How We Got Hundreds Of Customers Through Creative Cold Emailing

Published: January 18th, 2019

Hi, my name’s Neil and I’m the CEO and founder of Our company exists to make it easier for teams, events, and startups to get great quality merch and swag.

For too long it’s been a lengthy, drawn-out process. We use a mix of tech and print expertise to make it a quick, painless process. And that’s why we’ve rapidly been able to bootstrap ourselves to a six-figure business.

Automated cold emails as a massive sales channel

This is a summary of how we used cold email, personalization, automation and an awkward photo of me to find and convert new customers.

It’s also about how we managed to give it a second life beyond the email, as content. And then how it’s now having a third life as a presentation and talk.

This is a story about implementation

First off, it’s important to know that this isn’t the story of how we came up with the idea.

It’s the story of how we implemented it, and what you can learn from that. It’s the story of how we tested the idea without committing lots of money or resources to it before we knew it would definitely work.

Call us dirty growth hackers…

You can call this growth hacking, product or process validation, or just taking an iterative approach to building automated marketing systems.

But it’s important to understand that everything we did in the first part of this blog, is something you can do with no technical skills and free (or nearly free) micro services on the web.

Customer acquisition is hard

So, the problem that we were trying to solve was simple customer acquisition.

Ramp T-shirts makes it easy for companies, teams or events to get promotional merchandise quickly and easily. But we’re a bootstrapped company, in a very competitive market, so finding customers is not always easy.

Advertising is expensive, and SEO & content are slow. So we decided to try cold emails to get quick, measurable results.

Raising the bar for cold email

But we didn’t want to be spammy. Unlike a lot of cold emails we all receive every day, we wanted our emails to be relevant, targeted, and at least provide some positive reaction from the recipient.

After a lot of brainstorming for how to do better cold email, we thought that it would be amazing if we could send the recipient an example of what their logo would look like on a high-quality t-shirt.

So, we set to work.

But before we did we asked ourselves a fundamental question, that every startup should keep close to their heart - “What is the quickest way we can test our hypothesis (preferably for no money)?”

Our marketing assistant, Romina, and I spent a few hours researching possible targets, finding email addresses, and then manually photoshopping their logos onto a stock photo of a plain white t-shirt.


The whole process took about 4 hours, and required almost zero technical skill. We then wrote a quick sales email to each of the 50 recipients (“Hey, check out what your company t-shirts will look like if you buy from”), along with the unique t-shirt preview that we had created for them, and sat back and waited.

Testing our hypothesis

From these 50 emails, we received a 50% open rate (which is *great* for a first time cold email), and 6 positive replies. But no sales.

OK, so not a resounding success. But certainly, plenty to be positive about. We just needed to find a way to automate just a tiny amount and do it at a bigger scale. We broke it down into the three main elements so that we could consider the best way to approach it.

Running more tests - at bigger scale

Firstly there was the finding of emails: This was actually one of the easiest things to do. There’s a ton of great services like Hunter and DuxSoup out there that make it super simple. Getting 250 relevant emails was easy.

Then there was getting the logos. This was a little trickier, but thankfully Twitter or Facebook avatars are often the perfect shape for t-shirt prints. We also experimented with Clearbit as well.

And then the tricky part - creating the previews. We found a great service called PlaceIt, which allows you to upload images and creates professional looking previews of all sorts of products.

In our case, we found one of their stock images of a handsome guy in a white t-shirt, and uploaded 250 logos. We could have spent time coding this ourselves, but we didn’t want to commit to a full project - just yet. We had more validation to do, and measuring to undertake!


These 250 emails yielded another great open rate, another raft of replies and, crucially, one sale!

Yes, it worked!!

But the big question was whether it worked *enough* for the 10 or so hours of work that had gone into creating those 250 emails.

The answer was “Probably not”. It was clear that people were responding well to the campaign, but that it would only be worthwhile, and bring us new customers at the right cost of acquisition if we could automate it even further.

Consulting our CTO

And it was only at this point that we took the idea to our CTO. As a bootstrapped startup with limited dev resources it is vital to us that we don’t tie up our developers with stuff that we can’t prove will have a tangible return.

So we just spent those few days of our time proving that we at least had some validation of our hypothesis that we could generate sales through personalized t-shirt previews in cold emails.

Building more automation

Milen and the team then started building a simple system that would use a variety of APIs and systems to finding relevant email addresses (it automatically discarded generic emails such as “support@, info@, hello@...”) from a list of URLs, at the same time as pulling in the logos, and creating the previews with those logos.

One crucial change that we made was the “template” photo which we used to superimpose all the individual logos on to. We wondered if we could do better than just “handsome guy in a white t-shirt”.

After some careful thought we decided to go for a significantly less handsome guy in a white t-shirt, but hopefully, one that would resonate with the recipient - it was a photo of me.



I wasn’t keen on sending photos of myself to unknown thousands of company CEOs and marketing executives, but there’s no doubt that it would be a lot more persuasive for the preview to feature the guy that is actually trying to sell you custom t-shirts for your team!

