20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup

Aaron Levie is the Founder and CEO @ Box, the company incorporating the best of secure content collaboration with an intuitive user experience suited to the way people work today. Prior to their IPO in 2015, Aaron raised from some of the best in the business including the main man Mark Cuban, a16z, Emergence, DST, Coatue, DFJ and many more. Aaron founded the company from his dorm room at the University of Southern California and has led the company to 1,900 employees and over $770M in revenue, as of 2021 data.

In Today’s Episode with Aaron Levie You Will Learn:

1.) How Aaron founded Box from his dorm room at the University of Southern California? What was that founding a-ha moment? What did the first year look like? Does Aaron agree, “serial entrepreneurship is overrated”?

2.) Phases of Leadership and Company Growth:

• How does Aaron define the different phases of leadership required as a company grows?

• Which phase did Aaron find the most challenging? How did he overcome it?

• What are the first things to break when companies grow? What can founders do to prevent this?

• Does Aaron agree, “the best CEOs are the best resource allocators”?

3.) The Market:

• How does Aaron thinkj about the dislocation between private company valuations and public company market caps?

• What does Aaron believe are the biggest challenges founders face when they are over-capitalised?

• What does Aaron mean when he says, “raise when cash is cheap, spend as if it was expensive”? How does Aaron advise founders on fundraising today?

4.) The Team and Culture:

• How does Aaron create a safe space where all team members can come to him with anything?

• How does Aaron approach effective goal setting? How does one balance between achieveable and also aggressive goals?

• How does Aaron approach the art of delegation? What is his decision-making framework for what to delegate vs what to control?

Item’s Mentioned In Today’s Episode with Aaron Levie

Aaron’s Favourite Book: Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail (Management of Innovation and Change)