This week, we’re sharing our conversation with Chris Schierholtz, the creator of Rally Wednesday—a movement that’s part run club, part social experiment, and all about building community through shared experience. From helping launch Airbnb Experiences to reimagining hump day as the most fun day of the week, Chris brings his love of the outdoors, his background in brand-building, and his belief in the power of play to everything he does.
Some highlights from our conversation:
🧭 How growing up in a van life-before-van-life family instilled a deep love of adventure and connection
🏃♂️ The inspiration behind Rally Wednesday—reclaiming the week and creating a reason to move, connect, and explore
💬 What Airbnb and Lululemon taught him about building experiences that deliver on their promise
🌁 Why he picked Wednesdays—and why every day should be a little more fun
👨👩👧 How he and his partner juggle careers, athletic goals, and raising a daughter with grace (and a little chaos)
🧘 The importance of authenticity, “California radness,” and using tech to get people offline
🔁 How failure and collaboration helped him evolve his ideas and build something that lasts
🛠️ Applying lessons from counterculture sports and startup life to rethink how we gather
🤝 Why doing something active with others leads to deeper conversations and stronger bonds
📣 "Take the emergency brake off"—his advice for anyone thinking about joining the next Rally Wednesday
A conversation about movement, meaning, and building community on your own terms.
Join us on June 18... This one is gonna be good! A 12 mile MTB ride, a 5 trail run, or a 2 mile hike! Pick your Jam! After the run and ride, we’ll gather on the beautiful Filoli grounds for their Summer Nights series: food trucks, live music, art exhibits, and plenty of space to picnic and hang.Whether you’re new to Rally or a regular, this is the perfect night to run or ride, chat, and meet more of the community. Join to get the weekly Rally Wednesday text with all the details - www.rallywednesday.com
Check out Chris on Instagram and Strava, and follow Rally Wednesday on Instagram and sign up to join!
You can find us on Instagram and Twitter @runnersofthebay
Check out our website www.runnersofthebay.com and send us an e-mail at runnersofthebay@gmail.com.
Music is California by The Spectacular Fantastic.
Mixing and editing by Brian Walters at Singletrack Sound.