Glasswing Ventures was named one of America's top venture capital firms of 2026 by TIME and Statista.
“you and Glasswing Ventures were named as one of America's top venture capital firms of 2026 by Time and Statista.”
Person
Rana el Kaliouby
21 episodes · 93 quoted claims
- 16 Sep 2026The ROI on AI is obvious in these industries40m
- 9 Sep 2026Zapier wants to be the AI hub where all your agents connect38m
- 22 Jul 2026WorkLab: Culture, not tech, softens AI’s impact24m
- 20 May 2026How fast can you upskill in AI? We did a sprint to find out.36m
- 6 May 2026John Deere's AI vision for future farms39m
- 15 Apr 2026What is agentic commerce? Stripe’s CRO of AI explains.33m
- 1 Apr 2026How AI is reshaping Wall Street37m
- 11 Feb 2026The “ChatGPT moment” for agentic AI39m
- 24 Dec 2025AI’s journey from the lab to the marketplace27m
- 17 Dec 2025‘Like Disneyland when it just opened’: Arm CEO Rene Haas on the AI revolution24m
- 3 Dec 2025Walmart, AI, and the future of shopping, with Walmart CTO Suresh Kumar35m
- 26 Nov 2025Andrew Ng on winning the AI race, with DJ Patil26m
- 1 Oct 2025How Harvey is reinventing legal work with AI36m
- 17 Sep 2025How Microsoft is democratizing safe AI38m
- 27 Aug 2025Inside how The New York Times leverages AI40m
- 30 Jul 2025How Writer is helping Fortune 500 companies become AI-forward35m
- 12 Mar 2025Why AI agents are the future of work, with Marc Benioff30m
- 29 Jan 2025Your ‘AI crisis’ is totally normal but you’ll be fine, with Ethan Mollick34m
- 27 Nov 2024How to make AI more responsible, with Navrina Singh38m
- 20 Nov 2024How agentic AI will save customer service, with Bret Taylor38m
- 9 Oct 2024Debunking AI myths, with Jeremy Kahn39m
In fall 2020, during Covid, Rana el Kaliouby asked Rudina Seseri for advice on whether to raise more funding for Affectiva or explore an exit.
“This is about six years ago. Now it was the fall of 2020, so it was during Covid.”
Rana el Kaliouby says Harvey AI has developed AI products for law firms and has seen success.
“Companies like Harvey AI, right, have developed AI solutions for law firms, and they have seen success.”
Kaliouby says her fund has invested in Odyssey, a world models company.
“We've made an investment in a company called Odyssey, which is a world models Models, Yeah, company.”
Pioneers of AI is a Wait What original produced by Megan Tan, with Eve Trow as executive producer.
“Pioneers of AI is a Wait What original. Our executive producer is Eve Trow. This episode was produced by Megan Tan.”
Rana El Kaliouby says that when her firm couldn't find a PitchBook MCP on Zapier, PitchBook told them to use its own MCP directly.
“We couldn't find their MCP on Zapier, so we asked Pitchbook and they were like, No, no, no, you can just like use our MCP directly.”
Rana El Kaliouby says Microsoft cancelled Claude Code licenses over cost and that some companies spend about $7,500 per employee on tokens.
“So we've seen companies like Microsoft cancel their cloud code licenses because of costs, and also other companies are spending about 7,500 per employee on tokens.”
Rana el Kaliouby says she started Affectiva out of MIT in 2009, before smartphones were common, to bring computer-vision-based emotion algorithms to the world.
“So I started the company out of MIT, um, in 2009, and we were so early. We were basically pre-smartphones and trying to bring these, like, computer vision-based algorithms to the world”
Rana el Kaliouby says half of the Fortune 500 companies used Affectiva to test how people respond to content, products and services.
“So half of the Fortune 500 companies use us to test how people respond to content and products and services.”
Rana el Kaliouby says Affectiva was sold to a Swedish publicly traded company in the automotive space.
“We also, um, ended up selling the company to a Swedish publicly traded company in the automotive space.”
Rana el Kaliouby says Affectiva's technology was used in the automotive setting to understand driver engagement, attention and drowsiness.
“how are drivers engaged and driver attention and drowsiness, et cetera.”
Rana el Kaliouby says over 90% of human communication is carried in facial expressions, body language, gestures and vocal intonation rather than words.
“It turns out over, um, 90% of how humans communicate is in your facial expressions, your body language, your, you know, hand gestures, your vocal intonation.”
Rana el Kaliouby says AI is largely oblivious to nonverbal signals and focuses only on the words people use.
“AI's completely oblivious to these nonverbal signals. It's just focused on the actual words you're using.”
Rana el Kaliouby says her fund is an investor in Tough Day, whose conversational AI agent Tuffy helps people with workplace challenges.
“We're an investor in a company called Tough Day, and their conversational AI agent is called Tuffy.”
Rana el Kaliouby says Blue Tulip Ventures trained a chief-of-staff AI agent named Blue, which works on tasks overnight.
“We just trained a chief of staff AI agent for our, uh, for for my fund, Blue Tulip Ventures, and we call her Blue.”
Rana el Kaliouby says her fund's investment thesis is human-centric AI that augments and amplifies human abilities rather than replacing people.
“our investment thesis is human-centric AI. So we believe AI ought to augment human potential and amplify our abilities, not replace us.”
Rana el Kaliouby says current AI models have imperfect memory and a poor sense of time, such as not knowing what 'Monday morning' means, which complicates agent use in workflows.
“a lot of these models have memory today, but the memory is not optimal. The AIs can sometimes forget things, it'll s it doesn't have a good sense of time”
Rana el Kaliouby says applying AI to an already broken workflow will not fix it.
“if if your workflow doesn't work, using AI to optimize it is not gonna work.”
Rana el Kaliouby says AI coding and co-working platforms get work roughly 60 to 70 percent of the way, with the remaining 30 percent needing substantial effort for accuracy.
“a lot of these AI coding platforms and co-working platforms, that gets you maybe to 60, 70% of the way, but the remaining 30% is actually a lot of work”
Rana el Kaliouby says one of her fund's investment theses is applying AI in vertical, antiquated industries to reimagine entire workflows.
“one of our theses is, um, kind of the application of AI in vertical, like antiquated industries, where you can come in and reimagine entire workflows with AI.”
Rana el Kaliouby says she has two children, a 22-year-old daughter and a 17-year-old son, who sit at opposite ends of the AI adoption spectrum.
“I have 2 kids, my daughter's 22 and my son is 17, and, um, they sit on the opposite ends of the AI spectrum.”
Rana el Kaliouby says proprietary data, such as personal health data, can be a defensible moat for AI companies against off-the-shelf models.
“Data is a moat, right? Do you have access to proprietary data that off-the-shelf models don't have access to?”
Rana el Kaliouby says she will not invest in a business that the next version of AI models could make obsolete.
“if you are worried that the next version of these AI models is gonna render your product obsolete, that's not a defensible business”
Rana el Kaliouby names communication, critical thinking, creativity, collaboration and empathy as uniquely human skills that will stay important.
“So one is communication. We're gonna continue to need to be great communicators, whether in writing or in, like, in real life, so communication is an important one.”
Rana el Kaliouby says companies that succeed with AI have leadership commitment, an experimentation mindset, and keep testing the latest tools.
“one is, uh, commitment from from the leadership that sends a strong signal. Two is, um, this, um, experimentation mindset”
Rana el Kaliouby says she is most excited about AI in health and wellness, combining wearable sensors, multimodal data, and predictive and generative AI, which she says puts us at the cusp of a health-span revolution.
“I call it the trifecta of sensors, data, and AI.”
Rana el Kaliouby says empathy is one of the main ways humans build trust, so AI agents lacking it will affect how much people trust them.
“Empathy is actually one of the main ways humans build trust with one another.”
Rana El-Khalyubi compares Claude's single-user design to Microsoft Word rather than the collaborative Google Docs.
“it's basically not like Google Docs where multiple people can be in the document collaborating. It's kind of more like Microsoft Word, really.”
Rana El-Khalyubi says AI lets people build software by prompting in ordinary human languages rather than writing code.
“You can basically use just plain English or Arabic or Chinese to prompt the AI to build software on your behalf.”
Rana El-Khalyubi believes AI will both disrupt some jobs and create many new ones.
“AI will disrupt some jobs, but it is my fundamental belief that AI will also add a lot of new jobs to the economy.”
The host says OpenAI announced advertisements on ChatGPT and stated that the ads will not influence which products appear in answers.
“OpenAI announced that they are rolling out advertisements on ChatGPT, and they've actually said that these ads won't influence what products you see in answer to queries”
Rana El Kaliouby lists Eric Schmidt, Yann LeCun and Mark Cuban among Samaya AI's investors.
“that includes former Google CEO Eric Schmidt, Jan LeCun, Mark Cuban, who we've had on the show.”
Samaya AI recently announced new investment from Nvidia's venture arm NVentures and from Databricks Ventures.
“you also announced recently a new investment from N Ventures, that's Nvidia's, uh, venture arm, as well as Data Bricks Ventures.”
An ad in the episode states that 86% of the Forbes AI 50 run on Stripe.
“86% of the Forbes AI fifty run on Stripe, along with industry leaders like Salesforce and Pepsi.”
Rana El Kaliouby described an OpenClaw agent that, when stuck on a task, went to a social platform for AI agents (called Multibook in the transcript) to get an answer.
“one of these OpenClaw agents was struggling to complete a task. So it went to Multibook, which is the the social platform, the Reddit for AI agents, essentially.”
Rana El Kaliouby co-founded Affectiva as a spin-out from MIT; the company used computer vision to understand human emotions and facial expressions.
“when I spun up my company out of MIT Affectiva, and we did computer vision to understand human emotions and human facial expressions.”
Rana El Kaliouby interviewed Kyle Law, who is the CEO and co-founder of a company made up mostly of AI agents, over Zoom.
“He's the CEO and co-founder of an AI company. We hopped on a call and we had a Zoom call together.”
Rana El Kaliouby says the AI agents in Kyle Law's company lacked a world model, including a real sense of time.
“one of the epic fails, I would say, of these agents is that they didn't quite have a world model. And so they didn't have a real sense of time”
Rana El Kaliouby cited an MIT study reporting that 95% of organizations see no measurable return on their AI investment.
“there's this MIT study that found that 95% of organizations see no measurable return on their investment in AI.”
Rana El Kaliouby relayed Peter Diamandis's prediction that within a decade organizations will either have adopted AI or be out of business.
“in a decade, there'll be two types of companies or organizations, those that have adopted AI and those that are out of business.”