Digital Social Hour Podcast - Episode Summary

Episode: Chris Kubby: The Brutal Truth About Woke Branding, DEI & Why Big Brands Are Failing | DSH #1642
Host: Sean Kelly
Guest: Chris Kubby (Kubby)
Date: November 26, 2025

Main Theme

In this episode, Sean Kelly sits down with marketing agency founder Chris Kubby to dissect the rapidly changing landscape of marketing, branding, and social media, with a sharp focus on the pitfalls of “woke” branding, the impact of DEI (Diversity, Equity, and Inclusion) initiatives, and why many big brands are struggling to connect with customers. The conversation weaves through the influence of AI on marketing, insights into European and American business culture, strategies for creators and agencies in the AI era, and practical, no-nonsense advice for both startups and Fortune 500s.

Key Discussion Points & Insights

1. How AI Is Disrupting Marketing and Agencies

• AI is “crushing” agencies and forcing massive, industry-wide change.
  “Every agency is going to go through massive changes. We’re just going to see way more clients take stuff in house with their AI agents and things that they’re building… I think we’re going to see every major agency in the world just get flipped on its head in the next like five years.” — Kubby (06:22)
• Specialization is essential: Agencies must provide what AI cannot—unique access to people, creators, or exclusive distribution.
• Owning media is the new moat: “Owning media is going to be something that becomes way more valuable because it’s not done by AI.” — Kubby (09:10)
• Ad buying is close to full automation: Zuckerberg intends to cut out agencies, with platforms optimizing both creative and spend with AI. Still, human oversight is necessary for quality.

2. Changing Approaches to Targeting and Creative

• Move away from rigid personas: “You can put all of these things… these psychographics on top. You don’t need those anymore. Basically, you’re just running and the algorithms and the AI figure out where best to place it.” — Kubby (11:38)
• Focus on high-quality creative and iterating rapidly: Build lots of creative variations and let algorithms optimize.
• High ad costs and long sales cycles in B2B enterprise marketing; leads for Kubby’s agency average $200 but yield large contracts.

3. Brand Building and Creator Economy Strategies

• Organic > Paid: Audience trust is higher when people discover you organically (TikTok, viral content) than through ads.
• Monetize your expertise: Don’t be afraid to offer digital products, courses, templates. “I fucked up that so bad… I left so much money on the table.” — Kubby (20:04)
• Leverage “clipper” networks: Let young content editors clip and share your content for a percentage of sales.
• YouTube is the long-term winner: “YouTube’s the best. It’s just, it’s a place that’s going to pay you... higher investment time wise but you will get more brand recognition out of it.” — Kubby (18:56)
• Own your audience: Build messenger/subscriber lists, use ManyChat, and employ DMs to deepen relationships. However, don’t overdo call-to-action engagement, as platforms can lower reach if engagement farming is too visible.

4. Woke Branding, DEI, and Why Brands Are Failing

• Corporate activism is backfiring: Many brands misread culture and overcorrect, alienating core customers.
  “They didn’t read the room… American culture is not progress. It’s just progressive in a different way now.” — Kubby (29:08)
• Change is costly and often unnecessary:
  “Any kind of change will hurt. Unless the upside is double or triple what you’re doing today, it’s going to cost you more.” — Kubby (28:18)
• Rebranding usually doesn’t deliver ROI for big brands: Cracker Barrel and Jaguar suffered after “woke” changes.
• Disconnect between upper management and real customers:
  “There’s also a disconnect between the employees in general. I think we’ve been hearing so many times that employees want companies that are progressive… but that’s not necessarily what’s good for the business.” — Kubby (30:29)
• DEI initiatives are being dialed back: Brands are moving away from mandated diversity in ads and focusing more on core markets.

5. The Culture and Politics of Business in Europe vs. US

• Denmark has capitalist efficiency with strong social support: High taxes (50%+), employee protections (long maternity/stress leave), high cost of living, but great public services.
• Business is more employee-first: Firing can be tricky; long-term sick/stress leave is common.
• Different work-life balance culture: Europe is more “laid-back” but high taxes and social programs support that. Four-day work week is being tested in parts of Europe but is not yet widespread.
• Blue-collar jobs are resurging: Trades (plumbing, roofing, etc.) offer high incomes and resilience against automation.

6. Tactical Career and Agency Advice

• Degrees matter less than real results:
  “When I'm hiring people, I don’t care. We’d rather see a creator come to us and say, this is what I built.” — Kubby (49:07)
• Encourages employees to build personal brands and freelance: “More power to you. You’re going to be a more valuable employee to me.” — Kubby (51:29)
• For young marketers: Build, ship, and market your own projects; practical experience trumps theory.

7. On Writing and Publishing ("Hook, Line and Sinker")

• AI can accelerate content and book creation:
  “I just did voice notes driving to work every morning… get them transcribed in AI and then put them through AI to structure... while still keeping my tone of voice.” — Kubby (53:03)
• The book distills 10–15 years of marketing and content creation into a practical, actionable guide for building audience and sales.

Notable Quotes & Memorable Moments

"Owning media is going to be something that becomes way more valuable because it’s not done by AI."
— Chris Kubby (09:10)

"Any kind of change will hurt. Unless the upside is double or triple what you’re doing today, it’s going to cost you more."
— Chris Kubby (28:18)

“They didn’t read the room… American culture is not progress. It’s just progressive in a different way now.”
— Chris Kubby (29:08)

“They have to really do some serious analysis and say, will this 2x 3x or more our business… If it doesn’t, you don’t do that change.”
— Chris Kubby (28:57)

"There’s also a disconnect between the employees in general… Oftentimes, what the employees want isn’t actually good for the business."
— Chris Kubby (31:00)

“Degrees are crap. You shouldn’t have them… We’d rather see a creator come to us and say, this is what I built.”
— Chris Kubby (49:02)

“I totally agree. I fucked up that so bad. No, honestly, like I just went all in… I left so much money on the table.” (On not having early digital products)
— Chris Kubby (20:04)

Timestamps for Key Segments

• AI impact and agency future: 06:22–09:41
• Ad strategy & evolution: 11:27–12:55
• Organic vs. paid, lead costs: 13:02–14:37
• YouTube & digital offers for creators: 18:56–22:23
• Woke branding, DEI, and failing rebrands: 28:18–31:27
• Corporate management/customer disconnects: 30:29–31:26
• Pullback on DEI and cultural trends: 31:57–33:34
• European vs. US business/taxes/culture: 36:14–38:19
• Employee protections, work-life, stress leave: 39:03–43:16
• Rise of blue-collar jobs: 45:08–46:54
• Degrees vs. experience in hiring: 49:02–52:10
• Writing ‘Hook, Line and Sinker’ with AI: 53:03–54:07

Resources and Where to Find More

• Connect with Chris Kubby:
  • DM on Instagram for details on “Hook, Line & Sinker” and his custom AI tool
• Kubby’s Agency: Specializes in social content for Fortune 500/1000 brands (contact via agency site for CMO-level consulting)
• Further Reading:
  • Book: “Hook, Line & Sinker” (DM for PDF and access to accompanying AI/chatbot)
  • Inspired by recent shifts in branding, content strategy, and real-world marketing psychology

For more practical insights, agency CEO stories, and creator strategies, check out “Digital Social Hour” wherever you get podcasts.