Ep 447 · 13 min · Fri 20 Sep 2024

Aaron Woolf from Trendii | Checkout

Why is experiential shopping the future of retail? Trendii’s founder, Aaron Woolf, explains how unforgettable shopping experiences can give brands the edge.

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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.

Read the full transcript Auto-generated

[Ad]: I've got a question for you and I want you to be honest with me. Does your business partnership program go beyond snacks for your postie and contra with your local pub? I hope so. Forrester found out that brands with mature partnership programs grow revenue twice as fast and see 28% of their revenue come from emerging partnerships. I'd love to see your local pub do that for you. To get a kickstart and partner with some of the world's most credible content creators, influencers, mobile apps and other brands on a performance basis, check out Impact, a technology company transforming the way we do partnerships at scale, visit impact.com growth welcome to the Checkout. We catch up with previous, add two cart guests and ask them five quick questions to get to know them better and leave you with a little extra inspiration to get through your Friday. Here's your host, Bushy Today's checkout features Aaron Wolfe, the visionary founder behind Trendi. That's Trendy with two eyes at the end. Trendi is revolutionizing the way that we interact with content by seamlessly integrating shopping experiences directly into the media that we consume. With clients including Freedom, Maya, Temple and Webster, and integrated on networks such as news.com, domain and vogue living, Trendy is connecting content to with relevant advertising.

Nathan Bush: Aaron, welcome to the Checkout. We had a great conversation around everything that you're building at Trendi, from how we match products all over the publishing world, including fashion sites, to how to match paint colors for customers wherever they might come across them, even the future of tv and how we're going to shop on tv, which was fantastic to hear, but we've got five questions to hear more about you. Number one, what's the weirdest thing that you've ever bought online?

Aaron Woolf: I bought from Instagram a shoe cleaning paste and it took two months to arrive. It was stuck in customs for about three weeks and it came and it's all Chinese. Can't read a word of it. And it's, it's the best shoe cleaning product that you can buy. Honestly, it's unbelievable and I have absolutely no idea where to get it again.

Nathan Bush: Why was it stuck in customs for that long?

Aaron Woolf: Because it's, I mean, I mean, who knows what the hell it is. It's just some come in some weird bag. It's got like a Chinese official stamp on it, I reckon. God knows what, they thought it was

Nathan Bush: just a weird white powder that you can.

Aaron Woolf: But yeah, exactly. Right, yeah, it's a weird white paste. Anyway.

Nathan Bush: All right, well it was clean shoes. You could as well, you never know, just give it a taste. Number two, which retailer has most inspired you recently?

Aaron Woolf: So I love what Inku are doing in Australia. I think they've done incredibly good things with building a brand. Not only by bringing unknown premium overseas brands into Australia, like brands like Alexander Machuzzi, they do a lot of stuff with acne and other brands. Like these brands are growing obviously, but they, yeah, they've done incredibly well by kind of leaning on these overseas brands and then bringing them in. They also have their own brands. I think it's fantastic and obviously it's just, yeah, just absolutely crushing it. So I, yeah, love those guys. Farfetch'd. Another one I think are doing a lot of really interesting things in the experiential physical world. I'm a big believer in shopping should be experiential rather than just walking in and kind of picking something off a rack, trying it on and buying it. I think there needs to be more there. What that looks like, I don't know. But I'm not really in the bricks and mortar world but maybe one day I will be. But yeah, I'd say, I'd say that they're doing incredibly good things.

Nathan Bush: I think both of those pick up on the theme that we talked about in our main episode around the power of discovery. Those brands like Doug and what the team at Inku are doing is phenomenal because you walk into an INCU store and I'm definitely not cool enough to

Aaron Woolf: be a regular customer. It's so funny. I said that to my partner the other day. I said, do I, Am I dressed well enough to walk into Incu today and have a look? Am I, you know, in my shoes clean enough? Do I look good enough? It's like a bouncer on the door just looking you up and down and it's like, it's. They've created this, this brand that makes you, you want to feel like you're worthy of them and it's like, isn't that insane? It's incredible.

