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

Why would we spend time recording audio and leave it there when you can easily turn on your camera and start? Trevor Grimes is here with Benji Block to talk about video podcasts, trust building, and feeling like you’re a “fly on the wall” while Trevor and Benji are talking.

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Benji shares a simple content strategy: record a full season every six months, plus 30 minutes once a month to answer questions, cut video clips, and turn the rest into LinkedIn posts. The through line is pre-production: the stuff you do before you hit record—why you’re creating what you’re making, the first 30 seconds, titles, and thumbnail—so it’s less of a headache and more “you,” not an arms race for people’s attention.

Benji Block says he helps companies build impact through video. He’s spent the last five years helping build 55+ podcasts from scratch, and he’s coached 100+ business leaders on communication and using video to grow their businesses. Before that, he spent years in the agency and nonprofit church sectors, leading creative teams. In 2025, he launched his own venture through Signature Series, producing numerous video podcasts.

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• Podcasts in the business world skyrocketed when COVID happened, and a lot of people thought audio-only was “really easy.”
• Video is not for everyone—it depends on your strategy.
• “As soon as they can see your face,” there’s personalization: it feels like being a fly on the wall in the conversation.
• Two 30: record long-form content in a two-day sprint, then a 30-minute recurring meeting to ask 10 to 15 questions, cut clips, and turn the rest into LinkedIn written posts.
• “Your brain turns into mush” after too many topics—most people can’t record more than four in a day.
• Pre-production is the most important and often overlooked thing: hook / first 30 seconds/thumbnail/three to five different titles for YouTube.
• Three-by-three method: three main points and three mini points for each.
• Fear, curiosity, and desire drive people to click—and it’s not clickbait if the content is actually helpful and you deliver after that one line.

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• Scrappy ABM
• Chat GPT
• CapCut
• LinkedIn
• YouTube + YouTube Shorts
• TikTok
• Creator Hooks (Jake Thomas)
• My First Million (Sam Parr)
• Alex Hormozi + MrBeast
• iTunes
• Facebook
• Series of Unfortunate Events
• Jesus (parables)

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Low-Tech, High-Impact Account-Based Marketing

If you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving ABM program, check out Scrappy ABM. Led by a team of Scrappy ABM experts, they specialize in low-budget plays and programs that deliver high impact—no shiny tools required. Scrappy ABM has built account-based programs that have delivered millions in revenue, and you can build your first...

Content that actually resonates starts with telling the whole truth about what you can and cannot do right now. In this conversation, Trevor Grimes sits down with Tylor Jones, Director of Digital Acquisition at SIB Fixed Cost Reduction and 3X demand gen leader, to talk through category busting content, flopped campaigns, and building something that really matters.

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Tylor shares the long journey from 35 years of fixed cost reduction data to Spend Brain, a niche LLM that lets you “have a conversation with your spend,” plus how he borrows the B2C playbook, spends $100,000 a month on Meta, and uses UGC videos to make a complex offer feel simple.

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They walk through painful PLG and FBA reimbursement flops, the almond milk story, Reddit threads, cults, The Wandering Home Podcast, and why most teams under $20 million should stop chasing podcasts and ebooks and move the needle with honest structure, clear distribution, and real communities.

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Elder Emo, 3X demand gen leader, and self-described Gandalf of growth marketing, Tylor Jones is Director of Digital Acquisition at SIB Fixed Cost Reduction, a private equity–backed cost reduction and spend management firm. He builds and scales modern demand generation engines across high-growth B2B SaaS and B2B e-commerce, owning pipeline targets, budget, multichannel strategy, and executive-level reporting.

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Tylor also leads growth marketing for Getida, the largest FBA reimbursements auditor on the globe, and helps drive 3X inbound and 2X marketing-sourced pipeline. Outside of work, he co-hosts The Wandering Home Podcast, where a former pastor and a secular friend talk church, cults, and everything in between.

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• Content that actually resonates vs. content that just talks: why “stop mimicking and start making content that actually matters” is the starting point for both personal brand and company brand.
• Productizing fixed cost reduction into Spend Brain: how 35 years of enterprise spend data, an in-house AI and LLM, and “a conversation with your spend” turned a gray-hat-feeling service into extreme clarity for $100M+ businesses.
• Category busting content and the almond milk example: putting yourself “next to milk in the refrigerator” even when you don’t have to be there, fighting for that position, and using competitors’ categories as the comparison point.
• Borrowing the B2C playbook for B2B: why Tylor spends around $100,000 a month on Meta, runs UGC videos, blends product led and sales led motions, and treats category creation like a busy experiment instead of a static play.
• Two big flops and what they changed: a 10-video PLG onboarding series nobody watched, and an Amazon FBA reimbursement launch with a great deck, landing page, and CGO video—but weak distribution and wrong message order.
• UGC talent vs. “just use your webcam”: how Billo actors, stable spokespeople, consistent lighting, strong audio, and screen-cap product tours set the quality standard brands can’t drop below—while BDRs still use lo-fi 1:1 video in outreach.
• PLG, support, and that...