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This article was published on July 26, 2011

How Poppy Dinsey went from fashion blogger to startup founder

How Poppy Dinsey went from fashion blogger to startup founder
Paul Sawers
Story by

Paul Sawers

Paul Sawers was a reporter with The Next Web in various roles from May 2011 to November 2014. Follow Paul on Twitter: @psawers or check h Paul Sawers was a reporter with The Next Web in various roles from May 2011 to November 2014. Follow Paul on Twitter: @psawers or check him out on Google+.

Fashion by its very definition is something that’s constantly changing. And changing is something 24-year old blogger Poppy Dinsey knows all about.

Poppy set up What I Wore Today (WIWT) back on January 1st 2010, and it has always been a blog with a simple underlying  premise: Upload and share one photo each day of Poppy in a different outfit. Interesting idea…but why?

With a new year underway, Poppy pondered whether she could create a photo diary of herself in a different combination of clothes for the next 365 days.

It wasn’t so much about buying new clothes, it was more about making use of the extensive collection she had already amassed over the years.

Whilst many among us might dream up similar quirky plans and stick to them for a couple of weeks, Poppy didn’t miss a single day.

WIWT has developed beyond its initial remit, and Poppy now also interviews celebrities on what they’re wearing, and there’s even a section called The Lust List. Check it out for yourself.

With around 90,000 monthly visitors and a burgeoning reputation in the fashion blogging fraternity, Poppy has taken WIWT from a hobby through to a money-making business. And to capitalize on this, WIWT is about to relaunch as a community-based fashion website, where anyone can upload and share pictures of themselves in their latest clobber.

I caught up with Poppy to discuss blogging, business, estate agents…and her plans for WIWT as a fully-fledged startup.

The birth of a blogger…

Poppy is from near Guildford, Surrey, and 13-year old Poppy also had a penchant for blogging, using Open Diary, way back in 1999. By her own admission, her first flirtation with the blogosphere was “mainly fiction, made up stuff”,  and when she continued on through college and university, she moved over to Windows Live Spaces, before hitting the likes of Posterous and WordPress in recent years.

But it was during her time studying Economics, Business and East European studies at London’s UCL that Poppy’s blogging career really took off. And she wasn’t writing about fashion, either.

Zoomf is a UK property search engine, and Poppy worked there whilst still a full-time student, from May 2007 until September 2008. It was whilst a Marketing Executive at Zoomf that Poppy’s passion for blogging was flamed, and was where she got the opportunity to write about one of her other interests.

“I was one of these people who was obsessed with estate agent websites”, says Poppy. “A lot of girls are like that…they want to move house the whole time. I’d left home at 18 and at that point I’d lived in about 6 different flats in London and Brighton. I was also looking for a Web job, and when I saw a disruptive startup involving property search, I had to go for it.”

Poppy jumped ship for Zoomf’s competitor Globrix, where she worked between September 2008 and January 2010. But it was through both her roles at Zoomf and Globrix where Poppy managed to carve a niche in the property blogging sphere.

“I had studied economics, and I was reading a lot about the property market anyway”, says Poppy. “I managed to carve my niche through writing about the property market and its effects on the wider economy. But I wrote about it in this very cheeky, funny way. But, what shone through was a very in-depth understanding of what I was writing about.”

In October 2008, whilst at Globrix, Poppy was voted the fifth most influential property blogger in the world by Global Edge, and it was during this time that she was invited to write for websites in the US and attend conferences Stateside too. So now Poppy’s made the move from freeholds to frocks, does she miss it?

“Sometimes I still miss it, but there’s only so long you can deal with estate agents and write about property before you get a bit sick of it”, says Poppy.

After leaving Globrix in January 2010, Poppy worked as Marketing Manager at School for Startups with entrepreneur Doug Richard, at the same time as she was launching WIWT. She left School for Startups in June 2010 to commit to WIWT and it’s been an upwards trajectory since then.

It seems that working for the likes of Zoomf and Globrix gave Poppy the taste for the startup scene, something that may have been instrumental in her launching her own digital company.

“I got addicted to the idea of working in small teams, you really know who did what”, says Poppy. “And you see the outcome of your work immediately, I’d say I’m quite an impatient person.”

And you won’t get many smaller teams than what’s currently at WIWT. Whilst she does have support in the form of Shoreditch-based developers Caffeine Hit, Poppy manages and produces all the content by herself.

A passion for fashion?

So how much into fashion is Poppy?

“I’ve always been into style, but I’m not a slave to fashion”, says Poppy. “I’m not one of those people who buys hundreds of fashion magazines, but all my money has pretty much gone on clothes. I’ve always liked having completely different outfits every day. Before I launched WIWT, I was quite often tweeting pictures of my outfits, and I just realized they were going nowhere, sitting in my Twitpic account, and it seemed like a wasted concept really.”

When 2010 was over, Poppy didn’t feel the need to continue with her ‘new outfit each day’ philosophy, because strictly speaking, it was just a year’s challenge. But she still continued to upload new outfits on many days, and the content Poppy has built up over the past year and a half will soon be carted off into archive on a yet-to-be-determined website, to make way for the launch of WIWT v2.0:

The site is currently in beta mode and is invite only, and the site should be launched to the public some time in August, in plenty of time for Fashion Week which kicks off in September. Whilst the site could potentially exit closed beta now, a major part of the WIWT relaunch will be an iPhone app, which users can use to take photos of themselves and upload directly to WIWT.

And this is the main difference between the two sites. Whilst WIWT at present is largely all about what Poppy is wearing, the new site is about the community, where users follow each other and connect their profiles with Facebook and Twitter to share what they’re wearing with their own friends.

Will this mean that Poppy will be growing the company and taking on more staff and investments? It doesn’t seem so.

“I’m being really frugal with the money”, says Poppy. “Someone asked me recently why I don’t build-up my team now, but I’ve worked at startups that have 20 people at the beginning and you just don’t need that amount of people. These are the companies I think don’t do very well in the long-run, I think. They take on a lot of investment, and grow way too quickly. I’ve turned down investment, and it’s amazing how much I can get away with not spending and I get by just fine. If it’s your money, you do tend to be a lot more careful.”

Wise words from a young entrepreneur, who realizes that she’s in a very good position to really take off into the fashion blogging stratosphere. “This has the potential to be huge”, says Poppy. “Now’s the perfect time to do it. I’m single, I don’t have kids or a mortgage…it’s the most risk-free time for me to do this.”

And is Poppy back to buying more clothes now that her year’s challenge is over? “I get sent lots of clothes now”, she says. “But I do still buy clothes too.”

At 24-years young, Poppy seems to be living the dream. But as the sole proprietor at WIWT, she works 16/7, and on a recent ‘holiday’, her beach doubled as a surrogate office. “I don’t particularly like having to work the whole time, but I like what I do, so it’s fine”, says Poppy.