One Year Wiser: Harold and Kyleigh Smith

Published on
May 12th, 2022
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The company she was working for shut down, so she dove head first into her side projects. One year later she’s writing a book about what she learned.
Tyler Swartz is a Group Product Manager at Reddit and writes a product-focused newsletter called, One Year Wiser, where he interviews founders and product makers one year after their product launch. Subscribe to One Year Wiser here and find him on Twitter: @tylerswartz.
Kyleigh Smith started to build Harold as a side project in 2020, while she was working as a Product Manager at an early stage startup. One of her goals was to build something from scratch and launch it on Product Hunt. Harold helped her achieve that.
Kyleigh found that some people can track habits using journals, spreadsheets, or apps, but for many people those tools don't work – they are quickly forgotten. Harold is a text message based tracking app that “comes to you and does all the tracking for you.”
In January of 2021, Kyleigh shared Harold with the Product Hunt community. She got 200+ upvotes and over 300 signups for Harold. She also won the first ever $5k Product Hunt Maker Grant and was selected to present Harold at On Deck’s Demo Day. As she describes it, she “was learning, making progress towards [her] dream of being an indie maker, and still getting a full-time salary.”
But in March, her CEO called and told her the startup was shutting down. She would get three months of severance to find her next role. Kyleigh decided that instead of looking for a new role, she would go all in on being an indie maker.
I connected with Kyleigh a year after she had decided to go full time on her side projects. I had seen some of her Tweets where she shared stats and updates from building Harold. I was excited to hear about what she’s learned from the past year.
In our conversation, Kyleigh talks about:
  • How building in public on Twitter has helped her grow an audience
  • How she would have changed the approach she took to onboarding all of the new users from her Product Hunt launch
  • The importance of building a strong relationship with your first 100 users
  • How figuring out the best pricing strategies can be hard and that it’s important not to overthink it
  • The book she’s writing, called The Honest Guide to Indie Making, about everything she’s learned in the past year from going full time on her side projects
My questions are in bold; this interview has been lightly edited for clarity.
In your Product Hunt launch you mentioned that you were motivated to build Harold because you had a goal to build and launch a product on Product Hunt. Can you tell me more about that goal and how Harold came about?
Kyleigh Smith: I was following a lot of indie makers on Twitter and I always thought everything they were building was so cool. I really wanted to do that myself, but I never really started. Finally, I read this article by Steph Smith, who had written this article How to Be Great, Just Be Good Repeatedly where she explained how to stick to your goals. It's simple - you need to track daily progress and share it publicly. I was really inspired by that article and everything she was doing.
The only problem was I had never been able to stick with tracking my habits. I'd tried tracking apps in the past and nothing stuck. When it comes to habit trackers, I’ve tried so many things and nothing works. I had a journal where I had made this whole table to track my habits, but the table is empty. I never went back and logged anything.
Kyleigh's empty habit journal
Kyleigh's empty habit journal
The more I thought about what project I would do, the more I thought a better habit tracker that was SMS based was the right idea. As a user experience designer, I always subscribe to the framework, “meet the user where they are.” It's so hard to get people to go to your website or app, so meet them where they are, which is messages. It suddenly clicked. I had that habit tracking problem and the idea for a better solution that was SMS based.
‍I totally agree with your “meet them where they are” approach. I definitely made that mistake before. Tell me about the Product Hunt launch. What were your goals for it?
KS: I used the Product Hunt launch to get validation for my product. I come from a UX and product management background, which means I'm always thinking about validation and gathering evidence. I wanted to validate that Harold was a good idea and worth me working on.
You always hear that advice to launch before you're ready. I decided to follow that advice and post it right after New Year’s Day. It’s a habit tracking app, so I thought that would be the perfect time to share it. The product had a waitlist and I also had automated the signup process, so I thought I could handle the launch.
I went for it and posted it, but I didn't promote it. I mentioned it on Twitter + emailed a couple of people, because I didn’t try to overly manufacture a response. I wanted to measure the natural response.
‍A habit tracker and New Year’s resolutions is a perfect combo. I assume you got enough of an initial response to validate the idea and keep going?
KS: Yes, the launch was really exciting. I got 350 sign ups and a bunch of comments that were really supportive. I got my little bit of validation and realized that maybe Harold could be something.
Next, I started to follow Phil Libin’s process for managing a beta waitlist. As I improved the product every week, I would let in a new cohort, see how people used it and measure the key metrics. Then I would make changes, let the next cohort in and see if the key metrics improved.
I learned a lot, but, in hindsight I don't think that was the best approach for me. Phil had a great team behind him and all of these resources, and I think they were more equipped to iterate with large cohorts. Whereas I only had 350 signups and wasn’t able to move that fast. It was just me. I started with only letting in ten people at a time because I didn’t know if my little no-code app was going to hold up to the users or not.
