Kyleigh Smith: Habitual Harold-er

Issue 10

Hi friends! Welcome to the 10th issue of “Procrastineur”, a newsletter about struggles and successes in modern entrepreneurship. I can’t believe we’ve made it this far already. Thanks so much for following along!

It’s Thursday, July 1, 2021, and this week’s founder is Kyleigh Smith

Kyleigh’s Story


Show me a person with a degree in cognitive science and ask me to guess their current occupation. It won’t be an Entrepreneur.

Kyleigh shocked me when she said she had a degree from UCLA focusing on how we think, but it fits perfectly with her product, HeyItsHarold (AKA “Harold”), which helps form habits through gentle text reminders.

Kyleigh, of course, didn’t know where she was eventually headed, but knew she wanted to build things. So after her degree, she dove right into the startup ecosystem. 

Her first stop was user research at Scopely, a huge success in its own right. They raised a $340 million Series E round in October to continue building interactive mobile games.

After that, Kyleigh worked at a design agency, helping build out Minimum Viable Products (MVPs) for new founders. Then she freelanced a while, and followed that up with a job with a friend of hers at a startup called Moment that tracked screen time, before Apple and Google adopted the idea and effectively put them out of business.


Harold started with the pandemic. Prior to his creation, Kyleigh was working to track her habits in spreadsheets, without much success.

She needed something that fit into her typical workflow.

SMS text messages were the answer. With an AutoCode walkthrough and Twilio, Kyleigh was able to set up a workflow for herself to have a daily reminder to complete her habits.

A friend asked her what she was working on and got Kyleigh to add him to the flow. Two days later, her sister wanted in too. When Kyleigh added Harold’s website to her Twitter bio, she had someone join the waitlist on the first day.

She knew she was on to something, but entrepreneurship isn’t known for being easy. Kyleigh has a long road ahead.

The pressure is on

Kyleigh has been working full time on Harold for a few months now. She started with the On Deck No Code (ODNC) fellowship, launching on Product Hunt and at the ODNC demo day. Both events created a spike in users for Harold, but outside of that, growth has been more trickle than surge.

Kyleigh is working to improve organic growth for Harold. She is experimenting with his personality and image, meeting with a marketing agency to determine his look and his voice. She’s also testing out solutions through OpenAI to give Harold more varied responses.

Kyleigh is all-in on Harold. She’s in one of the hardest parts of the journey. Harold has proven to have some draw, but can it keep customers? Can Kyleigh build a brand that people connect with, share with friends, and grow from? Time will tell. We know she’ll keep building. That’s what Kyleigh does.

And as much work as she puts in to make Harold better, he’ll match by rooting her on in return.

Kyleigh’s Advice

  • Start with NoCode! You can build something so quickly and prove out an idea.

  • Use AutoCode! It’s a low-code tool to help you build logic and syntax for your application. The team is fantastic and helps out on their public Discord channel. Shoutout to Jacob!

  • Invest in branding! Mentors explained the value to Kyleigh. Customers connecting with the brand is key to growth.

  • Go slow to go fast. Be certain you’re learning and testing as you build. You’re going to be excited to build, but save yourself time by listening to users’ desires. Evaluate those critically too.

You can connect with Kyleigh on Twitter as @bagelsandgranola or on LinkedIn

A note: Harold is available in the USA only for now, but reach out to Kyleigh and let her know if you’re international and waiting to try Harold out!


That’s it for this week! I hope you enjoyed Kyleigh’s story. You can connect with me through my website, Twitter, LinkedIn, or send me an email at If you enjoy the newsletter, please share it with friends!

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