Duolingo's first investors admitted they didn't believe in the education market, which they considered a bad business. They invested solely because founder Luis von Ahn had a previous successful exit to Google, demonstrating that a founder's track record can be more persuasive to early VCs than the business idea itself.

Founders with deep market fit must trust their unique intuition over persuasive, but generic, VC advice. Following the standard playbook leads to cookie-cutter companies, while leaning into the 'weird' things that make your business different is what creates a unique, defensible moat.

Flock Safety was dismissed by VCs because its initial market of neighborhood associations seemed too small. This perception of a small TAM acted as a moat, deterring competition and allowing them to build a foundation to later expand into much larger government contracts.

Kyle York of York IE passed on Adhawk despite loving the founder because of a recent bad experience in the ad tech industry. The founder later pivoted the company into a SaaS platform for the flooring industry (Broadloom) and achieved a great exit, demonstrating that strong founders can escape challenging markets.

Figma's market initially seemed too small to attract major VC interest or intense competition, giving them space to build a defensible product. Founders can gain a significant advantage by working in overlooked spaces, provided they have genuine passion to sustain them for a decade or more.

Well-funded startups are pressured by investors to target large markets. This strategic constraint allows bootstrapped founders to outmaneuver them by focusing on and dominating a specific niche that is too small for the venture-backed competitor to justify.

The founders of Free Soul endured multiple rejections, including literally being laughed out of rooms. They frame this brutal process as a necessary filter that weeded out misaligned VCs and ultimately led them to investors who were personally connected to their mission.

A truly exceptional founder is a talent magnet who will relentlessly iterate until they find a winning model. Rejecting a partnership based on a weak initial idea is a mistake; the founder's talent is the real asset. They will likely pivot to a much bigger opportunity.

While it's crucial to listen to markets and clients, founders must also be prepared to stick to their convictions when investors, who may not be specialists in their niche, offer conflicting advice. Knowing when to listen and when to hold firm is a key startup skill.