Column Five

Cofounder: 2018 -
Cofounder/CEO: 2014 - 2018
Cofounder/Creative Director: 2009 - 2014

Cofounder

Columbia University

IKNS Course K4335 'Visualization of Information'

Instructor

Cofounder at Column Five

I'm a husband as well as father of five. I'm also a Cofounder of Column Five, my favorite creative agency (I may be a bit biased). 

Column Five is a B2B marketing agency that specializes in brand and content marketing for SaaS companies. We help our clients build their brands through world-class content that stands out and pulls people in because it's anchored to a company's special sauce and conveys a clear, distinctive, and memorable perspective.

The content we create and distribute shapes the story potential buyers tell themselves and others about your company, namely that their lives will improve simply by becoming your customers. 

This all takes place within the context of many other companies attempting to do the same, competing for the pole position in buyers' minds as the best option. And, the stakes are winner-takes-all. 

Ultimately, deciding which company wins any deal comes down to this story. We don't own it; the buyer does, but the better the job we do shaping the story, the more you will win. 

This is why we say, "best story wins.”

If you're on Design or Fin Twit (or X, whatever) you've probably come across these beautiful earnings call posters from Quartr - this one highlighting RobinHood is probably my favorite. So what is Quartr? They provide qualitative public market research. 

But the beauty of what this company is doing is in their visual storytelling - when you see their graphics you instantly want to learn more about them and what makes them unique. 

This is such a great - and simple - example of how to use story to differentiate.

Joshua Ritchie

Cofounder of Column Five & Host of Best Story Wins

The kids have spent the week making up games on the trails out back, drawing maps, and turning every stick into a sword.

No TV yet. No neighborhood friends yet.

Just… time.

It’s made me realize how rare boredom is, and how useful it can be.

Boredom forces you to make something out of nothing.

Last Saturday we moved from Orange County, CA to Columbia, TN to give our kids a slower-paced upbringing — fewer screens, less keeping up with the Joneses, and more room to lean into the everyday stuff. 

We’re still unpacking, so no TV yet — which means the kids are discovering new forms of entertainment. Current favorite: the leaf blower.

I’ve been feeling over-connected and overstimulated lately, and I’m intrigued by the quiet rebellion back to dumb tech.

So much so that I sold my Ram truck that was basically a big computer on wheels and bought a 2003 Toyota Land Cruiser as my daily driver.

(Just look at that media console!) 

It’s analog. Heavy. Unbothered. A screen that reminds me of a Commodore 64, no alerts, no app integrations - just a beautiful machine doing its job. And it's fun to drive, whether I'm taking the boys fishing, running errands or driving to the office. 

I don’t think the masses will U-turn here - just like most people aren't canceling their Spotify accounts in favor of vinyl. But, as with most things in life, the option to simplify is there if you want it.

And it might just save your sanity.

There’s something calming about less stuff going on.

“Do more with less” might be the most dangerous phrase in marketing.

Most CMOs already get that the job’s gotten harder. Budgets are shrinking, patience is thinner, and the seat itself is a revolving door. 

And most folks understand all of this, and that it's all happening, at a high level, but we wanted to go deeper. So Jason Lankow and I sat down with someone who probably talks to more CMOs than anyone - a person who sees the patterns firsthand. What’s actually working. What’s breaking. And what it really feels like to lead marketing in the pressure cooker right now.

This week’s episode of Best Story Wins could be thought of as basically the State of the Union for B2B marketing leaders. 

Our guest, Drew Neisser, Founder of CMO Huddles, lays out the real forces reshaping the role: PE and board pressure, CFO scrutiny, AI upheaval, and the erosion of marketing power inside the org. It’s blunt, unvarnished, and refreshingly honest about what it takes to lead marketing. 

We cover:
- Why “brand” is a budget-killing word (start saying “reputation”)
- How to align with CFOs on metrics that matter and end attribution theater
- Power plays that expand CMO influence—owning Partnerships and Rev
- The late-stage moments that actually convert (small dinners > trade shows)
- Why AI should first nuke your workflow before it ghostwrites your strategy
- And much more. 

A big thanks to Drew for coming on and for being a great guest - episode links in the comment below.

For most of the last decade, B2B marketing was easier than it should've been.

