The Hill I’ll Die On About Content | Ep. 12

The Hill I’ll Die On About Content | Ep. 12

Author: Trevor Grimes September 4, 2025 Duration: 23:57

Content often stalls before it even begins—not because people lack talent, but because they don’t know what to say or how to start. In this solo episode, Trevor Grimes shares how interviewing yourself can unlock new ideas, create momentum, and shift the way you think about content.

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Fresh off welcoming his second child and recording ahead of paternity leave, Trevor reflects on lessons he’s absorbed from past guests and how they’ve reshaped his own philosophies. He talks candidly about messy beginnings, why bad audio is worse than bad video, and why consistency is more about commitment than daily posting.

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Listeners will also get access to a free self-interview questionnaire template, a practical tool to help break through creative blocks and generate content directly from your own answers.

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📌 What We Cover

  • A simple technique for generating content ideas by interviewing yourself
  • Why describing what you do to a stranger is harder (and more helpful) than it sounds
  • The importance of recentering content to the right ICP or persona
  • How to stretch and repurpose existing content instead of starting from scratch
  • The balance between “just create” and raising your quality standards
  • Low-cost, DIY ways to improve audio and video setup for more professional content
  • Why consistency doesn’t mean posting daily—it means staying committed
  • The overlooked power of emails that simply ask for a reply

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🔗 Resources Mentioned


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There's a constant pressure to produce more, to follow every algorithm shift, and to mimic what seems to be working for everyone else. The Content Crowd steps away from that noise. Hosted by Trevor Grimes, this podcast is a conversation for anyone building a brand, an audience, or a creative practice who feels that chase is ultimately hollow. Instead of another list of quick tips, episodes delve into the substance behind sustainable work. You'll hear explorations of creative habits that last, storytelling approaches that actually resonate with people, and honest breakdowns of what goes into making content that means something. It’s for founders, marketers, and creators who believe that a more human-centered approach isn't just idealistic-it's effective. The discussions naturally span business strategy, the art of communication, and the practical education needed to execute ideas well. Tuning in means moving past the fatigue of empty output and finding a more thoughtful path to making things that connect.
Author: Language: English Episodes: 29

The Content Crowd
Podcast Episodes
The NoteCard Method for Endless Content Ideas | Ep. 19 [not-audio_url] [/not-audio_url]

Duration: 19:14
You block out time, sit down to batch content, open a blank document or camera app… and suddenly you’re deep diving on a Wikipedia page about soup spoons. That isn’t about talent. As Trevor Grimes says, creativity doesn’…
30-Day Content Sprint (with Phil Pilalas) | Ep. 18 [not-audio_url] [/not-audio_url]

Duration: 42:48
Guest slumps, last-minute reschedules, and still hitting publish—this conversation gets real about what it takes to keep creating when plans fall through. Trevor Grimes (host of The Content Crowd) sits down with colleagu…
Think Like a Content Creator (Before You Are One) | Ep. 17 [not-audio_url] [/not-audio_url]

Duration: 39:09
The loop of consuming, doubting, and delaying ends when you flip the switch from consumer to creator. In this solo episode, Trevor Grimes shares how to think like a content creator before you have an audience—turning dai…
There’s No Such Thing as a Flop (with Wael Davis) | Ep. 16 [not-audio_url] [/not-audio_url]

Duration: 30:58
No effort goes unnoticed. That’s the throughline as Trevor Grimes sits down with Wael Davis to talk confidence, being findable, and why social media should be fun. Wael shares how long-form writing on Substack, short-for…
Why the Messy Middle Matters in Content Creation | Ep. 15 [not-audio_url] [/not-audio_url]

Duration: 10:31
The polished “after” posts get all the attention—viral numbers, 100k followers in three months, a paid-off house from writing on LinkedIn. But as Trevor Grimes reminds us, that’s not the content people need most. What’s…
Why Most Content Doesn’t Resonate (and How to Fix It) | Ep. 14 [not-audio_url] [/not-audio_url]

Duration: 14:17
Hitting “post” and watching your content flop is a feeling every creator, marketer, or founder knows too well. In this solo episode, Trevor Grimes breaks down why most content doesn’t connect — and what to do about it.ㅤD…
Creating Sales Content That Resonates (with Amanda Hall) | Ep. 13 [not-audio_url] [/not-audio_url]

Duration: 30:11
Shifting careers isn’t always linear — sometimes it’s messy, surprising, and exactly what’s needed. Trevor Grimes sits down with Amanda Hall, Account Manager at Scrappy ABM, to unpack her journey from teaching every grad…
Why Consistency Beats Perfection (with Briana Yates) | Ep. 11 [not-audio_url] [/not-audio_url]

Duration: 39:11
Consistency, not perfection, is what actually keeps content moving forward. In this conversation, host Trevor Grimes sits down with Briana Yates, Project Manager at Vers Creative, to talk about wrangling creatives, build…
The Power of 30 Coffees in 30 Days (with Erika Bryant) | Ep. 10 [not-audio_url] [/not-audio_url]

Duration: 43:32
Not every business breakthrough comes from creating more content. Sometimes it starts with a conversation.ㅤIn this episode, Trevor Grimes sits down with Erika Bryant, marketing strategist and business advisor at Piece of…