I cofounded an app that made over $1 million in the last year. We pivoted 5 times and made one big mistake before finding success.

This as-told-to essay is based on a conversation with Alex Ruber, a 29-year-old cofounder and CEO, based in San Francisco. The following has been edited for length and clarity.

About five months after being in Y Combinator, my cofounder, Parth, and I thought we might have to give up.

We met through Y Combinator’s Co-founder Matching Program, a free resource to help people find potential business partners, in January 2024. We were both working full-time. After building some projects together, we launched an AI-powered shopping tool and were accepted into Y Combinator’s fall 2024 batch.

It became clear that the shopping app was not economically viable and was running at a loss, with no clear path forward. We entered what I call our three-month pivot hell. Within those three months, we tried out about five to six different ideas and almost gave up.

Then, we built a very simple game on a whim, and by August 2025, roughly five months after launch, our monthly revenue had reached $144,533.

We did not want to let go of our first app idea

Parth and I were both full-time engineers when we met and bonded over our love of building projects on the side. Also, we’re both really into fashion, especially thrifting.

We thought that the secondhand shopping market would only grow as concerns about the environment grew. Combining that with the advent of AI, we built a basic conversational search engine where users could type anything in natural language, like “I’m looking for a leather jacket under $500 with two stripes, and it has to be a little bit worn in.” The engine would search resale sites like Poshmark, eBay, Mercari, and ThredUp, then compile all the results into a single page.

We loved using the app and got some traction, but it was very expensive to run. People were browsing every day, but they weren’t necessarily buying. The commission we made on the final sale wasn’t great either.

We had poured so much time and energy into this, and wanted to continue because of that, but we hit a breaking point. Eventually, we made the call to explore other ideas as our main pursuit.

We spent 2 to 3 weeks on each new idea

We cycled through five to six fleshed-out ideas, up to 10, depending on how you define an idea execution. We tried everything from a therapy product to a self-journaling product to ideas for dating apps. We even went into the B2B side of the insurance and paper industries.

We’d constrain ourselves to build the solution in one to two days so that we could put it in front of real users through friends, family, Reddit, X, and online communities as quickly as possible.

For each of these ideas, we went super hard for maybe two to three weeks. We did user interviews. We’d also determine the product’s success metrics, and we were ruthless about them. We asked ourselves a simple question: Do people come back, or care enough to pay? If the answer was no, we’d switch to a new idea very quickly.

Constantly trying to dive into a new industry or space put a huge mental and physical strain on us, but we were really trying to find a problem we could help solve.

Right before we came up with our successful app, we hit a low point

We had cycled through so many ideas, and the metrics weren’t looking good. We were completely exhausted and didn’t know what to do.

There was one night when Parth and I decided to go for a walk. We both wanted to take a break and, honestly, get out of the startup world. We took two or three days off to reflect on what went right and what went wrong for each pursuit.

On the last day, we went back to the whiteboard. We decided we wanted to build in the consumer space. That’s one thing that we learned from that whole pivot hell: we didn’t love B2B.

We started making observations about the world around us. Being a founder is a very lonely experience, and we noticed that a lot of our friends and family were worried about us. Every time they checked in or called, we’d always be like, “Oh, we’re just working.” Same bland answer every time.

So we built a very early version of Candle, our social connection app, mainly to feel closer to our loved ones again. It gives a one-question-a-day prompt for both people to answer.

We didn’t have any metric goals when we first created our best idea

We were so strict about the metrics during our constant pivot cycle, but we didn’t have metrics for Candle right away because it wasn’t one of the ideas we took seriously enough to define metrics for before we built it.

Then it started making a big difference in our own relationships. The retention seemed really good organically among our family and friends. We started measuring it, and it was the best metric-wise of our ideas.

We published the app on the App Store in March 2025. We have a full-time team of four, and in our first year, we made over $1 million in revenue.

We don’t throw AI at every step, but it does help us

We have a large question library, and we’re actually opposed to AI-generated questions for our app. We feel like they come across as inauthentic, and this is an app for human connection, so we have human question writers. However, we do use AI to edit grammar.

We use Claude Code and Codex for much of our code generation and for building mini-games in the app. We don’t have a translator, so we’ve started using AI to translate into German, French, and Spanish. This has worked very well, especially using Gemini and Claude. We also have AI recommendations for activities that two users could do together.

Using AI to recommend content or information that helps two people connect is how I think AI should be used, not to replace the connections humans form with each other.

We pinpointed our biggest mistake and learned from it

We feel so passionate about our app. Looking back, the biggest mistake we made was making an industry pivot that was too large each time we explored a new product idea.

Instead of picking a problem space we really love, trying our solution, and, if it didn’t work, switching to a different solution, we kept switching industries. We lost our passion for what we were building as we did that.

My advice would be to pick the problem space and not change it very easily. How you approach that problem is what you should be changing.

Do you have a similar story to share? If so, please reach out to the reporter at aapplegate@businessinsider.com.