Interview Poppy Dinsey of ‘What I Wore Today’

A few weeks ago I was sat in the pub near to my university and Pete Cashmore’s face filled the television screen. He had seemingly come from nowhere and was now on the brink of selling his huge blog Mashable to CNN for hundreds of millions of dollars. His story inspired me to write a feature about the significance of blogging in 2012 and I emailed Poppy Dinsey, who has risen to fame from her blog-turned-booming-website (What I Wore Today), to interview her. She is lovely and gave me some great material – read below for the full article…

What Poppy Did Next


“One of the key differences between an Olympic swimmer and any other swimmer is that the Olympic swimmer is in the pool at 5am every morning 365 days of the year. My general advice to anyone wanting to succeed in anything is to work hard, then work harder. And ideally don’t have a mental breakdown along the way.” These are some words of wisdom from What I Wore Today founder and blogger-extraordinaire Poppy Dinsey, and probably a motto Pete Cashmore lives by.

Cashmore took the media by storm recently when it was reported that his blog, which he started from his bedroom in Scotland in 2005 at the age of just 19, had blossomed into a world-wide phenomenon. Dubbed ‘Brad Pitt of the blogosphere’ (supposedly he is an amalgamation of beauty and brains), Cashmore’s blog Mashable, a destination for digital, social media and technology news, is now one of the most profitable blogs in the world and has led to talks with CNN for a deal to purchase the blog for hundreds of millions of dollars.

It’s a dream come true. We all fantasize about sitting in our beds at home, a cup of tea on the bedside table and a packet of hobnobs not far from reach, all the while raking in money without lifting a finger or dealing with rude, fussy customers. Cashmore said himself that setting up Mashable was appealing: “it’s partly because it was something I could do in bed and feel like I was achieving something. I’m just not good at obeying authority figures.”

Poppy Dinsey is another British success story. She started her blog as a small-scale project at home. With a new year underway – 2010 – Poppy pondered whether she could create a photo diary of herself in a different combination of clothes for the next 365 days. The simple ideas are always the best. She stuck to it. What I Wore Today grew in popularity, with around 90,000 monthly visitors, and Poppy decided to take the website from a hobby through to a money-making business. University degrees aren’t enough any more; blogging can be a great way to show off writing skills. Another string to a writer’s bow, in the tireless trudge through the job market.

I scour the internet and find hundreds upon hundreds of blogs, many of which whose last post was in 2008 or 2009. Not very promising. I feel a little bit like I am looking in on a pond full of fish of all different strengths – it really is survival of the fittest. Thousands won’t make it, and then every now and again a sparkly, dogged blog rises to the surface and gets noticed. It doesn’t look as if a ‘proper’ blog can be born on a whim – it looks like a thorough business plan is what is needed.

I ask Poppy if this was the case for WIWT: “I’ve blogged since 1999. So it’s kind of normal for me to start blogs whenever I have a vaguely interesting idea, I’ve had so many I’ve lost count. Any project I did growing up usually involved a blog – or an ‘online diary’ as we called it then. WIWT was by no means my first blog, I’d been blogging for nearly a decade when WIWT started. My life was certainly made a lot easier by the fact I already had a relatively large readership from the property blogs that I wrote professionally. I was supposedly the fifth most influential person in the world of online property in 2008, so I’d be cheating if I said I started WIWT from scratch. But the original WIWT blog really was started on a whim, it was literally just a New Year’s resolution/challenge to get me to wear more of my old clothes.”


So, WIWT was indeed born on a whim. However, Poppy’s background in, and dedication to, blogging ensured her success. While working as a Marketing Executive at Zoomf, a UK property search engine, Poppy’s passion for blogging was inflamed, and there she got the opportunity to write about one of her other interests, property. Although Poppy was a successful property blogger, that didn’t give WIWT a fast track to overnight success. Like Cashmore, who worked on Mashable for six years before virtually anyone had heard of him, Dinsey’s blogging didn’t spawn real success until last year.

