20VC: Why Passion Is Overrated When It Comes To Starting Companies, Why VC Is Overrated As A Financing Mechanism & Why You Should Never Sell Your Company with Waseem Daher, Founder & CEO @ Pilot
Posted on 2nd August 2019 by Harry
Waseem Daher is the Founder and CEO @ Pilot, the startup that takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed. To date, Waseem has raised over $58m in funding from some of the very best firms and people in the business including Index, Stripe, Okta’s Frederic Kerrest, Gusto’s Josh Reeves, Stripe’s Patrick and John Collison and Lola’s Paul English, just to name a few. As for Waseem, Pilot is the 3rd business he has founded with his co-founders, the first being Ksplice and the second Zulip, which was acquired by Dropbox in 2014. He has also enjoyed spells with the likes of Oracle and Dropbox in the interims.
1.) How Waseem made his way into the world of startups over 15 years ago and how that lead to his founding of Pilot today, changing the world of accounting? Does Waseem agree with Joel Fernandez at JoyMode that “serial entrepreneurship is overrated? What has Waseem done differently this time as a result of his 2 prior founding experiences?
2.) Why does Waseem believe that “passion is overrated when it comes to starting companies”? If passion is not fundamental, what does Waseem believe is fundamental to ensuring one sticks the course? How does Waseem think about the craft of company building as a passion in itself?
3.) What is it about Waseem’s relationship with his 2 co-founders that makes it so successful for the third time around this time? What do they do to ensure that unity and trust remains? Where do they have weaknesses and flaws in the co-founding relationship as a result of it’s maturity? What advice does Waseem give to newer co-founding partners?
4.) Waseem has previously said that “VC is overrated”. What does he mean by this? How does Waseem think about the decision to bootstrap vs to raise VC? What are Waseem’s biggest lessons when it comes to investor selection? How much of a role does brand play? What core questions should the founders ask the VC?
5.) What does Waseem mean when he says, “never sell your company”? What were his biggest lessons from exiting two companies to Oracle and Dropbox? How did it shape his thinking on M&A and exits? How has Waseem seen his role scale and develop as a leader and as CEO? What are the biggest challenges he has found in his personal scaling?
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