George Kailas joins the show to discuss Fintech, options, and investing strategies that are shaping the landscape of finance. He shares how AI and alternative data are changing investing and leveling the playing field between retail investors and hedge funds. He explains how his company, Prospero, uses AI-powered signals that simplify complex market information, including options sentiment, social sentiment, technical flow, short pressure, and dark pool activity. George discusses the strengths and limitations of using AI for investment research, emphasizing that AI can identify momentum and analyze large amounts of information but may struggle to recognize when a trend is ending or accurately assess risk. He also explains how investors can build a repeatable research process based on their goals, time horizon, and risk tolerance, while using multiple sources rather than relying solely on AI. Today we discuss...
- How AI and alternative data are changing the investment landscape and giving retail investors greater access to sophisticated research.
- The evolution of hedge fund technology from expensive, exclusive information toward widely accessible AI tools.
- The strengths and limitations of using large language models for stock research and investment decisions.
- What investment signals are and how they can simplify complicated market data into easier-to-understand scores.
- How Prospero uses signals based on options sentiment, social sentiment, technical flow, short pressure, and dark pool activity.
- How options sentiment can help investors identify institutional positioning and potential changes in market momentum.
- How AI is used to improve and test signals rather than simply allowing AI to make investment decisions.
- Why investors should develop a repeatable research process based on their goals, time horizon, available time, and risk tolerance.
- The importance of using multiple sources of information instead of relying on AI or a single investment signal.
- How investors can track their decisions and results to determine which signals and strategies actually work for them.
- George's transition from working with hedge funds to becoming an entrepreneur focused on making financial markets more accessible.
- Prospero's business model and its long-term plans to build trust, expand into wealth management, and utilize alternative data.
- The potential for crowdsourced alternative data to create new insights into markets and economic conditions.
- How simplifying complex options data into standardized signals can make sophisticated market information easier for everyday investors to understand.
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Today's Guest: George Kailas
As CEO of Prospero.ai, I’m leading a fintech company on a mission to democratize Wall Street-level intelligence. We use cutting-edge AI—developed in partnership with NYU and refined over a decade—to deliver market-tested signals that empower both everyday investors and professionals. As of June 2nd, our free 2025 Newsletter Picks have outperformed the market by 120% annualized, 77% in 2024 and ~50% in 2023 and 2022. We also maintain remarkably consistent win rates against SPY, ranging between 58% and 61%. Over the years, our tools have helped many improve their financial futures.
I started in finance by teaching myself accounting to land a hedge fund job at 17. Since 2011, I’ve built predictive models across corporate bond demand, equity index additions, real estate pricing, and loan risk—often applying these methods to niche areas just for fun, from sports analytics to health-tracking motion models.
Prospero is the culmination of my life’s work: making elite financial tools accessible to all. I believe AI can be the great equalizer—and I'm passionate about building systems that prove it.
Outside of Prospero, I serve on the Fast Company Impact Council, a collective of creative leaders working on the most important opportunities and challenges in business. I'm also proud to be a Fellow at AI Circle, joining peers from OpenAI, NVIDIA, Anthropic, Meta, Cohere, and Perplexity in shaping the future of responsible, high-impact AI.
Previously, I was CEO of Instadat, an AI company focused on B2B predictive analytics primarily in the Financial Services space.
George's Online Presence: