The question in the room
Every leader is being asked to bet on AI. Fewer are asking whether the bet matches what they believe.
The pressure to have an AI strategy is everywhere. The harder question sits underneath it: what are you actually building, and is it what you'd choose if you were being completely honest with yourself?
I come at this as an entrepreneur first. I've co-founded and built companies, so I know what these decisions feel like from the founder's chair. I've also led technology as a CTO, and I've been building with language and data technology since the early 2000s, long before anyone called it AI. Today I lead development with teams of AI coding agents working in parallel, so I know firsthand what AI changes and what it doesn't. More often than not, the hard part of the decision is conviction, not code.
How I work
I don't hand you answers. I ask better questions.
My approach is Socratic. We take a decision you're facing and question it together until the assumptions underneath it are visible. Most leaders already know more than they realize. What's often missing is a thinking partner whose only job is to be curious, candid, and on your side.
- What would have to be true for this to be the right bet?
- If AI did this part for free tomorrow, what would still be yours?
- Which belief are you protecting by not deciding?
- Who on your team disagrees, and what do they see that you don't?
One-on-one
Ongoing, confidential conversations with a founder, CTO, or executive, working through real decisions as they come.
Leadership roundtables
Small, facilitated groups of peers working through one hard question together. No slides and no pitch.
About
An entrepreneur and technologist who cares most about the decisions.
I've spent 25 years building software and companies, as a founder, an architect, and a CTO. A few highlights:
- CTO of TZ United, the on-the-ground U.S. partner for institutions building on the Tezos blockchain. We design and build tokenized assets, settlement systems, and records modernization for government agencies, banks, capital markets firms, and fund managers.
- Lead technology at CIMA, an AI-first marketing platform for mortgage lenders. It follows each borrower from the first ad click to a funded loan, then teaches the ad platforms' algorithms what a real borrower looks like. It's built on ClickEngine, the attribution platform I created in 2019.
- Built Open Threat Exchange (OTX) at AlienVault, growing it from zero to over 100,000 users. AlienVault was acquired by AT&T.
- Architect at a security startup backed by Michael Dell, who drove its merger into Secureworks, where the product became Taegis.
- CTO of Tend, a neobank serving the US and Mexico, with deposit accounts in both countries and cross-border money movement.
- In 2010, built a call analytics platform that recorded, transcribed, and ran sentiment analysis on customer calls.
Along the way I noticed that the problems that mattered most were rarely technical. They were smart leaders heading in directions that didn't match what they believed, and not seeing it until much later.
I also stepped away from tech for two years to help a small city in Michigan become a better community of neighbors, working alongside city officials, schools, faith communities, nonprofits, and local businesses. It taught me that the best work happens face to face.
I started Alexandria Solutions to help leaders think clearly about what they're building and why. I'm based in Newport Beach and I prefer to meet in person, over coffee or across a table.
Also from Alexandria Solutions
Daimon Classics
Classical philosophy, from Seneca onward, adapted into clear modern English with reflection prompts. I edit the series.
Know Your Ethos
A voice-first journaling app that uses AI as a mirror, helping people see their patterns and blind spots and put their own ethos into words.