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This is a summary of an episode of Pioneers, an educational podcast on AI led by our founder. Join 2,000+ business leaders and AI enthusiasts and be the first to know when new episodes go live. Subscribe to our newsletter here.
TL;DR
- Cliff Lerner's startup, Saturday, uses AI to help people build meaningful relationships and combat loneliness exacerbated by the pandemic.
- The app matches users with potential friends nearby and facilitates offline meetups, using ML to refine recommendations based on user feedback.
- Unlike traditional networks optimized for screen time, Saturday leverages AI specifically to get people interacting in real life.
- Cliff sees AI as key to reinventing social networking to focus on creating human connections, not just driving engagement.
We live in the most technologically connected age in human history, yet 60% of Americans report feeling lonely. The COVID-19 pandemic only made the “loneliness epidemic” worse.
Cliff Lerner founded one of the first online dating apps back in the early two-thousands, growing the platform to over 100 million users. Fast forward to today, he’s again placing bold bets — this time on AI-powered social networking. His latest startup, Saturday, aims to help people build meaningful relationships both online and offline.
Cliff has seen firsthand how technology can undermine the very social fabric it aims to create. As loneliness reaches epidemic levels, he wants to leverage predictive analytics to help people forge new bonds focused on fulfillment versus addiction.
We sat down with Cliff to get his take on how AI can play a role in reducing loneliness, and he uncovered exactly how he’s implementing the technology into his app. Check out the full interview here:
The Post-Pandemic Desire for Social Connection
Cliff saw the issue of loneliness get heightened during the COVID-19 lockdowns, when digital connections replaced in-person interactions for over a year. He described this as creating “a lost generation” that will be “very lonely, sad, and depressed” unless new solutions emerge.
“When you think about your friends today, most people met in college and through their first or second job. And this entire generation, because of COVID, didn't go to college in person,” says Cliff.
Cliff recognized that remote work and hybrid learning — trends accelerated by COVID — will continue limiting the types of spontaneous connections that previous generations formed in college or early career stages. Without reimagining how networking happens in this increasingly virtual age, the loneliness crisis may only intensify.
Enter AI: Fostering More Authentic Social Bonds
Artificial intelligence can offer new ways to facilitate the types of social bonding experiences that technology previously struggled to nurture.
By combining user data with predictive analytics and natural language processing, AI can help surface potential relationships that may have otherwise remained undiscovered — then smoothly guide users into rewarding conversations optimized for connection.
As Cliff puts it, “What's missing is a feedback loop. You go out with someone and the product says, how'd it go? What did you like? What did you not like? And if you get enough information, you can feed it into a model where it can start to figure out pretty quickly if you’re going to connect or not.”
AI may even quantify the depth of certain relationships by assessing how often two people communicate and the engagement levels of their conversations. As machine learning models ingest more behavioral data (with appropriate privacy protections), they can continuously refine recommendations to improve connection.
This marks a profound shift — rather than viewing users as data and engagement engines, AI-powered social platforms can recenter distributed networks around human needs for purpose and companionship.
The First AI-Driven Social Network
Cliff’s app, Saturday, represents the forefront of this AI-first approach to social networking. Launched in 2022, Saturday leverages machine learning and geolocation data to answer three key questions:
- Who do I know nearby?
- Who should I know nearby?
- What should I talk about with them?
As Cliff explains, Saturday creates “magical moments in people's lives" by identifying friends, friends-of-friends, and like-minded strangers that users can readily meet up with in real life.
The app only shows users’ approximate locations, not precise positions, helping to alleviate privacy concerns. Saturday's algorithms generate custom icebreakers for starting conversations, easing social awkwardness. The app also facilitates deeper discussion by uncovering non-obvious commonalities between users.
Previously, dating apps would match you based on a series of questions, Cliff explains. These rigid questionnaires often fail to capture real compatibility.
Instead, Saturday’s AI models can also pick up on subtle cues.
As Cliff explains, “With AI, it's going to figure out the hidden commonalities … it was able to say, you two need to connect."
Plus, the app also avoids a pitfall Cliff witnessed firsthand as founder of a dating app company. Most networks fail to solicit user feedback, undermining product-market fit. But Saturday asks users directly: How were your meetups? What did you like or not like?
By factoring responses into its AI models, Saturday creates a self-improving feedback loop. Cliff predicts this will produce exponentially better recommendations over time – a pattern familiar to machine learning practitioners.
AI as Social Networking's Next Platform Shift
Apps like Saturday point toward a future where technology helps us spend less time with screens and more time with each other. Cliff believes AI can elevate digital and physical social networking into a hybrid model where technology expands — rather than limits — human potential.
