Interview with Charlie Osmond, CEO and Founder of Triptease, CEO of the Week

The internet is a wonderful thing, but it is often a very ugly, and very useless thing.  Luckily, to cheer ourselves up, we’ve taken it upon ourselves to highlight the bits of the internet that are brilliant, and beautiful, and useful- to give you alternatives to the grim world out there. You know TripAdvisor? This is the pretty one of that. It’s also, given the latest news on TripAdvisor, the factual, useful one of that.


Like holidays? Like beautiful things? Triptease is going to make you swoon. Triptease is the review website all travellers- casual or utterly committed to the globe-trotting bug- have been waiting for: simple, elegant, and so very useful. We loved it. We loved it so much, in fact, that we got in touch with Triptease founder Charlie, to pick his brains. In a beautiful and elegant way, obviously.

So, where did Triptease come from,Charlie?


(This is Charlie, in the picture. What a nice smiling man.)

Triptease was the product of two frustrations, Charlie tells us- a business frustration, and a personal frustration.

“During the six years I spent at Fresh Networks (the social media agency I founded), I always felt the travel industry had the greatest opportunity to get value from [social media], yet it continues to struggle to make it pay.”

“I also felt a consumer pain- that existing travel review sites were ugly, text-heavy and often anonymous. As an example, about a year ago I was booking a family holiday. I booked us into a beautiful French hotel with a great reputation. Excited, I checked some review sites to show my wife. It was at that point that the joy of anticipation instantly drained away. All I could find was poorly written, bad looking reviews that made even great hotels look awful. I had no idea if a reviewer had similar travelling habits to me and whether their review had personal relevance.”

Well, that’s Morris’ “useful” criterion- what’s Charlie got to say about beauty?

“People,” says Charlie, “will always care about great design. Online aesthetics are becoming increasingly more important, as more and more content moves online. The success of apps like Flipboard, challenging the bland online aesthetic of news sites, proves that people love good design. Much like Instagram, we think giving people the tools to make quick, beautiful creations is powerful. Empowering people to instantly feel like magazine editors is a large part of the emotional appeal.”

Morris would be proud. Probably. Being Enternships, however, we’ve got a few more questions before we can be totally satisfied: we want to know just how being a successful entrepreneur feels, how Charlie did it- and what you can do to get involved. Don’t say we never do nothing for you.

So, go on- what’s the best bit about running Triptease?

“The sheer size of the opportunity. Travel is a gigantic industry worth billions of dollars per annum. It’s exciting to start out with the ambition of becoming a major player in such a huge market which is, in my opinion, ripe for disruption. The support of the industry since launch has been hugely encouraging. This type of validation so early in our journey is very exciting.”

It’s not all roses, surely?

“It may sound clichéd but life at a startup is a real rollercoaster. There are tough moments, but the overall reaction to the product has been extremely positive. Our community is engaged, there’s a regular stream of high quality content being produced and the reception from hotels has been equally as enthusiastic. But the very nature of a startup means you have really good days and really bad ones.”

Who wouldn’t want to be involved with something this exciting? Not us- so tell us, Charlie- what do we have to do to work for you?

“There are some pre-requisites that apply to good hires at all startups and across businesses in general. The first is commitment. No matter how good your idea is, getting a company off the ground requires hustle. You need energetic, productive people around you who are committed to the cause. You won’t always be able to recruit the polished product and that’s OK. What’s important is that the people around you are willing to listen, learn and develop.”

But what would really impress you, personally, in a job application?

“First, it’s an absolute must that applicants take the time to check out Triptease. They should add a review, engage with the community, offer us feedback on the site. We also love people with a burning passion for travel, photography or writing (but preferably all the above). Applicants with high quality blogs always stand out.”

Brilliant. Well, we’re off to practice blogging- and idly peruse Triptease in our lunch hour. Our imaginary holidays are diverse and endless- and, should we not be totally dedicated to bringing you brilliant content, we’d be reviewing stuff ourselves. Before we go though, Charlie- what advice would you give someone wanting to launch a business online?

“Just have a go. There is no longer a valid reason to let an idea sit and fester. Build an MVP (minimum viable product), test it and learn from the experiment. From there you can decide whether your idea is business-worthy and worth bigger investments of time and money. Good luck.”
And with that, ladies and gentlemen, we’ll leave you- swooning over holidays, brushing up on your blogging, and (we hope) inventing some amazing, beautiful, useful things to make William Morris proud.

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