I had the pleasure of seeing Aziz Ansari, (an extremely talented comedian) sharpening his tools at the Comedy Cellar.

Comedy Cellar is a small comedy club in Greenwich Village, New York City. It fits ~80 people per show in a long, narrow basement venue. The comedians have a narrow, elevated red platform from which to deliver their jokes. It boasts Jerry Seinfeld, Dave Chappelle, Jon Stewart and many others as having performed there.

Each night at Comedy Cellar, there are 3 or 4 shows. There’s a host who warms up the crowd, and introduces each comedian. The comedians each perform a 15 – 20 minute routine.

We attended over Memorial Day weekend. Aziz Ansari was a surprise visitor. He had a stack of notecards with him. He wanted to try out some new material on us.

His bits were hilarious, but I was more interested in his approach (which I imagine is similar among top comedians):

Test jokes on smaller audiences

Aziz performs at large theaters. When he stands on stage with the bright lights on him, and a sea of faces, it’s hard to see reactions. In a smaller venue, you can see how many people are laughing (and how hard).

Zero-hype

Nobody in the audience knew he would be there that night. Judah Friedlander (from 30 Rock) who was also performing was clearly more rehearsed in his routine. Testing ideas out is better on fresh / unexpected minds.

Don’t overpractice the routine

Aziz had notecards to remind himself of what he wanted to say. He was practiced and he was fluid. But rather than spending time to perfect the routine, he decided to validate whether or not the jokes were funny before getting the delivery perfect.

In comedy, great comedians use lean startup-like thinking to answer the question “How can I know if this joke is funny?” without having to tell the joke to an auditorium of people. Opportunities to use “lean” to remove uncertainty exist in every industry and in every profession.

Whatever your job, whatever you do, look at a problem you’re trying to solve. Figure out how you can answer important questions in less time, with less money, and with less work. You are the lean ____.

I like to write and respond to emails at 1:00 am.

However, you don’t want to receive an email from me at 1:00 am. If you do receive an email from me, there’s a higher chance you’ll miss it. But for me, writing an email at 1:00 am makes great use of my time. I batch all of my email writing together to leave the day to focus on making.

One of the things I’ve realized is that the time someone receives an email affects whether or not they respond. So, how do you resolve the difference between personal efficiency and timing?

My solution: Separate the writing of the email and the sending of the email. I’ve been using Boomerang for Gmail to schedule sending my email. When I write an email, I hit “Send Later” and I usually click “Tomorrow Morning”.

Now, I can write my emails at 1:00 am and recipients receive them the next morning when they arrive at the office. I use this primarily for meeting or phone call follow ups. I try to write the follow up when it’s fresh in my mind, but send it when enough time has passed that our conversation isn’t fresh in their mind.

Some clever ways to use email scheduling:

• Send a follow up email to a customer.
• Send an email to your boss at 3 am to make it seem like you’re working late.
• Delay time-sensitive information to be sent to multiple people at the same time

Most efforts at user retention are post-cancellation. What if you could know someone was going to cancel before they did?

For subscription services, it’s pretty easy to identify who is about to cancel. Look at their usage data.

Let’s look at a simple example:

A user signed up 2 months ago and is paying for your site monthly. They are going to cancel at the end of the month.

How do you know?

Here is their usage pattern:

As you can see, they’ve used the site 4 times in the past 6 weeks. What’s most important is that they’re engagement is dropping. They have used the site 0 times in the past 6 weeks. If that’s far off your normal user engagement (and it should be), you want to be proactive.

What can you do to stop churn?

If the user doesn’t cancel before they receive their next bill, they probably will after they do. Here’s a great opportunity to identify this user and engage them with a re-marketing email establishing the value of your product.

Firstly, you want to be able to see these at-risk customers in aggregate. Once you’ve grouped all of your at-risk customers, you can start measuring if your customer retention efforts work.

