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


Waseem Daher is the co founder and CEO of the bookkeeping startup Pilot. He’s a a serial entrepreneur with 15 years experience and 2 prior companies (exited) under his belt.

In this interview on The Twenty Minute VC, Waseem shares his insights on entrepreneurship.

3 lessons…

  • Passion for the thing (accounting in Waseem’s current company) is not necessary. And passion alone won’t get you through the difficult times. Better to be passionate about talking to people, understanding their problems and building something to solve it.
  • Waseem sees a lot of entrepreneurs making the mistake that they think they know the market already. They plow ahead without talking to people first or running any experiments.
  • If you’re looking for funding, don’t think of it as transactional. You’re giving up a seat on the board so think of it as a long term relationship. You need to be able to work together.

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.

In Today’s Episode You Will Learn:

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?

Items Mentioned In Today’s Show:

Waseem’s Fave Book: Harry Potter

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