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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👤 Guest Bio
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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📌 What We Cover
- 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
- The context sandwich: “context to details, context,” so the reader knows where they are
- “Open loop and closed loop” writing—mention it, close it, and don’t leave the reader hanging
- “Write the way that I talk” vs. “structured and organized” content—and making a “boring blog” a “joy to read.”
- Creativity as tone and style vs. creativity as “constructs,” “organization,” and “solving problems.”
- Turning subjective decisions into objective ones: yes/no questions, flowcharts, and finding the bottleneck
- Getting started with personal content: topic → subtopic → type, building something repeatable, and the “shame bone.”
- “Content should build trust,” and “content should give value”—plus the conversion theory of cost of entry vs benefit
- 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.”
- “Not playing tennis” with clients and why “awkward working sessions” are the point
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🔗 Resources Mentioned
- Podcast sponsor: Scrappy ABM
- Scrappy ABM Case Studies
- Scrappy ABM Podcast
- Scrappy ABM Contact
- Greg’s company: BoostIdeal
- Tool mentioned: Lucidchart
- Platform mentioned: LinkedIn
- Reference mentioned: “the old school, A-Team” (“I love it when a plan comes together.”)
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