Gabe Velez has started multiple startups over the years, winning some competitions but also experiencing issues like co-founders leaving. He discusses various startups from 2012 to 2015, including WhatNow, Voutche, and Linesnap. Through these experiences, he has learned to deeply research problems before pitching ideas and building companies around solving them. He encourages taking risks and persevering through the entrepreneurial process of eating, sleeping, and repeatedly pitching ideas.