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How AI & Retail Investors Are Changing Wall Street

Retail investors have more choices than ever before. From traditional stocks and cryptocurrencies to prediction markets and AI-powered investing, today’s market is flooded with opportunities and plenty of noise. But how can investors separate genuine market insights from hype? In this interview, Anna Insana, Co-Founder and Head of Growth at Upside, and David Ma, Founder and CEO of Upside, explain how they’re building a platform designed to give everyday investors access to collective market intelligence.

Anna and David discuss how Upside allows investors to anonymously benchmark their portfolios against a community of verified retail investors, providing real-world insights into portfolio performance without revealing personal identities or account balances. Rather than following influencers or social media personalities, the platform focuses on actual investment behavior, helping users understand how their strategies compare with others who are actively investing in today’s markets.

The conversation also explores how artificial intelligence is transforming investing. While AI can rapidly analyze financial filings and automate trades, Upside aims to bridge the gap by combining AI with real investor behavior. Looking ahead, Anna and David share their vision of creating a new generation of investor-driven market indices based on the collective actions of Main Street investors, offering a fresh perspective on how retail participation could shape the future of investing.

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