In this episode of Technically Creative, Orlando Wood sits down with Dani Van De Sande, founder of Artist and the Machine — one of the most important gatherings anywhere in the world for artists, technologists, and creative leaders working with AI.

Dani has built a rare kind of event: a place where engineers, filmmakers, researchers, and creative directors share a stage and show what they’re actually making right now. Not predictions. Not hype. Real tools, real experiments, and real creative breakthroughs.

In this conversation, Dani and Orlando explore the rise of the creative technologist, why artists and engineers need to be in the same room, and how the most interesting work today often couldn’t have existed even a year ago.

It’s a thoughtful, optimistic conversation about the people building the future of creativity — and the communities forming around them.

🔍 Highlights include:

• Why the creative technologist is the defining role of the AI era
• How Artist and the Machine brings artists and engineers together
• The difference between AI hype and real creative practice
• Why the most interesting work today is happening at the edges of disciplines

🎙️ Meet the People Designing the Biggest Moment in Advertising

In this special post–Super Bowl episode of Technically Creative, Orlando Wood sits down with Mark Gross, Co-Founder and Co-Chief Creative Officer of Highdive, and Chris Bellinger, Chief Creative Officer of PepsiCo Foods USA - two of the creative leaders behind some of the most talked-about Super Bowl advertising of the last decade.

The Super Bowl has long been the most concentrated moment of attention in media. But what it means to advertise there has fundamentally changed. What was once a single 30-second TV event has become a multi-week, multi-screen cultural launch shaped as much by social feeds, memes, and war rooms as by what airs during the game itself.

Mark and Chris unpack how Super Bowl advertising has evolved in the second-screen era, from the rise of 60-second storytelling to the limits of celebrity-driven ideas, and the strategic decisions brands now face around timing, secrecy, and amplification. They go deep on the creative risks of emotion on the loudest stage in advertising, and how Lay’s “Little Farmer” became an unexpected, last-minute pivot that reshaped the brand’s tone and expectations moving forward.

The conversation also pulls back the curtain on game-day realities: war rooms, real-time decision-making, competitor overlap, and the uncomfortable truth that even the biggest ads can’t be fully controlled once culture takes over.

What emerges is a rare, honest look at how modern Super Bowl advertising is actually made not as a single moment, but as a system of craft, strategy, intuition, and risk.

🎧 Highlights include:

● How Super Bowl advertising shifted from a one-night event to a multi-screen cultural launch

● Why 60-second spots now outperform 30s on the biggest stage

● The celebrity arms race and when “no celebrity” becomes the real surprise

● The creative risk of emotion in the middle of a football game

● How Lay’s “Little Farmer” came together through late pivots and leadership conviction

● Why sequels are harder than originals in advertising

● What really happens inside Super Bowl war rooms

● Measuring success beyond views: shares, comments, and cultural impact

🔗 Visit KoobrikLabs: https://www.koobriklabs.com

🔗 Connect with Orlando: https://www.linkedin.com/in/orlando-wood

📍 Chapters:

[00:00] Meet Mark Gross and Chris Bellinger

[01:13] How Super Bowl advertising has changed over the last 20 years

[02:56] Is the Super Bowl still the most valuable media buy?

[04:48] Teasers, timing, and pre-game release strategy

[06:40] Celebrity saturation and creative risk

[10:07] Making emotion work on the biggest stage

[12:07] Inside the making of “Little Farmer”

[15:15] Media buying and late-stage creative decisions

[19:09] Does Super Bowl pressure change the work?

[22:26] When an idea only works on game day

[24:01] TV winners vs internet winners

[25:29] Designing for memes and long-tail culture

[26:45] Where agency and brand priorities collide

[30:45] Sequels, expectations, and creative pressure

[33:37] Holding spots vs releasing early

[35:32] Extending campaigns beyond the game

[38:50] War rooms and real-time decision-making

[42:49] Defining success after the final whistle

[44:18] Competitor overlap and creative collisions

[48:40] Final reflections and what comes next

#TechnicallyCreative #SuperBowlAdvertising #MarkGross #ChrisBellinger #Highdive #PepsiCo #CreativeStrategy #BrandStorytelling #Advertising #CulturalMarketing #KoobrikLabs #OrlandoWood

🎙️ Meet the Woman Helping Film Culture Make Sense of Itself

In this episode of Technically Creative, Orlando Wood sits down with Cara Cusumano, Festival Director of the Tribeca Film Festival — one of the three major American film festivals alongside Sundance and SXSW, and still one of the most important gateways to legitimacy for filmmakers worldwide.

Film festivals remain the first real hurdle for a film or filmmaker to be taken seriously. The place where work moves from being made to being seen, debated, championed, and absorbed into the cultural bloodstream. And in a moment when more creators than ever are making more content than ever — with near–studio-level tools available from their couch — that curatorial role has never mattered more.

Cara oversees one of the most complex and influential selection processes in global filmmaking, sifting through more than 13,000 submissions a year to find what’s audacious rather than merely loud. As the filmmaking system is pressured on all sides — economically, culturally, and technologically — this conversation makes the case that festivals, and the humans who curate them, are more essential than ever.

Under Cara’s leadership, Tribeca has also been notably forward-thinking about new tools, including AI. Rather than sidelining creators who experiment, the festival has created intentional frameworks that ask the same timeless questions: Is there a point of view? Is there a voice? Is there something human at the center of the work?

What makes this episode especially resonant is Cara herself. When asked whether she actually watches everything, she laughs and admits she lives in fear of missing something great. That moves beyond love and into dedication — a reminder that taste-making isn’t algorithmic. It’s human.

🎧 Highlights include:

● Why film festivals remain the path to legitimacy for filmmakers

● How Tribeca filters signal from noise in an era of infinite content

● The evolving role of curation as the film industry fractures

● Tribeca’s approach to AI, tools, and creative experimentation

● Why taste, restraint, and vision still matter more than polish

● How festivals balance indie discovery with major cultural moments

● “I live in fear of missing something” — dedication as a curator

🔗 Learn more about the Tribeca Film Festival: https://tribecafilm.com

🔗 Visit KoobrikLabs: https://www.koobriklabs.com

🔗 Connect with Orlando: https://www.linkedin.com/in/orlando-wood

📍 Chapters:

[00:00] Introducing Cara Cusumano and Tribeca

[04:00] Film festivals as the path to legitimacy

[09:00] Signal vs noise in the age of infinite content

[15:00] AI, tools, and Tribeca’s forward-thinking stance

[23:00] Discovery, innovation, and community

[31:00] Programming across film, TV, games, and podcasts

[41:00] Shorts, new voices, and emerging formats

[52:00] “I live in fear of missing something”

[57:00] Why festivals — and curators — matter more than ever

#TechnicallyCreative #CaraCusumano #TribecaFilmFestival #FilmFestivals #Curation #Filmmaking #AIinFilm #Storytelling #CreativeTechnology #IndependentFilm #KoobrikLabs #OrlandoWood