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...

Tired of chasing busywork over real impact? In this episode, Trevor Grimes sits down with Justin Price, principal and founder of Vers Creative, to explore a more meaningful way to lead creative teams. Drawing on his experience serving world-changing faith-based organizations and integrating AI into marketing, Justin reveals why “productive, not busy” should be every leader’s mantra. You’ll learn how to stop mimicking others and start making something that matters by embracing tight guardrails, using constraints as a gift, and ruthlessly editing toward excellence. Whether you’re an agency lead or in-house manager, you’ll leave with actionable takeaways for nurturing talent, driving innovation, and shipping your very best work—every time.

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👤 Guest Bio

Justin Price is the principal and founder of Vers Creative, a consulting agency helping faith-based nonprofits and for-profits grow through brand, marketing, and AI integration strategies. After 12 years as a creative director at top-tier nonprofits, Justin launched Vers to bring “special forces” expertise—tackling the hard stuff so clients can backfill and sustain success. He’s also the author of The Creative Squeeze, a leadership guide for getting the most from emotionally driven creative teams.

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📌 What We Cover

• How being “productive, not busy” fuels intentional growth for agencies and clients alike
• Vers Creative’s “special forces” model: advancing the line, then graduating clients to run on their own
• Why tight constraints and guardrails spark breakthrough creativity rather than stifle it
• Real-world budget examples: from $4,000 CAC on a $1 M spend to the challenge of a $50 CPA goal
• The power of “ship excellence”: ruthless editing and doing less, better, rather than more, mediocre work
• Lessons from The Creative Squeeze on leading emotionally driven creators versus other teams
• Balancing timeless brand DNA against fleeting trends in design, messaging, and voice
• Building a sustainable creative culture that prioritizes collaboration, risk-taking, and mentorship

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🔗 Resources Mentioned

• The Creative Squeeze by Justin Price: https://www.verscreative.com/book
• Justin Price’s LinkedIn: https://www.linkedin.com/in/justin-price-053a27b1/
• Trevor Grimes’s LinkedIn: https://www.linkedin.com/in/trevor-grimes/

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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.

How do you build brand trust when your audience isn’t even sure your founder is real?

In this episode, host Trevor Grimes sits down with Hannah Green, the internal marketing lead behind Patient Care Marketing Pros and Nick the Marketer, to unpack what it really takes to grow authentic, long-game content in a niche industry like urgent care.

Hannah shares what’s worked (a weekly podcast that clients quote in meetings), what hasn’t (an intricately folded direct mailer that got zero response), and how her team blends grassroots trust with digital presence to make clinics more findable and human. They also get real about content fatigue, internal buy-in, and why 4.7 stars beats 5.0 every time.

If you’ve ever struggled to keep showing up when no one’s clicking—or wondered how to make medical marketing not feel sterile—this one’s for you.

Hannah Green is the Internal Marketing Coordinator at Nick the Marketer and Patient Care Marketing Pros, where she leads content across social, email, podcast, and webinar channels. With a background in graphic design and a knack for getting things done even without a playbook, Hannah’s the human behind much of the brand’s approachable, personality-driven presence. She’s also the co-creator of Walk-Ins Welcome, a podcast for healthcare marketers.

• Why their “Doc in the Box” reputation still holds clinics back—and how to change that
• The one rule Hannah applies to all her content: educate, entertain, or engage
• How a hyper-targeted direct mail campaign completely flopped—and what she learned
• Why 4.7-star reviews are more trustworthy than perfect 5.0s
• The surprising power of Reddit for urgent care reputation research
• How Patient Care Marketing Pros uses content as a brand trust funnel, not a vanity metric
• What happened when their podcast listeners became their warmest leads
• The role of personal posts in building connection on LinkedIn (even if it’s just about counting dogs on a walk)

• Walk-Ins Welcome – their weekly healthcare marketing podcast
• MailChimp – used for their email newsletter
• Strava – mentioned in reference to personal walks + book recaps
• Urgent Care Association (UCA) – for community and event presence
• Alex Hormozi’s $100M Leads – referenced in a discussion on reviews and proof of concept

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 do cashflow, content, and Krispy Kreme have in common? According to Trevor Grimes and his longtime friend Chris Brown, more than you’d think. Chris, a solutions engineer at Trovata.io, helps companies understand where their money is—literally. But in this episode, he goes beyond bank accounts and into the messy, experimental journey of making content before you have it all figured out.

Trevor and Chris reflect on their early creative projects, lessons from Alex Hormozi and Gary Vee, and why cringey content is part of the process. They break down how to balance volume with authenticity, why capturing ideas matters more than polishing them, and what it means to keep showing up—even when the algorithm doesn’t care.

