Caitlin Smith wasn't ready with recipes or packaging, but when a Whole Foods buyer offered a meeting, she took it. This forced her to accelerate her process and land a crucial first customer, demonstrating the power of seizing opportunities before feeling 100% prepared.
Simple Mills founder Caitlin Smith's key advice is that entrepreneurship requires constant self-reinvention. She notes that if you succeed, your job will eventually outgrow you unless you are constantly learning and adapting. This makes continuous personal scaling the most critical leadership skill.
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.
In a venture climate dominated by tech, Simple Mills struggled to attract institutional investors. The founder succeeded by focusing on angel investors, who were more open to a consumer brand and funded her first three rounds, demonstrating their crucial role for non-tech startups.
The founder of Simple Mills pitched so many investors (8 per day) that two potentials randomly met in a Whole Foods aisle while looking at her product. This serendipitous moment led directly to her lead investor signing on, proving that sheer volume in fundraising can generate its own luck.
During post-COVID supply chain disruptions, Simple Mills viewed the chaos as an opportunity. While competitors struggled with an 80% fill rate for retailer orders, Simple Mills invested to maintain 96%. This reliability built immense retailer trust and ensured their product was always on the shelf, allowing them to capture competitor market share.
Convinced she only needed $200k, Caitlin Smith was proven wrong in her Chicago Booth "New Venture Challenge" course. Coaches had her analyze public CPG financials, revealing the massive marketing and working capital costs she'd underestimated. This academic exercise provided a critical reality check that reshaped her fundraising strategy.