Money was cheap, and "good enough" content and campaigns worked pretty well.

(And a lot of us got rewarded for playing the game, not for being great at it.) 

But, the last two years corrected everything. 

Budgets tightened. Teams shrank. Buying committees got cautious. And AI brought the cost of content creation to nearly zero. 

As a result, marketing is hard again. And for many, it's hard for the first time. 

There's been a lot of discomfort with this, and anyone saying there isn't is delusional or plain lying. But, if you we take a longer-term view here - maybe this is all a good thing. 

Because when marketing is easy, activity gets rewarded. When it gets hard, it rewards craft and impact. 

Today, you have to be really good at what you do to get results: you have to have taste. You have to know your story, and find new ways to tell it. You have to put yourself in your customers' shoes and figure out how to make something that people will care about and remember.

Easier said than done - yeah, I get it. But a lot of what we do and how we feel about it comes down to how we frame it.

Like baggy jeans, Storytelling is cool again. 

Unrelated: this is a pic of me and my daughter, Daisy Ann who’s obsessed with the BB guns I bought my sons when we moved to TN. She looks just like my wife in this pic.

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When we first started our agency, everyone was scrambling to "do SEO."

Now, two decades later, everyone's trying to "do AEO."

Talk to any marketing leader and they'll tell you: it's in their top 3 priorities for 2026.

But in the rush to "optimize for LLMs," droves of marketers are forgetting the cardinal rule of content marketing: serve your customer.

These are the ones chasing quick hacks and shortcuts, convincing themselves they're being strategic because it might drive visibility.

It's understandable — the market's tough, headcount is shrinking, and short-termism is everywhere.

But the early cautionary tales are already here. Every week, I see a story about a brand that saw early gains from gaming AI search, only to watch its visibility tank because the machines figured out what was going on. 

For the last two years, we've been building our own approach to AEO — using ourselves as the guinea pigs. And what we've learned is it's not about new tricks or shiny tools.

It's about fundamentals, done right. First for humans and then for machines.

Here are a handful of examples of what's actually moving the needle for us and our clients:

• Remove the fig leaf. Publish pricing and ungate your content - transparency trains models and customers to trust you. With search is collapsing into chat, your "critical for decision-making" info must be visible there.

• Replace fluff with real FAQs. No more keyword dumps, but rather structured, real answers to the questions your sales team hears every week. If you can answer them proactively, you should. 

• Lean into originality. The content that performs best in AI search has a pulse - it leverages proprietary data, human quotes, and a sharp POV that feels like it came from someone you like and respect.

• Be consistent everywhere you show up. LLMs synthesize your whole content footprint: your website, social media, review sites (eg G2 and even Glassdoor), press mentions, podcasts, and employee posts - and the more consistently your company is described/framed, the more serious a player you seem to be LLMs, which means the more often you'll be mentioned in a reply to a relevant query; alternatively, if your positioning and language shift across those 
surfaces, the model (and your audience) gets a fragmented picture of who you are. Treat every mention like part of your site architecture - it all feeds the exact source of truth.

• Choose quality over quantity. Flooding the internet with AI-written filler doesn't make you visible; it makes you average and replaceable. We've learned that one high-signal, valuable piece of content does more for long-term authority than any number of filler posts. With the cost of average content creation going to zero, high-taste, original content is becoming invaluable. 

Curious to hear from others - what else have you learned about what works / doesn't work?

LLMs are serving up what your brand is for would-be buyers.

Are you shaping that story—or leaving it to the machines?

In this week's on Best Story Wins, we dig into what it means to build a human brand in the AEO era.

In our conversation, Jason Lankow and I sat down with Ari Yablok, Head of Brand at Island, who unpacked how to: 

- Show up inside LLM answers and make buyers prefer you before they ever ask a bot.
- Lead with signals over slogans—booths, visuals, and copy that telegraph “category shift” without a single bullet point.
- Turn unscalable, unreasonable hospitality into retention and reputation.
- Create the “feeling of knowing”—brand confidence that shortens deals even when buyers can’t explain why.
- Use curated flaws and analog touchpoints to stand out as AI perfects the average.
- If you want to be chosen by people (and machines), start sending clearer signals.
- And much more. 

Thanks to Ari for coming on and being a great guest! 

(Links to listen / watch in comment below)

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