What do we do when we fall off the horse?

October 2019 Retrospective

Last month I was feeling pretty dejected about Pegasus. But in the immortal worlds of Jerry Stiller:

What do we do when we fall off the horse? We get back on!

So I’m back on the horse! Or in this case, the Pegasus.

But before getting into that, let’s jump into the October stats.


Project Profit Monthly Change
Place Card Me $2109.10 +6.5%
SaaS Pegasus $660.01 -11%
Chat Stats $207.02 +58%
Amazon Affiliates $16.54 -53%
Total $2992.67 +3.7%

Place Card Me up a bit, Pegasus down a bit, and totals staying approximately flat.

Still chasing that elusive $3k, but I think November might be the month I get there (fingers crossed…).


October 2019 Time

Time breakdown for October 2019

Still at 70% sponsored time due to wrapping up my short-term contracting project and putting in extra Dimagi time last month.

Still, I’m happy that I managed to put in a solid 30 hours on Pegasus and feel like I’ve got good momentum to keep pushing on it.

Last Month’s Goals

Back to a reasonable looking report card!

# Goal Grade
1 Talk to 3 Pegasus customers A-
2 Set a new product roadmap based on customer feedback A-
3 Ship the “making of Pegasus” blog F
  1. I had calls with two Pegasus customers and good email exchanges with several others. More on this later.
  2. Feeling good about the Pegasus roadmap right now, and I’ve started working on the next release. Also more below.
  3. Didn’t touch the blog—though I knew this one was a stretch.

Getting back on the Pegasus

Outside of my sponsored engagements—which continue to keep me busy—Pegasus is where all my energy is going. And it’s going pretty well!

Customer Development

This month I made a huge effort to talk to more customers.

I started with an email blast out to everyone who had purchased a license, but got very few responses.

So, I started sending super-personalized individual outreach and offering to do hands-on support and onboarding. This yielded a substantially higher response rate and led to several educational back-and-forths over email, as well as two phone calls.

And man, I know that “talk to your customers” is a classic startup trope, but it is so true. I learned so much in those few conversations and I continue to be surprised by the things people tell me.

Classic advice from PG

First off—it’s just super fun to hear and see what people are doing with it. For example, Patent Mark is an AI-powered way to analyze and compare patents. Live! And built with Pegasus! So cool…

But beyond that, just hearing the perspectives of people who aren’t as close as I am to the product has been super valuable. I’ve learned where the documentation is confusing because of assumptions I made, the types of things that are a struggle to customize, and also where Pegasus is adding the most value.

Jason Testimonial

One nice side effect of talking to customers: testimonials! Now featured on the Pegasus landing page.

I also learned a lot about what people want, which has helped informed the roadmap moving forwards.

Which brings us to…

What’s next?

I continue to have high hopes for Pegasus. But I also now feel that I have a ways to go before it will be simple, lovable, and complete enough to get to true product/market fit.

At a high level, there are two key big features I want to add:

  1. Sensible multi-tenancy out-of-the box.
  2. Recurring subscriptions.

For the first one, that means making it much clearer and easier to setup a project with either user-based or team-based data models and having each user/team have silo’d access to its own data.

Basically every web application in the world has some version of this feature. And Pegasus currently has all the building blocks for it, but how to put them together is left to the customer. I now know this is a big place where people are getting tripped up getting started.

As for subscriptions—they are something people have been asking for since day one. Basically the ability to setup recurring payment plans tied to Stripe and associate them with users or teams in Pegasus.

I’ve always wanted to build out recurring subscriptions, but the problem is that I’ve never actually done it before. Place Card Me, Chat Stats, Pegasus—they’re all one-time-sale products. So creating a sensible subscription model without that context has been daunting and so I’ve avoided it.

So now my plan is to build that out once for myself, and then build it into Pegasus.

Based on that plan, I have the following high-level roadmap for the next 9-ish months:

  1. November-December, 2019: Release overhauled multi-tenancy.
  2. January-February, 2020: Build subscriptions into one of my own products, once.
  3. March-April, 2020: Bring subscriptions into Pegasus.
  4. May 2020-onwards: Start cranking up the marketing engine.

So basically taking the next six months to get to what I believe is the real, high-quality simple, lovable, complete product, and then funneling my energy back into getting the word out. And as a bonus, if I’m successful I might get my first ever recurring revenue out of it!

I’ll still continue to do product development, marketing, and talk to as many customers as I can in the meantime—and I expect a trickle of sales to continue coming in—but that’s the plan!

This Month’s Goals

For reasons I don’t fully remember—at some point last month I decided to create OKRs for the rest of 2019.

Anyways, it was useful!

Here they are:

Project Objective Key Result(s)
Pegasus Make Pegasus a best-in-class SaaS starter kit experience 1. Release overhauled multi-tenancy support
2. Zero new refund requests
Writing Find my voice as a writer and create content that resonates with people Two major blog posts by end of year
Financial Achieve financial independence through passive income $3k average monthly profit for Q4

One interesting output from the OKR exercise was the realization that becoming a better writer is actually a primary objective of mine—completely independent of all this startup / passive income stuff. It’s also a goal that has mostly been neglected since I returned to part-time work two years back. So I’m going to try and find room to prioritize writing more moving forwards.

With that backdrop here are November’s goals:

  1. Version 1 of Pegasus’s new team-based multi-tenancy launched
  2. Talk to at least one Pegasus customer, and email with 3 more
  3. Zero Pegasus refund requests
  4. Publish one non-retro blog post


  • Product: Google Keep. I really love Keep and am surprised when people haven’t heard of it. It’s become my go-to todo list / note taking app and their sharing features are great for things like shared grocery or packing lists. I’ve actually started using Keep to jot down recommendations throughout the month so I have something to put here. Meta FTW!
  • Slack Channel: ZA Tech. For technologists somehow affiliated with South Africa. I’ve learned a lot and met some amazing people through this channel—created by n1c.
  • Keyboard Shortcut: Shift-Esc in Slack. This is only relevant to people who hang out in big non-work slack rooms like the one mentioned above. Will clear all your unreads in a single stroke! Can’t believe I only recently discovered this and it’s saved me so much time.

Happy Thanksgiving to my American friends! If you have any suggestions or feedback, let me know in the comments.