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.


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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.

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.

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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

Host Kaylee welcomes Anastasia Williams, the entrepreneurial community navigator at Iowa's West Coast Initiative, for a candid look at building a rural startup ecosystem across Monona, Plymouth, and Woodbury counties. Anastasia describes her "concierge" role connecting founders to resources, and how she's catalyzing a grassroots, founder-led community that now meets weekly to share roadblocks, surface values, and co-design support. They spotlight impressive student pitches at Morningside—supercharged by AI—and unpack West Coast Iowa's unique challenges: dispersed geography, tight-knit dynamics, and the need to lean into local strengths rather than copy larger hubs. Anastasia discusses integrating college talent, addressing brain drain through holistic community building (schools, wages, amenities), and draws inspiration from Norfolk, Nebraska's comprehensive retention playbook.

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Anastasia also shares her entrepreneurial journey—from a dog bakery and tutoring company to a yarn venture—where she discovered a passion for relationship marketing and collective success. Her core advice for rural founders: don't be your own labor. Prioritize revenue-generating hires, partner creatively, and consider bartering expertise within the founder network to offload key functions. Most of all, come out of the "basement"—community is a force multiplier. To connect, learn about events, or get involved, visit iawestcoast.com (and find Anastasia out in the ecosystem).