Behind Mary's Marketing Adventures – with Dan Holt

Marketing can feel like the wild west – no clear rules, constant chaos, and a never-ending stream of new trends to chase. And if you’ve ever sat in a marketing meeting thinking, why are we acting like this? - you’re not alone.

Dan Holt, managing director of Boss Digital and creator of Mary’s Marketing Adventures on LinkedIn, knows this feeling all too well. His viral LinkedIn comic series hilariously captures the madness of marketing – one ridiculous meeting at a time.

Behind the humor, the series shows real-life scenarios and lessons about focus, strategy, and what it takes to build a strong marketing foundation.

In this interview for the 9th episode of Marketing Mondays with Maria, Dan shares his journey from marketing newbie to agency owner, how Mary’s Marketing Adventures was born, and why most marketing strategies fail before they even start.

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From Clueless Young Marketer to Agency Founder

Fresh out of university, Dan found himself in a job he didn't enjoy, and when given the chance to switch to marketing, he took it – despite having zero experience. Shortly after, with no formal marketing training, Dan took a bold leap and started his own agency.

Spoiler: It didn’t take off right away.

Three months in, they still had no clients. But through persistence, hours upon hours of learning and hustle and a bit of luck after this rocky start, things started to turn around. The agency has since made of course huge leaps in its development, and has worked with hundreds of brands over the years to help them grow.

This experience gave Dan firsthand insight into the lack of structure in marketing. Unlike other industries, where formal training is expected, marketing can feel a bit free-for-all – something that later became a recurring theme in the Mary’s Marketing Adventures series.

The Birth of Mary’s Marketing Adventures

Like many marketers, Dan struggled to gain traction on LinkedIn. He tried multiple times to build a personal brand, but nothing really stuck.

Then, he had an idea: What if marketing struggles were told through a cartoon?

“I knew I wanted it to be in a story format, and what’s more obviously "story" than a cartoon? As soon as you see a drawing, your mind adjusts, and you immediately interpret the information in a story context.”

Enter Mary – the voice of reason in a world of marketing madness. Dan created Mary’s Marketing Adventures to highlight the absurdities marketers face daily.

Here's one of my favorite chapters as an example:

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But, other than the relatable topic, what was the key to Mary’s success?

Consistency.

Dan followed the principles of content marketing expert Joe Pulizzi:

• Have a clear content angle (the tilt) that differentiates you.
• Focus on one platform instead of spreading yourself too thin.
• Post consistently – don’t expect overnight success.
• Commit to at least 18 months before expecting results.

“The average B2B content strategy takes about 18 months to consistently monetize,” Dan explained. “Most brands don’t have the patience to wait that long, so they give up before seeing results.”

Following this strategy, Mary’s Marketing Adventures started small but steadily grew (in terms of both revenue Dan could attribute to the series and median amount of likes per quarter). By month 18, the series was bringing in consistent business, proving that long-term content strategies pay off – if you have the patience to stick with them.

Continuous Learning

It’s shocking how many people work in marketing without ever studying the fundamentals.

Dan's personal journey involved years of self-education, where he dedicated time every morning to reading, listening to podcasts, and reading books on his focus topics.

“For about three years, I got up at 5 a.m. every day and just learned. I read books, listened to every podcast I could find, and took detailed notes. It changed everything.” Now, he still spends at least an hour a day staying up to date.

If you want to dive deeper into marketing, Dan recommends following the work of the following Top 1% of marketers:

Resources

• David Aaker (Building Strong Brands)
• Mark Ritson (Mini MBA, various podcasts)
• Byron Sharp (How Brands Grow)
• Rory Sutherland (The Surprising Power of Ideas That Don't Make Sense, various podcasts)
• Joe Pulizzi (Content Inc.)
• Chris Walker (Revenue Vitals Podcast)
• Rand Fishkin (LinkedIn content)
• Marcus Sheridan (They Ask, You Answer)

The Focus Problem in Marketing

Many of Mary’s episodes tackle one core marketing issue: lack of focus.

In most companies, marketing teams get pulled in 20 different directions. One day, it’s social media, the next, a CEO wants to “go viral on TikTok.” The result is lot of half-baked initiatives with no real impact.

Marketers need to get ruthless about what they say NO to.

“Strategy is just what we say no to,” he says. “Most organizations don’t have the resources to do everything, so instead of spreading yourself thin, focus on doing a few things really well.”

During the interview we also touched on the relationship between marketing and sales, a notoriously tricky dynamic:

“There is generally a tension between sales and marketing. Sales teams tend to be more focused on the next 90 days, while marketing takes a longer-term approach. That gap creates friction.”

For this, his advice is for Marketing to take responsibility and align expectations from the start. Define clear KPIs and work together to ensure marketing efforts support sales goals. Also, align on what common terms are SQL (Sales Qualified Lead) actually mean for you and your colleages. Clarity is key.

The Short-Term vs. Long-Term Trap

Another common marketing mistake marketers make is over-prioritizing short-term tactics.

It’s understandable. Short-term tactics are easier to measure. They give you an immediate dopamine hit. But long-term brand-building is where real growth happens.

Instead of pouring all resources into direct response and lead gen, Dan advises businesses to invest at least 60% of their resources in brand-building – even during economic downturns.

Recessions make brands panic. They cut brand marketing and double down on performance marketing. But if fewer people are buying, your acquisition costs go up. Instead, you should be leaning even harder into brand.

Final Thoughts

Marketing doesn’t have to be as chaotic as Mary’s Marketing Adventures makes it seem – but let’s be honest, it often is.

Some key takeaways from this episode with Dan and his decade + long career are:

1. Consistency beats short-term hacks.
2. Focus is your biggest advantage.
3. Long-term brand marketing matters more than you think.
4. Marketing and sales need to align on goals.
5. Marketers should invest in learning, not just execution.

Dan’s final piece of advice? “Most marketers just need to learn more about marketing.” He stresses the importance of studying the fundamentals—brand strategy, behavioral psychology, and positioning – rather than just keeping up with the latest digital trends.

If you want to dive deeper, check out Mary’s Marketing Adventures on LinkedIn. And if you have any ridiculous marketing scenarios Dan should turn into a comic, send them his way – he’s always looking for inspiration.