‍Interesting, I really like Phil’s “State Machine” approach to metrics, but it makes sense that because your waitlist was smaller and you are a solo entrepreneur that it was harder to iterate each week. I agree that you probably needed a bigger cohort to get more meaningful insights.
‍What was the key metric that you were looking at? Was it the number of people completing a habit each day?
KS: The primary metric was retention, how long were people tracking for? I also looked at how many days per week were people responding. My goal was having over 50% of users responding at least three or four times per week. Those were the people getting value from Harold.
‍I spoke to another founder who had found that their waitlist approach led to stale leads. It was a business to business software product and as they worked their way through their initial launch day leads, they found that the likelihood of signing a contract decreased with each day. Did you find a similar challenge, as you let people in each week? Were they less likely to engage and retain a few weeks after the launch?
KS: Yes, totally. I ran the numbers at some point. If I sent access within a week, the signup rate was more than 60%. But after a week passed it dropped to about a 50% signup rate. And then it kept dropping after that. I had some people on there for months, which was not great. It might have been better to just let everyone in that first week.
I’d actually gotten that feedback from other indie makers at the time. Sharath, who was working at Product Hunt at the time and is now at On Deck, was telling me on Twitter to just let everyone in. I didn't listen to his advice because I was in product management mode, I was trying to do Phil Libin’s strategy. In hindsight, I think I should have tried to move everyone through faster. Maybe, I could have also spent more time improving the product before Product Hunt, but you don’t want to spend too much time doing that. It’s hard to find the right balance.
I was trying to do all this quantitative metric stuff because I’m a Product Manager. I had a little too much of a product management head on, and maybe I could have just iterated with the first core group a little bit better.
‍How has Harold changed over the past year?
KS: One of the biggest changes was that I added GPT 3 functionality. Before, when users responded to Haraold telling him they had completed their habit for the day, he would say the same thing back, “got it, your response is logged.” Now, with what I implemented with Open AIs API Harold responds with something quirky or funny… and it’s different every time. The goal with that change was to make it more engaging. People were telling me that they liked Harold and felt that he was a real person helping them with their goals. Expanding what he says really leans into that. The other reason for that change was to spur organic word of mouth. If people find the response funny, they may be more likely to screenshot it and share it on Twitter.
I’ve also made some other smaller tweaks, such as allowing the user to customize what time of day they get the text messages, or enabling more than one type of habit.
‍Let's talk about customer acquisition strategy. What have you found to be the most effective way at acquiring customers?
KS: You can see a breakdown of my acquisition in my book, The Honest Guide to Indie Making. In short, Product Hunt was definitely effective in the beginning. 350 signups from one launch. The other big one is Twitter. I build in public, meaning I share lots of details on what I’m building, sharing screenshots of my progress and learnings. Sharing all of that on Twitter has made it the most reliable and consistent channel. Also doing podcasts and newsletters, like this one have helped too.
‍What’s your advice for someone that’s starting to build a business and is considering whether or not they should build in public and share details on Twitter? Is there certain types of content that gets more engagement?
KS: That's a good question. Everyone loves the screenshots of Stripe dashboards that include revenue numbers. Those will get a lot of likes and impressions, but not necessarily engagement. But, my advice is to just start talking about what you are working on. For a while, I struggled with how I should talk about what I’m doing. Finally I got a push from Steph, who I mentioned earlier, she just said, keep it simple and tell people what you are building. It's that simple.
So my advice is to just talk about it and what it’s like working on it. Treat Twitter like your coworker or your friend. Also, let go of your ego. Sometimes you’ll share something and no one will respond. That’s okay. You’ll get better over time as you share more and more.
‍What is your monetization strategy and what are your goals for Harold in the upcoming year?
KS: I tried to monetize it this year and I’m at about $80 monthly recurring revenue (MRR). It’s $49 per year with a 7-day free trial. I maybe should have held off on monetizing and just focused on creating the value and worried about capturing it later. I was able to get some Twilio credits that helped cover the costs of it, so it was less critical for me to charge for Harold. But it was also a way of me validating whether people wanted Harold and whether they’d pay for this type of thing.
Looking back I’m not sure I took the right approach to monetizing it. When it comes to building habits, it can take a while for the habit to start to form and they might not see value before that point. Pricing strategy is hard and it’s stalled me for weeks. The most important thing I learned about pricing — don’t overthink it and keep it simple at the start. Because pricing is the lever closest to that shiny MRR number that we’re chasing, it’s tempting to think there’s just one small change that we can make to unlock higher MRR. But there’s a lot of other things to get right before we do that.
