I Built A Tool That Helps You Track Your Habits Long Term [With $100]

Published: November 2nd, 2021
Kyleigh Smith
Founder, Harold
from Denver
started March 2020
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Hello! My name is Kyleigh, I’m an Indie Maker and Product Manager living in Denver, CO.

I’m building Harold. Harold is an SMS-bot, powered by AI, that helps you stick with your habits via simple, convenient, and fun check-ins via text message.

My customers are people who are interested in self-improvement, specifically via tracking habits. Some users are new to tracking, some have tried before but didn’t stick with it, and some are experienced trackers looking for a better way.

The strongest indicator of success so far is retention. I’ve worked on mobile apps for 6+ years, and I’ve never seen retention this good!

There are also promising signs that customers are willing to pay for this solution as well.

Since launching on Product Hunt in January of 2021, I’ve had 838 people join the waitlist, 369 create accounts and 20 converts to a paid plan. That comes out to about $534 in total revenue and $58 MRR. It’s early, and there is still a lot to learn, but I’m energized by this initial traction.

What's your backstory and how did you come up with the idea?

I’ve worked in startups my entire career since I graduated from UCLA. I did everything from user research, product design, and product management. Because I worked mostly on early-stage products, I learned how to validate ideas early. When I started Harold I was working full-time at a startup, and I was eager to test my knowledge and skills on an idea/product of my own.

How I came up with this idea:

I read an article by Steph Smith, a creator that I admire, entitled, "How to Be Great? Just Be Good, Repeatably", where she wrote about the importance of being consistent with small habits that compound. In another article she spelled it out: "The best way to stay committed to your goals is to a) track progress daily and b) share your progress openly."

This sounded simple enough, but there was one problem: I had tried tracking my habits before and it didn't work. I would make a beautiful table in my journal, get all excited, track for a few days, and then never look at it again.

That's where the idea for Harold came from. I needed a habit tracker that would come to me and ask me for the data. That way I didn't have to remember to track. I had been interested in applications of SMS and this seemed like a great use case. The name Harold came later.

I decided the only way to validate the idea would be to build a prototype and see if it solved my problem. If I was able to consistently track with it, then I figured it might be worth putting more effort into.

How I decided to work on this idea vs other ideas:

At the time, I had a lot of ideas for products and businesses. I had so many that I was stuck in decision paralysis and I wasn’t making progress on any of them.

Luckily, at the time, I was working with a career coach who helped me tap into my intuition and select an idea that would move me closer to my goals and my ideal future self. It sounds cheesy, but it worked!

The problem I was solving:


Take us through the process of designing, prototyping, and manufacturing your first product.

To build the prototype, I googled “how to build an SMS bot”. That led me to this tutorial which walked me through how to build an SMS bot using Autocode, Airtable, and Twilio.

I’m not a developer by trade, but I knew enough programming fundamentals to piece these tools together and get something working. The customer support team at Autocode was also a huge help when I had technical questions or couldn’t figure something out.

For the website, I used Unicorn Platform ($9/mo) and bought a domain on Namecheap for less than $10. I like Unicorn Platform because it has beautiful pre-built components that you can use so it saves a lot of time on design.

A lot of these tools have free plans or discounts for indie makers and startups so I was able to get everything going for about $100/mo.

How I validated:

After I got the prototype working, I used it myself for a few weeks. Turns out, it was working! I was still tracking consistently 3 weeks after I started, which was WAY longer than I had ever tracked with other methods before. This was some validation, but I needed to test with people other than myself.

So the next validation step was to test it with other people and see if it worked for them. I showed it to some family and friends and a few wanted to try it, including my sister, who ended up tracking for 5 months straight.

This was great validation, but I still wasn’t convinced. Maybe she was only using it because she was my sister and she wanted to be supportive.

So the next big step in validation was to test it with an external audience. I posted a signup link in my Twitter bio and someone signed up! This was another clue I was on to something.

Then I posted the product on Product Hunt and slowly gave access to the 300 or so people that signed up. I set up Amplitude analytics to track their retention and saw it was working for other people too. Almost 50% of all users were still using Harold at least 1 month later. This was the last piece of validation I needed.


Describe the process of launching the business.

I launched on Product Hunt in January 2021. I didn’t feel ready at the time, but I wanted to capitalize on the timing--people were thinking about new year's resolutions and building new habits, and I wanted Harold to be a part of that conversation and help people succeed.



