5 startup PR lessons learned through trial and error



Often times – we’re asked about our “secret sauce.” The truth is, there isn’t a magic ingredient to pitching journalists nor is there a perfect science. As much as we’d like to write a lengthy ‘how to’ guide (trust us we’ve tried – they’re herehere and here) the real secret is that despite the existence of guidelines or step-by-steps – there is no secret code.

Sorry to burst your bubble. Of course, like anything in life, we have learned a thing or two from simple trial and error or simply just screwing up.

Here are 5 startup PR Lessons Learned from Trial and Error:

1. Set Expectations But Dream Big

Managing expectations is important but don’t be afraid to dream a little bigger. We recently proposed to a client that if they created content relating to a current big trending topic – 50 Shades of Grey (you may have heard of it) – we could potentially present the content to the author.

Full disclosure: our PR team had a valuable connection with E.L. James herself to begin with.

But the expectation that was set acknowledged that while it was do-able – there was no guarantee that E.L. James would like the content enough to share. With this in mind, time was spent on creating the content and despite some uncertainties – the gamble paid off. E.L. James loved it and personally retweeted it from her Twitter account, generating thousands of hits to the client’s blog.

Sadly, those thousands of hits didn’t lead to conversions. Lesson learnt. While it’s great to see your company’s name in lights, one must stop and consider who those lights are shining on. Sure E.L. James has hundreds of thousands of fans but are those fans your key demographic? In this case, they were not. In the end, it still secured some pretty great bragging rights.

This story of success was great but it wouldn’t be fair for us to suggest all large dreams for our clients are met every time. Though the sky is endless when dreaming, the ocean of rejection can be just as endless. And while we’ve scored some great wins – we’ve also gotten our fair share of rejection to content and pitches given a great deal of time and effort.

Lesson Learnt? Dream big but set reasonable expectations. Anything can happen.

2. Sometimes Journalists Don’t Give a Sh*t

Perhaps one of our more memorable passes on a pitch this year was when we cold pitched (I know – we broke our own rule) a writer who chose to respond with a witty insult rather than leave us with crickets. The media outlet was a last minute request from the client so our normal flow of researching the writer and getting to know him first wouldn’t suffice. We had to go in cold.

Following a lack of response to a media release sent his way, we sent a brief two sentence follow-up email to see if he’d had a chance to give it a read. His response? Quite literally – “I do not, in fact, care.”

Lesson Learnt? Sometimes journalists can be tough to deal with. Rightfully so. They get pitched a billion times a day. And that’s ok. But that shouldn’t stop you from trying. (Oh – and always follow your own rules. After all – you made them for a reason.)

3. Small Requests Lead to Large Gains

We encourage you to always dream a little bigger but sometimes even big dreams lead to greater ones. This year – we pitched a killer post on behalf of a client to a large content syndicate for consideration. As with all of our content, hard work was put into it with no guarantee on a return.

After a surprisingly quick back and forth – not only was the guest post accepted but they offered us a syndication agreement which has led to several great pieces from the client’s blog posted since. Small request. Big gain.

Similarly, after weeks of back and forth with a journalist at another large syndicate, we were beginning to lose hope that we’d secure the coverage we longed for. In the end, the piece was postponed until the new year but instead, we received an invite to become a guest contributor. A relationship that has led to greater lead generation and wider long term exposure for the client.

Lesson Learnt? Relationships are key. Never burn bridges. Just because something doesn’t come to fruition overnight doesn’t mean you should turn your back. An even greater outcome may be in the works.

4. Great Pitch. Wrong Target.

Sometimes even the greatest pitches will fall on deaf ears. Despite preaching the importance of researching each writer carefully and confirming that they’re the right fit for the job – sometimes we’re lazy and we fire off that great pitch to the wrong person.

We’re all guilty of it. On some occasions, said wrong person will be nice enough to respond and remind us of our shortcomings. Other times – we’re left with crickets. It may seem at the time that your saving time by firing off those pitches to any writer you can find at media outlet XYZ but think about the time spent crafting said pitch. Now think about your client’s expectations.

Wider reach and greater quantity over quality of pitches sent into the media universe isn’t the key to success and it won’t guarantee you better coverage. In fact, without the time and care put into identifying the right players – you’ve already lost the game.

Lesson Learnt? Always take the time to research the writers you’re pitching. If possible, get to know them first without asking anything of them. Build your network before you need it.

5. This Isn’t a Race – It’s a Marathon

Copy and Paste functions were created to save time and they do the job well. But they should never be relied on when pitching the media. While we encourage the creation of high level sample pitches – they should always be personalized for each media outlet and be extremely cautious when copy and pasting anything from previously sent pitches.

While you may think you’ve got the eyes of an eagle for spotting repetition from the last pitch – you’d be surprised how often the name of the last journalist or the publication accidentally slips into the new email. If you’re lucky, the journalist won’t notice but if they do – you can pretty much guarantee that you’ll get no response.

Lesson Learnt? If you’re going to attempt to copy and paste, always use a clearly defined [[ VARIABLE ]] to help flag personalized, unique info for salutations, mentions of the media outlet and any shout outs throughout the post. While this will take you longer, your odds of getting a response are much greater.

Though pitching and dealing with media can be fun, tedious and intimidating at the same time, it is incredibly rewarding if you do it right.

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About the author

Heather Anne Carson

Heather Anne Carson, Co-Founder, Onboardly. Heather’s focus is all things PR and Promotion – helping introduce Onboardly's portfolio of amazing startups to a wide variety of media outlets, influencers, and networks. She believes that good PR is all about good ideas and a ton of hustle; not a hefty Rolodex like your typical PR agency claims. As a result of that approach, she has helped her clients secure coverage in publications like Inc, Entrepreneur, Shape Magazine, New York Times Magazine, BetaKit, TechCrunch, PandoDaily, TechCocktail, and Mashable among other industry-specific outlets.

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