Nick Leeper‘s career embodies the Iowa tech ecosystem at its best. Starting as a software engineer at Pioneer (now Corteva), Nick spent nearly a decade building research lab software before catching the startup bug. In 2008, he and close friend Derek Brooks made a pivotal leap together to Chicago to work on the Obama campaign—a decision born from their friendship and mutual ambition that shaped both their trajectories. After the campaign, Nick landed at Dwolla, where he spent 11 years helping build real-time payment systems, working with institutions like the Federal Reserve and the Gates Foundation.
What strikes Nick most about his venture-backed experiences is how they’ve accelerated opportunity. “I was in rooms I had no business being in,” he reflects, describing how startups compress experiences that might take decades in corporate environments. But he’s also candid about the downsides: the emotional toll of building products that get scrapped, the constant pivots driven by investor expectations, and the cycles of hiring and layoffs that come with funding rounds.
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In 2024, Nick joined Hummingbirds as head of engineering, working alongside COO and Co-Founder Charise Flynn and CEO and Co-Founder Emily Steele. He was drawn to the company’s rare advantage of having product-market fit before scaling—and to the opportunity to build his own team and set culture from scratch. At Hummingbirds, he’s found better work-life balance and a woman-founded environment that brings a different energy.
(Check out our interview with Emily Steele here!)
The conversation pivots to AI’s impact on the next generation of engineers. Nick acknowledges that AI will reshape venture’s traditional playbook of “grow, hire, grow”—but argues that code was never the bottleneck. The real work is understanding problems and validating solutions. His concern: how will junior engineers build the pattern recognition and judgment that comes from shipping products and learning from failures? It’s a question without easy answers, but one that defines the moment we’re in.
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.