Richy brings big credibility to the conversation. You’ll hear the stories of a career that included helping launch CNN.com and its digital business, co-founding the IAB, and building an advertising infrastructure still used across the industry. He likes to build things.

And we’re the better for it. Because he’s THE person to help explain why privacy laws aren’t just legal issues—they’re structural ones. And why, if you work in marketing, advertising, media, or tech, these laws apply to you whether you realize it or not.

Richy breaks down what regulators are actually asking, why enforcement is picking up, and why brands are now responsible not only for themselves, but for their entire partner ecosystem.

What I appreciate most about Richy’s approach is that it’s practical, and empathetic. He understands the values and the limitations of AI. He knows human attorneys need to be involved.

He has made sure that SafeGuard is nimble and building systems that make compliance auditable, efficient, and—yes—actually helpful to growth, even when the rules keep changing. 

Why inboxes listed on privacy policies are now enforcement targets

How standardization saved digital advertising once before…and why it’s key to compliance now

Where AI fits into privacy workflows (and where it shouldn’t)

Why proving compliance matters more than promising it

If privacy still feels abstract or overwhelming, this conversation will give you clarity—and probably a healthy nudge to check a few things you’ve been meaning to look at. 

Speaking of healthy, I’m so honored to have Richy on for 23 million additional reasons: he is also a founding force behind BreastCancer.org, (did we mention they are matching donations through December?) It’s now one of the most recognizable, trusted, peer-reviewed health information sites in the world. Richy put his powers to use, from grabbing the URL to creating the revenue streams that are the foundation for its viability and ability to serve more than 20 million women globally, and counting.

Richy Glassberg works in a world defined by discretion and safeguards, yet remains an open book—grounded in purpose, devoted to his wife and best friend Katy, loyal to his Jack Russells, disciplined through 30 years of training in Shorin-Ryu Karate, and committed to making privacy compliance clearer, calmer, and more human.

00:00 – Why privacy compliance has become a business risk CMOs can’t ignore

4:10 – How data privacy laws impact all forms of digital advertising

8:55 – How Richy’s sneakers explain privacy really well

12:40 – Why brands are now responsible for vendors…and their vendors’ vendors

17:05 – What enforcement really looks like (and why it’s accelerating)

22:30 – How standardization turns compliance into a competitive advantage

26:15 – Using AI to assist privacy teams without replacing legal judgment

30:45 – From building CNN.com to how a pixel protected Ted Turner’s business

34:50 – The origins of BreastCancer.org and why it’s the work Richy’s most proud of

39:10 – Putting digital to good while keeping the open internet viable

41:55 – What’s next at SafeGuard Privacy

Connect with Richy Glassberg: https://www.linkedin.com/in/richy-glassberg-49a915

Visit SafeGuard Privacy for more resources: http://www.safeguardprivacy.com

LinkedIn: https://www.linkedin.com/in/mossappeal

Learn what “context” really means for advertisers (spoiler: consumers don’t experience media in silos), how the collapse of some Regional Sports Networks has created opportunities for local advertisers, and why “smart curation” is more than an industry buzzword.

But it’s not just the small business that needs to adapt: it’s agencies and brands, too.

Peter breaks down what full-funnel capabilities now available to SMBs—from maxing out brand awareness across Premion’s 210 DMAs, to measurable sales transactions, tapping 1st and 3rd party data. 

And, as we gear up for playoff sports, he reminds us how technology has leveled the playing field and that local advertisers can get in the game, too! So, sports puns are pervasive in Episode 44 since part of our conversation is about Premion’s new(ish) programmatic options to enable more inventory for all in live sports. Talk about a “game changer…!”

Understand how local car dealerships and furniture stores can now leverage the same targeting, data, and attribution tools that Fortune 500 companies use, all while reaching their specific communities with precision. But for everyone, it’s key to understand the importance of creative in driving outcomes, and omnichannel strategies (because yes, we’re all scrolling during halftime), and why advertisers need to embrace data-driven decisions over personal platform preferences.

Whether you’re a media buyer, agency leader, or local business owner trying to navigate the CTV landscape, this conversation delivers practical guidance on inventory, data, and measurement—the three pillars every advertiser should evaluate when choosing a CTV partner.

Bottom line? The local advertising opportunity in streaming TV has never been bigger—but only for those willing to adapt, measure outcomes over impressions, and follow consumers wherever they are.