Nathan Bush: Or you speak to any of the team and they are the most friendliest, down to earth people you've ever come across. So.

Aaron Woolf: And they sell all sorts of different price points. Right, so it's not all premium stuff, but yeah, no, I love it, love what they sell, love all the brands they sell.

Nathan Bush: But I can imagine in an environment around content, especially around fashion content, being able to put new Incu product up there against that kind of content as a discoverability medium by trendy would be really powerful.

Aaron Woolf: Oh, mate. Well, we'd love to work with Inku if they're listening, reach out, we'll see what we can do for you guys. But yeah, no, I'd love to, I'd love to work with them. They got. Yeah, absolutely. And, and to be honest with you, a lot of the stuff they sell would be matching incredibly well to a lot of the stuff that's being worn in all the events because let's be honest, it's very, it's very current and very cool stuff.

Nathan Bush: So yeah, I reckon I'm going to get a, get a text message from

[Ad]: Doug after this hopefully.

Aaron Woolf: Wouldn't that be cool?

Nathan Bush: Stop putting me in it. All right, number three, name a piece of tech that you or your e commerce business or trendy couldn't live without.

Aaron Woolf: So I'm a bit old school. I. I'm going to have to go with email. I know, I mean I know there's linear and I know slack and I know there's all these other things that people use all day, every day but to be honest with you, I have an incredibly good team that use all of that stuff and they do incredibly well using it all. I mean, look, slack obviously to you know, to put things in and then we've got, you know, linear to log tickets and everything else. But the reality is, you know, I'm doing 150, 200 emails a day and all day, you know, doing emails and without it I don't think I'd be able to function. So yeah, it's definitely got to be email for me. Forgive me for being perhaps a little bit old school.

Nathan Bush: No, no, no, I just feel sorry.

Aaron Woolf: That's where I'm at.

Nathan Bush: Many emails?

Aaron Woolf: Yeah, no, well, I think I've got some in the region. About 23,000 unread emails. So I do have to start, start cleaning up my inbox. But anyway, do you ever see a

Nathan Bush: future where trendy recommendations and product matching finds its way into promotional or campaign emails as well?

Aaron Woolf: Look, the email is going to come from a brand. The brand's going to already know the products that consumers wanted or clicked on

Nathan Bush: engaged with emails from publishers.

Aaron Woolf: An email from a publisher connects brands products an automation.

Nathan Bush: Maybe. Maybe, maybe. Yeah.

Aaron Woolf: You've just given me. You've just given me three sleepless nights. Thank you.

[Ad]: Add that on top of your emails.

Nathan Bush: You'll be right.

[Ad]: Yeah, just.

Aaron Woolf: I'm just gonna go and solve this problem now. Thanks. Thanks Nathan. It's a problem I didn't know. It's a problem I didn't know needed to be solved and Now I've got to go and try and figure it out.

Nathan Bush: It might not be. I mean,

Aaron Woolf: yeah, maybe dynamic. Dynamic email, HTML. Let me, let me.

Nathan Bush: Anyway, all right, I'll leave that with you.

Aaron Woolf: I'll come back to you if it becomes something. I'll, you know, buy lunch. How's that?

Nathan Bush: Buy me a new T shirt number four. Can you recommend a book or a podcast that our listeners should immediately get into?

