Money Tree Investing

How AI will Transform the Future of Trading with John Bartleman


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John Bartleman, the CEO of TradeStation, is here today to talk about how AI will transform the future of trading. John shares his background and the evolution of TradeStation from early backtesting software to a full-service broker, while explaining how its roots in systematic trading differentiated it from competitors. He outlines major industry shifts, along with the benefits and challenges of dark pools and institutional order flow. We also dive into how AI is transforming trading, as John describes his own use of MCP-enabled AI agents for research, portfolio analysis, trade structuring, and more. AI may radically reshape fintech analytics and asset management, enabling traders to work more efficiently and pushing the industry toward fewer traditional money managers and more AI-driven decision systems.

We discuss...

  • Record money market fund levels are being widely misinterpreted, as the balances often represent defensive positioning rather than pent-up buying power.
  • Many investors mistakenly assume large cash balances automatically signal a coming equity influx, ignoring the behavioral reasons people hold cash.
  • The tariff headline created rapid swings in futures markets, revealing how sensitive positioning is ahead of the election.
  • A sharp crypto drawdown triggered widespread stop-loss cascades across major tokens, amplifying downside pressure in a classic liquidity vacuum.
  • Seasonal trends typically provide a tailwind this time of year, but macro uncertainty is preventing markets from fully leaning into the pattern.
  • Investors are observing a notable rotation away from mega-cap tech and toward value-oriented and small-cap sectors.
  • The dispersion between the top seven tech stocks and the rest of the index remains near historic extremes.
  • Elevated cash levels and volatility suggest institutional investors are selectively adding risk rather than buying broadly.
  • Market breadth is improving modestly, but not enough yet to signal a durable trend reversal.
  • Short-term traders are capitalizing on intraday volatility spikes driven by headlines and algos.
  • Longer-term investors remain focused on earnings resilience and margin stability across sectors.
  • Companies with global exposure are expressing concern about potential policy shifts after the election.
  • Energy and industrials are gaining attention as potential beneficiaries of a reflationary environment.
  • Tech remains bifurcated between AI-driven leaders and more traditional software names experiencing deceleration.
  • Crypto markets continue to influence risk appetite, even among investors who do not directly hold digital assets.

Today's Panelists:

  • Kirk Chisholm | Innovative Wealth
  • Barbara Friedberg | Barbara Friedberg Personal Finance
  • Diana Perkins | Trading With Diana

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For more information, visit the show notes at https://moneytreepodcast.com/the-future-of-trading-john-bartleman-766

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