[01:15] CTV’s double-digit growth, challenges and opportunities for advertisers

[02:14] What Premion does – Nine years of helping local advertisers navigate CTV

[03:33] Leveling the playing field – Educating SMBs on using the same tools as national brands

[05:25] Challenges and Strategies for Outcomes in Omnichannel Advertising

[08:26] Tools and tactics – First-party data, pixels, attribution, and what SMBs need to track

[10:48] The role of creative – Sequential messaging, AI tools, and “message to market match”

[12:52] How Premion’s programmatic access to sports inventory is opening doors for local advertisers

[15:39] Smart Curation Explained and Full Funnel Options in 200+ markets

[20:22] The dynamic nature of live sports – Why planning can be tricky but opportunity is massive

[21:45] What to look for in a CTV partner – Hint: Inventory, data, measurement (plus the TAG seal of approval!)

[23:41] Emerging Trends and AI in Advertising

LinkedIn: https://www.linkedin.com/in/mossappeal

What becomes clear quickly is that Neil operates from a different premise than a lot of industry vets.

He doesn’t see change as something to fear or fight. Instead, he sees it as the operating environment: “We’re going to happen to things. Things are not going to happen to us.”

It’s a subtle shift, but it changes everything about how you approach strategy. He also refuses to accept the tired narrative that media is dying. “Media is a fantastic business,” he told me. “People are on media more now than ever before, and there’s more money being spent against media in various ways.” The problem isn’t media; it’s when companies cling to old business models instead of adapting the execution while keeping the core mission intact.

One of the sharpest insights from our conversation centered on the collapse of search dominance. When Dotdash was independent, 70 percent of traffic came from search. That was their “mall.” But the mall blew up. Search traffic dropped to 30 percent of total traffic over time. The expected outcome? Disaster.

What actually happened, thanks to Neil’s approach? Total traffic grew. They built. They diversified into direct traffic, email, social platforms, Apple News, and owned properties like recipe lockers.

A key lesson:

The restructuring of People, Inc. offers a masterclass in letting go of control. Before, one print editor-in-chief made every decision across every platform. But these days he wondered how a print editor could understand everything and all platforms, like TikTok.

They couldn’t. So they decentralized. Execs like Charlotte Triggs now set the brand direction—the ethos that drives all teams—and then fully independent editorial teams handle the magazine, website, Apple News, the app, and yes, Instagram and TikTok. There’s no forced repurposing. Each platform team creates natively for their audience. The result: People grew from six or seven million daily visitors to ten million, with explosive growth on social.

Neil’s Wall Street background shaped how People Inc. approaches analytics, but he’s careful not to let math override instinct, noting:

The real insight is this: strategic ad placement and clean design mean you can generate more revenue with fewer intrusions on the audience. Better experience. Better margins. That’s the math he wants to do. 

What makes this conversation valuable is that Neil isn’t selling a complicated theory. He’s demonstrating a mindset: stay forward-looking, embrace change, remain unsentimental, and never stop making things people genuinely want. 

LinkedIn: https://www.linkedin.com/in/mossappeal

Joaquin emphasizes that AI should be seen as a supportive tool to elevate creative processes, rather than a replacement for human creators. He argues, ‘We are the sum of our experiences. And that makes us unique.’ He explains the benefits of Freepik’s tools for reducing the time needed to execute creative ideas… but stresses the irreplicability of humans based on our individuality, even as AI continues to advance. Basically, AI is a tool for creators, not a replacement, because AI cannot replicate unique human experiences.

Following this, Alexia highlights the significance of human artistry and personal storytelling in using AI tools to generate immersive and engaging experiences. She points out  “in the world of copyright with AI you have to show human authorship. So if you’re creating a story or a film that’s a hundred percent generated by AI, you can’t copyright or trademark that. So, I’m documenting my whole process – showing where it’s from my vision, it’s from my sketches.”

The conversation concludes with the vision of a synergistic future where AI tools enhance creative processes without devaluing the human touch.