I got about 300 waitlist signups from the Product Hunt launch. From there I slowly let in batches of users at a time. For each batch, I had tweaked something in the experience so that I could measure if I had improved or not.

Sometimes, it would be weeks or months before people got their access, but I didn’t want to send access unless I had an experiment set up to measure. I learned this approach from the mmhmm beta that I was a part of. They made a change -> let in a new batch of customers -> measured the effects of that change. If you let in everyone at once, you can only measure one version of your product. But if you batch them, you can test multiple different versions. And when you're at an early stage, it’s more about learning, than growing.

I may have lost some customers due to the slow roll-out, but I knew the people who were interested would stick around, and those are the people I wanted to use the product and get feedback from.

Since launch, what has worked to attract and retain customers?

Growth has been the toughest part and is the biggest challenge I face today. My background is mostly on the product side, and I’ve largely relied on others on my team for marketing purposes. Now I have to figure out how to do it myself!

Some stats:

  • Almost 50% of all users are still using Harold at least 1 month later.
  • 45.5% of all users are still using Harold at least 2.5 months later.


I’ve concluded that it’s going to take a lot of elbow grease. A lot of writing (like I’m doing for this!) to get my story out there.

The most successful channels I’ve used so far have been Twitter and Product Hunt.


I’ve grown my Twitter to 1,270 followers by sharing my journey as I go and participating in the community.

Product Hunt (Front Page)

I have gotten on the front page of Product Hunt 2x.

There are a lot of great resources out there on how to launch on Product Hunt. I did a few things to try to make sure I had a successful launch:

  • I posted at 12:01 Pacific time
  • I tweeted about the launch on Twitter and LinkedIn
  • I emailed and DM’d a few high profile people who I had built relationships with and asked them to take a look

That’s about it! I know a lot of people put in a lot of effort in reaching out to people to try to get upvotes, but I was interested in seeing how the market responded without me meddling too much.

But I’m getting to a point where these are not enough. I need to grow faster and so I’m looking at other channels and strategies, including content marketing, SEO, and partnerships.

I don’t know much about these areas so I am learning as I go!

How are you doing today and what does the future look like?

Harold is not yet profitable but he is close. To cross the that profitable threshold, I need to:

  1. Figure out how to drive organic traffic to my website
  2. Experiment to find the right pricing and pricing strategy

While I am tempted to focus on growing revenue and increasing conversions because this is where I’m most comfortable, I need to work on filling the top of the funnel and creating more sustainable growth for Harold.

It’s just me working on it and I would like to keep it that way, although recently I’ve flirted with the idea of bringing on a Marketing partner, we will see!

Through starting the business, have you learned anything particularly helpful or advantageous?

I think the biggest thing I’m learning right now is how important marketing is. And how much time it can take. I’m struggling because it’s not the part that I enjoy the most, but I know it is necessary to do.

In the end, though, it’s a balance. You can’t just focus on a product, or just focus on marketing. It’s a classic chicken and the egg problem. You can’t successfully market a product until you have a really valuable solution. And you can’t successfully build a product until you have a stream of prospective customers coming in that can test out different versions and give you feedback + data.

What platform/tools do you use for your business?


What have been the most influential books, podcasts, or other resources?

Doing Content Right by Steph Smith - This book is helping me understand the basics of SEO so that I can start formulating a strategy.

Indie Hackers Podcast - I love listening to these episodes and hearing how other bootstrapped founders are finding their way to profitability.

Another article by Steph Smith that inspired the whole thing. This was a snippet from another, related article she wrote that helped me identify my problem of staying committed to tracking.


Advice for other entrepreneurs who want to get started or are just starting out?

It’s a long journey! Take your time. We all want those crazy MRR stats that are achieved in 2-3 months. But in reality, the work that went into those products took a lot longer than that because they are leveraging their experience from other products they’ve worked on.

Overnight successes are an anomaly. Embrace the learning curve and celebrate your small wins along the way. It helps to look back on them when you’re feeling stuck.

For example, currently, I’m feeling stuck around $58 MRR and stressing about how I can grow faster. But then I just saw this tweet:


And it reminded me how far I’ve come.

When I was just starting, the advice that kept me going was to enjoy the journey. It’s not always going to be easy, so if you don’t enjoy the process, then it might not be for you.

So when I hit a rough spot or feel like I’m not making progress, I remind myself how much fun I’m having working on my product and just keep going.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!