Outside The Box: Convos With Creators

I need your help making a decision.I'm building the sneaker community on Substack. Not hype. Not product drops. Something real. But I think I got the pricing wrong.68 people are paying for my newsletter. But since January 1st? Zero new signups. Two cancellations. My free subscribers are growing (+18 in two weeks) but paid subscribers are shrinking.TheSneakerNewsletter.com

Chris Kaufman co-founded StockX and helped build it from the very beginning in a Detroit office to a global marketplace. But this conversation isn't all about that origin story... it's about what he learned watching companies choose short-term profits over long-term culture, and why he wrote a book about empathy at work.We talk about the early StockX days when disagreement was productive, not destructive. About why firing people every 18 months to hit quarterly targets actually costs more than just keeping your best people. About the difference between being a CEO and being a leader. And about why the most powerful thing you can say as a leader might be "I dropped the ball on this."Chris has seen both sides... the scrappy startup that valued every voice, and the scaled company where efficiency replaced humanity. He's worked with founders who get it and founders who don't. And his take on what actually makes teams work is refreshingly honest.If you've ever felt like workplace culture is just corporate speak for "free snacks and ping pong tables," this conversation will change your mind. If you've ever wondered why your company keeps restructuring instead of just... building something, you'll recognize the patterns Chris calls out.And if you've ever tried to lead people while also being a human being yourself, you'll appreciate how real this gets.Topics:Why StockX's early chaos was actually its competitive advantageThe true cost of constant layoffs (it's way more than severance)What happens when "efficiency" becomes the enemy of innovationWhy vulnerability isn't weakness in leadershipThe Kanye visit, the first trades, and what it felt like when things started workingChris's book is "Empathy at Work," and yes, it's actually good. Not corporate handbook good... actually useful good.This is the first episode of whatever I'm calling this show. Outside The Box, Pursuit of Something, The Nick Engvall Podcast, Unplanned Entrepreneur... still figuring it out. Let me know what you think it should be called.Links:Chris Kaufman: https://www.christopherkaufman.com/Empathy at Work (book): https://fave.co/3NL54K3Subscribe to The Sneaker Newsletter for Deep Dives on Sneaker Lore, Business Analysis, and Industry Insider Insight.Chapters00:00 Introduction to Chris Kaufman and StockX01:41 The Birth of StockX: From UpTo to Sneakers04:54 Understanding the Sneaker Market and Culture10:16 Challenges and Doubts in the Early Days13:58 The Impact of Timing on StockX's Success16:30 Personal Reflections on Sneakers and Self-Expression20:05 Building a Team and Culture at StockX24:17 The Power of Diverse Opinions and Collaboration29:37 Learning from Feedback and User Experience35:27 The Importance of Passion and Engagement38:35 Celebrating Team Achievements39:26 The Value of Open Conversations40:56 Nostalgia and Personal Connections in Sneakers42:09 The Evolution of Fashion in the...

Outside The Box is back. I'm talking with people who are in the pursuit of something... building brands, chasing dreams, navigating the gap between passion and paying bills. This episode explains why I'm bringing the show back, what's changed, and how it connects to going full-time as a creator in 2026. If you're pursuing a passion that matters to you, these conversations are for you.Subscribe to The Sneaker Newsletter for industry deep dives and vault stories from 20 years in the business: https://www.TheSneakerNewsletter.com

In this conversation, Nick Engvall is joined by Brandon Edler and they discuss their experiences working in the content industry, particularly in the sneaker and media space. They reminisce about their time at Complex and the evolution of social media platforms. They also touch on the importance of storytelling and dynamic visuals in content strategies, as well as the challenges of measuring success in the digital age. The conversation in this part focuses on the success and impact of their work at Finish Line, the importance of authenticity in content creation, and the future of tangible media. In this final part of the conversation, Nick and Brandon discuss their favorite shows, the internet's impact on exploration, their experiences with sneakers, the changing landscape of content and social media, the concept of selling out, and the importance of in-person experiences and community.Brandon Edler: https://www.instagram.com/mrbrando3/Subscribe to our newsletter: http://outsidepods.substack.com/Please like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Nick Engvall:Twitter: https://threads.net/@nickengvallInstagram: https://instagram.com/nickengvall

In this conversation, Nick Engvall and Jacques Slade discuss the intersection of sneaker culture and golf. They explore the importance of consistency in brand campaigns, the need for change in the culture of golf, and the role of sneaker brands in driving that change. They also discuss the impact of collaborations in golf and the potential for creating a more inclusive golf community. The conversation highlights the importance of bringing street culture to golf and creating moments and social engagement in the sport. Finally, they discuss the future of golf and the role of Jacques Slade in the PGA Tour. In this conversation, Jacques Slade discusses the potential for golf to connect fans to moments and create a more inclusive and diverse culture. He shares his experiences working with the PGA Tour and how content creation can help shape the future of the sport. Jacques also highlights the importance of hip-hop artists in golf and suggests names like Jay-Z, Kendrick Lamar, and J. Cole who could bring a new energy to the game. He discusses his favorite golf sneakers and his dream foursome. Jacques also touches on Tiger Woods' move to TaylorMade and the potential for custom golf shoes to become a bigger part of the golf culture.Jacques Slade: https://www.instagram.com/kustoo/Subscribe to our newsletter: http://outsidepods.substack.com/Please like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Nick Engvall:Twitter: https://threads.net/@nickengvallInstagram: https://instagram.com/nickengvall

What does it take to turn your passion for sneakers into creative income? I talked to five creatives who each found their own unique niche in the sneaker space: Nightwing2303, Jacques Slade, Reina Koyano, Gary Lockwood, and Tamara Dhia.Connect with Panelists: Jacques Slade: https://www.instagram.com/kustoo/Freehand Profit: https://www.instagram.com/freehandprofit/Reina Koyano: https://www.instagram.com/_vivalareina/Tamara Dhia: https://www.instagram.com/tamaradhia/Nightwing2303: https://www.instagram.com/Nightwing2303/Please like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/Follow Nick Engvall:Twitter: https://twitter.com/nickengvallInstagram: https://instagram.com/nickengvall

Jacques Slade has done it all...hosting events alongside A-list celebrities, helping Nike and Kobe Bryant launch new sneakers, covering golf for the PGA tour, working with NBC on the Olympics, unboxing the most insane sneaker packages the world has ever seen, and he's done all that and more while continuing to be one of the most respected and appreciated creators amongst his peers. After over a decade of creating videos, working both on camera and behind throughout his journey, I had to ask him if it was too late to get started as an aspiring YouTuber.WATCH THIS EPISODE ON YOUTUBEConnect with Tamara:IG: https://www.instagram.com/kustoo/Twitter: https://twitter.com/kustooPlease like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/Follow Nick Engvall:Twitter: https://twitter.com/nickengvallInstagram: https://instagram.com/nickengvall

Tamara Dhia has a resume that includes work for companies like Complex, E!, MTV, NTWRK, and more but the path to success wasn't easy. In this conversation, she talks about being around the opportunities you want, staying true to your own passions and beliefs, and how she went from pouring drinks for Robert "Bobby D" De Niro to hosting red carpet events with Giuliana Rancic. Find out the routines, habits, and her tips to finding continued success on this episode of Outside The Box, hosted by Nick EngvallWATCH THIS EPISODE ON YOUTUBEConnect with Tamara:IG: https://www.instagram.com/tamaradhia/Twitter: https://twitter.com/tamaradhiahttps://www.thetamaradhia.com/Please like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/Follow Nick Engvall:Twitter: https://twitter.com/nickengvallInstagram: https://instagram.com/nickengvall