Key Moments:

02:11 The Role of AI in Creativity

03:19 Human Uniqueness vs. AI

04:47 FreePik’s AI Tools and Their Impact

08:56 Copyright and Legalities in AI

14:31 Future of Jobs…and Creativity in the AI Era

15:38 Voiceover Job Reclaimed from AI

16:21 Regionalizing Ads with AI

17:16 Alexia Adana journey from Footlocker to Edelman

20:51 Microsoft sAI Project at Edelman

27:08 BloomChild: An Artist’s AI Journey

30:16 The Future of Human-Generated Art

LinkedIn: https://www.linkedin.com/in/mossappeal

Doug went from a career in the tech side to the publishing side, ultimately running Meredith Magazines (think: “Time,” “People,” “Better Homes & Gardens”…) to NOW hangin’ with the digital natives doing bling-meets-social media, as Co-CEO of “Bomb Party,” with its TikTok-famous jewelry reveals! Bet you didn’t see THAT coming.

He discusses the evolution of Meredith, its major acquisitions, the partnership he headed with Walmart, and how Meredith navigated its own transition — adding digital to print media.

Doug also describes his transition to #BombParty, a thriving and unique jewelry company that uses social media to engage customers. 

I cannot even keep track of all the ways David has reinvented himself: from launching a magazine on DC society back in the 70s, which he sold 10 years later for a handy profit — and is now turning those archival images into songs and content! I kid you not.

But wait, there’s more. He helmed big PR shops, but is perhaps best know for founding one of the best magazines on events, called “BizBash.” And now? SO MUCH — from recently launching an online events mag, “GatheringPoint.news” to yet another startup.

He highlights how he is an unabashed #AI acolyte and explains how it has revolutionized his latest ventures, supporting creative storytelling and increased efficiency. But David is also stopping to smell “The Roses”, making the most of his author father’s legacy by helping enable that current box office hit!

Like roses themselves, these guests exemplify the concept of ‘perennials,’ described by David as individuals who continuously evolve and remain curious, regardless of generational labels. Their stories illustrate the importance of adaptability, lifelong learning, and embracing new technologies in media or just for mental well-being!

00:00 Meet Doug Olson and David Adler

02:44 Doug Olson: From Tech to Media Mogul to…

05:36 The Better Homes & Gardens / Walmart Omnichannel Strategy

08:03 The Future of Print Publications

11:20 Golfing or Jewelry? Doug Olson’s New Venture: Bomb Party

14:56 David Adler: A Perennial Journey Through Media

19:55 Adler on AI and Innovation

24:09 Washington Insider, A Big Screen Legacy and MORE Current Projects

LinkedIn

Bomb Party

LinkedIn

LinkedIn: https://www.linkedin.com/in/mossappeal

Peter explains Pantheon’s effort at launching music-oriented podcasts, netting maybe 10 listeners on day. He and his other partners were not inclined to quit their day jobs. But then when Spotify entered podcasting, suddenly everyone searching for artists was discovering their content alongside the music.

And Pantheon went on to becoming one of the world’s biggest music podcast networks with 150 shows featuring top-tier bands like Metallica. 

Peter’s now pioneering interactive podcasting with Spooler, a platform created by former Apple Podcasts and Megaphone executives. This isn’t just another tech upgrade; it’s completely reimagining what audio content can be…and do.

But thanks to a combo of  new tech enablements from large language models anticipating conclusions to voice recognition and more, the team has raised the bar on what’s possible. Try out the beta version of what the team has dubbed a “Podcast Puzzle” and try a brain game! 

They’re enabling everything from choose-your-own-adventure stories that adapt to your location in real-time, to walks through decades of San Francisco with The Grateful Dead, and even talks with Benjamin Franklin using his complete writings. As I proudly punned to Peter, it’s “electrifying!”

LinkedIn: https://www.linkedin.com/in/mossappeal

“I’m a guy that’s had no focus for 30 years,” Jim told me with characteristic humility. “I am a transport category pilot. I’m a professional glass artist with industrial designs in MoMA and the Smithsonian. I’m a computer scientist. I was on the Federal Reserve and used to vote on interest rates. That was fun. I built the hardware for Square, which we now call Block. I’ve started a bunch of other companies…Ugh. Look, basically, what I do is I build tools.”

His “lack of focus” has actually been his superpower, creating a truly unique lens on innovation, branding, and problem-solving that most specialists simply can’t achieve.

Our conversation revealed how Jim transforms everyday frustrations into industry-changing innovations. The Square story began with something as mundane as being unable to accept American Express at his glass studio. That simple pain point sparked a billion-dollar disruption that fundamentally changed mobile payments forever. 

