What were the toughest problems you faced when starting Taro?

The early days were tough: we knew we wanted to help software engineers, but we didn't know how to turn it into a business. In the first few months of 2022, we struggled to answer basic questions:

• Would we charge consumers or businesses?
• Would we create tools (in the flow of work) or content?
• How can we convince investors that we could take VC funding? Is that the right move for us?

I remember we did user interviews through a platform called Tegus, where we spoke to various enterprise leaders at various companies, e.g. Head of Learning, or HR Lead, or a CTO. Access to these people was great, but we became increasingly frustrated because:

• We didn't know how to properly interview these folks to identify problems that were worth solving for them.
• Our misguided expectation was that we'd be able to get "design partnerships" or Letter of Intents (LOIs) from these conversations, but we were still very far from having that kind of trust with enterprises.

We got rejected by YC (and a few other accelerators) the first time we applied, but ended up getting in for the Summer 2022 batch. Don't assume that seniority in FAANG makes it easier to get into YC -- it helps, but you're still much more likely to be rejected. Y Combinator was really powerful in helping us ship a product that we finally started charging for.

The core Taro team is still quite small: 3 engineers in the Bay Area (me, Alex, and Charlie), and we have one contractor abroad to help with operations.

For a trip down memory lane, here's a video from the early days of Taro (Sep 2022): "How did you decide to quit your job and make a startup?"

Fundraising after YC was challenging: hundreds of calls across 3 months, starting in August, with many unique characters in the investing world. Also a lot of disappointment and frustration, but that's a story for another time 😇 Overall, I'm actually grateful for the investors and amount we raised, and also that we don't have to fundraise anymore.