Instead of coaching unconventional founders to be more palatable for mainstream Series A investors, early backers should encourage them to lean into their unique traits. The investor's role is to help them find the right future partners who appreciate their peculiar worldview, not to change it.
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Limited Partners, much like VCs searching for outlier founders, are often looking for fund managers who are "a little off." They value investors who think differently and don't follow the consensus, as this non-traditional approach is seen as the path to generating outsized returns.
To win the best pre-seed deals, investors should engage high-potential talent during their 'founder curious' phase, long before a formal fundraise. The real competition is guiding them toward conviction on their own timeline, not battling other VCs for a term sheet later.
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.
The hardest transition from entrepreneur to investor is curbing the instinct to solve problems and imagine "what could be." The best venture deals aren't about fixing a company but finding teams already on a trajectory to succeed, then helping change the slope of that success line on the margin.
Competing to be a founder's "first call" is a crowded, zero-sum game. A more effective strategy is to be the "second call"—the specialist a founder turns to for a specific, difficult problem after consulting their lead investor. This positioning is more scalable, collaborative, and allows for differentiated value-add.
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.
Unlike operating companies that seek consistency, VC firms hunt for outliers. This requires a 'stewardship' model that empowers outlier talent with autonomy. A traditional, top-down CEO model that enforces uniformity would stifle the very contrarian thinking necessary for venture success. The job is to enable, not manage.
Venture capital should focus on what a founder does exceptionally well, rather than penalizing them for past failures or weaknesses. Ben Horowitz uses the Adam Neumann example to illustrate their principle: judge people by their spectacular talents (like building the WeWork brand) and help them manage their flaws, which is a more effective strategy than seeking perfectly flawless individuals.
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.
