Indie Hacking Week 2 Recap – TimelineGPT Progress, LearnGPT Decision Time

For Martin Luther King weekend my family and I headed to Boone, North Carolina and stayed in a cabin for a few days. We went snow tubing at Beech Mountain while we were there, one of the many ski resorts in the area.

As is common on vacations, I spent way too much time thinking about work. But on the bright side, at least now I’m thinking solely about my own projects and not contract work as well 😅.

TimelineGPT Progress

TimelineGPT – the name of the AI content generation feature I’m working on for Preceden – is coming along well:

My tasks this week included:

  • Moving the actual content generation to a delayed job because it can often take 20+ seconds and I don’t want to tie up Heroku dynos or have the request timeout while the user is waiting
  • Lots more work to parse the myriad of date formats that GPT returns
  • UI work with Milan, Preceden’s designer, including figuring out where the place the buttons, managing their states (like disabling them when appropriate), etc
  • Giving users a way to bulk delete all AI suggestions they’ve previously added to their timeline
  • Handling the UX for users on the free plan who are limited to 10 events per timeline

Lots more to to do though including:

  • Rate limits (per user, and overall) to avoid bad actors racking up excessive OpenAI fees for me
  • Better duplicate identification so if the user already has the same event on their timeline, this tool doesn’t recommend they add it again
  • Giving users a way to choose which layer they want the suggestions added to

Coming along well, but probably another week or two of work before it’s live.

LearnGPT Decision Time

Earlier this week I announced that LearnGPT was for sale. I’ve received 2 offers so far and the deadline to get an offer in is the end of today. At that point I’ll have some big decisions to make: sell it or keep it, and if I decide to keep it, what does its future look like? We will see.

I would not recommend entrepreneurship to anyone who doesn’t want to face a never-ending series of hard decisions.

Adios for now 👋.

Indie Hacking Week 1 Recap: Starting TimelineGPT, Ending LearnGPT

Today marks the end of my first week of full-time indie hacking. I feel like I’m getting in a good groove as far as my daily routine, but I don’t think it’s quite sunk in yet how much flexibility I have in terms of my daily schedule. For example, I’m still waking up early to workout and still mostly working 9am-5pm, despite having the flexibility to make my own hours. That said, keeping a normal routine and structuring my workday like a normal job might work best for me. We’ll see.


On the Preceden front, I started work on a promising new feature that uses GPT to suggest events to add to your timeline.

For example, imagine you want to create a timeline of World War II. In the past, you would have to research and manually add events to your Preceden timeline to populate it. With this new feature, you can hit a button and it will generate a list of suggestions for World War II or any other topic:

And with the click of another button, you can add those suggestions to your timeline:

Neat, right?

Preceden’s free plan limits users to 10 events per timeline, so making it easier to populate timelines should lead to more paid conversions and help me grow the business.

And while trickier to do, eventually I’d love for this to support project planning too. Imagine being able to say you want to plan a marketing campaign for your SaaS and it automatically generates tasks and suggests dates.

The v1 will be an in-app tool that people can use, but after I work out the kinks I’ll likely make it a standalone tool that logged out users can use, with an option to sign up to continue working on whatever timeline the tool generates for them.

Codename for this whole project: TimelineGPT :).


Shortly after ChatGPT launched in late November, I launched, a site for browsing, sharing, and discussing ChatGPT prompts:

On launch day I posted it on HackerNews where it received over 350 upvotes and earlier this month it made it to the top 10 again thanks to an interesting prompt about a leaf falling that someone posted.

My initial vision for the site was to start with prompts, then expand it into GPT news, tutorials, apps, and more, and eventually offer paid courses to monetize the site.

There’s this famous graph showing the typical path that a successful startup takes over its lifetime. I’ve added an arrow showing where LearnGPT is in this journey:

I honestly believe that with a lot of work, I could push LearnGPT past this “trough of sorrow” and build it into a big business along the lines of PyImageSearch or WPBeginner.

But, continuing with it would consume a lot of time and headspace that I could be putting into Preceden.

And unlike other products I’ve started, LearnGPT would require building a community and creating a lot of unique content which doesn’t terribly excite me. I enjoy building products, and writing a lot of content or managing people to write that content is not something I want to spend my days working on.

I considered trying to sell LearnGPT to someone better suited to take it to the next level, but because it’s pre-revenue (and actually burning money thanks to the contractors I’ve had helping with it), it’s not likely to fetch much, and would likely require a fair amount of time to finalize the deal, so I’m just going to throw up a banner about the closure, turn off new sign ups, and shut down the site in a week or two.

And with that, I’ll finally, truly be full time on Preceden and not splitting my time with contracting or other projects.

