5 Lessons For When Your Pitch Bombs (Like Mine Did)

When I say that my pitch bombed, I'm really giving it more credit than it deserves. My pitch didn't even get a chance to bomb, because it never even ignited in the first place. I'd like to tell you what I did, where I think it went wrong, and what I learned as a result.


If you've had an important pitch fail on you, you're not alone. Sometimes your timing is off, and sometimes they're just plain old not interested. 

For many freelancers, the cold pitch is part of the daily routine, it's how you win the work you really want. How much time you spend on each pitch, depends on how much time you've got and how willing you are to put yourself out there to be noticed. You could spend a few hours pulling together the most relevant parts of your portfolio for a hiring manager to see, or you might spend days, even weeks putting together a bespoke collection of work aimed specifically at the company you want to work with. That's what I did (and what I generally tend to do for most of my pitches.)

The pitch I'm talking about is this one, a 50-piece creative portfolio aimed at California-based tech giant FitBit. At the time, I was big into FitBit for a number of reasons, and so determined was I to land some work with them, that I spent three weeks brainstorming, writing, editing and designing a range of creative for everything from the Alta to the FitBit One. Once it was done, I looked up as many names and email addresses at FitBit as I could, and I launched. 

And do you know what I got back? A couple of lukewarm 'Nahs' and then dead silence. 

So, what went wrong? Are FitBit just a bunch of rude monsters? Probably not. Was my approach all wrong? Not entirely, but was right? Hell no. 

Why create so many pieces in the first place?

Right. Let's start with the obvious question which is, 'Why would you spend three weeks making 50 copy ads for a company which spends millions on advertising and which never asked you for anything?'

Fair point, and I could've just applied for one of their advertised jobs, right? Kind of. FitBit HQ is based in San Francisco, roughly 5,323 miles from when I am in Cambridge. I could've moved there, but the likelihood of my beating out the competition in the local area from way over here, is tiny. And so if I wanted to make a splash big enough for the Californians to see, I couldn't be content with a folio of 10; it had to be 50 (also #50forfitbit had a nice ring.)

Lesson #1: Do the work

But you just said that you did the work and it was a waste of time. 

No, I didn't say that it was a waste of time. The work is the work, and the work is never a waste of time. If I hadn't spent those days and weeks writing and designing, I would never have had this experience, and I wouldn't have a portfolio of work that I'm still incredibly proud of. 

Doing the work is about being an unshakable optimist. If you went through life not doing things because you were afraid, or even 90% certain they'd fail, you'd never give life to any of the ideas you're truly in love with. 

I'll say it again: Do the work, even if you think that 9/10 it will fail to meet your expectations for it. If you don't do the work, then you've got no chance at all. 

The approach: Sometimes the cold pitch stays cold

Here's where I went drastically wrong. I assumed (moron), that because I had put in the work, that I was guaranteed a positive response. The mistake I made here, was that I forgot that nobody at FitBit owes me a damn thing. 

Nobody, not James Park, not the head of HR, not a single person on the FitBit talent acquisition team, had (or has) any obligation to acknowledge anything that I did for them.

My generation has grown up believing that if you work hard, you will achieve greatness. Sure, if you work hard, there's no reason why you can't get a great job that you love. You can get money and influence and followers and anything else you want, but don't be surprised if sometimes you work your ass off and you get nothing. The world doesn't owe you shit. 

Lesson #2: Accept some shit and move on

Sometimes you'll work, work, work and get next to nothing in return. That happens sometimes, because, to quote Walter Sobchak in The Big Lebowski:

"Life does not stop and start at your convenience, you miserable piece of shit." 

Does it matter how you pitch?

Let's be real, it's not like I was pitching for millions of VC money. All I was asking for was a chance to write copy for FitBit. If you're pitching for money for your startup, then good luck to you, that's something that I know nothing about. As a freelancer, how you pitch can have an effect — positive or negative — on how your request is received. 

As a general rule, I tend to believe that there's no better way of showing that you're serious about working with someone, than to track down their email address or Twitter account, and to reach out directly. Some people think that that's invasive, but in my opinion, wanting the right person to see your work is a mark of respect for both them and the work. 

If you followed your own rules, then why did it fail?

In this case, I went all in, sending out emails, following FitBit influencers on Twitter and even previewing the work on social media with paid advertising boosts. There are two reasons I believe it didn't work (and I truly believe this, because I think the work is good):

  1. There was no call or need for the work or my services.
  2. They just weren't interested.

That doesn't mean the work isn't worthwhile, it just means that at that time, your pitch isn't in the mindset or position to accept your work. Did the work not Wow the people at FitBit? Maybe it didn't, but I may never know. 

Lesson #3: Be thorough with your work, and be humble

If you've done all you reasonably can to reach out to the people you're pitching to and you still get no response, accept it as a loss and move on. It might not be the work's fault, but if it is the work's fault, then work harder next time. 

Follow up, then stop following up

People these days are busy. Everyone's got an idea they're working on and when you try and get them to look at yours, it can be hard. Once your pitch is out there, you'll be eager for a response, which might lead you to send follow-up emails and tweets. That's ok, you should. You've put in the work and it's reasonable to want to know whether it's been seen.

If, however, you've done your rounds on the follow-ups and you're still not getting any returns, it's safe to assume that whoever you were pitching to is not interested. 

Lesson #4: Know when to quit

You might get the opportunity to pitch again later on, but for now, this one is dead. Find another thing to work on. 

The work goes further than you think

Remember at the start when I said that doing the work regardless was important? After I finished this 50ForFitbit thing, I received offers for work from people who were not FitBit, but who had seen the work. When you pitch semi-publicly like I did, you're pitching to more than your primary target. 

You do the work, sometimes you get nothing, sometimes you get something you didn't expect. So do the work. 

Lesson #5: Be generous, be grateful

When the pitch doesn't go the way you expected, use the work to your advantage, and be grateful of any positive feedback or unexpected work that comes as a result. 

The bottom line here, is that a failure is only really a failure if once it drops to the ground, you just let it sit there. If you're proud of it, then pick it up and use it. 

Have you had a pitch or project fail on you? How did you respond? Leave a comment, or follow me on social media and let's talk.