Everything a scaleup founder should know about the media, from a journalist 

Everything a scaleup founder should know about the media, from a journalist 

When startups and scaleups approach the media, there’s often a noticeable gap in understanding that can hurt both sides. Startups frequently underestimate journalists, and with that miscalculation come missed opportunities, misunderstandings, and at times, damaging consequences. Orlando Crowcroft, a seasoned editor, shares his perspective on these common missteps and offers insights that can help founders foster a more productive and mutually respectful relationship with the media. Here’s a look into his advice on the most common mistakes founders make, how to fix them, and why the media might be more of a critical friend than an adversary.

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What's the most important thing that startups and scaleups often overlook or misunderstand about the media?

There are many things, but I think the most important mistakes that founders and others at start-ups and scale-ups make when it comes to the media is underestimating them. 

It’s funny, because we are actually quite similar. Journalism is a difficult trade: it is badly paid, it is competitive, it’s unstable. More often than not, journalists are decent, smart people who could have done a lot of [better paid] jobs but *chose* journalism. Just like a lot of founders could have made good money and stability at a big corporation but *chose* to start a start-up. 

And a lot of people hate us, and we know that, and it fosters a bit of a siege mentality - us vs them - but it doesn’t need to be like that. So my advice is: be the outlier, be the founder that is open and decent to journalists. Treat us well, treat us as equals, and we’ll give you a fair hearing: which is all we can do. 

And don’t bs us, ever. We always know, and if we don’t we will eventually find out [probably when one of our rivals writes the story we missed], and then believe me you’ve made an enemy for life. The only thing we hate more than being scooped is being lied to. 

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Tell us about your most memorable founder interview? What made it stand out?

I’ve mentioned this before but I really enjoyed interviewing Cliff Obrecht from Canva. I went into the interview as I go into most interviews: ready for a fight. But I needn’t have: he didn’t try to spin me, he didn’t use any fluffy tech jargon. He was willing to discuss the good and the bad (including a big drop in valuation), and fundamentally - I think - understood what the media can be when it comes to startups and scale-ups: a critical friend. It was suggested to me by a colleague that he had charmed me, and that I should have been harder on him. Maybe he did. But in a funny sort of way that didn’t make me angry: I thought, fair enough. 

What is/are your PR pet peeves?

Honestly, laziness. I can't stand it when I get an email that I know has been sent to a million other people and often has nothing to do with the area I edit or report on. It happens *so* often, I can't tell you. It literally takes five seconds to find out who the opinion editor is, or who covers health tech at a particular title. Just do your research and then spend time crafting an email, and spell my name right and know who I am before you send it. I think it is one of the major casualties of the email age: this spray-and-pray attitude to PR. 

‍What would you prioritise if you were the head of communications or CMO of a start-up for a day?

I would probably sit down and take a look at all of our people - both our employees and our customers - and think about the stories that they tell. Does our founder have a particularly interesting background? I mean, a background other than good school-wealthy parents-MBA-startup-massive VC round from our mates, etc. Who at the company has something interesting to say? Who is the right person to put in front of the press (it often isn’t the founder)?. Then I would think about all the things that are coming up that would be interesting to the press: investment rounds, genuinely relevant news hooks, data, data, data. After this I would work out which titles and journalists would be interested in all of these potential stories -  once you’ve done that you can reach out to them and take them for a coffee. 

What is your one piece of advice for dealing with a journalist?

Be honest, always be honest. Give them the bad stuff as well as the good. If you have a downround coming up, get in front of it. If you have layoffs coming, get in front of it. And remember that it isn’t all ‘if it bleeds, it leads’. We like good stories too, they just have to be genuinely compelling, human, non-jargony, non-promotional. Good agencies and PRs know this, and they get these stories told in awesome publications like WSJ and Harvard Business Review and so on. It is possible to get good press, but you have to take the rough with the smooth.

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Orlando has spent the last two decades as a reporter and editor at titles including Sifted, Newsweek, and the Guardian. He advises startups and agencies on content and media strategy. Get in touch on LinkedIn.

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