# Stack to Street

> Stack to Street brings finance and technology into the same room to understand the problems being solved and what they mean for the people working across all segments of finance and banking.

Stack to Street is a video podcast hosted by Michael McLaughlin (https://www.path66.com/). Each episode is a conversation with a builder (a founder, engineer, or executive) about the problem they are working on and what it means for people in finance and banking. Many guests build open-source software for finance.

About the host: Michael McLaughlin is a financial services executive with more than 30 years in structured finance and private credit. He is the founder of Path66, an advisory firm for private credit managers and financial institutions, and the host of Stack to Street, a video podcast that brings software builders and finance leaders into the same room. At Macquarie Group from 2008 to 2023, Michael built the credit markets business from inception into a portfolio financing platform that averaged a $5 billion portfolio and generated more than $1 billion in cumulative net revenue. Before Macquarie, he was Global Head of the Structured Securities Group at Banc of America Securities, a business consistently ranked among the top five global arrangers of CLOs and other structured credit products. He has also served as an advisor to Hebbia, which builds AI research software for financial services. Michael started out as a CPA before moving into banking. He holds an MBA from Penn State and a BS from Villanova, along with certificates in entrepreneurship, blockchain, AI and machine learning, and Python from Stanford, MIT, UT Austin and Carnegie Mellon. Through Path66, Michael advises private credit and direct lending funds, business development companies, banks, insurers and broker-dealers on asset finance, liquidity, capital raising and data-driven due diligence. Michael is also a hands-on builder. Working with AI coding tools and open-source software, he designs and ships his own applications, often aimed at problems he knows firsthand from finance. His projects include a credit agent that reads new credit agreements, extracts the covenants and flags what changed from the prior version, and a research engine that monitors sources such as SEC filings and identifies and scores genuinely new information. He has also built and shipped a privacy-focused iOS app. That experience shapes his view that the distance between financial expertise and working software is shrinking.

- Website: https://stacktostreet.com/
- About the host: https://stacktostreet.com/about/
- Insights (articles by the host): https://stacktostreet.com/insights/
- Host on LinkedIn: https://www.linkedin.com/in/michael-p-mclaughlin
- YouTube: https://www.youtube.com/@StacktoStreetPodcast
- Apple Podcasts: https://podcasts.apple.com/us/podcast/stack-to-street/id6819263656
- X: https://x.com/stacktostreet (show), https://x.com/mike_path66 (host)
- Contact: hello@stacktostreet.com
- Episode data (JSON): https://stacktostreet.com/episodes.json
- Full text of every episode, including transcripts: https://stacktostreet.com/llms-full.txt

## Insights by Michael McLaughlin
- [Why Don't Textbook Pricing Models Match the Prices on a Trading Desk?](https://stacktostreet.com/insights/textbook-vs-trading-desk-pricing/) (2026-10-28): Michael McLaughlin on Why Don't Textbook Pricing Models Match the Prices on a Trading Desk: Formula → Conventions → Calendars → Price.
- [Why Is Meeting Data the Most Underused Asset Inside a Financial Institution?](https://stacktostreet.com/insights/meeting-data-institutional-knowledge/) (2026-10-27): Michael McLaughlin on Why Is Meeting Data the Most Underused Asset Inside a Financial Institution: Capture → Own → Interpret → Share.
- [How Banks Can Deploy AI Agents Without Losing Control of Sensitive Data](https://stacktostreet.com/insights/ai-agents-sensitive-data/) (2026-10-20): Michael McLaughlin's four-layer framework for deploying AI agents at banks without losing control of sensitive data: capture, model, storage and permissions.
- [Can Financial Institutions Rely on Open-Source Pricing and Risk Models?](https://stacktostreet.com/insights/open-source-financial-models/) (2026-10-20): Michael McLaughlin's four tests for relying on open-source pricing and risk models at financial institutions: can we read it, does it match the market, does it run in time, and who stands behind it.

## Episodes
- [Episode 3. Aceiss: Cybersecurity Is a Business Problem](https://stacktostreet.com/episodes/aceiss/) with Lloyd O'Connor, Founder and CEO of Aceiss (2026-10-28): Lloyd O'Connor helped pioneer Chase Quick Deposit and worked on cybersecurity at JPMorgan and Barclays before founding Aceiss. We talk about why companies of every size struggle to know who has access to their systems, why AI agents make that problem harder, and what leaders can do first. Transcript: https://stacktostreet.com/episodes/aceiss/transcript.txt
- [Episode 2. FinancePy: From Physics to Wall Street](https://stacktostreet.com/episodes/financepy/) with Dominic O'Kane, Creator of FinancePy (2026-10-18): Dominic O'Kane went from theoretical physics to Wall Street derivatives, led quantitative research in Europe at Lehman Brothers, and wrote the book on credit derivatives. We talk about what a sell-side quant actually does, and why he built FinancePy, a free, open-source Python library for pricing derivatives. Transcript: https://stacktostreet.com/episodes/financepy/transcript.txt
- [Episode 1. Vexa: Your Firm's Most Valuable Data Is Trapped in Meetings](https://stacktostreet.com/episodes/vexa/) with Dmitry Grankin, Founder of Vexa (2026-09-21): Dmitry Grankin built Vexa so companies can turn live meetings into usable, searchable text--and keep that data in an environment they control. We talk about why he took this approach, and what it may mean for finance teams that care about privacy, supervision, and recordkeeping. Transcript: https://stacktostreet.com/episodes/vexa/transcript.txt