Joe Zawadzki is CEO of MediaMath, ad tech pioneer and noted investor, mentor and visionary. A floppy-haired, Tesla-driving, intensely affable Harvard grad, he came to NYC in the late ’90s and joined a real estate firm as an analyst. Rapidly, his interest turned to e-commerce and personalized shopping apps using ASP. (In this episode, he reminds us that in the pre-SaaS stone age, start-ups had to buy their own servers and security systems.) Through the time of the dot-com boom and bust, he bravely founded Poindexter, a Silicon Alley firm that provided technology to agencies. Poindexter was originally focused on website personalization and optimization, and customers such as AOL and American Express asked them to deliver better prospects in the first place (aka, ad tech). Zawadzki adapted optimization to ad targeting and serving, was involved in the ideation of Right Media — his own ‘origin story’ and cautionary board-handling tale is dramatically told here — and saw Poindexter rebranded to [x+1]. In 2007, he founded MediaMath, a leading DSP, which continues to rock and roll today. He’s also a co-founder of MathCapital, an investment fund.