Waseem Daher

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

Waseem Daher, Co-founder and CEO of Pilot, brings insights from the trenches of early-stage startups. He discusses the delicate balance founders face when setting their salaries amidst investor pressures. The conversation dives into the impact of economic changes on founder compensation, especially across different regions and sectors, including the AI landscape. Waseem also tackles essential metrics like burn rate and runway, while emphasizing the emotional challenges of financial austerity and the importance of clear storytelling to attract venture capital.

Exploring successful exits, billion dollar company ideas, and getting Jeff Bezos to invest. From software updates to accounting, the journey to securing investments, growing followers on LinkedIn, and navigating AI in entrepreneurship. Strategic funding considerations and prioritizing emotional resilience in business challenges.

Waseem Daher, Co-founder of Pilot, discusses Pilot's beginning, first customers, pricing, building a GTM team, advice for founders. They delve into their approach to targeting the right customers, founder-led sales, and the importance of shipping a product quickly.

Waseem Daher, the Founder and CEO of Pilot, previously initiated Ksplice and Zulip, highlighting his prowess in tech startups. He believes passion is overrated in entrepreneurship, advocating instead for organizational discipline and effective team dynamics. Waseem shares insights on the importance of co-founder relationships and emphasizes empathy in leadership. He also critiques traditional fundraising methods, arguing for a reevaluation of how companies should approach growth versus personal well-being.