Everything has to have a caveat. Every circumstance has to be accounted for. That’s the tension Trevor Grimes and Greg Toler keep coming back to: how to make content that actually matters, while still being practical, structured, and worth someone’s time.

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Greg talks about shifting from managing content teams to actually writing again—and realizing how different that muscle is. Trevor shares how Greg’s “context sandwich” changed his own writing: if you stop in the middle, you should know where you’re at and why you’re there. They go from open loops and closed loops, to flowcharts and yes/no questions, to the “cost of entry versus the benefit of entry.”

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Through it all, Greg’s two tenets remain simple: content should build trust and give value—and people buy from people.

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Greg Toler is a consultant on operations and go-to-market and the founder of BoostIdeal, an early-stage startup. He’s been consulting for almost 10 years and has worked in and out in a few different ways—most recently as the fractional COO at Scrappy ABM, transitioning into full-time, then back into fractional. He’s kicking off the new year doing full-time consulting and also full-time work on Boost.

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1. Why writing “very strategically” feels different than actually being in the writing seat—and why the same piece can take “hours” for one person and “days” for another
2. The context sandwich: “context to details, context,” so the reader knows where they are
3. “Open loop and closed loop” writing—mention it, close it, and don’t leave the reader hanging
4. “Write the way that I talk” vs. “structured and organized” content—and making a “boring blog” a “joy to read.”
5. Creativity as tone and style vs. creativity as “constructs,” “organization,” and “solving problems.”
6. Turning subjective decisions into objective ones: yes/no questions, flowcharts, and finding the bottleneck
7. Getting started with personal content: topic → subtopic → type, building something repeatable, and the “shame bone.”
8. “Content should build trust,” and “content should give value”—plus the conversion theory of cost of entry vs benefit
9. A real experiment that didn’t land: a bot with “super high value,” and the feedback that changed everything—“I didn’t come to work with your bot. I came to work with you.”
10. “Not playing tennis” with clients and why “awkward working sessions” are the point