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Water Cooler with Devyn Olin

Water Cooler with Devyn Olin

A Q&A with the Cache founder.

By Quinn Henderson

May 5, 2026

Give our readers the elevator pitch for Cache.

Cache is AI-powered resale for influencers. We turn influencer closets into storefronts.

What’s the origin story of Cache?

I was working in corporate law. I was finally making real money and I wanted to invest that money. I looked at the stock market and I thought, I don't really want to invest in tech stocks or mining stocks. I wish there was a way that I could buy stock in a Birkin bag or a Chanel bag because I fundamentally understand the value of those assets.

So, I kind of had this nagging idea, “What if I could buy stock in these luxury fashion items instead of actually owning them and benefit from the appreciation over time?” That nagging idea is what inspired me to decline my full-time offer to go back to my law firm and ultimately start building this fractionalization platform for luxury fashion goods. 

Is that what Cache still is?

After interviewing hundreds of women, what I started to realize was that the problem isn't so much the need to fractionalize these things, but it's the friction in resale that prevents us from buying and selling clothes and fashion items in the same way that we would trade stocks.  So I pivoted and ultimately set out to build this mass-market resale product that eliminated the friction in resale. 

Why target influencers? 

I started testing going to market, and did that by doing influencer closet sales. After two events for five different influencers, I started to get inbound interest from other influencers who were excited about what I was doing and wanted me to sell for them. I followed the momentum, and ended up selling for 17 different influencers in the span of four months. 

The light bulb went off in my head where I thought, “You know what, I need to rebuild this product and focus on the influencer as my customer.” They have three to five times the amount of stuff as the average person. They have a higher turnover of their closet. And, most meaningfully, they have this built-in distribution that no platform has been built to capture. And so that is the gap in the market that Cache is looking to fill. 

You have several degrees, including an MBA and a JD. Was becoming an entrepreneur always the endgame of your educational journey? 

I wouldn't say it was the endgame, so to speak, but it has always been an aspiration of mine. I really did not expect to start a company this soon. I knew that when I went and did my JD and my MBA at the same time that, long term, I would love to do something entrepreneurial and I didn't necessarily want to practise law. I come from a family with a couple of lawyers who barely or never practised, so I saw how they parlayed the education into other things and I knew that no matter what I did, that dual degree would set me up for success. 

What are the advantages of building a startup like this in Toronto versus New York?

I realized that our ecosystem has everything that a New York has, just on a smaller scale, and I do think that in many ways that can work in your favour. It is easier to make your mark in that way. You do become known more quickly. 

There are also major incentives to building in Canada, whether it's the SR&ED credits or the student wage subsidies, all of which I'm taking advantage of. And then there is also the access to world-class talent, especially coming out of the University of Waterloo. I have an engineer on my team right now who is a student there.

What’s one of the most interesting pieces that has been sold on Cache?

There was a pair of these Chanel pink ladybug heels, and I remember when we listed them, my friend actually ended up buying them. She scored them for a good price and now we've been seeing them pop up all over other vintage resellers for a major premium. I told her, “If you wanna resell them again we can list them for double,” and she said, “Honestly, now I wanna hold on to them.”

Have you personally scored any great finds on it?

I kind of had to make a rule for myself early on where I decided that I won’t buy anything until our users shop first, otherwise I'd be cannibalizing all of my own sales. And I've tried really hard to maintain that for myself, but because it's genuinely tempting, I'm sure I'll break the rule at some point. But I haven't gotten anything other than a merch T-shirt from Sky Ting Yoga. It says Sky Ting Boyfriend, which I thought was funny. 

Do you have any podcast recommendations?

I've been listening to Maggie Sellers' Hot Smart Rich podcast lately. I specifically listened to three episodes of note: Cat Goetze, she goes by CatGPT on Instagram, is an expert in all things AI and I found it really informative; [Shopify president] Harley Finkelstein; and Senada Greca, Kim K's trainer. The whole show focuses on successful people, what made them successful, and what keeps them successful within their own niche. But I especially love Maggie’s focus on the female perspective.

Any restaurants you want to shout out?

Coffee shop-wise, I am obsessed with Dua’s Coffee in Midtown [Toronto]. The thing to get there is the freddo cappuccino or the iced matcha latté with sugar-free vanilla. We're actually doing a collab with them all May, so if you visit, make sure to try the Cache Freddo Matcha Latté and tag us!

This interview has been edited for length and clarity.

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