Jim shared his methodology for spotting opportunities hiding in plain sight and building products that resonate deeply with audiences. More importantly, he explained how he predicts business disasters before they happen – and his track record is impressive! Hint: his accurate predictions about Southwest Airlines and other major corporate meltdowns, made it into his book “The Innovation Stack” years before its current challenges. Then he shares how and why brand associations can make or break a company (hello, Bud Light disaster. Listen for how that motivated his current project, PwrScore.ai.)

What struck me most about Jim was his fearless approach to high-risk, high-impact projects. “I work on projects that are right now, sort of long shots because I’m in a position where I can take a long shot,” he explained. “I’ve made way, way more money than I ever expected. My wife and I have taken the giving pledge, so we’re gonna give all the money away, but in the meantime, I can take crazy risks.”

That’s not just talk – Jim and his wife have literally committed to giving away their entire fortune for the betterment of the world. It’s a level of commitment to pro-social behavior that’s both inspiring and rare in today’s business landscape.

Jim pulled back the curtain on his current ventures, and they’re both fascinating for completely different reasons.

First is PwrScore, a that tool that measures and assesses brand resonance and compatibility using AI to minimize research bias and enhance brand capabilities through better data. The kicker? He’s giving it away for free. Yes, really. This isn’t some limited trial – it’s a genuinely useful tool that most companies would charge thousands for, and Jim is just handing it out because he believes it can help businesses make better decisions.

The second project might sound unusual, but it could change the world: plastic-free diapers.

“Diapers last for a thousand years and they become these horrible microplastics that are bad for the world, and I just thought it could be possible to do it without plastic. So I’ve been working on it for five years with a team. We’re this close to a breakthrough…”

Think about it – billions of diapers end up in landfills every year, taking centuries to decompose and creating environmental havoc. If Jim cracks this code, the sustainability impact could be massive. (Hint #2: Catch my previous episode with the founder of Sustainable Brands for more.)

What makes Jim truly special isn’t just his business acumen – it’s his genuine curiosity about everything. He flies “small, crappy airplanes” for fun, creates glass art displayed in world-renowned museums, and casually mentions voting on Federal Reserve interest rates like it’s a weekend hobby.

This broad range of experiences gives him perspectives that pure business specialists simply can’t match. When he talks about innovation, he’s not just drawing from MBA case studies – he’s pulling from art, aviation, monetary policy, and manufacturing.

Whether you’re in media, marketing, or building the next big thing, Jim’s approach to problem-solving offers a masterclass in thinking differently. He doesn’t just spot trends – he creates them by identifying problems everyone else has accepted as unsolvable.

His insights on brand compatibility, disaster prediction, and sustainable innovation are particularly relevant right now. Plus, his commitment to giving away his wealth while still actively building and creating is a refreshing take on success and legacy.

This episode is packed with inspiring stories, clever insights, and tactical wisdom that will help you rethink what’s possible in your own work. Jim McKelvey proves that true innovation comes from embracing diverse interests, taking calculated risks, and always asking “what if we could do this better?”

00:00 Jim McKelvey’s Eerily Accurate Business Predictions

02:15 Hall of Famer but a Career with No Focus — On Purpose

03:02 The Plastic-Free Diaper Project

03:36 Giving Away his Fortune

05:55 Giving Away his Power (Score).ai Tool

08:05 What Makes for Dangerous Brand Associations

11:17 Writing the Book on Innovation

14:17 Why McKelvey Only Solves Unsolved Problems

15:12 Trading News Consumption for Data Capture

16:30 Humble Pie, Hobbies and Heroes

LinkedIn: https://www.linkedin.com/in/mossappeal

Guests include Brittany Bigelow of Bigelow Creative, Dawn-Michelle Lewis of Salutations Media, filmmaker and podcast host Vergie Rodriguez, and James Starace of Focus 360/Creator Square. 

We covered strategies for podcast concept development, the value of niche topics and micro-influencers, technical execution, and effective marketing strategies. The panel also explained their monetization techniques, from securing brand partnerships to leveraging subscriber models.

The whole PopCon event was eye-opening, by the way, with more people lined up to meet the faces behind their favorite voices than the known faces playing TV characters! Ti, who graciously captured the video of the panel, Vergie and I also won Best Podcast awards from the organization!

Next year, we’re looking forward to a day dedicated to #podcasting, but for now, take advantage of the wisdom captured by this panel of pros on Making, Marketing, and Monetizing Podcasts!

