Jason Chatfield is an award-winning cartoonist, author, and stand-up comedian based in New York City. For 16 years, he wrote and drew the 102-year-old internationally syndicated comic strip Ginger Meggs. His work has appeared in The New Yorker, Esquire, MAD Magazine, Variety, Wired, and more. He’s a former President of both the National Cartoonists Society and the Australian Cartoonists Association, writes the award-winning Substack New York Cartoons with over 19,000 weekly subscribers, and serves as the portrait illustrator for Sam Harris’s meditation app, Waking Up.

But what struck me most in this conversation wasn’t his résumé — which he will massively downplay by the way. It was his discipline and entrepreneurial drive that sets him apart.

Jason talks about treating creativity like a business. About working from a calendar instead of a to-do list. About how jokes evolve from overheard subway moments to stand-up bits to New Yorker cartoons to full book series. And about what it really means to build a creative life over decades, not days.

We talk about failure, imposter syndrome, about backing yourself anyway, and about why chasing algorithms is a losing game compared to serving the people already in the room.

He’s an absolute beast of a creative force.

If you’re interested in the arts not just as expression, but as a way of living, building, and sustaining a career, this episode is for you.

Join Tad Crawford—author, publisher, and attorney—as he explores the emotional core of his latest novel, A Woman in the Wild. Through the journey of its protagonist, Thea, Tad reflects on family estrangement, the healing power of nature, and the tension between creative instinct and practical reality.
Tad’s multifaceted career includes decades of work supporting writers and artists, notably as co-author of The Writer’s Legal Guide: An Authors Guild Desk Reference, a foundational resource on copyright, contracts, and publishing law. His background as an advocate for creators informs this deeply personal and literary conversation.
The episode also touches on the ethics of AI, the philosophy of money, and the role of storytelling as a means of understanding and healing. A thoughtful exploration of creativity, independence, and what it means to build a life on one’s own terms.

Join us in this captivating episode as we sit down with Paulette Perhach – an acclaimed author, essayist, and writing coach. Paulette shares her journey of helping writers through her innovative tools and community initiatives, such as the Writer's Mission Control Center and The Finishing School for Writers. Dive into the emotional aspects of the writing process, the struggles with ADHD, and the importance of community in overcoming writer's block. Paulette also discusses her viral essays, the evolution of her writing career, and her unique perspective on balancing creativity with the business side of writing. Whether you're a budding writer or a seasoned author, this episode is packed with insightful advice and inspiration.

Emmy and Tony-winning producer Joe Plummer, President of Wavelength, joins Login to explore the intersection of storytelling and media innovation. Joe dives into how he crafts authentic narratives across film, theater, and branded content, emphasizing the need for genuine connection in an advertising-allergic world. He shares his journey from journalism to producing award-winning content and his approach to fostering collaborations where authenticity and values alignment drive the story. Joe discusses leveraging AI not as a threat but as a tool to enhance storytelling, drawing parallels to the early days of YouTube's transformative impact. Gain practical insights into adapting storytelling for modern audiences, the art of creating brand stories without losing audience trust, and the importance of embracing change to stay ahead of industry trends.

Join Sarah as she sits down with Justin Marlowe, the author of "Perfect Strangers: Echoes of a Black Suburban Youth." In this captivating conversation, they explore Justin's experiences growing up as an African American in suburban America, his literary journey from student athlete to author, and the profound themes of race and identity that underpin his debut memoir. Drawing from his unique upbringing and educational background, Justin sheds light on the complexities of societal integration post-Civil Rights era and reflects on the dualities that shaped his life and career. Discover how his insights into sociology, history, and media enrich his narratives, and gain a glimpse into his aspirations to further influence culture through future literary and media endeavors.

Hal Rosenbluth and Marnie Hall join Login to talk about the hidden world of health anxiety — and why so many of us slip into self‑diagnosis without realizing it. Hal, a hypochondriac CEO who once sold his travel company for hundreds of millions and built a retail‑clinic business sold to Walgreens, shares how living with illness anxiety shaped his career in healthcare. Marnie brings a creator’s perspective on research, narrative, and how we build empathy by naming what most people keep quiet.
They dig into the emotional and financial cost of health worries, how advertising and information overload fuel anxiety, and the practical tools that actually help. Expect insight on writing a book rooted in vulnerability, using technology without losing humanity, and what it takes to strip away stigma in a culture obsessed with symptoms.

Two Texas girls on a couch talking grit, elegance, and the real work of building a brand. Mair, founder of Mair Fragrance, shares how a handwritten signature sparked a decade-long journey, why she designs soft scents to complement you not overpower you, and what almost ended her company this year. We cover distribution, contracts, influencer fatigue, and the mantra that guides her now, think slow, move fast.

What if exhaustion isn’t a badge of honor, but a signal that something deeper needs attention? In this episode, Sarah talks with Lindsay Scola - former White House staffer turned sleep and productivity expert, about her journey from decades of undiagnosed narcolepsy to becoming an advocate for better sleep and self-understanding.Lindsay shares how rethinking sleep changed her entire life and career, why burnout culture is so hard to unlearn, and how we can all build a more compassionate relationship with rest. They dive into Lindsay’s new course, Sleep Is The Power Move in addition to many other valuable sleep insights. They also explore Lindsay’s new book AI for ADHD, how technology can both hinder and help focus, and what it really means to design a life that works with your brain instead of against it.Whether you’re running on caffeine and chaos or just craving more balance, this one will make you rethink what “rest” really means.