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Why 83% of Shopping Still Happens In-Store (And Why Most Stores Run Blind)

Guest: Simon Molnar — Founder of Flagship.ai

Most retail stores operate with almost no data.

This week, we break down how Simon Molnar (founder of Flagship.ai) is giving brick-and-mortar the same funnel visibility that e-commerce has had for decades.

At the core: visual merchandising as retail's most overlooked lever, why 83% of shopping still happens in-store, and how to build A-player teams that raise the standard.

We cover:

Why 83% of shopping happens in-store yet most retailers run blind — with almost zero data on what's actually working inside their four walls
The "money map" concept: how Flagship built square-foot-level intelligence that shows exactly which products, placements, and displays drive revenue
Why visual merchandising became retail's most underestimated lever, and how brands completely misjudge store performance without objective data
Simon's leadership philosophy shaped by Afterpay's $29B rise — hiring for humility, building teams of A-players, and the personality traits that matter most
Behind the scenes of building Flagship.ai: the biggest lessons from scaling from Australia to the USA, and why every retail store will eventually need this technology

This conversation is a masterclass in retail reinvention. Enjoy!

Chapters:

00:00:00 Trailer
00:01:26 When Did You Realize Retail Was Broken?
00:02:58 What is Flagship.ai?
00:05:36 What Exactly is Visual Merchandising?
00:09:00 The Real Comparison of Retail vs. E-Commerce
00:16:08 What is The Biggest Unlock Retailers See Using Flagship.ai?
00:21:05 What Are The Macro Trends on How People Shop Differently Globally?
00:23:05 What is Your Biggest Prediction on Flagship.ai in 5 Years?
00:27:05 What's Your Thesis on Analyzing Data Online vs. In-Store?
00:30:16 Do You Think Every Retail Store Is Going To Be Using Flagship AI?
00:31:32 What's One Thing The Internet Doesn't Know About Being With Afterpay?
00:34:29 What Was The Most Underrated Part of Afterpay's Success Story?
00:35:22 What's The Secret To Building A Great Team?
00:41:45 What's The Key Trait That The Best Employees Share?
00:43:09 What's the Most Difficult Lesson You Learned?
00:45:42 What's The Most Important Hire in Tech and SaaS?
00:50:00 The Importance of Personality Tests in Hires
00:53:59 What's The Biggest Leadership Tip That Founders Must Know?
00:57:28 What Did Your Jewelry Business Teach You About Customers?
01:03:38 What's The Single Greatest Habit That Makes You A Better Founder?
01:11:20 What's The Biggest Misconception When Raising Money?
01:15:36 What's One Thing Marketers Should Stop Doing Immediately?
01:17:17 What's A Timeless Marketing Strategy?
01:21:39 What Was The Biggest Challenge With Afterpay?
01:26:19 What's The Biggest Lesson From Taking Flagship.ai From Australia to USA?
01:29:42 Quickfire Questions

🎙 Guest: Simon Molnar, Founder of Flagship.ai
LinkedIn: https://www.linkedin.com/in/simonmolnar/
Website: https://www.flagship.ai/

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