In this episode, I sit down with Elisa Miller-Out, Managing Partner at Chloe Capital, to unpack her journey from a Gilded Age lineage and a childhood on food stamps to serial founder and investor with 65+ portfolio companies and multiple M&A, including a $100M exit. We dig into how her theater-to-tech operating background shapes founder empathy, sales/storytelling, and practical company-building.

Elisa shares candid wins and stumbles, from a risky bridge round that became a marquee exit to hard-earned lessons on the perils of venture debt, and why “founders to funders” is the flywheel the ecosystem needs. We close on Chloe Capital’s mission of inclusive innovation, their accelerator work across NY (and beyond), and how Upstate’s growing network is opening real pathways to customers, capital, and community.