The most successful venture investors share two key traits: they originate investments from a first-principles or contrarian standpoint, and they possess the conviction to concentrate significant capital into their winning portfolio companies as they emerge.

Despite strong early metrics, Huntress was rejected by over 60 VCs for its Series A. The primary objections were its SMB focus, its Maryland headquarters (outside Silicon Valley), and its fully remote model in 2018. This demonstrates how VC pattern-matching can cause them to miss high-growth opportunities.

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.

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.

To identify non-consensus ideas, analyze the founder's motivation. A founder with a deep, personal reason for starting their company is more likely on a unique path. Conversely, founders who "whiteboarded" their way to an idea are often chasing mimetic, competitive trends.

McInerney's success comes from profiling founders, not just markets. He seeks deep domain expertise combined with a unique, often unconventional, perspective, believing this combination is key to building disruptive companies.

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.

When evaluating revolutionary ideas, traditional Total Addressable Market (TAM) analysis is useless. VCs should instead bet on founders with a "world-bending vision" capable of inducing a new market, not just capturing an existing one. Have the humility to admit you can't predict market size and instead back the visionary founder.

Huntress founder Kyle Hanslovan leveraged his nine years at the NSA creating offensive cyber warfare tools. This 'offense to defense' path gave him a deep, intrinsic understanding of how hackers infiltrate and persist in networks, providing an unfair advantage in creating a product that could effectively hunt them.