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Ten years across private equity, retail, and asset management. Real technical experience covering infrastructure, cloud, security, and trading systems. Written plainly to help other engineers navigate this world.

Michael Harlow
Michael Harlow // sys.ghost  ·  Boston, MA
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AI tools are genuinely useful, and I use them daily. But in an environment that touches money movement and client data, 'it worked in the demo' is not a risk assessment. Here's what careful actually looks like.
Aug 4, 2026 · 10 min read
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Security Aug 4, 2026 · 10 min read

Why We Have to Be Careful With AI: The Risks That Don't Show Up in the Demo

Why We Have to Be Careful With AI: The Risks That Don't Show Up in the Demo

I want to say upfront that this isn't an anti-AI post. I use these tools every day - for drafting, for debugging, for chasing down an obscure error message at 2am. They've made me faster. What this post is about is the gap between "faster" and "safe to hand a decision to," because in financial services that gap is where the incidents live, and I've watched teams walk straight into it because the demo looked so convincing.

The demo is not the risk assessment

Every AI vendor pitch follows the same shape: a clean example, a confident answer, applause. What you don't see in the demo is the 1-in-50 case where the model is equally confident and completely wrong. That failure mode - fluent, well-formatted, wrong - is the single most dangerous property of these systems, because it doesn't look like a failure. A stack trace looks like a failure. A hallucinated compliance citation formatted in perfect house style does not.

I've seen this firsthand: an internal tool summarizing regulatory filings produced a summary that was clean, well-organized, and referenced a clause that did not exist in the source document. Nobody caught it in review because it read like every other correct summary that tool had produced. The fix wasn't a better prompt. It was accepting that anything downstream of that tool needed a human checking against the source, every time, not just when something looked off.

Where this actually bites in a financial environment

  • Hallucinated specifics presented with total confidence - numbers, clause citations, API parameters, account details. The model doesn't have a "low confidence" tone; overconfidence is uniform across correct and incorrect output, which is exactly why it's dangerous in a context where a wrong number moves money.
  • Data leaving the boundary you think it's inside - pasting a client statement or an incident writeup into a consumer AI tool to "just clean up the wording" can mean that data is now sitting on infrastructure you have no contract with, no audit rights over, and no idea how long it's retained.
  • Prompt injection through untrusted content - if an AI agent reads incoming emails, tickets, or documents and takes action based on what it finds, anything in that content can potentially steer the agent. A support ticket that contains instructions aimed at the model rather than the human reading it is not a hypothetical anymore.
  • Automation bias - the more often a tool is right, the harder people stop checking it. This is a people problem wearing a technology costume, and it gets worse exactly as the tool gets better, not better.
  • No audit trail for a decision that needs one - "the model suggested it and I approved it" is not the same as documenting why a trade, an access grant, or a client communication happened, and in a regulated environment that difference matters when someone asks later.

What "careful" actually looks like day to day

None of this means don't use the tools. It means the controls have to match what's actually at stake, not what's convenient.

  • Match the check to the blast radius. A model helping draft an internal wiki page needs a light touch. A model whose output can trigger a wire transfer, change an access policy, or go out under the firm's name needs a human who verifies against the source before anything happens - every time, not spot-checked.
  • Treat AI output as a claim, not a fact, until verified. Especially anything with a specific number, date, or citation attached. The specificity is exactly what makes it convincing and exactly what makes it worth checking.
  • Know what data is allowed where. Client data, MNPI, anything covered by a client agreement's confidentiality terms - that has a defined set of approved tools with actual contracts and data processing terms behind them, and "I pasted it into a chatbot to save time" should not be a sentence anyone on the team can say without it triggering a real conversation.
  • Give agents the least privilege that lets them do their job, nothing more. If an agent only ever needs to read a ticket queue and draft a response for a human to send, it should not also hold credentials that let it send unsupervised or touch a production database. Scope the blast radius before you scope the prompt.
  • Log what the model saw and what it did. When something goes wrong - and eventually something will - "I don't know what it was looking at" is a much worse position than having the input, output, and the human decision on record.
  • Red-team the thing before it's customer-facing. Someone on the team should be actively trying to get the agent to do something it shouldn't - follow an injected instruction, leak a system prompt, take an action outside its intended scope - before an actual adversary does it for free.

The part that's easy to get backwards

The instinct in a lot of orgs is to treat "AI governance" as a committee that meets quarterly and produces a policy document nobody reads until an incident forces them to. That's backwards. The controls that actually work are boring and operational: least-privilege credentials, logging, a verification step sized to the actual risk, and a clear list of what data is and isn't allowed near which tool. That's the same playbook as every other system that touches money or client data - AI doesn't get a different set of rules just because it's newer and more impressive in a demo.

