To determine if a startup will succeed, analyze the sequence of events. Did organic customer demand and behavior exist before the startup created its supply (product, messaging)? If the startup is trying to force motion with its supply, it's a sign of conjuring demand and a higher risk of failure.

After finding their ideal manufacturing partner, the Free Soul founders' open admiration for the products and team prompted the supplier to immediately raise prices, making the order unaffordable. This serves as a cautionary tale about maintaining leverage in early negotiations.

Contrary to popular belief, successful entrepreneurs are not reckless risk-takers. They are experts at systematically eliminating risk. They validate demand before building, structure deals to minimize capital outlay (e.g., leasing planes), and enter markets with weak competition. Their goal is to win with the least possible exposure.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

Unlike pure software, freight logistics involves complex physical realities that tech-first founders consistently underestimate, leading to massive failures. Successful ventures in this space almost universally have a founder who deeply understands the industry's nuances from direct experience.

Getting too many "yeses" indicates your product is an incremental improvement within existing playbooks. True category creation involves pushing boundaries so far that you inevitably hear "no" from people who can't yet grasp the new paradigm. Rejection is a signal of innovation.

Investors warn that when potential customers delay adoption because your product isn't a top priority, it's a major red flag. This feedback almost always means 'never' and signals a fundamental lack of product-market fit, suggesting you are solving a 'nice-to-have' problem, not a 'must-have' one.

The search for an initial manufacturer required contacting hundreds of potential suppliers. This quantifies the immense and often underestimated volume of outreach necessary for a new brand to find a partner willing to accommodate small, early-stage production runs.

Paranoid about quality control with their first Alibaba supplier, Unbound Merino's founders flew to the factory for the initial production run. This seemingly inefficient act of being physically present built a strong personal relationship that became their primary safeguard for quality.