What I Learned from Sending 300+ Emails Manually

I could have automated everything instead of staying up late reaching out to every new user. 

But I went with the old-school option. 

Here's why...



Growth is just.....so......damn......tempting. 

But it's almost impossible to realize that you're not as far along in your understanding of the people, problem, and product as you think you are.

So we usually end up aiming for growth before we really know what it is we’re even actually doing. 

Here's how I started down the flawed path of trying to grow too soon, realized it was a huge mistake, and  then managed to change course in time to gain a ton of actionable insights from new users and make valuable new relationships...



Before I did anything public, I signed up a nice list of early users, curating exactly who came onboard.

But for the actual kickoff, I wanted more users. So a few weeks ago I posted Dwilly on Betalist, a site for startups looking for beta users. 

We ended up getting more than 1,000 pageviews in a few days as a result. 

The folks were from all over the world:

And after a day or so, Dwilly got picked up by the Product Hunt of China (not its real name): 

Knowing there’d be some level of traffic surge from the two sites, part of me really wanted to build in a viral sharing component to capitalize on the moment.

In fact, a well-known investor and entrepreneur I got connected to recommended this as well


The easiest thing I could’ve done would be to set up a simple email automation referral program. As soon as someone signed up, I could send them a welcome email. It could still sound personal, and could include a call-to-action like click-to-tweet, or share on Facebook, or forward for a free ebook, or something. 

Trying to straddle the personal and sharing, I started by sending the first 50 or so people who signed up the following email:

It was manual, and it was also sort of indecisive, like an ask without a super simple next step. Half-committed is never the right approach.

I was copying and pasting the content and customizing it where I could, since I'd only collected email addresses in order to boost conversions.

This process was time-consuming but fun and helpful. I got to check out people’s design portfolios, startups, blogs, etc. 

I’m not sure how to explain it, but after around 50 emails, something clicked. 

This realization would never have happened if I had everything automated.

I realized it didn’t make sense to get referrals or to aim for compounded growth. At this point, I needed to not think about growth. I needed to figure out why people were coming onboard.

If I didn’t know why they were joining, I’d most likely lose them in no time anyways.

When you’re building a community, the most important thing you can have is a feel for the people. 

I knew the makeup of the 75 or so people I signed up on my own. They’re the ones I used in writing the copy for the landing page:

 - Icons from  http://icons8.com

- Icons from http://icons8.com

But I was signing up around 100 new people each day. Apart from the fact that they likely had an interest in new startups and had clicked through a couple of content filters (Betalist blurb, landing page, signup), I didn't know exactly who they were or why they signed up. 

So I took a nod from Alex Turnbull’s commitment to his users at Groove.

With each new signup, there were two things I specifically wanted to gauge:

1. Interest in being part of a community of great people; and 

2. Interest in the individual practice of idea generation.

These two components didn’t come from nowhere. 

When I ran the alpha test for Dwilly with a small group of friends and family, I included a little experiment. On the first day, I sent a recap email to everyone that highlighted some of the most promising creative ideas from the day, gave an overview of common themes, and a couple unique findings. 

On the other days, I didn’t share anything with anyone and people missed it. 

The more I thought about what this meant — and talked to potential users in real-life — the more I realized the community interaction needed to be a critical component. 

So I updated the site’s heading from:

To the current one:

While the new copy was helpful for drawing in more people, the site still had some intentional vagueness on it, so it was critical to find out which parts actually stood out.

So I started asking something different. 

While I did get a small number of direct referrals from the first email, it also produced almost zero direct responses. This email led to tons of responses. And they mainly fell into two buckets:

  1. “Compulsive innovators” (to use one user’s term) who generate tons of ideas 
  2. People looking to connect with other people doing cool stuff

There’s definitely overlap between the two groups, which seems only natural when you have people who want to generate new ideas in pursuit of new products/services.

They also matched up pretty closely with the two main concepts I was curious about: idea generation and community.

Plus there were a small number of people who offered helpful unsolicited advice and feedback:

Calling out the vagueness:

Identifying a conversion killer:

  (for the record, we definitely don't own 'em . The ideas are public domain  ☺ )

(for the record, we definitely don't own 'em . The ideas are public domain  ☺ )

Pointing out valuable copy:

Community and personal benefit:

Intriguing concept:

The practical payoff of these types of comments is incredible. 

I’d argue they’ll lead to more conversions over the long-term than if I opted instead to have them refer one or two people to a service they hadn’t even used yet. 

This feedback loop makes Dwilly better.

Something I actually hadn't anticipated was the number of references to some of the related services out there, and the enthusiasm people felt for something better/different. 

I’m keenly aware of the problems related to how people use ideas to innovate

But what I liked most was the reminder that this is a really interesting and challenging space. It’s a nice place to call home, especially with all of these incredible people. 

I definitely could have sent 300 automated emails instead of staying up late everyday reaching out to every new user. 

But as I see it, freeing up those few days would’ve meant running in the dark for months. 

Manually sending hundreds of emails, and customizing where appropriate, is anything but practical. The value is something simultaneously tangible and intangible.

I can feel the group’s pulse. 

And for that, I’d send every email again.