In this episode of the Iowa Tech Podcast, host Kaylee Williams interviews serial entrepreneur Matt Ostanik about his 20-year journey building four startups and his evolution from chasing profit to creating social impact.
Matt begins by sharing his origin story: after studying architecture at Iowa State, he launched Submittal Exchange in 2003 – a SaaS platform that digitized document management for commercial construction projects. The company grew from a bootstrapped side project to 35 employees and $3-4 million in annual revenue, ultimately selling to Chicago-based Textura in 2011. After the acquisition, Matt watched the business scale to 110 employees and $10 million in revenue before Textura went public on the New York Stock Exchange in 2013, later acquired by Oracle. His original product still powers construction software across the industry today.
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Following this success, Matt launched two more ventures: FunnelWise, a marketing analytics platform that failed in 2018 despite raising millions, and CVG (later sold to employees), which provided business services to architects. Matt openly discusses the painful lessons from FunnelWise’s shutdown: underestimating required capital, product-market fit challenges, and the emotional toll of disappointing investors, employees, and customers. He reflects on the lack of guidance around how to fail gracefully.
This failure catalyzed a shift. In 2019, Matt founded Grateful Giving, a nonprofit charitable platform combining technology with social mission. The app—described as “Venmo for gratitude”—has raised over $1 million for 3,300 charities across all 50 states. Matt and Kaylee explore concepts like “generativity” (the psychological drive to give back), the triple bottom line (profit, people, planet), and why younger generations expect businesses to measure success beyond financial returns.
The conversation underscores how failure, life challenges, and personal reflection can redirect an entrepreneur toward more meaningful work—and how technology can amplify impact at scale.