Simon Molnar’s entrepreneurial journey started in his family’s jewelry business in Sydney, where he developed an early understanding of retail, sales, and consumer behavior. While still a teenager, he experimented with selling Pandora jewelry on eBay, unknowingly laying the foundation for what would later become Ice Jewellery, a fast-growing online business he co-built with his brother, Nick Molnar.

As Ice scaled, Simon developed expertise in SEO, digital marketing, and e-commerce automation, eventually systemizing operations to free himself up for new ventures. Around this time, Nick transitioned to launching Afterpay, and Simon found himself running Ice independently. He soon realized he wanted to move beyond e-commerce and into a role with greater impact. This led him to Afterpay, where he initially contributed informally before officially joining the team to help scale marketing and data-driven sales strategies.

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His experience at Afterpay reinforced the importance of customer psychology, growth hacking, and the power of leveraging data to drive business decisions. However, as Afterpay expanded and was later acquired by Block, Simon found himself disillusioned with the bureaucratic structures of a large corporation. He thrived in fast-moving, high-impact roles, and corporate life didn’t suit his style. This prompted him to leave and start Flagship, with the goal of bringing digital transformation to in-store retail.
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Flagship’s initial concept was a smarthanger that tracked customer interactions with products in physical stores,allowing retailers to gain real-time insights into shopping behavior. Simon raised capital based on this vision and built an early version of the product. However, as he began selling to retailers, he faced long sales cycles, high costs, and operational challenges. After months of frustration, an investor,Georgie Turner from Tidal, challenged him to rethink the business: could he achieve the same goal—helping retailers optimize product placement—without hardware?
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This led to a dramatic pivot. Instead of tracking product movements with sensors, Flagship focused on digitizing the visual merchandising process. Traditionally, brands used static PDF documents to tell stores where to place products, leading to inefficiencies and inconsistent execution. Flagship transformed this into a dynamic, cloud-based platform, allowing retailers to map store layouts, track compliance, and analyze performance with real-time heat maps.
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Once Simon validated this new direction, he quickly signed contracts for a prototype, secured fresh funding, and scaled the software. His fundraising approach was strategic—he built long-term relationships with investors, ensuring that by the time he needed capital, they had already witnessed Flagship’s progress.
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As a solo founder, Simon has built a strong network of advisors and internal leaders to cover his blind spots. His leadership style prioritizes quick decision-making, customer-driven development, and a relentless focus on execution. He emphasizes that startup success isn’t about knowing everything upfront but about learning fast and adapting.
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Looking ahead, Simon envisions Flagship becoming the foundational operating system for brick-and-mortar retail, much like Shopify for e-commerce. With U.S. expansion on the horizon, he advises founders to test new markets in the lowest-risk way possible, proving demand before fully committing.
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Watch Episode 11 now.