one dimension and weak in another [1].
  • The transformer was clever and effective but essentially stumbled upon, and the shift from an elegant architecture to layered agents and add-ons is a warning sign that scaling alone stopped delivering on its promise [1].
  • His main concern is not that the current approach is wrong but that its dominance will starve funding and attention from people pursuing other routes to machine reasoning [1].
  • The primary value of academic research is training a community of young people equipped to attack problems across society, not generating companies; cuts made on the company-formation logic misunderstand what the money buys [1].
  • He backs that view in practice through Open Athena, which places AI engineers with university research teams to improve their research infrastructure [1].
  • Two Sigma's culture was modelled on the MIT AI lab environment, on the principle that you get the most from people by making them curious and unafraid to push boundaries [1].
  • Western film has consistently coded AI and robots as dangerous where Japanese culture codes them as helpful; the point is not that fear is right or wrong but that it is an inherited bias [1].
  • In investing there is no six sigma confidence available, so you must pick the confidence level you are willing to act on, well above the coin-flip of half a sigma [1].
  • He argues internet communication has collapsed into context-free snippets, and that getting society to digest information more slowly would be a meaningful change for the better [12].

Media & appearances

  • The TreatmentApple Podcasts
    The Treat: David SiegelWriter-director David Siegel has collaborated on films with Scott McGehee for more than three decades. Their most recent feature is 2025’s 'The Friend,' starring Naomi Watts with a very large and well behaved co-star. But for The Treat, Siegel goes so
  • Invested by AlephApple Podcasts
    David Siegel, Former CEO of Meetup & Investopedia, on Solving the Loneliness Crisis, Rescuing Meetup from WeWork, and Why Israelis are Happier than AmericansOn this episode of Invested, Michael Eisenberg sits down with David Siegel, former CEO of Meetup, former CEO of Investopedia, former President of Seeking Alpha, author of Decide & Conquer, and founder of the Israel Tech Mission. David has spent more th
  • The OpinionsApple Podcasts
    David Brooks, E.J. Dionne and Robert Siegel Take Stock of 2025The Conversation convenes this week with the Opinion columnist David Brooks, the contributing Opinion writer E.J. Dionne Jr. and the former host of NPR’s “All Things Considered” Robert Siegel to unpack a week of turbulent news across the globe, in
  • Becoming a CEOApple Podcasts
    David Siegel on Culture, Kindness, and the Cost of LeadershipWhat does it really mean to lead at the highest level? For David Siegel, former CEO of Investopedia and Meetup, leadership isn’t about titles or power. It’s about culture, kindness, and carrying the weight of decisions no one else wants to make. In
  • Tom NelsonApple Podcasts
    David Siegel: Comparative thinking and motivated reasoning | Tom Nelson Pod #295David Siegel is a tech entrepreneur from Silicon Valley. He has been researching and writing about climate since 1990. X: https://x.com/PullNews Longevity: https://www.infinitegameoflife.com/ ========= AI summaries of all of my podcasts: https://tomn.substack.com/p/podcast-summaries My Linktree: https://linktr.ee/tomanelson1
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    How to Turn Any Idea into a Real MovementThe Ryan Meetup group has nearly 2,000 members whose common bond is simple: their first name! David sits down with founders Ryan Rose, Ryan Cousins, and Ryan Le to hear the amazing origin story of these three partners spreading the Ryan gospel. The Ryans reveal how they were able to take a Meetup of just three members—themselves—and turn their first big event into a viral blowout with hundreds of attendees including journalists from the New York Times, NPR, and The New Yorker. Plus, the Ryans discuss how they’ve actually helped people legally change their name to Ryan, and their future plans to break the world record for the largest gathering of people with the same first name. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    An Entrepreneur’s Guide to Community BuildingBefore he was a co-founder of General Assembly and founder of Common co-living spaces, Brad Hargreaves was a Meetup organizer hosting tech events in New York. In this conversation with David Siegel, a legendary entrepreneur talks about how he’s made community building an essential part of his business strategy. Learn how the right community can help you make a major change in your life, whether it’s a long-distance move or a career change. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    How to Grow from Traumatic ExperiencesAmnoni Myers has persevered through addiction, abuse, abandonment, homelessness, and the many difficulties of the foster care system to become an author and nationally recognized child welfare advocate. Her success story (recounted in the new memoir You Are The Prize) is not only a tale of resilience and self-discovery but a brilliant guide for anyone struggling to thrive after a difficult past. Amnoni and David sit down to discuss how to be proactive in your own healing, the truth about safe spaces and why they matter, interdependence as a core value, and so much more. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    Platonic Longing: Make the Friends You WantKat Vellos is a certified connections coach and the author (plus illustrator!) of We Should Get Together: The Secret to Cultivating Better Friendships. She and David sit down to discuss why platonic relationships between adults are so important, why they’ve become difficult to maintain in the modern social landscape, and how to buck that trend through intentionality. Their conversation includes everything from the growing fear of awkwardness and online parasocial relationships to original ideas for replacing the old small talk and overlaying friend time with your other commitments. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • The How of Business - How to start, run, grow and exit a small business.Apple Podcasts
    Avoiding Partnership Disputes with David SiegelAvoiding the Partnership or Founder Disputes that can ruin your small business with attorney David Siegel. David is a partner at Grellas Shah, LLC - a full-service boutique law firm, with a focus on startups, technology, and venture law, as well as...
