So Many Questions...

Join us as we dive into the world of sports and LGBTQ+ representation with Ken Schultz from Outsports! 🌈 In this episode, we discuss the recent San Francisco Giants Pride Night and the importance of inclusivity in sports. Ken shares his journey as a queer sports writer and the challenges faced by LGBTQ+ fans in the baseball community. Key takeaways: The significance of Pride Night in baseball and...

Jonny Hoffner turned a philosophy degree into a 17-year wedding photography career and then, during COVID, started a golf apparel brand built around a single idea: good doesn't have to mean safe. Jonny is the co-founder of Paper Antler Photography and Good Lion Golf. He and his wife Michelle have been full-time photographers since 2007, working exclusively from natural light and word-of-mouth refe...

Craig Calcaterra is the author of Cup of Coffee, a daily newsletter about baseball and pretty much everything else. In this episode, Craig traces the unlikely path from litigation attorney to sports blogger to NBC Sports writer to newsletter creator—and talks honestly about the luck, timing, and self-sabotage that shaped all of it. They talk about writing authentically when the world feels overwhe...

A brief episode wrapping up 2025 with huge amounts of gratitude to you, our listeners. So so grateful that you've come along on this ride, and very excited about 2026 and all the great conversations we'll get to have, and share with you all. Thank you!

This week on So Many Questions... , Kendall talks with author and designer Joshua Graves about why tough conversations are so hard, how kindness differs from “niceness,” and the tools we all need to navigate conflict with more clarity, compassion, and confidence. Joshua shares stories from his upbringing in the South, how workplace dynamics and power structures shaped his communication style, and...

Marketing executive and Contentful CMO Elizabeth “EMax” Maxson joins Kendall to talk about the pivotal career moves, personal risks, and honest moments that shaped her leadership journey. From a life-changing cross-country internship, to navigating male-dominated industries, to building a mothers’ community that now supports nearly 1,000 women , EMax shares what it means to lead with vulnerability...

Director of Photography Ken Seng (Deadpool, Terminator: Dark Fate) joins Kendall to talk about his journey from business school to shooting massive IMAX action films, including the upcoming Street Fighter movie now filming in Australia. Ken shares how he fell in love with cinematography through the French New Wave, how his time with the National Outdoor Leadership School (NOLS) shaped his leadersh...

In this episode of So Many Questions, I sit down with Rob Bell—author, speaker, and former pastor—for a wide-ranging conversation that begins with memories of church-basement punk shows in suburban Chicago and stretches into creativity, vulnerability, and how suffering shapes the art we make. Rob talks about discovering the sermon as an art form, moving through criticism, and learning to surrender...

Baseball writers Jake Mintz and Jordan Shusterman (a.k.a. Cespedes Family BBQ ) join me to talk about life inside the clubhouse, their journey from teenage bloggers to covering MLB for Yahoo! Sports, and what it’s really like to build a career in baseball media. We talk about: A friendship that led into a career The evolution from baseball tomfoolery to being members of the Baseball Writers Associ...

Ethan Marcotte, the pioneer who coined the term "Responsive Web Design", joins So Many Questions... for a deep and thoughtful conversation. We explore the early web, inclusive design, tech worker power, and the values that shape Ethan’s work. From designing websites in the '90s to writing You Deserve a Tech Union , Ethan shares how community, justice, and craft guide his approach to...

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