So other than self-satisfaction and some potentially hefty profits, what else is there to be gained? “The best perk is probably the people I’ve met, whether they’re celebs, designers, entrepreneurs, WIWT users… it’s amazing really. The travel isn’t half-bad either, next week I’m in Cannes and then I’ve got to go to Milan for a party. That’s not a bad perk.”

But Poppy does give a word of warning: “I do always feel the need to point out though that the good stuff comes with plenty of bad. The blood and sweat and tears that have gone into WIWT would be measured in bucket loads. Running your own company is somehow the most rewarding and horrific experience all at once. I suppose the good does weigh out the bad really though, or no entrepreneurs would bother!”

The question is, how does one keep from becoming disheartened when you’re not getting the hits you want after two months of tapping away at your keyboard every evening. Why did Poppy’s blog do well when there are so many that flop because of little, or no, hits? “I’m lucky to have a good business brain and a creative brain, a lot of people only really have one or the other. You really do have to be a good writer with original ideas to stick out in the ever-exploding world of blogging, but my success in a commercial sense comes from being able to see and exploit opportunities. There are plenty of people who can write but can’t see how to turn that talent into something they make a living from, and similarly there are lots of business minded people who lack any real creativity or imagination. I’m very persistent though and that certainly helps. And I can’t deny for a second that I had a huge head start by getting into this crazy world of blogging early on.”

It all seems very overwhelming, but Poppy is optimistic that there is still space in the blogosphere for new, original blogs: “There are zillions of blogs, the majority of which have very few readers. Does it matter? I don’t think it does. Everyone goes into blogging for different reasons, if you started a blog because you’d just had a baby and you want your extended family to be able to see your latest baby news – then it would be ‘a success’ if your cousins in Australia could see a YouTube video of his first steps. That’s not going to be interesting to anyone outside of friends and family, but it’s still successful in terms of what it set out to be. The people that will come unstuck are the people who think blogging is going to make them a millionaire. It’s not.”

It may not make you a millionaire, but it might just give you an advantage over the next Joe Bloggs with a first-class university degree. “It’s normal for employers to ask for blog and Twitter links now and if you want to work in something to do with social media, yet aren’t actively using social media personally, then you’re unlikely to get very far. That’s fair though. For many people their blog has become their CV or portfolio: it proves you have the skills you say you have. An employer can see what you can do rather than just take your word for it, so it’s very important. I still look at what degrees people have though and where they got them from and what grade they achieved, a blog won’t replace experience and education – it’s in addition to.”

I ask Poppy’s best advice for budding bloggers out there, and those who need a little nudge in the right direction: “Write about something you care about, write consistently (that refers to tone, style, length, frequency of posts etc) and just keep going with it. Even if nobody ever reads it you’ll hopefully be improving your writing skills and picking up some HTML knowledge along the way. But if you don’t enjoy it, don’t bloody do it! The love has to be there as blogging really is a labour of love with, generally, very little reward in a commercial sense. Blogging isn’t a get rich quick scheme, but sometimes the media portrays it as that. The only people I know who have made a commercial success of their blogs are people that have worked at them all around the clock, every day of the week for YEARS. That shouldn’t put you off, but it should help put into perspective that if you haven’t been able to jack in the day job by your third post- you’re in the same boat as everyone else.”

You wouldn’t expect to get a promotion at work after a matter of months without a exceptional dose of luck, and the same can be said of blogs. However, if you can take everything with a pinch of salt and appreciate that all good things come to those who wait, you may end up writing for more than just your mother and the pet dog. Like Poppy, you might one day write for nationals – Poppy has since been asked to write for the Financial Times and the Sunday Times Style section. Poppy and Pete Cashmore are intelligent people but their success took time and hard-graft. And the most inspiring nugget us university students can take from that is that it all started from a teeny-tiny blog. Something we all have the ability to do.