Aaron Woolf: I mean, I love reading autobiographies of people that have achieved things. I recently read Phil Knight's autobiography, Shoe Dog, and thought that was absolutely just mind blowing. And I think one of the reasons why I loved it so much is because there's so much it's not. Losing my virginity was probably one of the first I read, which is Branson's, and I read that and it's very. It's very self indulgent. It's very fluffy. Hope he's not listening. He's a regular. Okay. I love this book. Best book I've ever read. It was a little bit, kind of everything just went according to plan. Of course it is. Or hang on, did it, did it really? No business goes according to plan. I don't care who you are. I don't care how big and successful you are. You know, you got stories about Amazon having a phone call away from bankruptcy. The little things that you kind of know about from these people that have built these businesses. And there's a lot in that book that's really raw and real and honest. And I think it's just one of those books you absolutely have to read. And then Chimp paradox. Haven't gotten too into it yet, but I don't know if you're familiar with the chimp paradox, but the idea is that there's three parts of your brain. There's the chimp, the human, and then there's your robot or your storage. And storage is essentially everything that you know to be true. Like, you know that you have to pull down on a door handle to open a door, that sort of thing. But the idea is that the chimp is five times stronger than the human. And so the chimp part of your brain is very much about impulse, instincts, reactionary, got to do things, blah, blah, blah. And it can be very overpowering to the human. So the chimp paradox is all about not controlling the chimp, but managing it and basically having a way of managing your sort of mind and those other things. Was recommended to a friend by a friend of mine that's done about 50 Ironmans. So it Obviously helped him. So I'm gonna, yeah, give that a

Nathan Bush: go and then go do an ironman.

Aaron Woolf: And they're all. Well, he keeps pushing me, but I don't know if I've got the legs for it. Anyway, love it.

Nathan Bush: Last question. I've got for you, Aaron. What is your biggest challenge today?

Aaron Woolf: I think the biggest challenge is sometimes switching off and the importance of switching off to reframe, refocus and come back to what you were doing. A lot of focus in my young years, when I was sort of in my 20s and early 30s, was very much about work. Long hours, work, big weeks, hustle culture, work, work, work, work, work, work, work. And I think what I've realized in the trendy journey is that it doesn't make you better, more productive, deliver a better product and have a better outcome. Because remarkably, some of the problems you solve might be ones you think of while you're sitting under a tree staring at the sky. And if you're so busy focusing on what's happening, you can't actually take a look at what's happening. You're just so busy in the zone. So that's probably. For me, one of my biggest challenges is actually remembering to do that, because by the time I realize that, it's 4 o' clock on a Friday afternoon and I've only had lunch once that week, you know, and so it does get a bit tricky. But I do try and find time to, you know, to get it, get away from it, just completely switch off, turn my phone off for an hour and, you know, do. Do other things.

Nathan Bush: Such a good tip. I once had a business coach who would always start our calls of, are you in the blue zone or the red zone?

Aaron Woolf: Oh, really?

Nathan Bush: Yeah, Literally, like, if you're in the red zone, the red zone is the doing zone. It's the. You're pumping out emails. It's like you're making decisions, you're going, you're going, you're going. Blue zone is that safe space, the sitting under the tree where you can think of new ideas and you have space for other ideas to come in. So she had a bunch of exercises to move us from the red zone when we're rushing to finish an email, whatever, to jump on a call to move us into the blue zone, which I think is really important.

Aaron Woolf: Yeah, agreed. I mean, you can't, you can't rush solutions either. You know, sometimes they do take as long as they take and you've just got to. To wait for that. But I think, you know, been around the block a bit. You know I've worked in the industry now 20 years so I know things eventually do come so it's trusting that process. But yeah, finding finding time to do it and you know dedicating to it's really crucial. But yeah, love it.

Nathan Bush: Aaron, thank you so much for joining us on the checkout.

Aaron Woolf: My pleasure. Thanks so much for having me.

[Ad]: To hear more from Aaron, jump back into episode four 433 where Aaron shares how Trendi reduces friction in the purchasing journey by embedding relevant products directly to inspirational content. We also look at the various ways that publishers and brands can leverage Trendy's technology to drive engagement and sales, especially through the middle part of that funnel. And we look into the future with some stargazing strategies on the future of contextual content commerce including potential streaming service integration, social media and who knows, maybe even a bit of VR. Thanks for listening and until next time

Nathan Bush: keep adding to cartoon.

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  • Technology and Platforms
  • Brand and Storytelling
  • Marketing and Acquisition
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