The Jay & Tony Show Show - Vertically Challenged

Part 2 of Jay & Tony's chat with Isabel Drean gets brutally honest as she explains why so many award-winning writers faceplant in vertical while newcomers run laps around them. They break down the real mechanics of how cliffhangers actually work, why slow-burns collapse in this format, and how ego, elitism, and quiet contempt for female-driven audiences keep the industry stuck.
 
Then it gets real, as they break down vertical money, survival, contracts, burnout, and why speed is now a creative skill. They tackle AI head-on too. Not as a boogeyman, but as a tool. Because refusing to adapt might be the fastest exit ramp out of the business.
Website: https://isabeldrean.com
Courses & resources for vertical training:
https://21dayscreenplay.com
Book: How to Write a Vertical Series in 10 Days
https://books2read.com/verticals
Social media (all platforms): @isabeldrean
 
Contact:  [email protected]
Instagram:  @vertically_challenged_pod_jtss
TikTok:  @vertically_challe5
YouTube:  @vertically_challenged_pod_jtss
The Jay and Tony Show:  www.jayandtonyshow.com

Jay and Tony sit down with screenwriter and vertical-storytelling juggernaut, Isabel Drean, to trace her weirdly perfect path from acting to entrepreneurship to writing hit scripts at record speed. Isabel breaks down why "tight boxes" (Christmas movies, vertical dramas, all of it) don't crush creativity, they force it to show up.
 
They get into why tropes aren't the villain, how the first five seconds decide your fate, and why the smallest constraints demand the biggest swings. This one's about craft, discipline, and the uncomfortable truth that great storytelling doesn't just come from freedom. It comes from focus.
Website: https://isabeldrean.com
Courses & resources for vertical training:
https://21dayscreenplay.com
Book: How to Write a Vertical Series in 10 Days
https://books2read.com/verticals
Social media (all platforms): @isabeldrean
 
Contact:  [email protected]
Instagram:  @vertically_challenged_pod_jtss
TikTok:  @vertically_challe5
YouTube:  @vertically_challenged_pod_jtss
The Jay and Tony Show:  www.jayandtonyshow.com

In this episode, Jay and Tony tear into their inbox and answer listener questions, from whether Quibi would still faceplant in 2026 to exactly how many vertical dramas they've actually watched for research. They argue about AI replacing actors, the real downside of the vertical gold rush, and whether filming your breakup in portrait mode counts as "content" or just a cry for help.

Along the way the get into what people consistently misunderstand about this format, why the same taboos keep printing money, and the very real ways this whole ecosystem could still go up in flames.
 
Contact:  [email protected]
Instagram:  @vertically_challenged_pod_jtss
TikTok:  @vertically_challe5
YouTube:  @vertically_challenged_pod_jtss
The Jay and Tony Show:  www.jayandtonyshow.com

In the second part of their conversation with Kasey Esser, Jay and Tony shift from origin story to industry reality. Kasey breaks down how careers actually move forward in the vertical space, from agents and leverage to boundaries, sustainability, and long-term strategy. They talk candidly about what creators get wrong once momentum hits and how visibility can become a liability.

Protect your hours, your values, and your leverage… or the next "win" becomes your slowest leak. This episode is a blunt, inside look at what it really takes to build something that lasts.
 
Contact:  [email protected]
Instagram:  @vertically_challenged_pod_jtss
TikTok:  @vertically_challe5
YouTube:  @vertically_challenged_pod_jtss
The Jay and Tony Show:  www.jayandtonyshow.com

Breaking into vertical content isn't about talent, it's about understanding the game you're playing.

In this conversation, Jay and Tony sit down with Kasey Esser to unpack what it really takes to survive and succeed in today's vertical game.


Kasey shares hard-earned lessons from inside the industry, the misconceptions that derail creators early, and why so many smart people still get it wrong. From career paths to platform realities, this episode pulls back the curtain on how vertical storytelling actually works and not how people think it works.
 
Contact:  [email protected]
Instagram:  @vertically_challenged_pod_jtss
TikTok:  @vertically_challe5
YouTube:  @vertically_challenged_pod_jtss
The Jay and Tony Show:  www.jayandtonyshow.com