EXCLUSIVE: People Will Let AI Trade Their 'Robinhood Money'— But Not Their Retirement

At the Benzinga Fintech Day & Awards 2025 in New York on Monday, a rare moment of honesty cut through the industry hype: people trust AI with their pocket change, not their life savings. That moment came courtesy of Chris Josephs, co-founder of Autopilot, best known for its viral Pelosi Tracker — and it summed up the mood of a panel titled "A New Era of Trading Tech," presented by WealthCharts.

"People might let AI swing-trade their Robinhood money," Josephs said, "but when it comes to their retirement accounts, they want a human."

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In an era when chatbots pick stocks and AI models build funds, Josephs' point hit home. He's seen it firsthand: millions of Autopilot users follow algorithmic traders or "creators" who run AI-driven portfolios, but few are ready to let automation touch their 401(k)s or IRAs.

"This whole idea that AI will replace financial advisers? It won't," Josephs said. "Trust is going to matter more, not less."

The Trust Premium

The panel — featuring WealthCharts CEO Rob Hoffman, TradeStation's VP of Product, James Putra, and Josephs — explored how AI and automation are redrawing the map for traders and investors alike. While Putra revealed he now trades entirely through Anthropic's Claude, and Hoffman described intuition as the "one algorithm machines can't replicate," Josephs offered the counterbalance: trust remains the final frontier.

Read Also: Anthropic Has A Sharp Edge Against OpenAI—Cheaper Chips

He cited Robinhood's recent acquisition of TradePMR, a firm specializing in adviser-led portfolios, as proof that even digital-first platforms are preparing for a human-AI hybrid future.

"That's the early signal," Josephs said. "No one wants an AI blindly doing everything for them — they still want to know someone's on the other side."

Backing that up, Hoffman — who's famously beaten trading bots in 35 of 42 real-money competitions — reminded the room that markets still reward instinct over code. "If the market were just math," he said, "the P/E ratio would never go past 15."

For Hoffman, AI can crunch numbers, but it can't feel fear — and that's what still separates traders from terminals.

AI May Be Fast — But Trust Compounds

For all the talk about machine learning and market automation, the conversation circled back to one simple truth: the most valuable currency in fintech isn't speed — it's credibility.

Or as Josephs put it, the future of investing won't be AI versus advisers — it'll be the humans who know how to use AI best.

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Photo courtesy of Corynn Egreczky.