Most loop failures are not loop-design failures. They are model-capability failures wearing a design problem's clothes. Your termination logic was sound, your goal was testable, your spine tracked state correctly, and the loop still drifted, because the model running inside it could not sustain coherent reasoning across the number of cycles the task required. Claude...
John O'Connell was recently featured in The Wealth Advisor on a fiduciary risk that emerges as AI gets better, not worse. Firms have spent two years worrying about whether AI gives advisors bad answers, but his concern is what happens once the tool is reliable enough that advisors gradually stop checking its work. John...
John O'Connell was recently featured in Professional Wealth Management with an article on a risk most firms aren't pricing into their AI rollout. Firms have spent two years worrying about whether AI tools are accurate, but the bigger question is what happens to advisor judgment once the tool is reliable enough to trust most...
The $5 block trade allocation fee looks manageable in isolation. Run the math across your full account base and it looks very different. Whether your firm runs a simple ETF model or a high-intensity tax-loss harvesting strategy, the economic impact of Schwab’s Block Desk fee depends on three variables working simultaneously: the number of client...
John O'Connell was recently featured in InvestmentNews to talk about how advisors should handle client questions about prediction markets like Kalshi and Polymarket. John says that event contracts can be a legitimate investment thesis, but only when sized for their unusual risk profile: the loss is capped at the position size and resolves on...
John O'Connell was recently featured in The Adviser Times for an article on what AI does to junior advisor training. His core concern is that the "grunt work" new advisors used to cut their teeth on, researching client questions, drafting emails, prepping meeting notes, was never busywork. It was the reps. Building out a...
Your AI pilot will look cheap. That is the trap. The per-task cost that looked trivial in a controlled test does not hold when you put the tool in front of your whole firm, and the gap between the two is not small. Enterprises that scaled past the pilot stage discovered the real cost only...
John O'Connell was recently featured in a ThinkAdvisor Q&A on estate planning now that the estate tax cliff has been repealed. For two years, advisors prepped clients for a 2026 deadline that would have halved the exemption. Then the One Big Beautiful Bill Act erased the sunset and set it permanently at $15 million...
John O'Connell was recently quoted in Wealth Solutions Report on why integrating advisory tech stacks hasn't solved firms' data problems. According to John, integration moves data between systems, but it doesn't create intelligence across them. Tools like Zapier sync fields, not behavioral context. Take CRMs and email platforms. They were never designed to work...
John O'Connell was recently featured in Advisorpedia arguing that firms misdiagnose the advisor shortage. 37% of advisors are planning to retire within a decade and demand is outpacing the talent pipeline, yet most firms treat it as an HR problem when it's an operational design problem. John's prescription is to stop competing for experienced...
