Venture with Grace Jon Callaghan, True Ventures MP on Early-Stage VC & AI Innovation
Nov 13, 2025
Join Jon Callaghan, Managing Partner at True Ventures and co-founder of the firm, as he shares his wealth of knowledge in early-stage investing. He discusses spotting founders who create generational companies and emphasizes the significance of empathy and integrity in the data-driven VC world. Jon argues that AI represents a transformational opportunity akin to the internet revolution. He explains how True Ventures evaluates and sources founders while maintaining robust, supportive relationships with them throughout their journeys.
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Founder Origin Story Shapes VC Lens
- Jon Callaghan started a mountain-bike shop as a teenager and built it for eight years before selling it.
- That founder experience shaped his belief that founders are visceral creators worth supporting for decades.
AI Is A Singular, Long-Term Vintage
- AI is the biggest technology shift seen in decades and opens enormous market and productivity opportunities.
- Short-term investing behavior can still be bubbly and non-contrarian despite the long-term certainty of AI's impact.
Back Contrarian Founders With Ambiguous Markets
- Do back founders with contrarian visions that most people don't yet see.
- Seek founders who imagine large, ambiguous markets and who can tolerate uncertainty.
