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Andy Dunn identifies two core issues crippling Chicago's tech ecosystem: a near-total lack of a local angel investing community for early-stage startups, and a local VC landscape where the vast majority of capital is deployed into coastal companies. This creates a funding desert, forcing local founders to look elsewhere.
The VC landscape has split into two extremes. A few elite firms and sovereign wealth funds are funding mega-rounds for about 20-30 top AI companies, while the broader ecosystem of seed funds, Series A specialists, and new managers is getting crushed by a lack of capital and liquidity.
The greatest danger of building outside the SF bubble is not a lack of capital, but the absence of a peer group that normalizes struggle. Without that support, founders are more susceptible to the surrounding skeptical culture and more likely to give up during inevitable downturns.
Y Combinator's model pushes companies to raise at high valuations, often bypassing traditional seed rounds. Simultaneously, mega-funds cherry-pick the most proven founders at prices seed funds cannot compete with. This leaves traditional seed funds fighting for a narrowing and less attractive middle ground.
Despite high returns, large VCs avoid seed investing because it's operationally intense (requiring 10-25x more meetings), access to top founders is a bottleneck, and their large funds require deploying big checks that are incompatible with small seed round sizes.
In capital-intensive sectors, the idea is secondary to the founder's ability to act as a magnet. Their primary function is to relentlessly attract elite talent and secure continuous funding to survive long development timelines before revenue.
Iterion CEO Rahul Aras argues that being outside a major biotech hub is a real fundraising hurdle. The issue isn't overt investor bias, but rather the loss of natural networking opportunities—like bumping into investors at a local coffee shop—that are common in dense ecosystems and must be overcome with proactive outreach.
The focus on AI among institutional investors is so absolute that promising non-AI companies risk "dying of neglect" and being unable to secure follow-on funding. This creates a potential opportunity gap for angel investors to fund valuable businesses in overlooked sectors.
The early-stage firm succeeded by identifying a market gap—VCs writing large checks while cloud-based startups needed smaller amounts. Their timing was perfect, launching during the 2008 financial crisis when capital was scarce, just as the iPhone ignited the mobile app boom.
Michal Preminger reflects that her former company, located outside a major biotech hub, had to invent solutions in isolation. It lacked the mentorship and deep market and business wisdom that permeates ecosystems like Boston, which would have accelerated its progress.
Caitlin Smith discovered that Chicago was ideal for her consumer goods company, not for its VCs, but for its deep, affordable talent pool from major CPG headquarters. Being where industry-specific talent resides proved a massive advantage over being in a more expensive, tech-focused city.