Onward 🚀

Updates: Preceden Trends, Training Help Scout’s New Analytics Engineer, Don’t Look Up, and Ray Dalio’s Principles

Photo by Ivana Cajina


  • Recurring Revenue: In January 2021 I introduced automatically recurring annual plans to Preceden. Prior to that the annual plans did not renew automatically which was an intentional (but bad) choice I had made because most users did not user Preceden for more than a year. However, the lack of recurring revenue made it really hard to grow the business because each year I’d basically be starting from zero (though some customers did manually renew). The changes I made last January were meant to address this: annual plans automatically renew by default, but users can easily disable that. I also email them a reminder 15 days prior to renewal, and a receipt when the charge happens, and also offer a 15 day refund window. This has worked well: most users who have no intent to use it long term wind up cancelling prior to renewal, those that forget can get a refund, and those that want to maintain their access can let their subscription automatically renew. Needless to say, this month (January 2022) has been stellar for renewal revenue.
  • New Revenue: This has been a challenge recently and is what I’m primarily focused on at the moment. Despite my best efforts, Preceden has languished at the top of page 2 for years for most key search terms. While I very much prefer product work over marketing work, I also recognize that marketing work to drive more quality to the site can move the needle much more than product improvements at this point. I have a few projects in the work that should help here.
  • Balance: This raises an important question though: how much of my day do I spend on potentially high impact marketing work (which I don’t terribly enjoy) vs low impact product work (which I do enjoy). This goes towards the question of what my goals are: do I want to grow the business as much as possible or enjoy my day as much as possible? Of course there’s some healthy middle ground, but I’ve been thinking a lot about how to balance the two.

Help Scout

We recently hired a new Analytics Engineer and I’ve been spending a good chunk of my contract work at Help Scout getting him spun up on everything. That brings Help Scout’s data team to 3 folks: a full time lead, a full time Analytics Engineer, and me (a contractor). We’re also work on hiring a full time product analyst which should round out our team very well.


In my last update I mentioned I was diving into Solana application development.

I’m glad I played around with it, but it just didn’t hold my attention very long. It would have helped if I had come up with some interesting use case for it besides speculation, gambling, DeFi, and NFTs, but that’s 99+% of what crypto is these days.

Plus, splitting my professional work between Preceden, Help Scout, and Solana was just too much to juggle well.

What I’m Watching

One movie I keep thinking about is Don’t Look Up on Netflix:

Of course there’s the obvious and important climate change metaphor, but it has me also thinking a lot about the shortness of life and not focusing on trivial things.

What I’m Reading

Ray Dalio’s Principles for Dealing with the Changing World Order. It’s a brilliant book where he looks at various long term economic and political cycles and how they explain in part the dynamics happening in the world today, especially with respect to US and China.

That’s it for now, hope y’all are doing well.

Friday Updates: Crypto, Solana, Preceden Improvements, and the Madness of Crowds

Photo by Lenstravelier

Hey friends – it’s been a while since I posted an update. I’ve been heads down on a number of things and just haven’t been prioritizing blogging, but figure it’s good to do every now and then. Shout out to the ~3 of you who read these :).


For anyone who follows me on Twitter, you may have seen me periodically retweeting or favoriting bearish crypto tweets. For a long time I have been super bearish on crypto and honestly still am. I think we’re in a massive bubble at the moment that’s due to pop in a big way in part due to the mania wearing off and in part due to the massive amount of fraud in the market right now. And blockchain technology just doesn’t seem super useful.

There’s a famous chart called the Gartner hype cycle that always comes to mind:

I’m of the opinion that we’re near the top of that Peak of Inflated Expectations curve, both in terms of crypto expectations and coin prices. But I do think there’s a chance that in the coming decade after the coming crash that we’ll see practical applications come out of all this.


In order to be more educated about crypto I’ve been investing a few hours each day into learning how to develop on the Solana blockchain. I’ve found it to be a pretty steep learning curve – I’m having to learn about blockchains, Solana, TypeScript, Rust, and how it all fits together. I don’t have any practical applications in mind yet, but am enjoying learning nonetheless.

I’m trying to keep an open mind – we’ll see what comes out of it all.


I’ve made a ton of progress on Preceden in the last few months. Things like:

I haven’t been working on it as much the last few weeks because I’ve been putting time into learning Solana instead, but still have a lot planned for Preceden in the coming months.

Also, at the end of December 2020 I switched Preceden’s pricing to have recurring annual plans (whereas before they didn’t renew automatically), which means those renewals will start hitting in a few weeks. It should help drive a lot of revenue growth for Preceden in 2022. Fingers crossed the renewal rate is decent – we will see.

Help Scout

Mostly status quo for my contract work at Help Scout. Recent projects have included:

  • Reworking the Daily Metrics Email that goes out to the entire company
  • Setting up reporting to estimate cash payback (ie, if we spend $X acquiring a cohort of new customers, how long do we expect it to be paid back when looking solely at cash payments).
  • Updating Account Executive commission structures
  • Analyzing how customers are interacting with new pricing we introduced for Messages
  • Helping a bit with hiring: we’re currently in the process of hiring an Analytics Engineer and Product Analyst

I will be reducing my hours from 18/week to 12/week starting in January which will free up more time in my schedule for Preceden, Solana, and whatever else piques my interest in 2022.

What I’m reading

Speaking of crypto, I’ve been reading Memoirs of Extraordinary Popular Delusions and the Madness of Crowds by Charles MacKay, a fantastic book about past bubbles. It’s amazing how many parallels there are between previous bubbles and what we’re going through now in crypto. And things will probably end just as badly.

On that happy note, I’ll end this update :).

Hope y’all are doing well 👋