Take on Goliath — and win, w/Dropbox's Drew Houston

Sep 5, 2019

Drew Houston, Co-founder and CEO of Dropbox, shares his journey of competing against tech giants like Google and Apple with his nimble cloud storage solution. He emphasizes the importance of recognizing unique strengths in a crowded market and highlights innovative hiring practices. Drew explains how Dropbox's referral program propelled user growth and discusses the balance between ambition and caution when navigating startup challenges. With engaging anecdotes about friendly rivalries and team dynamics, he illustrates how agility and strategic thinking can lead to success.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

ANECDOTE

Rock Band Rivalry

Drew Houston's Dropbox team engaged in a Rock Band competition with Mosey.
This anecdote highlights Dropbox's competitive spirit and focus on details.

INSIGHT

Identify Your Advantage

To win against larger competitors, know your advantage.
Focus on talent and anticipate potential challenges.

ANECDOTE

Accolade's Origin

Drew Houston started Accolade, an SAT prep company, in a Chili's.
Accolade capitalized on the SAT format change, making established prep books obsolete.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

Founders at Work

Jessica Livingston

Founders at Work offers a firsthand look at the early days of influential startups, featuring interviews with founders like Steve Wozniak (Apple), Max Levchin (PayPal), and Caterina Fake (Flickr). The book provides insights into the challenges, strategies, and lessons learned by these entrepreneurs as they built their companies. It emphasizes the importance of perseverance and adaptability in startup success.

High Output Management

Andrew S. Grove

High Output Management is a seminal book by Andrew S. Grove that outlines his management and productivity concepts developed during his tenure at Intel. The book introduces the 'management by objectives' approach, also known as the objectives and key results (OKR) framework. It covers techniques for creating highly productive teams, methods of motivation, and the importance of measurable processes, performance reviews, and training. Grove emphasizes the role of managers in leading and motivating teams, and his book is praised for its practical advice and timeless relevance in various professions and industries.

Becoming Steve Jobs

The Evolution of a Reckless Upstart into a Visionary Leader

Brent Schlender

Rick Tetzeli

This book provides a rich and revealing account of Steve Jobs' life, drawing on exclusive access to his family, former inner circle executives, and top people at Apple, Pixar, and Disney. It humanizes Jobs by explaining his behavior and highlighting his growth from a brash founder to a mature and effective leader. The narrative includes stories never told before and offers a fresh perspective on Jobs' career, particularly his time at NeXT and Pixar, and his return to Apple. The authors, who had close relationships with Jobs, detail how he learned to trust his inner circle, became more patient, and developed a more mature management style, ultimately transforming the daily life of billions of people.

The hard thing about hard things

building a business when there are no easy answers

Ben Horowitz

In this book, Ben Horowitz shares his personal and often humbling experiences in the tech industry to offer essential advice and practical wisdom. He addresses various hard decisions and challenges that business leaders face, such as firing friends, managing company culture, handling layoffs, and making tough strategic decisions. Horowitz emphasizes the importance of honesty, resilience, and adaptability in leadership, drawing from his experiences with companies like Loudcloud and Andreessen Horowitz.

Hard Drive

Bill Gates and the Making of the Microsoft Empire

Jim Erickson

James Wallace

This book is a detailed exposé of Bill Gates' life and the early days of Microsoft. The authors follow Gates from his childhood as an unkempt thirteen-year-old computer hacker to his present-day status as the most powerful and feared player in the computer industry. The book provides a balanced analysis of Gates' business triumphs and his driven personality, including his singular accomplishments, brattiness, arrogance, and hostility. It also delves into the intense atmosphere at Microsoft, the company's strategic positioning, and key events such as the partnership with IBM and the development of MS-DOS and Windows[1][3][5].

Competing Against Luck

Clayton M. Christensen

David S. Duncan

Taddy Hall

Karen Dillon

In 'Competing Against Luck,' Clayton Christensen and co-authors introduce the 'Jobs to Be Done' theory, which posits that customers 'hire' products to solve specific problems. The book provides real-world examples and tools for entrepreneurs to innovate effectively and create products that customers are willing to pay premium prices for. It offers insights into how companies like Uber and Airbnb have successfully applied this approach.

The Effective Executive

The Definitive Guide to Getting the Right Things Done

Peter Drucker

In this book, Peter F. Drucker identifies five essential practices for business effectiveness: managing time, choosing what to contribute to the organization, knowing where and how to mobilize strength for best effect, setting the right priorities, and making effective decisions. Drucker emphasizes that these habits can and must be learned to achieve true effectiveness in an executive role. The book draws from his extensive experience in organizational management and consulting, offering insights that remain relevant despite the passage of time since its original publication in 1967.