Listeners will walk away with permission to create something imperfect, refine it later, and build a body of work that actually means something.

👤 Guest Bio

Chris Brown is a Solutions Engineer at Trovata.io, a cash management platform that helps companies gain visibility across multiple banks. With a background in finance and a long history of experimenting with writing, freelancing, and creative side projects, Chris shares a rare blend of practical clarity and creative courage.

📌 What We Cover

• Why “just testing it” matters more than finding your perfect why
• How Chris helps companies like Krispy Kreme manage cash across dozens of banks
• The tension between financial privacy and building trust through content
• Why writing became Chris’s go-to format for processing and sharing ideas
• How capturing your thoughts (not just publishing them) builds momentum
• The underestimated power of showing up—accent, cringe, and all
• Balancing full-time work and family life with sustainable content creation
• Why expressing yourself matters, even if it’s just 7 minutes a day

🔗 Resources Mentioned

• Trovata.io
• The Total Money Makeover by Dave Ramsey
• Gary Vaynerchuk
• Alex Hormozi
• The 4-Hour Workweek by Tim Ferriss

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.

If your content feels bland or forgettable, this might be why: you're playing it safe. In this episode, Trevor Grimes sits down with Phil Pilalas, a fellow “content dork” and messaging strategist at Scrappy ABM, to talk about the one thing too many brands overlook—point of view.

Phil unpacks why content that tries to “be a friend to everyone” often ends up resonating with no one. He shares how safe messaging erodes brand voice, why marketers must fight to keep the founder’s original intent intact, and how to translate brain dumps from subject matter experts into content that actually says something.

Whether you're building a brand guide or trying to write one strong LinkedIn post, this conversation reminds us that meaningful content starts with a clear perspective—and the courage to stick to it.

👤 Guest Bio

Phil Pilalas is a messaging and content strategist at Scrappy ABM. He helps companies say important things to important people—by turning subject matter expertise into clear, compelling content. With a background in broadcast communications and leadership roles in marketing, Phil’s known for distilling messy brain dumps into tight, audience-ready narratives.

📌 What We Cover

• Why content needs a clear point of view to matter
• How trying to “stay safe” waters down your message
• What to ask when building a brand voice (that actually reflects your brand)
• How to distill hours of SME talk into a week’s worth of content
• The role of the CEO’s voice in brand communication
• Why marketers need face time with product and sales teams
• How to validate your tone with real customer language
• What “dying on the wrong hill” looks like for content distribution

🔗 Resources Mentioned

• Simon Sinek – Start With Why
• LinkedIn (as a key content platform)
• TikTok, YouTube – as examples of finding the right hill for your content
• “Brand archetypes” (mentioned, not followed)

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.

“If you don’t draw a hundred thumbnails first, was it even real design?” That’s how The Content Crowd host Trevor Grimes kicks off this deeply personal and professional conversation with longtime friend and creative peer Jessica Jackson Tait, now VP of Business Operations at WITH.

What unfolds is part origin story, part playbook for how creative minds can build meaningful systems without sacrificing heart. Jessica shares how her background in graphic design and art direction shaped her transition into creative operations—and how she’s redefining leadership by respecting both creative time and business goals.

You’ll hear why WITH dropped “agency” from their name, how they structure timelines around real data (not guesswork), and why project managers are the unsung heroes of creative work. Jessica also breaks down her move from agency ops to business ops, including how she helped launch a strategic advisory model with major clients like Coca-Cola and AT&T.

This episode is a guide for anyone trying to balance artistic integrity with sustainable, human-centered strategy.

👤 Guest Bio

Jessica Jackson Tait is VP of Business Operations at WITH, a strategic and creative firm based in Atlanta. Starting her career in graphic design and art direction, Jessica brings a rare blend of creative intuition and operational precision to her role. With over a decade at WITH, she now oversees systems, tools, and business decisions that help teams do great work—on time and with purpose.

📌 What We Cover

• Why WITH stopped calling itself an “agency”—and what that shift unlocked
• How to build project plans around real creative timelines (not just client deadlines)
• The power of time tracking as a creative growth tool—not a policing tactic
• Tips for bridging the gap between creatives and project managers
• What it actually means to operationalize value-driven content strategy
• The human reason behind WITH’s new advisory offering
• How to balance efficiency with empathy when managing creative teams
• Why content must earn trust—not just attention

🔗 Resources Mentioned

• monday.com (project management tool used by WITH)
• Harvest (time tracking tool)
• QuickBooks
• Jessica’s LinkedIn: https://www.linkedin.com/in/jessicajacksontait/
• WITH on LinkedIn: https://www.linkedin.com/company/with-agency

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.