We go into a lot more detail on the technicalities of the process on our own blog, but let’s just say that the results were pretty instant. Within days of starting to send emails, we were making sales.

And as we tweaked and refined the email copy and the targeting, it only improved.

One other big change we made that massively helped with open and click-through rates was to start using the Subject line “I’m wearing a <your company> t-shirt!”. For some of the campaigns, we were reaching 75%+ open rates!

Writing the perfect email


As you can see, there’s a bunch of stuff in there that engenders trust, offers social proof, and hopefully encourages people to click. Once they are actually on, then it’s the site’s job to convert them to customers.


It was such a success that we were asked to write up exactly how we did it. And that, in turn, became a fantastic piece of content marketing!

We seeded it on Reddit, Facebook groups, and Twitter. Before we knew it, it had been shared countless times, translated into French, German, and Japanese. And also tweeted about by some major players.


We’ve also been asked to write guest blogs (like this one on Starter Story!), that all feed into backlinks and SEO, and drive even more traffic for retargeting.

We’ve also been asked to speak at conferences in 6 countries so far, and in delivering our tale of how we bootstrapped and hacked our way to great revenue with this campaign, we’ve hugely increased our profile around the world, and brought in even more customers.

In terms of the actual, measurable successes:

  • Averaged over 50% open-rates.
  • Regularly clears double-digit clickthrough rates, with one well-targeted campaign hitting 25% CTR.
  • Thousands of visits to the site from the emails.
  • HUNDREDS of thousands of people have read the blogpost about it.
  • Final conversion rates and actual revenue are more difficult to provide actual details for, as most companies only tend to buy t-shirts once or twice a year, so we can’t measure the true success of any mailshot until over 6 months later. (Top tip - we use multiple different keywords throughout the email to ensure we’re easily found in their inbox when they search for us 6 months later!). But we’re happy to say that it’s paid for itself many, many times over.


And then there are the conference talks. I’ve now been asked to tell our tale all over Europe of our growth-hacking and quick wins.

It’s like one big feedback loop, and it all drives great quality traffic to our site, and it all feeds into our position as an authority in the world of innovative marketing and custom t-shirt printing.

So… What did we learn?

1 - Email is a funnel

Like any other sales and marketing process. For us, it was firstly getting the email into their inbox - i.e. not get marked as spam.

The next stage of the funnel is to get them to open it (our killer subject line helped here).

Next up the photo of me was the “hook” to get their attention and read it, which is something that never happens for most cold emails. And finally, we need them to go to the website, which is achieved through good calls to action, and sales copy.

At that point, they enter the website’s own funnel, and it’s up to the site to do its job. But hopefully, the email will have warmed up the reader.

On that note, at every stage think to yourself “What would make me open an email? What would grab my attention? What would make me read the next sentence?”.

There’s a notable journalist that says he receives over 1,000 emails a day, and that the best way to get him to even open your email is to put a massive, all-caps, filthy swear word in the Subject line! 😉But guess what - that’s not going to work if you’re selling wedding dresses. So you’d better know your customer pretty well.

2 - There are a ton of micro-services out there

These micro-services allow you to bootstrap/growth-hack/whatever your way to proving that your idea works. Zapier, Hunter, Gmail plugins, DuxSoup etc etc.

We spent less than £50 on subscriptions and licenses to prove this approach worked. From there, we knew it was worth committing the technical resource.

3 - You don’t need to be a tech genius.

We pretty much proved the concept between the few of us with our hand in marketing before we moved it “up the foodchain” to Milen and the tech team.

Remember what I wrote near the top? “What is the quickest way we can test our hypothesis (preferably for no money)?”.

There will almost certainly be something you can use to simplify or automate your great idea, even if it’s just a clunky, inefficient way to prove your hypotheses.

And it doesn’t need to be technical? I was advising a young startup recently who was thinking about building an online service for travellers, and were trying to build a simple app for use at bus stations to demonstrate value.

But they could get the same results from asking two non-leading questions in a survey at bus stations. And they can do that in a few hours, instead of days, weeks or months.

4 - Personalised cold sales emails aren’t just something for tech companies.

I mean, we’re a tech company in most respects, but we’re selling something fairly “traditional”.

You could sell your consultancy service with this very same email – “See how I made you open and read this email? I could do this for all your prospective clients, too!”.

Does your company sell drones or drone software? Why not send them a Google Maps satellite image of their office… What we do is just an evolution of the “Hello <firstname>”personalization, and there are countless ways that this can be done.

In summary

This whole campaign was hard work, and took several months of ongoing tweaks and changes to really get it humming and delivering good revenue.

And it was definitely a great blend of the team’s creative skills to come up with the idea, and then to deliver it in an automatable, scalable way.

But we always took the next, simplest, smartest step before we committed any further time, money or energy to it. And you should do too, whether building a product or a marketing process.

If you want customised t-shirts for your company, team, or friends, then head to** - if you have any questions, me or a member of my team are on hand to help via livechat, anytime.**

Check out some of the emails HUNDREDS of emails we got back!