Vince Sirico has photographed the likes of Aleali May, Gucci Man, James Harden, Zion Williamson, WizKid, as well as brands like adidas, Reebok, JD Sports. His work speaks for itself. On this episode we discuss the challenges of navigating the world of freelance photography, how to learn from the opportunities that present themselves, the value of always trying new things, and much more.WATCH THIS INTERVIEW ON YOUTUBEFollow Vince: IG: https://www.instagram.com/vincesirico/Twitter: https://twitter.com/vincesiricohttps://vincesirico.com/?ref=outsidepodsPlease like, subscribe, review, and share this episode if you enjoyed it. It goes a long way to helping us grow the podcast 🙏[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

Ryan Trembath made the most of the pandemic by writing his first book, Signature Shoes - The Athletes Who Wore Them and Delightful Pop Culture Nuggets. In this interview, he discusses how the book came about, some of his surprising discoveries while researching signature sneakers over the last 100 years, and what his tips for aspiring authors are.WATCH THIS INTERVIEW ON YOUTUBEBuy The Book: https://eckhartzpress.com/?ref=outsidepodsFollow Ryan: IG: https://www.instagram.com/olechapcollectibles/Twitter: https://twitter.com/trembath_ryan[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

Lucy Crivelli is a hustler at heart. From working as a freelance photographer in the sneaker world to starting her own creative agency, to building communities for startups like Aglet, her work speaks for itself. We discuss the challenges of starting your own business, how to find freelance work, how building communities isn't about short-term metrics like likes and comments, and showing up in all the ways you can.WATCH THIS EPISODE ON YOUTUBEFollow Lucy: IG: https://instagram.com/lucycrivelliTwitter: https://twitter.com/lucycrivelli[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

Tiffany Beers is one of the most important footwear designers in the sneaker world with shoes like the Nike Air Yeezy, Nike MAG, and countless others. In this conversation, we discuss her upcoming footwear design project, how to learn from your failures, finding your way in the footwear industry, "Air" bag design at Nike, and how being from a small town is actually a competitive advantage that many people see as a disadvantage.WATCH THIS EPISODE ON YOUTUBEFollow Tiffany: YouTube: https://www.youtube.com/watch?v=Rib8e8Hap6AIG: https://instagram.com/tiffanybeersTwitter: https://twitter.com/tiffanybeersPhoto: The New York Times - https://www.nytimes.com/2017/07/20/fashion/nike-back-to-the-future-sneaker.html[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

Reham Habib has been a part of making brands like Nike, Jordan, and even 50 Cent's G-Unit, some of the most recognizable names on the planet. Her path to the top of the corporate world is "looks less like a ladder and more like a jungle gym," and that includes living in China for 4 years working for Jordan Brand. Find out how she's managed to balance work with a healthy dose of travel, and how she thinks the perfect work schedule could look a lot different than tradition determines.We also discuss some incredibly important topics like addressing the lack of diversity in leadership levels in the footwear industry, how fans and consumers can hold brands accountable, and how environmentally friendly choices are happening behind the scenes.WATCH THIS EPISODE ON YOUTUBEFollow Reham: IG: https://instagram.com/rehamhabibTwitter: https://twitter.com/rehamhabib[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Want to buy me a coffee in support of the pod? https://www.buymeacoffee.com/nickengvallProudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

The Profitable Hobbyist, Darrin "DJ" Willingham Jr, joins Nick Engvall for a conversation about turning your sneaker reselling hobby into flipping houses for a living.WATCH THIS EPISODE ON YOUTUBEWe discuss:Becoming A Profitable HobbyistThe Benefits of Selling High Dollar SneakersHow Doing What You Love Creates Accidental OpportunitiesSelling Sneakers to Professional AthletesWhat to Consider when Buying Your First HomeFollow DJ: IG: https://instagram.com/dj_sneakerhead[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Proudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

Nick Engvall talks with Megan Ann Wilson about being on the first-ever sneaker reality show, her work as a creative, stylist to professional athletes, and as a designer. WATCH THIS EPISODE ON YOUTUBEWe discuss:Dealing With Professional Athletes As A StylistHer Experience at Parsons and Pensole Design SchoolNot Being Too Hard On Yourself About SustainabilityHow Creators Can Avoid BurnoutHaving The Courage To Change Your PathFollow Megan: IG: https://instagram.com/shegotgameWebsite: https://www.meganannwilson.com/Podcast: https://podcasts.apple.com/us/podcast/the-shegotgame-podcast/id1529222049[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Proudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

