Lessons From Scaling Pilot to a $1.2 Billion Valuation with Co-founder and CEO Waseem Daher

The Peel with Turner Novak

Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox.

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Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors.

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Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3FoYm52

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In this episode, we discuss:
• Why Waseem’s building a startup that does your accounting
• The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders
• When startups should build something themselves and when to outsource
• All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox
• How to avoid “fake work”
• How to get ROI from conferences
• His disastrous first ever meeting with a VC
• Why the best fundraising advice is to build a business that doesn’t need to raise money
• “Companies are bought, not sold” and his framework for startup M&A
• Why it’s a mistake to build your startup just to be acquired
• Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet
• Why tech-enabled service businesses are so hard to scale
• How Pilot got its first customers
• Pilot’s unique approach to raising its Seed round
• The initial scare when raising their Series A
• Why its Series B was half of what they could have raised

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Where to find Waseem:

• Twitter: https://twitter.com/waseem

• LinkedIn: https://www.linkedin.com/in/wdaher

• Newsletter: https://waseem.substack.com/

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Where to find Turner:

• Newsletter: https://www.thespl.it

• Twitter: https://twitter.com/TurnerNovak

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Production and distribution by: https://www.supermix.io

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For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform