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.

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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.

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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.

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• 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

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• Scrappy ABM Workshop
• Built Rewards
• Venn

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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 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.

Social media is your testing ground—flops vanish, wins multiply. Host Trevor Grimes sits down with LinkedIn devotee Kate Erwin (a self-described “I live on LinkedIn for a living” writer) to trade honest stories about content that lands—and the plenty that doesn’t. Kate moved from “typical content marketer” to guiding B2B tech brands and their executives on LinkedIn, armed with twelve years of writing, slam-poetry stage chops, and a mindset of “test the weird thing.”

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Together they unpack why social posts are low-risk labs, the three must-haves for ghost-writing an exec’s voice, and how memes can “sneak vegetables into mac-and-cheese” by serving insight without the hard sell. Expect straight talk on pricing creative work, turning “not right now” into future deals, and why self-advocacy beats viral wish-casting. Actionable, human, and refreshingly unpretentious.

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Kate (Brady) Erwin is an extroverted writer who has “lived on LinkedIn” for over twelve years. An English major turned slam-poetry award-winner, she now helps B2B tech brands and their executives grow reach and mindshare on LinkedIn—often via her consultancy, Ghost Megaphone. A big performer and part-time karaoke DJ, Kate blends storytelling, meme culture, and honest strategy to make business content actually resonate.

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• Why social media is the safest place to experiment—if a post flops, almost nobody sees it.
• Kate’s “big three” for successful ghostwriting: firm executive buy-in, an internal project manager, and leaders with real stories.
• Using memes to “sneak in your message without shoving it down their throats.”
• The value of “test the weird thing” and letting LinkedIn lag on trends so you look original.
• Pricing creative work: why ghostwriting for execs “always costs more—higher, higher.”
• Turning a “not right now” reply into future business through consistent, chill follow-ups.
• Lessons from Chili Piper and Close on brand voice, collaboration, and embracing edgy ideas.
• Self-advocacy: posting your wins and simply asking past contacts for new work.

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• Scrappy ABM – ABM in a Day workshop – free live session, Aug 7
• Chili Piper
• Close
• Ghost Megaphone
• Will Aitken & Travis Tyler
• Gong
• ThePath
• Silicon Valley (TV)
• TikTok & YouTube Shorts
• Facebook Marketplace
• Ted Lasso (TV)

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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 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.

What if you could bring the fun right where people already are—no need to chase trends, just deliver what they want? Jakob Eliason, co-founder of Pickleball Popups, shares how a mix of marketing strategy, bold execution, and relentless documentation transformed an idea into a traveling pickleball phenomenon. Hosted by Trevor Grimes, this episode dives into how Jakob and his team mastered the logistics behind portable courts, the importance of listening to real audience needs, and how “making noise” and capturing authentic moments powers lasting growth.

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Jakob breaks down their go-to-market journey, from buying portable courts before even getting approval, to turning temporary activations into scalable events at breweries, festivals, and trade shows. Along the way, he shares insights on product-market fit, the value of iterative feedback, and why content should come from what’s genuinely happening—not manufactured for the sake of it. If you want practical takeaways on connecting with your audience, building momentum, and growing with authenticity, Jakob’s story is packed with actionable wisdom.

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👤 Guest Bio

Jakob Eliason is the co-founder of Pickleball Popups, a company that transforms empty spaces into pickleball courts for events nationwide. Based in Memphis, Tennessee, Jakob leverages his marketing background to build a unique business blending logistics, community-building, and event activation.

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📌 What We Cover

• How Jakob and his partner pivoted from launching a permanent pickleball facility to creating a mobile popup concept, buying portable courts before even securing venue approvals.
• The logistics challenge behind transporting modular pickleball courts nationwide and the role of operations leadership in their success.
• Branding strategies for events: from decals on courts and nets to custom paddles and backstops that enhance sponsor visibility.
• Why “making noise” through memorable events and documenting everything has been central to growing their brand and audience.
• The importance of product-market fit validated through inbound leads and customer feedback before investing heavily in advertising.
• Insights on managing wait times and manufacturing crowd excitement to build energy and anticipation at free events.
• Jakob’s marketing philosophy: balancing quality and quantity in content, using paid ads to amplify authentic moments rather than manufactured posts.
• The role of continuous iteration and humility—embracing feedback, testing variables carefully, and evolving based on what people actually want.
• How the temporary popup model informed opening an indoor facility without costly renovations, using the same modular court system.
• Why Jakob plans to stay focused on pickleball rather than expanding into other sports, emphasizing pickleball’s unique accessibility and growth potential.
• The power of community-building through events, whether in-person or virtual, as a source for creating meaningful, resonant content.
• Jakob’s “hill to die on”: Make lots of good noise, document everything authentically, and create something worth capturing.

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🔗 Resources Mentioned

• Pickleball Popups website and events (implicitly referenced)
• Pickleball 901 — the Memphis-based pickleball facility Jakob co-founded
• Gary...