In this inspiring conversation, host Kaylee Williams sits down with serial entrepreneur Matt Ostanik to explore his 20-year journey through the startup ecosystem. 💡 Find this show on your favorite player: https://iowapodcast.com/Matt-Ostanik 🐖 Get a free $30 gift card from Jethro's BBQ: https://iowapodcast.com/jethrosbbq

Matt shares his origin story - from architecture school in Iowa to launching Submittal Exchange, a SaaS platform that revolutionized commercial construction document management. He walks through the full arc of his entrepreneurial career: the early wins (selling Submittal Exchange to Textura, which later became part of Oracle), the front-row seat to a major IPO, and the painful failure of FunnelWise, a marketing analytics platform he shut down in 2018. Through it all, Matt reflects on hard-won lessons about product-market fit, capital strategy, and the importance of doing right by employees and customers, even when things fall apart.

But the conversation takes a meaningful turn as Matt reveals what drew him away from traditional for-profit ventures: a deep desire to create social impact. He introduces Grateful Giving, a nonprofit tech platform (and his first charitable venture) that makes giving easier and more gratitude-driven, already supporting over 3,300 charities across all 50 states and raising more than $1 million for causes. Matt and Kaylee dig into the concept of "generativity"—that universal human desire to give back—and discuss how the next generation of businesses will be measured not just by profit, but by their impact on people and planet. It's a conversation about failure, redemption, and building technology that genuinely makes the world better.