As Cliff explains, “Great products make something much easier to use by providing more value and less effort for the user."
Saturday exemplifies this maxim by facilitating IRL meetups. Cliff dubs this “solving the IRL problem” of loneliness and disconnection.
However, the key is prioritizing recommendations that get people offline while transparently conveying how data is used.
As AI permeates aspects of everyday life that were previously filled by human intelligence, products like Saturday will increasingly harness predictive modeling and decision support systems to help individuals and groups find connection.
Cliff envisions an app facilitating shared dinners, serendipitous run-ins, and deeper bonding by discovering latent signals in user content and behaviors.
Legacy social networks focus on maximizing engagement within their walled gardens. But as Cliff notes, their algorithms are “hyper-optimized to keep you glued to your computer.” Facebook has even been labeled an “anti-social network” for displacing real world interactions.
In contrast, Saturday leverages AI specifically to get people off their devices.
As Cliff explains, “It's a social app that is engineered to get you off the device...It helps you basically make that [in-person meeting] possible."
Keys to Adoption: Efficiency and Killer Use Cases
AI enables startups like Saturday to quickly build and test cutting-edge social features unimaginable just a few years ago.
As Cliff explains, founders today can streamline development by tapping readymade language models like GPT. His team feeds Saturday’s corpus of user data into a customized GPT to auto-generate polls, icebreakers, and other micro-content.
Rather than large development teams, Cliff can use conversational AI to quickly write marketing copy, formulate growth experiments and discuss new features. He explained how prompt engineering lets him deploy customized social modules tailored to college users in minutes — functionality impossible for legacy platforms.
Modifying prompts directly on his phone, Cliff can deploy new AI-powered features instantly, conducting “live A/B tests” to gauge user engagement.
When combined with rigorous user testing to identify killer use cases, AI-native startups gain an enormous advantage. Cliff shared an example of Saturday users demanding that personalized location-based dining recommendations (which initially seemed extraneous) become a standalone app helping people pick restaurants.
He sees this real-time iterative approach as vital for startups riding the AI wave. It may also require founders to wholly reimagine legacy approaches rather than tacking-on AI into existing systems.
As Cliff explains, "When you have a disruptive technology such as AI, everything you've done before that you've been telling investors is your moat is no longer.”
True transformation may emerge from scrappy startups unconstrained by old ways of operating.
A Reckoning for Traditional Social Networking
Today’s dominant social networking models paradoxically undermine the social cohesion they’re designed to create. Platforms like Facebook, Instagram, and TikTok employ highly addictive algorithms to maximize engagement metrics — often promoting controversial content to grab attention.
Not only do these platforms extract large amounts of personal data, they leave users feeling anxious, isolated, and divided. Plus, by keeping people glued to screens, existing social platforms restrict the time and space for nurturing real-world relationships.
Cliff compared the rise of AI to past platform disruptions led by mobile apps and e-commerce, where "every company that didn't quickly adjust to location and building an app would ultimately die.”
Incumbents wedded to maximizing screen time face existential questions about their societal impact. Saturday's success would force difficult reckonings around whether algorithms deliberately addicting users for financial gain remain tenable.
Cliff pulled no punches in describing this dichotomy: "I want to create magical moments in people's lives. And the magical moment is … There's probably 10 people within a mile from us that we would love to grab a beer with or dinner. And we don't have that information.”
Rather than fearing an isolated future dictated by machines, Saturday offers an inspiring glimpse into AI improving lives by bringing people together. Cliff is betting innovative models emphasizing offline bonds will triumph over attention-maximizing giants lacking social purpose beyond profits.
Prioritizing Human Connections Over Technology
Looking ahead, Cliff stresses that AI should remain firmly anchored to Saturday’s fundamental purpose – creating human connection.
“My vision for Saturday is to create magical moments using location and AI to connect you with the right people," he says. While back-end machine learning does the heavy lifting, users need only appreciate the experience of meeting someone new.
Cliff believes this human focus distinguishes Saturday from more technology-centric networks. He aspires to build "a product that made it very simple to say, ‘who do I know that's nearby and who should I know?’"
In this sense, Saturday's machine learning is a means rather than an end. It remains in the background, enabling more meaningful foreground experiences. Cliff believes keeping the human benefits primary will attract wide adoption beyond early tech adopters.
He dreams that one day Saturday’s AI will power a global network facilitating friendship, romance and collaboration. Cliff explains: “If you happen to be a half mile from me three days from now, shouldn't technology be able to say, hey, you were at that event last week, [she’s] nearby–why don't you grab a coffee?”
