Sep 9, 2026
Margo is joined by Dan Scott, co-founder and CEO of Spotlight Advisory Group, musician, lawyer, and longtime advisor to creatives. After decades spent both making art and advising some of the world’s wealthiest individuals, Dan came to a powerful realization: having enormous wealth and experiencing financial freedom...
Sep 2, 2026
Margo is joined by Louie, better known as Louie’s Loops, a self-taught crochet artist, designer, game creator, and founder of Club Crochet. For nearly 20 years, Louie has been turning his love of crochet into an ever-expanding creative world of amigurumi, tutorials, games, characters, and stories—all rooted in...
Aug 26, 2026
I’m bringing you a preview of the new series of Death of An Artist. In February 2024, celebrated children’s book author and illustrator Petra Mathers and her husband, photographer Michael Mathers, mailed letters to dozens of friends and family members to let them know they had died by suicide. Petra and Michael...
Aug 26, 2026
Margo sits down with Daniel Boettcher, founder of The Intrepid Wendell, to explore the intersection of storytelling, craftsmanship, and legacy—and how the most meaningful creative paths are rarely the most straightforward ones. Daniel’s journey has taken him through music, law, aspirations of diplomacy, and...
Aug 19, 2026
Margo is joined once again by New York Times bestselling illustrator, artist, and now author Andrea Campos, the creative force behind DreasDoodles. Since her first visit to Windowsill Chats, Andrea’s creative career has continued to evolve—from a pandemic doodling practice that began simply as a source of joy...