01:12 Meet the Panelists

Links/Connections:

LinkedIn: https://www.linkedin.com/in/mossappeal

Jim Mullen (Mullen Media) and Yossi Kimberg are the real deal – we’re talking Seinfeld, Food Network, Super Bowl halftime shows, and decades of work on Lorne Michaels shows. These guys aren’t just talking theory; they’re actually using these tools in production right now.

Yossi’s journey into AI started by making masterful still images with Leonardo, as in Leonardo.AI. As he put it:

“The idea that text generates an image was beyond imagination. I was just amazed by it.”

But then he progressed to motion, face-swapping himself into different editing scenarios (find those in this episode, too!), and even bringing children’s artwork to life. But learn what happened next that was “a bridge too far” for one particular client.

Now, while Yossi’s moved on to scripted motion videos all AI-generated, Jim’s been experimenting with ElevenLabs for voiceovers, though he hit a hilarious snag on a project about a lack of libraries:

“I couldn’t get the bot to say ‘desert’. It kept saying, New York City has book desserts.”

Not so funny to me, because once it learns contextual pronunciations, my gigs doing voiceover will dry up like a desert. (Note: I found out just today while producing this episode that I literally lost a job to an AI-generated voice. True story.)

Both producers agree we’re not just approaching a tipping point – we’re already there. Yossi believes that within 2-3 years, even the very role of managing AI might become obsolete. The technology is learning to be funny, dramatic, and emotional without human instruction.

Jim pointed out something that made my stomach drop: if you can create an entire commercial with AI actors and voices (which is already happening), you eliminate hair and makeup artists, grips, gaffers, location scouts – entire production crews become unnecessary. 

As such, we talked about the fear factor. You know how I feel about voiceovers. Though AI helped me immensely in honing these show notes. But it’s not just job displacement we’re facing; it’s questioning our creative thumbprint and what makes us uniquely human in this process. Plus…

We touched on some fascinating legal territory that’s still being sorted out. Yossi mentioned reading legal briefs about using copyrighted images in AI training, and the emerging trend of celebrity estates licensing deceased stars’ likenesses for AI projects – Steve McQueen’s estate is apparently leasing his character for AI-generated content. The whole landscape of intellectual property, name-image-likeness rights, and even the ability to deny you said something (“I didn’t say that, it was AI”) creates a complicated web that we’re all navigating in real time.

But here’s what gives me hope: Yossi shared how his client loved his AI-enhanced children’s artwork until clients pushed back, saying it wasn’t authentic to what the kids actually created. They pulled back some of the AI elements. It reminded us of the vinyl comeback – sometimes we crave imperfection and authenticity. He thinks we’ll find our middle ground once this trend becomes trite.

For anyone starting out, Jim recommends experimenting with the free trials but warns against buying credits with “one-trick ponies” – platforms that only do one gimmicky thing. Yossi suggests testing the same prompt across different platforms since each has unique strengths.

The tools they’re using: ElevenLabs (voice), Runway, Kling, Higgsfield, Leonardo.ai (images), and the premium Veo3 — for dialogue-driven video at $250/month. I was simply wow’d by the basics of NotebookLM that I used in my intro. But I hope you’ll still call ME for doing the real deal as a human.

As we face this rapid evolution, seems many will become “AI wranglers” rather than traditional producers. The question isn’t whether this technology will change everything – it’s how we adapt while maintaining the humanity that makes content actually connect with people.

I have a feeling we’ll need to revisit this conversation in six months because everything will be dramatically different again. 

[01:36] – AI voices fool me twice – shame on me — on client websites

[05:13] – Yossi’s journey from Leonardo still images to motion graphics

[08:34] – Scholastic project: bringing children’s artwork to life

[11:12] – Jim’s Eleven Labs experiments and the “desserts” problem

[13:58] – Discussion of celebrity estate licensing for AI (Steve McQueen example)

[18:57] – Who gets replaced first: voice actors, then editors

[25:01] – Too much of a good thing: Client pushback on AI-enhanced artwork

[28:17] – Tool recommendations and experimentation advice

LinkedIn: https://www.linkedin.com/in/mossappeal

Overall, great experiences that showed how valuable experiential marketing can be!

00:32 Fresh Direct Pop-Up

LinkedIn: https://www.linkedin.com/in/mossappeal