HeyJaredSupercompanies with Greg & Taylor
Your practical guide to becoming a Supercompany – strategies, frameworks, and real examples for leading the AI transformation.
- Indexed issues, last 90 days
- 8
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- Sep 25, 2026
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- Jul 10, 2026
Latest issues
From Anxiety to Awe (opens the original)
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Hi, it’s Greg and Taylor. 👋 Welcome to Supercompanies, our weekly newsletter about building the world’s most valuable companies.When it comes to technology disruption cycles, Gartner’s Hype Cycle described the third phase as the “trough of disillusionment” - a necessary but painful phase, prior to enterprise adoption and value creation.For AI, I think we are in the “trough of anxiety” - maybe even panic. And for good reason. We just learned that GPT hacked the Australian government - and that it
AI is good for entry-level workers, actually (opens the original)
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Hi, it’s Greg and Taylor. 👋 Welcome to Supercompanies, our weekly newsletter about building the world’s most valuable companies.There’s a lot of handwringing right now about early-career employees and AI. If AI does the entry-level work, how do junior people learn? If they outsource their thinking to AI, do they ever build real judgment? Will the entry level job that launched your career exist in 3 years?I get these concerns because this was my path to leadership. I spent the first 3-4 years of
I spent $1,000 on AI in one day. It was a bargain. (opens the original)
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Hi, it’s Greg and Taylor. 👋 Welcome to Supercompanies, our weekly newsletter about building the world’s most valuable companies.Last week I needed to answer a strategic question that’s been blocking our pipeline: What are the actual pain points that prospects are coming to us with right now, and how should we be framing our products against each one?We had anecdotal answers from different people on the leadership team, but no systematic view.So I did what feels natural at this point - I opened C
Why your AI agent sucks (opens the original)
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Hi, it’s Greg and Taylor. 👋 Welcome to Supercompanies, our weekly newsletter about building the world’s most valuable companies.Everyone’s talking about the context layer right now - connecting your AI to Slack, email, calendar, Google Drive so it actually knows what’s going on in your company. We did that months ago. Slack, Google Calendar, Google Drive, Salesforce, Hubspot, etc. - it’s all connected to AI via MCPs. About 80% of Section’s institutional
AI ROI (Part 1) (opens the original)
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Hi, it’s Greg and Taylor. 👋 Welcome to Supercompanies, our weekly newsletter about building the world’s most valuable companies.We all know AI ROI is elusive and hard to measure most of the time - even if you work at an AI-enabled startup where it’s obvious AI is doing meaningful work.If you’re six to twelve months into your AI program and frustrated that you can’t produce convincing ROI numbers, you’re not failing. You’re probably just looking for evidence at the wrong level and at the wrong ti
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