Strategic thinker. AI specialist. Data specialist. Educator. And an athlete, magician, and musician. Every chapter of my life has been about picking up a new craft, practicing it until it clicks, and then helping someone else learn it too.
“You'll use everything you ever knew.”
“You cannot step into the same river twice.”
Constantly thinking about the economic drivers and disruptors in society.
An early adopter of GenAI. Now I build AI tools and teach others to use them.
Seven years turning real estate data into real decisions.
Taught 7th grade math, and I still use those techniques when working with others.
Disciplines that require problem solving, patience, and thousands of hours of practice.
I began my career teaching 7th grade math with Teach For America, then worked in education nonprofits. Long conversations with a friend about how development shapes communities pulled me into real estate. At Skanska I saw firsthand that profitable projects and positive community impact can go together.
In every role, my job has come down to being the translator: sitting with the people who do the work, understanding how their process really runs, and turning that into data models, reports, and increasingly AI tools that make the work easier. My biggest lesson from AI so far is that understanding the business problem still matters more than the prompt.
I started my career in a Bronx classroom, and teaching never left the job. Today I help people and teams put practical AI to work, the same way I once helped 7th graders work through a tough math problem: meet people where they are, and make the next step feel doable.
Teach For America · Urban Assembly for Applied Math and Science
Tracked student progress in Excel against the NYC math standards to see exactly where each student was strong or struggling, co-planned lessons with a fellow teacher, and ran after-school tutoring for anyone who needed more time. It was my first data project.
Rural middle schools, Taiwan
With four other teachers, I built a curriculum to teach English to middle school students in a rural part of Taiwan. I taught my class through music, and we visited schools across the country to learn how their education system works.
University of Southern California
President of the Economics Graduate Student Association.
Skanska USA Commercial Development
Ran a hands-on session teaching the development team how generative AI could help with their real work: zoning research, offering memorandums, comps, tenant reports, and Excel. See the session →
Conferences · workshops · this site
Most recently, I led Copilot training at GID/Windsor Communities and taught colleagues to build their own agents. Today I’m speaking on AI in real estate, and writing plain-English answers to the AI questions people ask me most.
Five years on Skanska's commercial development team meant my analysis was tied to real buildings, from transit tunnels under construction to topping-out ceremonies where the crew signs the final beam.
Joined a panel of people putting AI to work in real estate, representing multifamily operations at GID/Windsor Communities.
With Connie Chan (Andreessen Horowitz), Amit Koren (JLL), and Wan Li Zhu (Suffolk Technologies). Moderated by Richard K. Green, Director of the USC Lusk Center.
Discussed the ethical questions raised by new technology in real estate, representing Skanska.
With Richard Harvey Jr. (Beneficial State Bank) and Francis Janes (Beneficial State Foundation). Moderated by Mhare Mouradian (Husch Blackwell).
I started using ChatGPT in February 2023, just as the generative AI boom took off. By that summer I was presenting to real estate investment leaders about why the industry needed to pay attention. The talk asked three questions: Why should we pay attention to AI? How can it be applied to commercial real estate? What does an AI-integrated future look like?I also covered prompt engineering and predicted that AI would significantly change analyst-level work. I look back at how those calls held up in my Continued Thoughts on AI.
My first conference talk. I showed how I turned 400+ million rows of Spatial.AI social media data into a Power BI tool that maps demand trends down to the census tract, and how a "thumbprint" score built from LA's Arts District tracked with asking rents across U.S. cities. Read the full project →
Before ChatGPT: using social media data and Power BI to predict where demand is heading.
Began with idea generation and coding help, always looking for practical business uses.
From Hype-Free AI. It even appears on a slide in my PREA talk a month later.
Presented "AI Within Development" to real estate investment leaders.
Predictive modeling and turning data into decisions.
An “AI for CDUS” session with live demos on zoning, OMs, comps, and Excel.
Ethical implications and applications of new technology in real estate.
Led efforts to use generative AI for variance analysis and written summaries of what the numbers show. Partnered on a company-wide Copilot rollout and trained colleagues to build agents.
Kept learning, and shared what I’d learned alongside leaders from a16z, JLL, and Suffolk Technologies at the USC Lusk Center.
Completed four courses, including AI Fluency: Framework & Foundations and AI Capabilities and Limitations.
A PSA analyzer for acquisitions, a metric-definitions agent, and AI classification in Snowflake Cortex.
The rest of the picture: I perform magic, both on stage and up close at the dinner table. I play piano and guitar. I've competed in fencing, and I finished the 2024 Cambridge Half Marathon. None of it is in my job description, and all of it shows up in my work anyway: holding a room, practicing until something looks effortless, reading the person across from me, and going the distance.
“I had the pleasure of working with Chris Cashdan at Skanska, where I came to know him as an exceptionally knowledgeable, curious, and generous colleague. Chris has a rare ability to connect technology, data, and emerging trends with the strategic challenges and opportunities facing the real estate industry.”
“Chris approaches work with curiosity, initiative, and creative problem solving. He takes ownership of challenges and supports associates in building analytical capabilities and developing in their roles. He is a true team player.”
“Chris has an exceptional intellectual curiosity and a passion for creative problem solving. He has a knack for applying new technologies to existing problems to drive better outcomes. On a personal level, he's also a joy to work with and a great team member.”
“Chris has a profound ability to work collaboratively across a wide variety of business units in a world that is rapidly integrating AI into work flows. His ability to hear a business problem, quickly digest it, and propose a tech-enabled solution is an asset to all who work with him. Along with his individual skills, Chris leverages his background as an educator to empower others to learn new technologies in a thoughtful way.”