On this episode of the Outside The Box Podcast, Nick Engvall talks with Ross Brodsky and Alex Goldenberg, two high school students who founded the non-profit Sole Purpose NYC, an organization that is collecting and refurbishing sneakers to give back to the New York City homeless.WATCH THIS EPISODE ON YOUTUBEWe discuss:The Challenges Of Donating When You're Under 21Winning A $3,000 ScholarshipThe Process Of Sanitizing SneakersHow You Can Help Support The CauseFollow Sole Purpose: https://instagram.com/solepurposenychttps://www.solepurposenyc.com/[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Proudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

On this episode of the Outside The Box Podcast, Nick Engvall talks with Justin Valley, owner of Prospect, a brand and boutique based in San Diego, California, always after a good laugh, Justin showed up wearing an original Kanye West Dropout Bear costume from 2004. WATCH THIS EPISODE ON YOUTUBEWe discuss:The Power of Hiring From Within The CommunityPaying Attention To Trends That Aren't OnlineFinding Inspiration and Creating For Your CityShould You Open A Sneaker Store In 2021?Follow Prospect: https://instagram.com/prspctsdhttps://twitter.com/prspctsd[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]Proudly Recorded Using Riverside: http://www.riverside.fm/?via=outsidepodsHosting By Captivate: https://www.captivate.fm/signup?ref=nickengvallFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

On this episode of the Outside The Box Podcast, Nick Engvall talks with Jeremy Green, Founder of Calling All Creators, a global design collective that is poised to change the way the footwear industry thinks about democratizing design work, making sustainability more than a buzzword, and more.WATCH THIS EPISODE ON YOUTUBEWe discuss:The Democratization Of DesignGetting More Access For All CreatorsHow Verzuz Changed More Than Just The PandemicMaking Sustainability More Than A Marketing TermThe Loss Of Creative Freedom That Comes From Working At A BrandFollow Jeremy: https://instagram.com/callingallcreatorshttps://instagram.com/jeremym.greenFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

On this episode of the Outside The Box Podcast, Nick Engvall talks with Liz Beecroft, who has collaborated with Nike, The Hundreds, and more, while combining two of her passions and inspiring conversations about mental health and the worlds of sneakers and streetwear along the way.WATCH THIS EPISODE ON YOUTUBEWe discuss:How She Became Such A Huge Allen Iverson FanHow Men Can Be Better Allies In Supporting Women In FootwearUsing Sneakers In Her Work As A Licensed Clinical Social WorkerThe Challenges Of Collaborating With Big BrandsHow Stigmas and Trendiness Hold Us All BackFor More Info On Mental Health:24/7 Confidential Support - https://suicidepreventionlifeline.orgText Someone To Talk - https://crisistextline.orgAffordable Therapy - https://openpathcollective.orgFinding The Right Therapist - https://mywellbeing.comFollow Liz: https://instagram.com/lizbcroftFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/

On this episode of the Outside The Box Podcast, Nick Engvall talks with Barry Ancheta, aka VERSEONE. Barry runs Soleworks sneaker cleaning, was a partner at United Kicks sneaker boutique, and runs a charity car show called the Classick Sleighride that will celebrate its 10th anniversary later this year.We discuss:Turning Your Passion For Sneakers From A Hobby To A BusinessThe Importance of Constantly CommunicatingStarting A Sneaker Cleaning BusinessPrioritizing Your Mental HealthLearning To Work With Business PartnersThe Power Of Community WATCH ON YOUTUBEFollow Barry: https://instagram.com/verseonehttps://www.instagram.com/soleworks_/https://instagram.com/stayclassickFollow Outside The Box:Twitter: https://twitter.com/outsidepodsInstagram: https://instagram.com/outsidepodsSubscribe to our newsletter: http://outsidepods.substack.com/