Anyways, a year from now, I think Harold might look a little bit different. I'm playing around with some positioning right now. The target audience is really broad. People who are interested in self improvement feels like almost everyone. So, I’m trying to figure out if there’s a better niche to start with. I've been experimenting with focusing on creative habits and helping people be more creative in their life.
‍As a solo founder, how do you stay motivated and focused after the excitement of the initial launch has worn off?
KS: For me, it’s curiosity. I'm so curious and I always think of new things to try that might improve the product.
There have been times when I think, “oh nothing is working, maybe it’s not the right product.” But eventually, I learn about something from another business or product that gets me excited about mine and pulls me back in. That's kind of where I'm at now with the positioning of the product. I think if I better positioned it to focus on a niche audience then I could start growing faster.
So, I think it’s my curiosity that pulls me back in and gets me excited to continue working on it. I’m learning all the time about other products and get excited to apply those learnings to Harold.
‍Let’s go to the quick fire round. Short, less than a minute answers. What are you most proud of from the past year?
KS: It’s that I've started writing this book, The Honest Guide to Indie Making. It’s about everything I’ve learned in the past year from going full time on my side projects. Hopefully it helps other indie makers increase their chances of success. It's not quite done yet but it’s available for pre-sale and will be launched on April 19th!
I’ve always wanted to write a book. It’s such a big undertaking and I’m proud that I jumped in and started doing it.
‍That’s cool. Why don't you tell me more about that book?
KS: Yes, so it covers everything I’ve learned from going full time on my side projects. People can learn from the mistakes and successes of my journey so that they can start from a better place than I did.
It’s also been a really good exercise to put down everything that I've learned, because this past year and a half has been a huge learning experience. I started thinking, “Oh I’ll just make this product, launch on Product Hunt… and then I'll add Stripe and I'll have $5k monthly recurring revenue.” That was such a simplified picture of what it actually takes to build a business. This book is everything that I wish I’d known before I left my job to go full time on my side project.
‍What’s been one of the biggest pitfalls of the past year or something that you wish you had done differently?
KS: I think the biggest pitfall was that I moved too fast and didn’t spend enough time to really build relationships with those first 100 users. We sort of talked about this earlier in relation to the Product Hunt launch, but when I launched I suddenly had 400 signups and I couldn’t build relationships with them. Instead I switched to focus solely on metrics.
Before the launch I was talking to some users. I’m a UX designer at heart so I know the importance of speaking with your users. But, with the broader launch I forgot to focus on truly talking to my users, not just asking them for feedback, but engaging them in conversations.
Now we're seeing more and more products that are supported by a community. The community is the differentiating factor and a competitive edge. If you're an indie maker, you really need to build a community of supporters because you don’t have a huge marketing budget.
‍Interesting. It sounds like with the bigger launch you turned all of the people using your product into a weekly number and lost touch with the underlying people.
KS: Totally. For example, I started a separate project last fall that helps people build in public. In the sign up process I ask them a bunch of questions about how they intend to use the product and what their Twitter handle is. Next, I’ll DM them on Twitter and start a conversation with them about what they’ve tried in the past, what’s worked, what hasn’t, etc. Starting those conversations has made a world of difference. I’ve been able to more quickly valide the problem and identify the target audience.
‍What book do you recommend the most and why?
KS: Besides my book, the one I recommend all the time is The Four Tendencies by Gretchen Rubin. It's so awesome. It's a personality framework around how you respond to expectations for yourself and others. For example, I'm a rebel and so I don't respond to inner expectations very well or outer expectations. So it can be hard to get myself to do things. When I read that book it explained so much about myself. I think everyone should take the quiz, know what type they are, and most importantly understand how you best interact with others.
‍What do you know now that you wish you'd known a year ago?
KS: So many things, everything in my new book! We already talked about a big one which is building relationships with customers.
I've also learned a lot of tactical marketing skills that I wish I had known a year ago. I didn't know anything about SEO when I started but now I know a lot more. If I had known all of that at the start it would have been a game changer.
‍Last question, what's the advice you have for someone who wants to start a company in 2022?
KS: Build relationships with your first 100 customers. Don't worry about growing or capturing value or monetization until those first 100 people are recommending your product. Especially for indie makers, you're going to need those people to be your advocates and promote your product.
I hope you enjoyed my interview with Kyleigh and learned a few things. If you did, give it some love on Twitter and pre-order Kyleigh’s book! I got a sneak peek of the book and it’s full of helpful and actionable advice. -Tyler
This article was originally published on One Year Wiser, a newsletter from Tyler Swartz, who interviews founders and product leaders one year after their product launch to learn how their products and businesses have evolved, their ups and downs journey along the way, and what their experiences over the past year have taught them.
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