Benjamin Humphrey - Blog https://benjaminhumphrey.com Blog posts by Benjamin Humphrey, CEO and co-founder of Dovetail. en-US Wed, 15 Jul 2026 00:00:00 GMT Context creates better AI outcomes https://benjaminhumphrey.com/blog/suns-out-launch/ https://benjaminhumphrey.com/blog/suns-out-launch/ Wed, 15 Jul 2026 00:00:00 GMT Generic AI tools produce generic results. The real differentiator is context—private business data, customer interactions, and strategic research insights. Everything in our latest Dovetail product launch, Sun’s Out, is built around this idea.

]]> From compile time to run time: the new architecture of customer insights synthesis https://benjaminhumphrey.com/blog/run-time-synthesis/ https://benjaminhumphrey.com/blog/run-time-synthesis/ Wed, 27 May 2026 00:00:00 GMT Customer insight is shifting from compile time to run time. With AI, the research function can move from producing static reports to maintaining a live, queryable corpus of customer signal that the whole organization can draw on when making decisions.

]]> How can young Australians afford a home if we tax their risk-taking? https://benjaminhumphrey.com/blog/young-australians-risk-taking/ https://benjaminhumphrey.com/blog/young-australians-risk-taking/ Wed, 20 May 2026 00:00:00 GMT The CGT changes in this Federal Budget break the risk-to-reward ratio for all small business owners, entrepreneurs, and young Australians—not just tech.

]]> Australia’s CGT changes will hurt startup hiring https://benjaminhumphrey.com/blog/cgt-changes-startups/ https://benjaminhumphrey.com/blog/cgt-changes-startups/ Tue, 19 May 2026 00:00:00 GMT The newly proposed CGT changes scrap the 50% discount for future equity grants, effectively halving the value of startup equity for employees and making it harder for Australian startups like Dovetail to compete for talent.

]]> How will OpenAI win any of their three fronts? https://benjaminhumphrey.com/blog/openai-three-fronts/ https://benjaminhumphrey.com/blog/openai-three-fronts/ Fri, 27 Mar 2026 00:00:00 GMT OpenAI is competing on infrastructure and cloud services, business solutions, and mass consumer adoption. In each they face incumbents with significant advantages.

]]> Nakasendo Trail https://benjaminhumphrey.com/blog/nakasendo/ https://benjaminhumphrey.com/blog/nakasendo/ Thu, 04 Dec 2025 00:00:00 GMT Film photos taken with my Canon New F-1 when hiking the Nakasendo Trail, a historic route through the Kiso Valley connecting Kyoto and Tokyo during the Edo period.

]]> Hypotheticals https://benjaminhumphrey.com/blog/hypotheticals/ https://benjaminhumphrey.com/blog/hypotheticals/ Mon, 08 Sep 2025 00:00:00 GMT In a rapidly evolving software landscape, thinking too far ahead can be wasted energy.

]]> New tools, old rules https://benjaminhumphrey.com/blog/new-tools-old-rules/ https://benjaminhumphrey.com/blog/new-tools-old-rules/ Sun, 24 Aug 2025 00:00:00 GMT After getting caught up in the AI hype machine, a European sabbatical reminded me that while tools evolve, the fundamentals of building a software company remain unchanged. From floating in ancient Turkish waters to unfollowing everyone on LinkedIn, here’s what stepping away taught me about staying grounded in an age of artificial intelligence.

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