Ryan Holiday and The Daily Stoic: B2B Marketing Lessons on Making Content That Matters with VP, Head of Marketing at FourKites, Amanda Dyson

Since 2014, Ryan Holiday’s The Daily Stoic newsletter has landed in inboxes every single morning, offering ancient wisdom in bite-size, highly clickable form.

It’s also a masterclass in content marketing. In this episode, we’re unpacking what B2B marketers can learn from The Daily Stoic with the help of Amanda Dyson, VP, Head of Marketing at FourKites.

Together, we explore how to break the marketing mold, why the most impactful content is also the most practical, and how anchoring your message in core values makes it stick. Stoicism isn’t just a philosophy; if done right, it’s a blueprint for modern marketing.

About our guest, Amanda Dyson

With 20 years B2B software and SaaS marketing expertise, Amanda specializes in go-to-market strategy; consultative marketing; change and people management; lead generation; account based marketing; partner co-marketing; integrated digital marketing; email marketing; live and virtual events; corporate branding and storytelling; account segmentation and targeting; project and budget management, and strategic advisement.

Amanda has run regional and global teams. She has a passion for people and results and a proven track record of success delivering on KPIs and OKRs. She has held successively responsible, cross-functional leadership positions in sales and marketing, including alliances, partnership marketing, ABM, demand generation, field marketing, solutions marketing, events, communications, and corporate marketing for global Supply Chain Management (SCM) and Enterprise Resource Planning (ERP) software companies.

A California girl at heart, Amanda happily resides in Charlotte, North Carolina with her family of five. When she’s not growing people or pipeline at leading tech companies, she enjoys spending time with her family in the mountains or at the beach, running daily, and practicing mindfulness. Amanda has an MBA from the W.P. Carey School of Business at Arizona State University with a focus in Marketing, Finance and Supply Chain, and a Bachelor of Arts degree in Business Economics with a Minor in Professional Writing from the University of California, Santa Barbara.

What B2B Companies Can Learn From Ryan Holiday’s The Daily Stoic Newsletter:

• Break the marketing mold. Stoicism may be ancient, but Ryan Holiday has made it feel new and modern. Amanda sees that reinvention as a creative north star. She says, “Let’s do something wild. Some of my favorite marketing campaigns have just been weird stuff. It breaks the mold and it gets something done.” Ryan Holiday didn’t market stoicism by copying academic textbooks, he made it approachable and surprising. B2B marketers should do the same. Surprise earns attention. A little weirdness, done with purpose, goes a long way.
• Make it usable, not just insightful. Ryan Holiday’s greatest trick isn’t sounding smart, it’s making stoicism actionable. Amanda says,  “He does things in such a bite-size, practical way that you can hold onto it.” That’s exactly how B2B content should work. Don’t just publish thought leadership that nods at trends. Give your audience tools they can actually apply. Teach them something they’ll remember at 4 PM on a chaotic Tuesday. If it doesn’t help them do their job better, it’s just noise.
• Anchor your content in core values. The Daily Stoic isn’t random. It’s rooted in four core tenets: courage, temperance, justice, and wisdom. Amanda draws the parallel for marketers: “It’s all fostered and rooted in these core values or the stoic virtues, which you could look at your brand pillars in the same kind of light.” B2B content should be more than campaign-deep. When your content reflects your company’s true values, it resonates longer and travels farther. Think less about filling the calendar, and more about reinforcing what you stand for. 

Quotes

*“ I really challenge my teams to get back to storytelling. You gotta break out of the box, so let's do something wild. Some of my favorite marketing campaigns I've ever done have just been weird stuff: bobbleheads, robots on the beach. Random things that are not B2B software, but it breaks the mold and it gets something done. I think Ryan's done that with his marketing of stoicism. He's broken the mold, right? He reinvigorated this ancient philosophy, and so that's definitely a lesson I think we can learn from him too on content.”

*“ So we are all about how do we take one thing and reuse it in different ways. I think if we look at Ryan and his newsletter, I kind of mentioned his repetition. I don't think he sends the exact same newsletter, you know, multiple times. But there's certainly similar messages where you can go back in your archives and dig those things up again and present it in a different way. Content is huge. It drives, internally and externally, all of our activities. But you gotta be really smart about how you do it and how you use it, 'cause you're competing with so much noise. It can definitely be challenging to again break that mold.”

*“ Something that makes him a tremendous marketer is that he really believes in what he's selling us, right? He's created this brand that is a lifestyle. Stoicism is a philosophy, so there's a lot of high value attached to it and how you live your life.”

Time Stamps

[0:55] Meet Amanda Dyson, VP, Head of Marketing at FourKites

[00:58] Why Ryan Holiday's The Daily Stoic Newsletter

[03:04] The Role of VP, Head of Marketing at Four Kites

[04:18] Origins of Ryan Holiday's The Daily Stoic

[09:27] Understanding Tucker Max

[13:12] Stoicism 101: Old Ideas for Modern Chaos

[20:23] Building a Daily Ritual

[22:21] Strategies for Writing Like a Pro

[25:35] Inspiration as a Driver for Your Content

[35:55] Creating Marketing Tactics That Actually Matter

[39:00] FourKites' Content Strategy

[40:31] What's Working for Amanda Now?

[44:15] Measuring ROI at Four Kites

[49:49] Advice for Marketing Leaders

[51:27] Final Thoughts and Takeaways

Links

Connect with Amanda on LinkedIn

Learn more about FourKites

About Remarkable!

Remarkable! is created by the team at Caspian Studios, the premier B2B Podcast-as-a-Service company. Caspian creates both nonfiction and fiction series for B2B companies. If you want a fiction series check out our new offering - The Business Thriller - Hollywood style storytelling for B2B. Learn more at CaspianStudios.com. 

In today’s episode, you heard from Ian Faison (CEO of Caspian Studios) and Meredith Gooderham (Head of Production). Remarkable was produced this week by Jess Avellino, mixed by Scott Goodrich, and our theme song is “Solomon” by FALAK. 

Create something remarkable. Rise above the noise.