I procrastinated 2 years. Then AI was invented.
Why I'm both impressed and terrified by what AI just did.
Hi, it’s Melissa, and welcome (back) to “your founder next door”, a weekly publication with stories and tidbits of my human journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
A quick note before we move onto today’s topic…📋
This is my first short-form piece on “your founder next door”. I’m shifting my time to focus on Substack instead of LinkedIn, so I wanted to give you a heads up on what’s changing.
Instead of sharing two long-form pieces a month (like the articles I’ve always written), you’ll be hearing from me once a week. Every month, I’ll be sending you one long-form article, two short ones on whatever’s on my mind (like this one), and one end-of-month piece with a quick thought and resources I enjoyed.
Why the change? I want to spend my time writing for people who enjoy my writing, my founder journey, and intentionally opt-in to receiving it.
Thank you for your support. It means a lot to me. 🙏
I’ve been procrastinating rewriting our product emails for two years. Yes, you read that right.
These aren’t just ordinary emails. They’re 33 onboarding, activation, and nurturing emails that every customer sees when they sign up for an eWebinar trial, convert to a paying subscriber, and/or hit the cancel button ☹️.
The last time I did this was 4.5 years ago when we first launched. It took 4 months with a product marketing consultant after doing deep customer discoveries and extracting content from those interviews. I’m not a product marketer, so this kind of writing is mentally draining and sucks the life out of me.
The problem was, after a couple years, those emails no longer matched our product nor spoke to our ICP (ideal customer profile) which we had honed in on later. They were all over the place and didn’t sound like our brand voice because they mimicked the tone of the person who helped me with them.
Two years ago, I decided to update them but the thought of going through that process again felt harder than climbing Mount Everest. It’s one of those things you start doing…then realize you need to go organize your sock drawer.
So I did what any other founder in my position would do: I avoided doing it altogether. There are enough things on my to-do list to keep me busy for a decade.
Now that we’re entering the next phase of growth, I could no longer ignore this. Frankly, I was embarrassed the original content was still being used.
A friend told me to try Claude for writing content. I was skeptical because I had tried using ChatGPT before and it wasn’t generating business content I could publish without significant editing. But, desperate times called for desperate measures… I just needed to get this project done.
I just spent two weeks rewriting all 33 emails with the help of Claude. I kept about 50% of the elements from the original emails, and updated the rest to match our current features, benefits, and ICP. I’m mindblown by the result. How quickly and accurately it was able to communicate everything I wanted it to, in a conversational tone that sounds like me.
Two weeks. 🤯
Without Claude, this would’ve taken me a year, at least. Probably longer. I might have even quit my own startup to keep avoiding the task. That’s how much I was dragging my feet.
Here’s how it actually worked…
To help write our onboarding emails (during trial period), I told it:
I want to write a series of onboarding emails for users who sign up to my service, eWebinar. Here is the URL.There is a 14 day free trial, during that period, I will send 9 emails to convince users not to cancel their trial, so they can continue their subscription and convert into a paying customer. Let’s write one at a time so I can give you more context.
It said:
Before I write it, I’d love to know:
Who is your typical trial user?
What’s the main reason people sign up for your trial?
What’s the most important first action you want them to take in the first 24-48 hours?
What’s your brand voice/tone?
Do you have any onboarding data?
Then, for every email, it asked me this set of questions for context:
Timing and focus:
When does Email x go out?
What’s the main goal of this email?
Where are users typically at this point in their trial journey?
Content direction:
Are we following up on anything?
Focusing on anything?
Introducing a specific feature?
Addressing common objections or hesitations?
Any specific elements you want included?
Particular features to highlight?
Success stories or social proof?
Specific calls-to-action?
What is your vision for this email?
Is there previous content you want to reuse?
I still had to put thought into each email, but I only spent about 10 minutes at most editing each one afterwards. Every email it wrote was near perfect. Much better than if I had to write it from scratch, and 50x faster.
I procrastinated for 2 years. Until AI was invented. That’s epic. 🤩
On one hand, as a content creator who started writing 3 years ago, I hate what AI is doing to content. You can’t really tell anymore if you’re reading something a human wrote. It’s making everyone a writer the same way Instagram made everyone a photographer. It’s commoditizing a craft that people took years to perfect. Originality is harder to spot. Creativity is everywhere.
On the other hand, I can’t ignore what just happened. It helped me accomplish something I had been avoiding for two years, and did it with flying colors. 😳
While I’m not using AI to write my personal content, I am using it to edit my pieces before it goes to my COO, who edits everything before it goes out. It helps me restructure sentences that sound awkward, put an idea down that I can’t articulate, and improves my writing because I’m learning from it at the same time.
As I’m writing this, I’m wondering: what does this mean for writers and the future of content?
I’m not sure. But I’m guessing we will find out soon.
What I do know is that AI isn’t going away, and it’s only going to get better.
Perhaps the skill isn’t writing anymore. Perhaps it’s knowing how to direct AI to produce valuable content that sounds human, authentic, and “exactly like you”?
The thought of that is exciting and terrifying at the same time.
I’m so glad I finally got those damn emails done.
My procrastination station is temporarily closed for business.
Till next time,
— Melissa ✌️
💌 PS…
This was my prompt for our activation emails (post trial conversion):
I want to write a series of 12 emails that go out over 60 days to trial users who converted to paying customers. This will be a set of emails that dive deeper into eWebinar’s product features, benefits, customer stories, and use cases, to make sure new customers fully understand the value of the product and will continue subscribing. What do you need from me to write the first one? Let’s write one at a time.
This was the one for our nurturing emails (did not convert, or churn):
I want to write a series of 12 nurturing emails for eWebinar that go out over 360 days to customers who cancel their subscription, trial users who didn’t convert post trial, and people who watched the demo but didn’t sign up after 45 days. This will be a set of emails that dive deeper into eWebinar’s value propositions, the benefits of automating webinars versus doing them live, customer stories and case studies, general check-ins, to make sure people who saw value in eWebinar but didn’t get far enough to become paying customers fully understand the value of the product, the problem we are solving (doing repetitive webinars live), and will come back and subscribe when they are ready. This is a way to remind them that we are around so they don’t forget us. What do you need from me to write the first one? Let’s write one at a time.
What did you think of this article? Let me know!
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This spreads the word and keeps me writing content that will inspire founders to keep doing what they’re doing, knowing they’re not alone.
Thank you 💜 The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give.
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As usual, Melissa, your writing is refreshing, relatable and practical. Claude's value, for me, is that you can count on it to break through inertia. Even if my prompt is sloppy and its response is slop, it gets me into the process and out of "procrastination station."
Wait until you move from copywriting assistance to a trusted colleague and partner! Mindblowing.