Acquisition #9 -

Acquisition #9 -

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This week we completed the acquisition of what was formerly MailBoat and now

Userping - Send Emails easily
Userping makes it easy to send emails to your customers with a simple rich text editor

What's the bet here?

This is one of our bets on boring. Setting up trigger based emails for your saas app is still a pain in the ass and expensive. Just within our current portfolio, we will be saving money by acquiring this tool and using it ourselves. So right off the bat we already have a win just on cost savings alone. I'm increasingly interested in becoming vertically integrated. I.E. we own and use the tools we buy to operate our portfolio. We're customer's of our own tools and know problems and feature gaps better than our paying customers do. We're 1 step ahead because not only do we have wide variance in scale (some products have 100s of users, others have > 70,000) but managing multiple product means our pain tolerance for clunky UIs and complexity is about zero (mine is probably a negative number).

So the bet is that this statement is true:

SaaS companies will continue to need to message users based on events that happen in their apps

I don't see this changing (yes even with all the AI kerfuffle) anytime soon.

Use Cases:

  • new user signs up -> send drip email sequence (onboarding)
  • user takes action X in the app (but not action Y, etc)  -> inform them of the next step
  • user signed up but did not take the first step to activate -> send an email letting them know how to do it.

Where it's going

Email tech is old, saturated, and boring. But necessary. Perhaps I can get into this another time but it's actually quite difficult when signing up for a new product to tell if the lights are still on or if you just signed up to a zombie project. Onboarding emails can help. You can link to the community behind the app, etc. Just let people know you're home and welcome them! Imagine walking into a friends house and it's just empty, and all the lights are off. Weird right! That's what I think it feels like to log in to most applications.

Most founders pay for a tool like this. Again, super saturated, but we're okay with that. At worst, we will just outlast all the cool kids on the block (Loops), and at best we will just go market based on our differentiators (price usually at first). Part of my mission with XO is to first make it un-killable. I want to be able to make an infinite number of small but meaningful bets. This risk is asymmetric. The downside is in this case a tool we use internally to save $ (a win). Any paying customer above zero is a win for the price at which we acquired this. Unless we decide to shut the product down, we will win on this deal.

So back to where it's going. We're going to add in-app notifications (i.e. pop ups or other UI elements in-app to also notify users of stuff). Intercom has a banner product that does this.  We will build a simplified version of that. So userping, fully formed, will provide saas companies the ability to send emails and in-app notifications / banners contextually, based on stuff they have or have not done inside the app.


I still struggle with where a product like this properly ends and where an analytics product begins. I don't know that we will build complete reporting into userping but in theory we will have all the necessary data to do so. I've tried and failed once before to build an analytics product for PLG companies. I always just reverted back to using my trusty (and free) reporting tool But metabase doesn't quite cut it unless you're intentionally creating tables for product usage. In which case, you mind as well store those separately in another tool that's more robust so I don't have to copy and paste this code into 9 different products, and hence the loop I keep finding myself in.


We've bought userping, colddm, and support guy all within a short timeframe. We also built salesvid and recently launched another thing called saas deals.

We're now bottlenecked on engineering as well as on growth. We're not in a position to hire additional resources so we will necessarily be relatively slow to explore growth opportunities for each of these. There are some items that can be done in parallel, for example, loading up a bunch of leads into super send and doing a drip sequence over 30 days only needs to be set up once, and can then just run on auto pilot. We can set up cold email campaigns and cold DM campaigns relatively quickly which will free up some headspace to work on content and owned channels.

It's times like these where I feel like it would be better if we bought a bunch of tools we could sell to the same audience. That would be helpful. Not only can we build once and sell twice, we'd be able to acquire a customer once and sell twice.  So between being vertically integrated, acquiring tools that have the same audience, buying bigger or smaller, we're still just experimenting with what works even after nearly 3 years of running.

if this isn't enough I still have:

  • cold email studio
  • content crew
  • super send
  • docwise

Business is a beautiful sport.