Craig Calcaterra: Leaving Law, Baseball Analytics, and Writing Honestly About the World

Wedding Photographer Builds a Golf Brand on "Good > Safe" | Jonny Hoffner | So Many Questions

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 referrals. Good Lion Golf launched four years ago after a single sentence on a golf course sparked an idea he couldn't shake. In this conversation: how he accidentally fell into wedding photography, what 42 weddings in one year taught him about sustainability, why Good Lion exists in the narrow space between bland country club culture and loud fratty golf aesthetics, and what therapy and a very simple question from a counselor changed for him. 🔗 Paper Antler Photography: https://www.paperantler.com/ 🔗 Good Lion Golf: https://www.goodliongolf.com/

Craig Calcaterra: Leaving Law, Baseball Analytics, and Writing Honestly About the World

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 overwhelming, how sabermetrics changed baseball and then started to ruin it, his book Rethinking Fandom, and the strange feeling of being genuinely content with your work.

2025 End of Year Recap

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!

ep0006: Joshua Graves

This week on So Many Questions... [http://somanyquestions.show/], Kendall talks with author and designer Joshua Graves [https://joshuagraves.me/] 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 what he learned while researching and writing his book. They explore generational shifts in communication, boundaries vs. requests, and how to listen without losing yourself. They also talk about mindfulness, trauma-informed approaches, why younger generations communicate so directly with leaders, and why giving yourself grace might be the most revolutionary practice you can adopt. In this episode:• Joshua’s path from jukebox-obsessed kid to designer and author• How culture and power dynamics shape how we handle conflict• “Nice” vs. “kind” — and why the difference matters• Why difficult conversations feel so scary• How to listen with presence (without disappearing)• Setting boundaries that protect you• Generational shifts in workplace communication• Why many people fear talking to people in power• How to prepare for a tough conversation• What gives Joshua hope right now• Joshua’s powerful question of the week About the book: We Need to Talk: A Survival Guide for Tough Conversations [https://bookshop.org/a/13593/9781959029113] offers practical, human-centered tools to help anyone approach high-stakes conversations without scripts, gimmicks, or forcing yourself into “fake” authenticity. A quick, accessible read packed with real stories and flexible frameworks.

ep0005: Elizabeth Maxson (EMax)

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, courage, and clarity. She opens up about advocating for women and caregivers, the mental load of parenting, redefining boundaries, and why she rejects “work-life balance” in favor of harmony. EMax also talks self-care routines, slowing down, improv’s “yes and” mindset, and how to build a career grounded in humanity. Whether you're a parent, leader, woman in tech, or someone trying to find stability in a chaotic world, this conversation is full of wisdom, humor, and heart. #Leadership #WomenInTech #WorkingMoms #Caregivers #MarketingLeadership #CMO #CareerGrowth #WorkLifeHarmony #BoundarySetting #Vulnerability #CommunityBuilding #Contentful #SoManyQuestionsPodcast