20VC: Dropbox's Drew Houston on Leadership; Hiring, Firing, Breakpoints in Company Scaling, The Story of Nearly Getting Acquired by Steve Jobs and Apple, How Founders Should Think Through Potential Investors and Acquisitions

20VC: Dropbox's Drew Houston on Leadership; Hiring, Firing, Breakpoints in Company Scaling, The Story of Nearly Getting Acquired by Steve Jobs and Apple, How Founders Should Think Through Potential Investors and Acquisitions

Drew Houston is the Co-Founder and CEO @ Dropbox, for over 700 million users and +600,000 teams, Dropbox is the choice for storing and sharing their most important files. Prior to their IPO in 2018, Drew raised funding from some of the best including Sequoia, Index, Greylock, and IVP to name a few. Drew also currently sits on the board of Meta and is a seasoned angel with a portfolio including Gusto, Scale AI, Pilot and Superhuman to name a few. Prior to Dropbox, Drew founded Accolade, a bootstrapped online SAT prep company he started while in college.

In Today's Episode with Drew Houston We Discuss:

1.) Entry into Startups and Y Combinator:

  • How did Drew make his way into the world of startups with an SAT prep planning startup?
  • How did Drew convince Paul Graham to accept him and Dropbox into Y Combinator?
  • If we are all a function of our pasts, what is Drew running towards and what is he running away from?

2.) Drew Houston: The Leader and CEO:

  • How does Drew define "high performance" today?
  • How would Drew describe his style of management? How has it changed over time?
  • How did taking an enneagram test change how Drew leads? What did he learn?
  • What have been Drew's biggest hiring mistakes? What mistakes does he see others make?
  • What have been Drew's biggest lessons in how to let people go the right way?

3.) Crucible Moments: Getting Sequoia, Acquisitions and Steve Jobs:

  • How did Drew convince the Sequoia team to invest in Dropbox? How did it all start in a rug shop thanks to Pejman Nozad @ Pear?
  • Has Drew had opportunities to sell the company? Why did he not take them? How does he advise founders on the decision to sell or not?
  • How did Drew come to meet Steve Jobs? How did the meeting go?

4.) Drew Houston: AMA:

  • Is Dropbox a B2B company or a B2C company?
  • What is the hardest element of Drew's role with Dropbox?
  • What has Drew recently changed his mind on?
  • When press cycles were against him, how did Drew get through those tough times?
  • What is Drew's biggest takeaway from joining the Meta board?

Items Mentioned In Today's Episode:

Drew's Fave Book: High Output Management by And

Episoder(1387)

20 VC 003: Bob Ghoorah on Startups, The Pitch and Uber

20 VC 003: Bob Ghoorah on Startups, The Pitch and Uber

On today's episode I am thrilled to welcome Bob Ghoorah, Managing Director at Columubus Nova Technology Partners. Bob has experienced both sides of the table having been an early employee at three technology companies in Silicon Valley; LoudCloud (Nasdaq: LDCL), Opsware (Nasdaq: OPSW) and Ning, a privately-held software platform (sold to Glam Media in 2011). In this episode we find out: The benefits of having a legal knowledge in the Startup community. What characteristics make the best entrepreneurs? Who does Bob think of, when the word 'success' is mentioned and why? Where Bob sees the future of Uber? What aspects of a Startup are essential in order to obtain VC funding? Is it important for Startups to be located in Silicon Valley? What books Bob woulg give to an aspring entrepreneur and startup founder? What advice Bob would give to anyone looking to get into the Venture Capital Industry? Finally, we head to the quick fire round. Here, we get Bob's immediate reactions to the latests tech topics including tech bubble, company valuations and the first trillion dollar company. For all the resources mentioned in todays show head over to The Twenty Minute VC.

13 Jan 201522min

20 VC 002: How to become a VC with Kris Jones

20 VC 002: How to become a VC with Kris Jones

In this session of The Twenty Minute VC, I'm so excited to have the opportunity to interview Kris Jones. Kris has enjoyed an amazing career in the technology industry, founding PepperJam, an internet marketing agency in 1999 and later selling it to Ebay in April of 2010. More recently, Kris has made his transition into the Venture Capital Industry through the founding of an early stage technology investment fund, KBJ Capital, which includes portfolio companies Highlighter.com, French Girls App, ReferLocal.com, LSEO.com and many more incredible companies. In this session you'll learn: Why Kris decided to make the transition from the Startup ecosystem to the world of Venture Capital. How did it feel for Kris, selling his company to Ebay? What was the most important lesson Kris learnt in the journey from having the idea for PepperJam to being acquired by Ebay? What is the key characteristic a Founder must have? What can an individual do to get employed in the Venture Capital industry. Kris is also a prolific writer here are some of his articles, you can check out! Forbes: 15 Steps to Set Your Company Up for a Successful M&A Mashable: 9 Ways Social Media Marketing Will Change in 2014 Citibank: How to Impress a Potential Investor

13 Jan 201522min

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

20 VC 001: Guy Kawasaki of Apple, Motorola and AllTop.com

Welcome to the 1st episode of The Twenty Minute VC, on today's show we have Guy Kawasaki, Guy is the Founding Partner of Garage Technology Ventures, a seed & early stage venture capital fund investing in extraordinary entrepreneurs with unique technologies. Previously, he was Chief Evangelist of Apple Inc and an advisor to the Motorala Business Unit of Google. Guy is also the author of many best selling books including the recent best seller, The Art of Social Media: Power Tips for Power Users. In this episode we delve into: Why Guy made the transition into the VC industry? What is the most important aspect for a startup to have? What drives Guy insane about startup founders today? What books Guy gives to aspiring entrepreneurs? What software & apps Guy cannot live without? We then finish on a quick fire round where we discover Guy's thoughts on the future of Amazon, Tesla and whether we really are in the midst of a tech bubble. All of the products mentioned in todays show can be found at www.thetwentyminutevc.com If you love the show, please do leave a review on the iTunes store and don't forget to subscribe!

13 Jan 201519min

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