Our 🗝 Lesson from Seeding Attentive

By Hadley Harris

I’d love to tell you a story about the deep thesis my partners and I had that drove us to lead Attentive’s seed round. The story would talk about how in 2016 we were spending a lot of time in the marketing tech stack and saw an unmet need in the market for businesses to utilize messaging to communicate with their customers. I’d tell you how almost every business in China used WeChat for Business to interact with their customers at scale over messaging. And how we felt a company that optimized that use case for the western world’s messaging ecosystem could be a massive company. I could tell you all this but it would be 100% bullshit.

When Brian and Andrew first told us about what they were thinking of building it was not a problem or solution we were thinking about. If anything we didn’t think it was a particularly good idea. My partner Nihal had built and sold a business in the early 2000’s that let companies text their customers, so this didn’t feel particularly novel or exciting. Obviously we were very much wrong about that.

What we did know was that Brian and Andrew absolutely knew how to crush being some of the very very best founders we had ever worked with. We had been lead investors and a board member in their first company that sold for $100M after the series A. So despite the fact we weren’t even spending time in marketing tech, investing in Attentive was one of the easiest decisions we’ve ever made.

People say all the time “it's all about the team.” We at Eniac have been saying it our whole investing careers. But it’s only when you get to see founders execute like we’ve seen over the last 4 years with Attentive that you really understand how true that is. As an early-stage investor it's easy to get caught up by looking at the world through the lens of your theses. But when you have the chance to back a team you know is exceptionally good, don’t overthink it, just say yes and enjoy the ride! 🚀

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