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.

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.

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.

📌 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

🔗 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
How Going Viral Starts With Being Honest  | Ep. 29 [not-audio_url] [/not-audio_url]

Duration: 58:03
Some of the most powerful content ever created was never meant to go viral. It was just someone telling the truth. That is the thread running through Trevor Grimes's conversation with Joshua Harrell, Chief Revenue Office…
Why 85% of Podcasts Are Already Dead | Ep. 28 [not-audio_url] [/not-audio_url]

Duration: 44:41
Most marketers are told to pick a lane. Adam Sockel has built a career doing the opposite, and the results speak for themselves. That is the mindset Trevor Grimes unpacks with Adam Sockel, VP of Marketing at Share Your G…
Free Work Is Not Bad Work (with Kaleigh Schouten) | Ep. 27 [not-audio_url] [/not-audio_url]

Duration: 50:01
Turning a hobby into a full-time career often strips away the glamour. You get to "do the dang thing," but you also lose your creative outlet. That is the reality Trevor Grimes explores with Kaleigh Schouten, a creative…
100 Loyal Fans vs. Viral Fame (with Wanda Wesolowski) | Ep. 26 [not-audio_url] [/not-audio_url]

Duration: 52:35
You can have a million followers on TikTok and still play to an empty room. Trevor Grimes talks to Wanda Wesolowski about the reality of building a career versus chasing a viral moment. Wanda explains that if you can fin…
How to Create Better Content in 2026 | Ep. 25 [not-audio_url] [/not-audio_url]

Duration: 18:53
What if your content isn't failing? It might just be unemployed. It lives online, but it doesn't have a job. It isn't creating conversations, leading to opportunities, or building toward anything specific.ㅤThat aimlessne…
How to Create More Content in 2026 | Ep. 24 [not-audio_url] [/not-audio_url]

Duration: 11:03
What was the reason that you kinda sucked at creating content in 2025? Not fear, not imposter syndrome or perfectionism, not a lack of confidence—just friction. The moment you finally have time to create, you sit down, a…
Content Should Build Trust and Give Value (with Greg Toler) | Ep. 23 [not-audio_url] [/not-audio_url]

Duration: 47:48
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, st…