How Do You Scale a Made-to-Measure Business? | Ryan Lui

Can you scale custom clothing without sacrificing fit, quality, or the personal experience that made it valuable in the first place? In this episode of Deep Current, Andy Monge sits down with Ryan Lewey, Head of Operations at Proper Cloth, to explore what happens behind the scenes of a made-to-measure business. From custom sizing and supply chain complexity to omnichannel retail, in-house technology, AI, and customer experience, Ryan breaks down how Proper Cloth turns thousands of unique orders into a scalable operation. In this episode, you’ll discover: → How Proper Cloth scales made-to-measure clothing → What happens operationally after a customer places a custom order → How technology helps manage thousands of unique sizes and configurations → Why getting customer data right at the beginning matters → How the Perfect Fit Guarantee impacts operations and customer experience → How online shopping and physical showrooms work as one connected system → Where AI creates real value in retail—and where it doesn’t → How operations teams balance speed, quality, cost, and flexibility CHAPTERS 00:00 — Scaling made-to-order without sacrificing quality 00:51 — Meet Ryan Lewey and Proper Cloth 01:22 — What does a Head of Operations manage? 01:57 — Why custom clothing creates a unique operational challenge 02:40 — How made-to-measure clothing actually works 04:35 — Managing thousands of customization possibilities 06:28 — Getting customer data right from the start 07:18 — Finding the root cause of fit problems 08:25 — What is Proper Cloth? 08:50 — The economics behind the Perfect Fit Guarantee 10:37 — Speed vs. getting the fit right 12:28 — Connecting online and showroom experiences 13:59 — What physical showrooms teach you about customers 16:02 — Scaling personalization across locations 17:45 — How technology makes made-to-order scalable 19:14 — Where AI actually works in retail 21:33 — The biggest operational bottleneck 22:45 — Balancing speed, quality, cost, and flexibility 24:25 — Building an operational culture around craftsmanship 25:39 — Lightning round 27:20 — Solving the returns problem in custom apparel 28:31 — Where to find Proper Cloth 28:48 — Final thoughts MEET THE GUEST Ryan Lewey is Head of Operations at Proper Cloth, where he works across supply chain, inventory, shipping, customer support, and the systems behind the company’s made-to-measure experience. His work sits at the intersection of operations, technology, customer experience, and custom retail. [Ryan’s LinkedIn] [Proper Cloth website] ABOUT DEEP CURRENT Deep Current goes beneath the surface with leaders building, adapting, and solving the challenges shaping today’s industries. Real conversations on technology, business, operations, and the ideas driving what’s next. KEEP EXPLORING ▶️ Watch more Deep Current episodes: [YouTube playlist] 🎧 Listen on Spotify: [Spotify link] 🌊 Explore Oceans Code Experts: [Oceans link] 💼 Follow Oceans Code Experts on LinkedIn: [LinkedIn link] If this conversation gave you a new perspective on personalization, retail, or scaling complex operations, share it with someone building customer experiences at scale. #MadeToMeasure #RetailOperations #Ecommerce #CustomerExperience #DeepCurrent