Wasim: The first three to six months before a company gets started is one of the most underexplored or misunderstood parts of company creation. He says he and his co-founder Jeff, Jessica met at MIT; they all worked together on case blights that did software updates without rebooting. They bootstrapped it, grew it to six figures in revenue, seven figures in revenue,. Oracle acquired it and we were at Oracle for a year and a day to transition over the tech and then hit eject. After that first company, literally the day after we left Oracle, we all got together again and said, we want to do another company.
Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014. In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers. Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite. Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies. You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack:
https://waseem.substack.com/ You can email us questions directly at
review@firstround.com or follow us on Twitter @
twitter.com/firstround and
twitter.com/brettberson