Creating Content People Actually Care About (with Sydney Webber) | Ep. 9

Creating Content People Actually Care About (with Sydney Webber) | Ep. 9

Author: Trevor Grimes August 14, 2025 Duration: 46:55

Why do so many marketing campaigns fall flat, even when the content is strong? Trevor Grimes sits down with Sydney Webber to answer that question through the lens of storytelling, distribution, and authenticity. Sydney, a B2B SaaS marketer specializing in Proptech at Venn, shares her unconventional path from ballroom dancing to leading marketing in the multifamily real estate tech space.

ㅤ

In this candid conversation, Sydney explains why the heart of a successful campaign lies in people’s relationship to the story, not just the story itself. She reveals how to create content that makes people stop scrolling, why apps may disappear in the next five years, and the one hill she’ll die on: distribution is everything. Listeners will leave with a fresh perspective on what it means to create content that truly resonates and how to bring others along for the ride.

ㅤ

👤 Guest Bio

Sydney Webber is a B2B SaaS marketer specializing in Proptech and currently leading marketing at Venn. With over a decade in the multifamily real estate industry—from leasing agent to tech marketing leader—Sydney blends deep industry expertise with a passion for storytelling. Her background in theater and podcasting fuels her ability to craft authentic marketing strategies that connect with audiences on a human level.

ㅤ

📌 What We Cover

  • The surprising reason your content may not resonate (and how to fix it)
  • Why apps might disappear within five years and what this means for marketers
  • The difference between a great story and a story people actually share
  • How to build authentic relationships that power distribution
  • Sydney’s creative process—big ideas, deadlines, and lessons learned from both wins and flops
  • Why understanding your customer’s motivations is non-negotiable
  • The freedom of creating content knowing “nobody cares” (and why that’s a good thing)
  • The power of consistency and why distribution is just as important as the story

ㅤ

🔗 Resources Mentioned


ㅤ

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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.


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…
The Hill I’ll Die On About Content | Ep. 12 [not-audio_url] [/not-audio_url]

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 idea…
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…