Jenny Fielding is a former double founder turned investor who has made 300+ first-check investments across more than 50 countries with a deliberate thesis of venture everywhere, backing founders outside traditional hubs including emerging markets and overlooked ecosystems. As longtime Managing Director of Techstars NYC, she personally led or oversaw investments in hundreds of startups and runs a founder-and-operator-driven investing community that functions as a collaborative village where founders, operators, and angels co-source, co-support, and often co-invest rather than following a traditional GP-LP power structure.

• A strong preference for direct action and cold outreach over warm introductions or standard etiquette. She highlighted a success story where a cold LinkedIn message led to investing in a company that later signed a term sheet for a major round, and she encourages founders to ignore advice about waiting for the "right time" to email busy people.
• Focus on price discipline and skepticism toward inflated early-stage valuations. She has repeatedly noted that high entry prices, such as pre-seed rounds with twenty-five million dollar caps, make the math unworkable for her fund model, leading her to pass on otherwise great founders simply because the valuation did not make sense.
• Openness to investing in solo founders and non-technical teams leveraging AI tools. She admitted to breaking her own historical rules by backing a startup without a CTO, recognizing that AI coding applications now allow non-technical builders to create viable software companies without a technical co-founder.
• Appreciation for radical candor regarding exit strategies and business health. She specifically praised a founder who admitted he would accept an early acquisition offer if it benefited his team, noting that this level of honesty is rare and preferable to the standard pitch where founders pretend they only want to build a massive unicorn.
• Willingness to back non-consensus or "weird" deals outside of the current industry hype cycles. She pushes back against the idea that investors must be in the top handful of AI infrastructure companies to succeed, noting that she continues to wire funds to healthcare and non-software companies even when peers comment that her deals are strange.
• Pragmatic advice on fundraising momentum and efficiency. She suggests that founders should stop raising if they haven't secured a lead investor after two months and observes that the most effective way to raise capital is often asking for advice rather than money, citing a founder who oversubscribed a round purely through advice calls.