What I Got Wrong Building My First Startup

What we were trying to build

Kaptanos started with medium-sized construction companies. Their routine indirect-material purchasing ran through Excel, WhatsApp, email and phone. We wanted to automate it: enter a need, find suppliers, compare offers, place the order.

What we did

We talked to experts first: construction project managers and sector leaders with procurement experience. They were easy to reach. From those talks came our hypothesis, then market sizing and a pitch deck.

We passed the first of two selection stages for a Singapore-based VC's accelerator program. Their feedback was to talk to more potential customers. The people who would actually use the software were hard to find online. Many weren't on LinkedIn. So we went office to office.

What we learned

One of them opened up like this: "I'd want to learn Excel, but I don't have the time." The same person wanted to learn the software but had no time for it.

So the product had to need almost no learning. I drafted a two-month roadmap around finding the single most painful problem and keeping the product that simple. Some firms asked to join the test period. That was interest, not validation.

Where we went wrong

• We sized the market before we knew which problem hurt enough, and for whom.
• Experts explained the industry, but they weren't the users. We reached the users late.
• We still hadn't settled the most painful problem when our disagreement about how to build became fundamental.

Why it ended

My co-founder wanted to build the software first, without testing it with users along the way, and spend the rest of the year selling it. I wanted to stay close to users, find the most painful problem first, and build in steps. We caught this problem early, and we decided to end the project before it grew any bigger. Kaptanos ended there.

What I'd do differently today

• Check that one specific problem hurts before sizing the market.
• Go to the actual users first, even when experts are easier to reach.
• Launch fast around the most painful problem, as YC keeps telling founders. Then watch who uses it, who comes back, who finds it useful and who pays. We never got that far.
• Take the co-founder choice slowly; a16z's advice is not to rush it. Before committing, agree on how we will build: validation, speed, customers, and when to start writing code.