Once you segment users then create triggered emails to communicate why they should keep paying you. At the very least, it’s an opportunity to start a dialogue about how you can improve your product. Users who feel a connection to you are less likely to cancel. Try different techniques to see what works. And as with all your marketing efforts, measure conversions to see how successful you are at re-engaging customers.

If you measure your efforts, you’ll know what works and what doesn’t. Churn is an issue for every company, and with the right tools in place you’ll beat it.

Here’s a trick question for you: “What’s the cheapest way to get a new user?”

If right now you’re thinking about the price differentials between Facebook Ads and Google Ads, you’re doing it wrong.

The cheapest way to get a new user is to fix that giant gaping hole in your bathtub that leaks users after they sign up and before they become valuable.

Remember: Your job doesn’t end when someone gives you their email address

User acquisition is easier than user retention

Facebook and Google have built fantastic tools to help you understand how well your ads are driving clicks and even conversions to a sale. But most companies are about relationships, not transactions. And ad platforms just feel transactional and even a little sleazy.

But, people use them because they are easy to set up, easy to understand and easy to show results with. They just cost you.

Traditional strategies for retention

In the early days of a company, it’s common for the CEO to email every new person who signs up at one time or another. They check to see if they need help and if they got stuck. The CEO might reach out if someone created an account but hasn’t done anything. As companies grow, this behavior stops.

A good rule of thumb is to do things that are not scalable first – like reaching out personally. But then what? It’s all too common that these highly personalized interactions stop as a company grows.

Automatic emails to the rescue

Automatic emails can let you scale the personal touch of those early emails to a great scale. Done right, they feel unique, personalized and not like a marketing email.

Customer retention email examples:

• The user got stuck setting up the product.
• The user hasn’t been back an a while.
• The user viewed the upgrade page, but didn’t upgrade
• A few more days left in the trial
• User hasn’t uploaded a photo in 1 month.

Want more? Here are some great user retention email examples from real companies

How well do customer retention emails work?

Here are some stats from email marketing reports:

• Bank of America report that event-based trigger emails are 250% more effective than broadcast promotional emails
• VIE at home get £250 in revenue for every £1 invested on abandoned shopping basket emails
• 75% of registrations for Roku’s referral program are driven by triggered emails to new customers
• People who purchase after getting cart abandonment emails spend 55% more than those who buy straightaway
• “Happy Birthday” emails from Epson produce 840% more revenue per email than the overall email program
• Gaylord Brothers convert half of their cart abandoners using multiple message remarketing emails
• Trigger emails sent after relevant on-site searches got 200% higher open rates and 50% higher CTR than LowFares.com’s standard newsletter
• One study found abandoned cart mails getting 20 times the transaction rates and revenue of standard email campaigns
• Tafford Uniforms earn 20% higher revenue per email from post-purchase survey emails than through standard broadcast messages
• S&S Worldwide drive 40% of email revenue through trigger/transactional emails that account for just 4% of email volume

Create automatic emails

The first step with creating automatic emails to retain customers is to figure out where the sticky points are. One great thing to do is to map out your signup / key flows in your product and identify how many people are stuck in those different parts of your product.

Once you have your users in clearly defined groups, it’s a little easier to think about how to target an email to that group when an issue occurs. For example: A “paid user” (group) “hasn’t been back to the site in 3 weeks” (trigger). I’d consider this user an “At risk user”. They are paying you but not using your product. They’ll probably cancel unless you establish the value of your product with them.

Your product is full of opportunities for highly targeted messaging to engage your users more.

How to set up automatic emails

I’m not going to lie to you. This is a hard problem to solve. Most companies spend months building tools for lifecycle emails if they do anything at all. But what happens as your product evolves. You have to go back in and spend more months to update all the lifecycle emails.

The ideal situation is to have a tool thats easy for a marketing / community manager to define business rules and update the email copy. They might want to test new emails and turn off poorly performing ones. They may want to tweak copy and test one version against another. You could build all this yourself. Or you could build just a few emails. Or you can use a third party.