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.