The honest version of "be careful with AI" isn't fear of the technology. It's the same discipline we already apply to anything with access to production and a client's money - we just haven't finished admitting that this counts as that.

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Hey, I'm Michael Harlow.

Senior Systems Engineer · Boston, MA · Writing as sys.ghost

I have spent over a decade building and maintaining infrastructure at the intersection of technology and financial services. My career has taken me through three distinct sectors -- technology, private equity, and asset management -- and each one changed how I think about what reliable infrastructure actually requires.

I started in general IT, which is where most engineers who did not go straight into software end up. Data centers, networking, on-call rotations, learning to label cables properly because unlabeled cables are a promise that someone else will suffer later. The work taught me that almost every sophisticated system is, one layer down, a collection of unglamorous fundamentals that either hold or do not. I still believe that. I still label everything.

Private equity came next, and it was a different world. The infrastructure stakes there are less about uptime and more about data integrity. When deal teams are making acquisition decisions based on data you are responsible for, and when a due diligence process has a hard deadline that does not move regardless of what broke overnight, your relationship with reliability changes. A wrong number in an LP report does not cause an immediate incident. It causes a conversation in a partner meeting six weeks later, and by then you need to reconstruct what happened from imperfect records. I became obsessive about data provenance in PE and I have not stopped.

For the past several years I have been in asset management, supporting trading and investment operations infrastructure. This is the environment I find most technically interesting. The compliance requirements are demanding, the legacy systems have long institutional memories, and the tolerance for operational errors is genuinely low -- not just in terms of business impact, but in terms of regulatory consequence. When markets are open, there is no fixing it after the weekend.

I started Packet & Profit in January 2026 because I kept looking for the kind of writing I wanted to read and finding it mostly did not exist. There is a lot of content for engineers online. There is much less written by engineers working specifically inside regulated financial services firms, being honest about what that actually involves day to day. The compliance conversations, the legacy constraints, the incident management in front of stakeholders who measure downtime in dollars per minute. That is what I write about here.

Outside of work I have been running a Saturday morning robotics course at my local YMCA for kids aged 10 to 14. It is one of the better decisions I have made.

Certifications

Red Hat Certified Engineer (RHCE)
Certified Kubernetes Administrator (CKA)
AWS Solutions Architect -- Associate
CompTIA Security+
HashiCorp Vault Associate

My Stack

RHEL / Ubuntu
Kubernetes
OpenShift
Terraform
Ansible
Prometheus
Grafana
Python / Bash
AWS / Azure
Cisco / Palo Alto
PostgreSQL
Redis
HashiCorp Vault
Fluent Bit
Helm
ArgoCD

Career

2022 -- Present
Senior Systems Engineer, Asset Management -- Boston, MA
Leading infrastructure for trading operations and investment management systems. Responsibilities span network security, cloud migration strategy, Kubernetes platform engineering, and incident response. Deeply involved in T+1 settlement infrastructure work and the shift from overnight batch processing to near-real-time event-driven architecture.
2018 -- 2022
Systems Engineer, Private Equity -- Boston, MA
Built and maintained data infrastructure supporting deal teams, portfolio monitoring, and investor reporting. Managed infrastructure through multiple due diligence cycles with hard deadlines and high data integrity requirements. Led a major data platform migration from on-premises to cloud-hosted infrastructure, including security controls satisfying LP and regulatory requirements.
2015 -- 2018
Infrastructure Engineer, Retail Technology
Supported inventory management, real-time pricing, and supply chain integration systems across a high-SKU retail environment. Operated under peak load conditions where scale was a concrete engineering problem rather than an abstract one. Built out monitoring and alerting infrastructure from scratch and managed a full data center relocation.
2013 -- 2015
IT Engineer, Technology Sector
Established the professional fundamentals: data center operations, network infrastructure, endpoint management, and the on-call rotations that teach you more about system fragility than any textbook. Developed an appreciation for cable labeling that has never left me.

Get in Touch

If you are an engineer working in financial services, curious about the career path, or have a question about something I have written, I would genuinely like to hear from you. Use the and I will get back to you. If something here has been useful, a coffee is always appreciated.

A note on anonymity: I write under my own name but keep my current employer private. The financial services industry is small, the regulatory environment is real, and I want to write honestly without those constraints. All incidents and case studies on this site are anonymised. The technical content is real; identifying details are not.
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Whether you are an engineer in financial services, have a question about something I have written, or just want to say hello - feel free to reach out. I read everything.

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