Toast has raised more than $900 billion and is reportedly valued at over $5 billion. But back in 2011, no one knew this startup would see such meteoric success. It had a few things going for it, of course — founder Aman Narang hailed from Endeca, where he was a software engineer and product lead with a reputation for being able to ship a lot of software quickly.
But the ambitions behind Toast were big and complicated, and enough to give pause to any investor. Kent Bennett was one such VC, and while he had conviction in the founding team, he wasn’t convinced that they could tackle such a big problem.
Toast is a restaurant POS system that acts as a sort of operating system for an establishment, managing everything from online orders, deliveries and marketing to payroll and team management as well as the actual point of sale. Being able to do all that requires building a number of complex products, such as payments.
Early on, Bennett had told Narang not to build a restaurant POS. To him, it was too complicated and nuanced, which is why the systems from the ’90s were still deeply entrenched 20 years later. However, he did offer space in the Bessemer office for the Toast team to work on their product.
“I caught up with Aman and he told me that they did this interesting thing after hearing that a lot of their customers were frustrated by payments platforms, which are separate from the POS,” said Bennett. “Aman said they built their own payments platform. Once again, I was like, ‘You did what? You’re not allowed to build payments.’ But he told me that they built it and it improves their products, and that, by the way, they make a margin on it.”
Bennett said that when they added up the margins from the payments and the POS, it was impactful.
“It hit me like a ton of bricks,” said Bennett. “This is a really good business.”
From there, it became his obsession. And though it took a few more quarters to close the deal, they eventually got there. Bessemer led the company’s Series B financing in 2016.
We spoke to Bennett and Narang recently on an episode of Extra Crunch Live to explore the story of how they came together for the deal, what makes the difference for both founders and investors when fundraising, and the biggest lessons they’ve learned so far. The episode also featured the Extra Crunch Live Pitch-Off, where audience members pitched their products to Bennett and Narang and received live feedback.
Extra Crunch Live is open to everyone each Wednesday at 3 p.m. EDT/noon PDT, but only Extra Crunch members are able to stream these sessions afterward and watch previous shows on-demand in our episode library.
Despite the complexity of the Toast system, or maybe because of it, Narang says the fundamentals are the most important part of communicating the business, especially when fundraising.
