This Checkout episode features Aaron Woolf, Founder and CEO of Trendii. This innovative, AI-powered platform connects consumers with products they love by matching products in images and videos to real-time shopping experiences, allowing people to shop directly from moments of inspiration.
Aaron shares his personal shopping habits, ecommerce inspirations, the challenge of switching off in a fast-paced industry and offers valuable advice on finding balance between hustle and well-being.
The Unexpected Gem: A Mysterious Shoe Cleaning Paste
When asked about the weirdest thing he’s ever bought online, Aaron mentioned a mysterious shoe-cleaning paste he bought on Instagram a while back. “It took two months to arrive, was stuck in customs for about three weeks, and came all in Chinese—I can’t read a word of it—and it’s the best shoe cleaning product that you can buy,” he shared.
Despite the long wait and the mysterious packaging, the product turned out to be exceptionally effective. A timely reminder of the sometimes unpredictable yet rewarding nature of online shopping, especially when venturing into international purchases spurred by social media ads.
Retail Inspirations: Incu and Farfetch are Leading the Way
Aaron spoke passionately about retailers that have caught his attention recently, specifically Incu in Australia and global fashion platform Farfetch, two brands known for creating memorable retail experiences.. “I love what Incu are doing in Australia. They’ve done incredibly good things with building a brand… they’ve done incredibly well by leaning on overseas brands and then bringing them in.”
He also admired how Incu has created a sense of exclusivity and aspiration.
“They’ve created this brand that makes you want to feel like you’re worthy of them.”
Nathan chimed in, sharing his own experience: “You walk into an Incu store, and I’m definitely not cool enough to be a regular Incu customer.”
Aaron also praised Farfetch for their innovative approach to experiential retail, highlighting the importance of forging a deeper connection between brands and customers. He believes shopping should be more than just picking items off a rack—it should be an experience. “I’m a big believer in shopping should be experiential rather than just walking in and kind of transacting,” he explained.
For ecommerce brands, this underscores a critical lesson: it’s not just about having the right products, but about creating experiences that make shopping feel special. In a crowded market, retailers that can offer discovery, immersion, and emotional engagement are better positioned to succeed.
The Surprising Tech Aaron Can’t Live Without: Email
Despite leading a company built on advanced AI technology, Aaron’s go-to tool is simple: email. “I’m a bit old school… it’s got to be email for me,” Aaron revealed. While his team relies on more modern tools like Slack and Linear, Aaron finds that managing his 150-200 daily emails is the most efficient way to control his workflow and keep things moving.
For Aaron, email remains one of the most effective communication channels, not only for internal workflows but also for customer engagement. For ecommerce leaders, this is a powerful reminder that while new tools and platforms are essential, sometimes the simplest tools remain the most effective. This is a great reminder that we should focus on what works best for our business rather than chasing trends, striking a right balance between old and new tech.
Must-Read Books: Finding Inspiration in Honest Narratives
When the conversation turned to book recommendations, Aaron highlighted his preference for autobiographies that offer raw and real insights rather than those that are too polished (such as Losing My Virginity by Richard Branson). He appreciates narratives that delve into the struggles and challenges faced along the entrepreneurial journey, finding them more relatable and inspiring.
He highly recommended Shoe Dog by Phil Knight, the founder of Nike, as an inspirational read. “It’s raw, real and honest…it’s just one of those books that you absolutely have to read,” he emphasised, appreciating how the book exposes the highs and lows of building a global brand and showcases the power of resilience. Aaron also mentioned The Chimp Paradox by Dr. Steve Peters, which explores how the human brain works and how managing impulses in high-pressure environments can lead to better decision-making.
The Art of Switching Off: Balancing Work and Well-being
One of the biggest challenges Aaron faces isn’t related to tech or ecommerce—it’s learning how to switch off from work.
“In my younger years, I used to work long hours, big weeks… but I’ve realised it doesn’t make you better or more productive.”
These days, Aaron makes a conscious effort to step back, finding that some of his best solutions come when he’s away from the daily grind, giving his brain space to rest and recharge.
This is a vital takeaway for ecommerce leaders, particularly in an industry that’s always on. The constant drive to push forward can sometimes backfire, leading to burnout and missed opportunities for reflection. Aaron’s approach suggests that finding balance is key—not just for personal well-being, but also for fostering long-term creativity and innovation.
Innovating with Purpose
Aaron’s insights offer a roadmap for staying ahead in an increasingly competitive market. As the ecommerce landscape continues to evolve, brands that can combine innovation with authenticity will be well-positioned for long-term success. His emphasis on balance, continuous learning the importance of authentic experiences that resonate with customers, reminds us that growth comes from focusing on the fundamentals, building trust and creating value for consumers at every touchpoint. Moreover, his reflections on the necessity of taking time to switch off and unplug serve as a timely reminder in today’s hyper-connected world.
The Checkout is a short snippet of our conversations.