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    How to Handle StressDeborah Gilboa (aka “Dr. G”) is a family physician, as well as a frequent feature on TODAY, Good Morning America, and The New York Times. She’s fluent in American Sign Language, a leading expert on stress management strategies, and the author of From Stressed to Resilient: The Guide to Handle More and Feel It Less. Dr. G and David sit down to discuss why change of all sizes is so hard for people to cope with. They chat about everything from anxiety-relief life hacks, brain chemistry, and runaway feelings to Dr. G’s mission to redefine the word “resilience” in everyday usage. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • United States of DramericaApple Podcasts
    Episode 89 - David Siegel, former LA Dodgers exec and President of LA Sports CouncilWe talk to sports exec (and sports fanatic) David Siegel. We discuss his love of sport, pitching to his heroes and how bad some of the national anthems were at Dodgers Stadium. David tells us about a career in a baseball front office, sport as entertainment and his greatest memories with the Los Angeles Dodgers. We talk about LA's sporting riches, his work with the LA Sports Council and what is coming next for this sports-mad city. And we talk Johnnie Walker Blue, Sandy Koufax and Tommy LaSorda.
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    From Bankrupt to Better than EverDavid Meltzer is a three-time international best-selling author, top 100 business coach, host of top entrepreneurial podcast The Playbook, and so much more. It’s easy to see why David Siegel thinks he “may be the busiest person alive!” The two Davids sit down to discuss Mr. Meltzer’s transformative path from multi-millionaire business prodigy to losing it all, then building his life and career back the right way. They touch on the dangers of arrogance, the power of an open heart, how to stay energized, and how to move on from mindsets that are holding you back. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    The Power of Language in BusinessArjay Ruggles has done it all. He was a self-described Neopets supernerd, a successful makeup artist, an IT specialist, and a sex worker before founding HomeRoom, the first-ever Discord community management agency. These days, Arjay is on the cutting edge of community-centered business, helping companies navigate the evolving tech landscape while retaining real-world values. He and David discuss the dos and don’ts of startups, user experience versus human experience, and how to stay true to yourself in a business context. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Success Story with Scott D. ClaryApple Podcasts
    David Siegel - CEO of Meetup | Decisions That Make or Break All LeadersListen to and watch David Siegel - CEO of Meetup | Decisions That Make or Break All Leaders from Success Story with Scott Clary on Apple Podcasts. April 5, 2022. Duration: 52m.
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    Friendship Advice for Every Life StageDanielle Bayard Jackson taught high school English for six years, where she learned a thing or two about coaching people through interpersonal issues. Now, as a certified friendship coach, Danielle helps adults improve their overall wellbeing by teaching them how to make new connections and create more depth in their relationships. She and David chat about why adult friendships are a necessity, not a luxury. From there, they dive into parents modeling healthy friendships for their kids, how to be more intentional with social plans, and the often overlooked value of loose ties. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    Becoming a Proactive IntrovertGerald Soriano grew up in Hawaii, then lived in Milwaukee, Cleveland, and the Bay Area. Everywhere he’s gone, Meetup has played an important role in his story. From helping him land a pivotal internship to making lifelong friendships, Meetup became a constant in Gerald’s life. These days, he’s using the platform as a leadership opportunity through co-organizing the AR/VR Creators Meetup group. Gerald chats with David about spreading the aloha spirit through Meetup, how to pinpoint and pursue your own reason for being, and why you should keep smiling through these difficult times. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Order your copy today!
  • The Art of CharmApple Podcasts
    A Guide to Leadership Decision Making | David SiegelIn today’s episode, we cover leadership and decision-making with David Siegel. David is the CEO of Meetup, the largest platform for finding and building local communities, and the author of Decide & Conquer: 44 Decisions that will Make or Break All Le
  • Changing Lives Selling KnivesApple Podcasts
    David Siegel - Building CommunityDavid Siegel is the CEO of Meetup, the largest platform for finding and building local communities. He has 25 years of experience as a technology and digital media executive leading organizations through innovative product development, rapid revenue...
  • Keep Connected with Meetup CEO David SiegelApple Podcasts
    Awkward Isn’t Awkward, It’s NormalJenn Bane and Trin Garritano are the duo behind the cult favorite podcast Friendshipping, as well as a book of the same name that explores the art of finding friends. No strangers to the Meetup community, Jenn and Trin’s Meetup Live event had the most RSVPs of 2021. They’re back to discuss creating new friendships, deepening current friendships, and reconnecting with friends from your past. The conversation expands to the parallels between friending and dating, the do’s and dont’s of workplace friendships, and what you can learn from 42 seasons of Survivor. Ranked as one of the top 25 CEO podcasts on Feedspot, Keep Connected with Meetup CEO David Siegel is a podcast about the power of community. For more details on other episodes, visit Keep Connected on the Meetup Community Matters blog. We hope you’ll keep connected with us. Drop us a line at podcast@meetup.com. If you like the podcast, be sure to subscribe and leave us a rating on Apple Podcasts and Spotify! Learn more about Keep Connected host David Siegel’s experience as a leader and decision maker in his book, Decide & Conquer. Pre-order your copy today!

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