The Kid from Mitchellville: Nick Leeper on Startups, AI, and Betting on People

Building for Impact: Matt Ostanik on Startups and Giving Back

In this inspiring conversation, host Kaylee Williams sits down with serial entrepreneur Matt Ostanik [https://www.linkedin.com/in/mattostanik/] 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.

Knowing and Growing Economic Power: Joey Beech on Angel Investing and Financial Literacy

In this episode, host Kaylee Williams sits down with Joey Beech, aka the Financial Lit Lady, an author, speaker, and one of the driving forces behind Ankeny Angels. 💡 Find this show on your favorite player: https://iowapodcast.com/Joey-beech 🐖 Get a free $30 gift card from Jethro's BBQ: https://iowapodcast.com/jethrosbbq Joey shares her journey from teaching financial literacy at local high schools to building a thriving angel investment group that's backing some of Iowa's most promising startups. In their conversation, Joey shares what she looks for in founders and pitches—spoiler alert: it's less about the perfect financial projections and more about founders who've solved a problem they personally understand. Joey also opens up about her own financial mistakes, including overspending on a car, and explains why emotion plays such a huge role in our financial decisions, no matter how much we know about spreadsheets. But the real heart of this conversation is about Iowa's untapped potential. Joey makes a compelling case for why the state's "doer mentality" and tinkering culture give local startups an edge, and she challenges the ecosystem to stop playing small. She argues passionately that Iowa's biggest opportunity lies in engaging younger people—starting in high school—in entrepreneurship and innovation, rather than waiting until college to expose them to real-world business. By connecting students with local companies, breaking down silos between startups and established businesses, and investing in early-stage talent, Iowa can not only retain its best minds but build the next generation of founders right here at home.

The Kid from Mitchellville: Nick Leeper on Startups, AI, and Betting on People

Nick Leeper has spent the last two decades building meaningful products in Iowa's tech ecosystem—from the Obama campaign's fundraising systems to Dwolla's real-time payment infrastructure to Hummingbirds' creator platform. In this episode, host Kaylee Williams sits down with Nick to explore how a kid from Mitchellville ended up in rooms with the Federal Reserve, the Gates Foundation, and some of the brightest minds in fintech. 💡 Find this show on every app: https://iowapodcast.com/nick-leeper 🐖 Get a free $30 gift card from Jethro's BBQ: https://iowapodcast.com/jethrosbbq Nick shares the origin story of his friendship with Derek Brooks and their leap to Chicago for the 2008 Obama campaign, a pivotal moment that led him to Dwolla, where he spent nearly 11 years helping design systems that process billions of dollars. Along the way, he reflects on what it means to work at venture-backed startups: the exhilarating opportunities to work on problems you never thought you'd touch, the heartbreak of shipping projects that get shelved, and the importance of people and community in tech. Today, Nick leads engineering at Hummingbirds, a woman-founded creator platform where he's building his own team and setting culture from the ground up - something he always wanted to do. But as the conversation evolves, Nick and Kaylee dig into a bigger question: what does the future of tech look like in the age of AI? Nick explores how artificial intelligence is rewriting the venture playbook, the risk that the "people in the middle" of their careers face as AI disrupts how we work, and why human creativity and problem-solving (not just code) remain the true bottleneck in building great products. Tune into this thoughtful, wide-ranging conversation about ambition, mentorship, and what it takes to leave a mark in tech.

Best of the Midwest: Why Iowa's First-Ever Startup Week Is a Big Deal

In this episode of the Iowa Tech Podcast, host Kaylee sits down with co-organizers Safiya Lee-Evans and Tej Dhawan to introduce Iowa's first-ever Startup Week — a multi-day event celebrating and platforming entrepreneurs from across the state and the broader Midwest. 💡 Find this show on every app: iowapodcast.com/iowa-startup-week 🐖 Get a free $30 gift card from Jethro's BBQ: iowapodcast.com/jethrosbbq The trio breaks down the vision behind the event, including four days of programming spanning tracks in biosciences, advanced manufacturing, and IT/SaaS, all woven together with an AI thread. From fireside chats and workshops to an expo showcasing Iowa founders and their innovations, Iowa Startup Week is designed to bring together entrepreneurs, investors, universities, and corporate partners in one place — because as Tej puts it, a thriving ecosystem requires not just energy, but persistence over 20+ years. The centerpiece of the week is the Best of the Midwest pitch competition, culminating in a grand prize on the main stage at Hoyt Sherman Theater on October 1st. Startups from Iowa and neighboring states can apply across three categories, with top finalists earning the chance to pitch in front of a curated room of venture and angel investors — making the opportunity valuable well beyond the cash prize. Early bird tickets are available at $149 through July 1st, and sponsorship packages are open for organizations looking to get involved. To learn more or buy tickets, visit www.iowastartupweek.com [https://www.iowastartupweek.com].

Building products people touch (and having fun doing it) with Derek Brooks

Des Moines-based technologist and builder, Derek Brooks has a career that spans Fortune 100 roles, scrappy startups, and high-stakes political tech for the Obama campaign. Broox, as his friends know him, traces his path from growing up in eastern Iowa and discovering software at Cornell College to early work at Pioneer (now Corteva), a pivotal stint at Red 5 Interactive, and becoming a remote engineer before it was cool. 💡 Find this show on your favorite app: https://iowapodcast.com/derek-brooks [https://iowapodcast.com/derek-brooks] 🐖 Get a free $30 gift card from Jethro's: https://iowapodcast.com/jethrosbbq [https://iowapodcast.com/jethrosbbq] Brooks shares inside stories from the Obama 2012 campaign—building integrations and the high-pressure Call Tool used for millions of voter contacts—and how that experience led to a post-campaign startup in "contextual commerce" that was acquired by PayPal. He pulls back the curtain on acquisition realities, his time across PayPal/Braintree/Venmo, and why seeing products people actually touch fuels his work. Chapters: 00:00 - Meet Derek Brooks 01:57 - Midwest Roots to Remote Work 05:00 - Obama Campaign to PayPal 16:06 - Early Web Hustles 17:34 - Sabbatical Reset 20:12 - Rocket AI Advice