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Ross’s #1 Lesson for Marketers Heading Into 2026 | Vol 274

Free Content

Welcome to Volume 274 👋

Happy Thursday! 

In this week’s newsletter, we cover: 

Let’s get into it.


🔮 Ross’s #1 Lesson for Marketers Heading Into 2026

GetUplift recently asked 18 marketers and experts one question: What’s the ONE thing from 2025 you’re taking into 2026?

Ross’s answer: Assume everything can be automated — until proven otherwise.

“The most important thing that I’m taking into 2026 is the importance of having an open mind to augment everything,” Ross shared. “Every month in 2025 I came across a new tool, new use case, or new way of leveraging AI to be more efficient and effective.”

From Distribution.ai turning podcast episodes into multi-format assets, to Wispr Flow for narration, to Fathom for call recordings, to Claude and Perplexity handling tasks that used to take hours — Ross’s default has shifted. Instead of assuming something needs a human touch, he now assumes it can be automated and works backward from there.

That doesn’t mean replacing people. It means freeing up your best thinking for the work that actually requires it.

The full article features insights from Crystal Carter, Andy Crestodina, Rand Fishkin, Amanda Natividad, and more — each sharing the single lesson they’re carrying into the new year.

👉 Read the full roundup on GetUplift to see what 18 industry leaders are betting on for 2026.


🎤 Ross is Speaking at Digital Cut 2026

Ross is taking the stage at Digital Cut 2026 — a three-day online conference bringing together the sharpest minds in AI, marketing, and digital innovation.

Ross is Speaking at Digital Cut 2026

His session, “Unlocking Reddit: What the World’s Conversation Data Means for AI-Driven Innovation,” will explore how Reddit’s massive conversation dataset is shaping AI tools and what marketers need to understand about this shift.

He’s joining a lineup that includes Seth Godin, Neil Patel, Ali Abdaal, and Sophia Amoruso.

When: February 6-8, 2026

Where: 100% online (recordings included)

Get your tickets now


🤖 Reddit Unveils AI-Powered Media Buying Tool at CES

According to Trishla Ostwal of AdWeek, the company unveiled Max Campaigns at CES on Monday — an AI-powered media buying tool that automates targeting, bidding, creative optimization, and budget allocation directly within Reddit Ads Manager. The goal: simplify campaign setup while giving advertisers something Reddit believes its competitors can’t — transparency and access to what it calls “Reddit community intelligence.”

That intelligence draws on more than 23 billion posts and comments spanning two decades of human conversation. Max Campaigns uses machine learning to predict impression value, rotate creative, and optimize placements without constant manual adjustments. Early testing reportedly showed improved efficiency and engagement.

The tool also includes AI-assisted creative features tailored to Reddit’s discussion-driven format: headline suggestions based on trending language, auto-generated thumbnails for in-feed placements, and upcoming AI-powered video cropping for repurposing content from other platforms.

According to Marketing Interactive, one standout feature is “Top audience personas” — an AI-driven reporting layer that clusters users into segments, like new parents or home cooks, and surfaces which groups are engaging most, along with what topics they’re currently discussing.

Reddit Unveils AI-Powered Media Buying Tool at CES

“We’re not just making ad management faster — we’re making it smarter and tailored to our community,” said Jyoti Vaidee, Reddit’s VP of Product

For marketers already exploring GEO and AI-driven discovery, you shouldn’t miss this one. 

Reddit has not-so-quietly become an irreplaceable source for LLM training data and AI-generated answers. Now it’s packaging that same conversational data into an ad product designed to help brands reach high-intent audiences and influence how they show up across AI platforms. As the battle for performance budgets intensifies, Reddit is betting its community depth can compete with the scale of Google and Meta.


👀 What’s the Latest in B2B SaaS This Week? 

🤖 EXCLUSIVE: Reddit Takes on Google and Meta with New AI Media Buying Tool | AdWeek

🌎 OpenAI’s International Conundrum | The Information 

🖥️ December Core Update: More Brands Win “Best Of” Queries | Search Engine Journal

💰 xAI says it raised $20B in Series E funding | TechCrunch

🩺 OpenAI launches ChatGPT Health, encouraging users to connect their medical records | The Verge


🚨 New Podcast Alert: Winning with Intention in the Age of AI

In the latest episode of The Ross Simmonds Show, Ross sits down with Wil Reynolds — founder of Seer Interactive and a legend in the world of search — for a no-holds-barred conversation on playing the long game in marketing, leadership, and entrepreneurship.

