The Only Problem You Can't Fix Is the Problem of Market Size

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Sally Kohn: I was interested in maybe having you talk about what you heard from customers and how you approach those conversations. She asked, is this a niche problem or a general purpose problem? How many people or how many businesses have the problem? And the third question is, how much does it cost? It indicates how much pain there is because if there's a lot of pain there should be willingness to pay. The way we landed on the problem for the first company is we were like, well, we have this tech and it happens to have a problem we have. Let's go do it.

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