Harry, Rory & Elliot from Checkmate: Hot Deals and Red Doc Martin’s | #265

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Harry, Rory and Elliot talk mobile extensions, going viral on Tik Tok and founder chemistry.

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Nathan Bush is a director at eCommerce talent agency, eSuite. He has led eCommerce for businesses with revenue $100m+ and has been recognised as one of Australia’s Top 50 People in eCommerce four years in a row. You can contact Nathan on LinkedIn, Twitter or via email.


CEO of Checkmate, Harry is a Perth, Western Australian-raised entrepreneur living in the US. He has worked in Technology for the past 8 years working for Frank Gehry (Trimble Consulting), Skyryse, Flint Capital & EasyPost. Harry most recently left EasyPost as Director of Partnerships to bring his eCommerce experience to starting Checkmate.

Formerly on Triple J as Elk Road, Rory did a double degree in Law and Engineering and left the music industry behind to work at Apple in California on the iPhone. Deeply passionate about consumer products, Rory has spent the last many months building Checkmate as the Co-Founder and CTO.

Since obtaining his Master's degree in Data Science, Elliot has worked between the USA and Perth in both data-oriented and pure engineering roles. Elliot most recently left a role at DataRobot as a Data Scientist to start working on Checkmate with Harry and Rory.

In this episode of Add To Cart, we are joined by three mates from WA. Harry Dixon, Rory Garton-Smith and Elliot Rampono are Co founders of Checkmate, an app that plugs into safari on your mobile to automatically provide savings while you shop.  The team has an eclectic mix of talents and backgrounds – one is an entrepreneur and partnerships expert, another a trend setting data scientist and the third, a former musician who’s played Splendour and competed in Ninja Warrior!   In this chat, the lads share why they swapped traditional marketing for a different approach, how Checkmate reached number 1 in the US global app charts and how the dream-team started taking shape thanks to a pair of red DM’s.

It seemed to us like the whole world was looking at Web3 and AI as the big thing right now and we were like, holy shit you can build extensions on mobile?!”

Rory Garton-Smith

Red DM’s

(Rory) Elliott was wearing really bright red Doc Martins in a lecture. And I don’t know why, but I was just drawn to sit next to him and that’s the honest truth really. 

(Elliot) I remember that. I think Rory added me on Facebook afterwards and I looked through his profile and realized he was this famous Australian artist called Elk Road and I had a little freak out. I was like, oh my God, the guy who likes my Doc Martins played Splendour (in the Grass). This is crazy!”

Under the radar

(Harry) “…an extension lives in your browser. So if you imagine Safari or Chrome, there are two applications that are called browsers. So for your mobile Safari is the native one.  It’s created by Apple. And so with that they’ve released this product, it’s very new to market. So it was only released last year. You install the app, which gives you the ability to have an extension. We built this extension and then you have to activate it. And so that gives you permissions. When you are browsing on any website, Patagonia, Sephora, whatever you want to browse on, we just pop up inflow. So you don’t need to go to a dedicated, native app on your phone, you just go to your regular browser.  Through customer surveys, we realize most people shop through a browser rather than a native application.”

(Rory) “It’s interesting because I almost feel like developers that we speak to don’t know this exists. They don’t know that the ability to build in this ecosystem exists. I spoke with a lot of large tech companies last week while negotiating contracts for our internal billing.  And I’m speaking to like segment century amplitude. They don’t know this exists. And these are like top tier silicon companies. I feel it’s going under the radar.  I think over the next two years it’s gonna explode because mobile traffic just continues to go up and there’s a massive market to be captured there.”

Founder power

(Rory) “Well, we consider what they’re taking a bet on at seed stage is often not the actual company you’re putting in front of them, because they assume this is seed stage, they may well pivot direction. And even the product, some completely pivot, right? They’re essentially taking a bet that the founders have the ability to rapidly iterate and find what works and therefore they’re taking a bet on the founders.

It was a fascinating fundraiser round to do because they’re far less interested in metrics at that round. And even though we did have a beta out in market, it was like, cool, you’ve got a beta that just shows us you can build something, but who are you guys?  We actually had personal reference checks at our seed round by one of the first checks into the round because it seems like it’s such a crucial element of the seed round.”

Questions answered in this episode include
  • How did you get Checkmate to the top of the app charts?
  • Why did you swap traditional marketing for student ambassadors?
  • What’s the secret to a successful pitch?

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