Wil opens up about how AI is reshaping content creation and discovery, shares tactical workflows using tools like PhantomBuster and Claude Code, and gets candid about what he’d do if he had to start over from scratch. This one is packed with real talk on imposter syndrome, agency building, and why the most resonant content is often the most uncomfortable to post.

Here’s what Ross and Wil cover:

  • Respect the audience’s attention. Wil’s gut-check before posting anything: “Would I actually want to see this in my feed?” If the answer is no, it doesn’t go out.
  • Raw beats polished. The posts that build trust aren’t the curated wins — they’re the broken processes, the hard lessons, and the behind-the-scenes truth most people are afraid to share.
  • Distribution over perfection. Over-engineered content processes mean nothing if nobody’s sharing the output. Optimize for conversation first, then adapt for search once you know it lands.
  • AI as a leverage tool, not a replacement. Wil walks through how he uses PhantomBuster and Claude to turn LinkedIn into a research and lead engine — tracking who engages, pulling insights for outreach, and blending paid and organic data to spot opportunity.
  • Future-proofing through adaptability. The real edge is in remaining unsatisfied with the status quo, making it safe to break things, and preparing your team for automation shifts through constant experimentation.

Listen to the full episode on Apple Podcast or Spotify to hear Wil’s playbook for building trust, leveraging AI, and staying ahead when the rules keep changing.


🧠 This Week’s Brain Food  

New research from Technical University Berlin reveals a critical blind spot in how we work with AI tools — and it has major implications for marketers operating under constant time pressure.

The study (n = 228 participants across 8,200+ task evaluations) found that when people are rushed, their ability to distinguish between accurate and faulty AI outputs drops significantly. Participants without time pressure correctly evaluated AI responses about 70% of the time. Under time pressure, that number fell to 62.5% — with the drop driven primarily by a failure to catch AI errors.

Even more concerning: trust in AI increased over time regardless of actual performance. Participants gradually relied more on outputs — even without any feedback suggesting the AI was reliable.

With roughly 40% of the US workforce now using generative AI on the job, the takeaway is clear: the faster you’re moving, the worse you are at catching AI mistakes. And the more you use these tools, the more you’ll trust them — whether that trust is warranted or not.

Build in review checkpoints. Don’t let deadlines override diligence. 

If you’re interested, check out the full open-access paper here


🎙️ Ross on AI For U: The New Rules of Search Discoverability

Ross recently joined Brian Piper on the AI For U podcast to break down how AI is reshaping content marketing and search strategy.

The conversation covers why most content strategies fail (hint: it’s not a creation problem — it’s a distribution problem), how to optimize for “answer engine optimization” as AI-generated overviews replace traditional search results, and why 60% of ChatGPT search results now cite Reddit threads.

Ross with Brian Piper on the AI For U podcast

Ross also explores what’s coming next: a world where AI agents apply to schools, make purchases, and choose brands — based entirely on what they can find online.

👉 Listen to the full episode


Want to sponsor our next issue? Reply to this email, and we’ll share how you can reach more SaaS founders and marketers today. 


🏅 Reddit Post of the Week

An Open Letter to Marketing Directors Everywhere (A Friendly PSA from Your Agency) In r/marketing

🎖️ LinkedIn Post of the Week

Nobody’s Clicking Anymore by Amanda Natividad


🤳🏽 Nice Finds You Should Binge

What Readers Want to See in the Workplaces of the Future | The Walls Street Journal 

Can a social app fix the ‘terrible devastation’ of social media? | TechCrunch

The Future of Digital Marketing: 7 Shifts That Will Shape What AI Says About You | Foundation Marketing 

Is Craigslist the Last Real Place on the Internet? | Wired


💻 Job Postings Worth Checking Out

Looking for a new opportunity? Here’s a round-up of some exciting job openings in the B2B SaaS space. 


Want us to include your job postings in our next issue? Reply to this email, and we’ll share how you can reach more SaaS professionals today. 


🎧 What We’re Wired Into This Week

Massive Attack – Angel

This SaaS news smattering is brought to you by Ethan Crump!

If you have any feedback, suggestions, or ideas you want to see in this newsletter, feel free to email me at ethan@foundationinc.co. We’re always looking for ways to improve and provide the best B2B SaaS marketing resources. 

Have a great weekend!

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