Builder. Operator. Investor.
I’ve spent my career starting and scaling technology companies. Today, I invest in founders - and still like to tinker with new ideas and technologies.
Built one of the first advertising platforms designed specifically for streaming audio, connecting advertisers with audiences across hundreds of internet radio stations.
Backed by Union Square Ventures, CBS Radio and Bain Capital Ventures. TargetSpot was acquired by Radionomy. The business later became part of Vivendi and ultimately Azerion.
I even made it into Billboard. (Sadly, not for my guitar playing.)
Built a technology-enabled residential real estate platform combining brokerage services with proprietary software designed to make buying and selling homes more efficient and transparent.
I even appeared on CNBC’s Squawk Box. (Suit on top. Jeans under the desk.)
RealDirect was acquired by Zillow Group.
Partner
I invest at the pre-seed to seed stage in exceptional founders building across tech-enabled consumer, software and frontier technology. I’m particularly drawn to ideas that garner an emotional response, and founders who are exceptional storytellers.
Selected investments
01 / Vertical AI Software
While much of the market is chasing revolutionary AI technologies at billion-dollar valuations, I think there’s a significant opportunity in vertical software: domain experts using efficient AI models to solve specific problems more elegantly and cost-effectively than Big AI.
02 / Tech-Enabled Consumer
The best consumer products connect with people at an emotional level. I’m interested in how consumer AI can amplify that connection—helping products tell their story, become easier to use, and create stronger relationships with their customers.
03 / Company Building
I often think the most valuable role I can play as a VC is as a bench coach—helping founders work through the hundreds of decisions that come with building a company. I’m exploring how to make that kind of support more systematic and scalable.
04 / Building with AI
The best way I’ve found to understand AI is to build with it. I’m using today’s tools to turn ideas into working products, solve problems I encounter, and learn firsthand what’s becoming possible.
For years, I believed domain experts would always beat big tech in vertical software. My experiences competing with Google at TargetSpot and RealDirect reinforced that view. AI may be changing the equation.
Forward Deployed Engineers are becoming indispensable to AI companies. But much of what makes the role necessary today is friction—and AI is very good at eliminating friction. The job may disappear. The skills won’t.
As AI abstracts more of software development, the hardest problems increasingly become what to build, for whom, in what order and why. That could fundamentally change the role of the CTO.
Brooklyn born, New York based. Before starting companies, I was an Assistant New York Attorney General and served as counsel and chief of staff to local elected officials.
I’m a longtime guitarist and collector of 1980s Charvel guitars. I was once the lead guitarist for LP. Her music career worked out considerably better than mine.
I serve on my co-op board, spend an increasing amount of time in northwest Connecticut, and remain an inveterate tinkerer—usually with a new business idea, product concept, or something I’m trying to build.
I’m also usually accompanied by the dog you met at the top of this page. He’s less interested in startups, more interested in squirrels.