Startup CEO

You’re only a startup CEO once. Do it well with Startup CEO, a "master class in building a business."
—Dick Costolo, Former CEO, Twitter

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

Author Matt Blumberg has been there, and in Startup CEO he shares his experience, mistakes, and lessons learned as he guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path's 20-year journey but a thoughtful CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You'll learn:

• How to tell your story to new hires, investors, and customers for greater alignment
• How to create a values-based culture for speed and engagement
• How to create business and personal operating systems so that you can balance your life and grow your company at the same time
• How to develop, lead, and leverage your board of directors for greater impact
• How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company.

Foreword xi

Acknowledgments xiii

About the Author xvii

Introduction xix

Chapter 1: The Importance of Authentic Leadership in Changing Times 1

Part One: Storytelling 11

Chapter 2: Dream the Possible Dream 13

Chapter 3: Defining and Testing the Story 21

Chapter 4: Telling the Story to Your Investors 31

Chapter 5: Telling the Story to Your Team 39

Chapter 6: Revising the Story 49

Chapter 7: Bringing the Story to Life 59

Part Two: Building the Company’s Human Capital 69

Chapter 8: Fielding a Great Team 71

Chapter 9: The CEO as Functional Supervisor 83

Chapter 10: Crafting Your Company’s Culture 89

Chapter 11: The Hiring Challenge 99

Chapter 12: Every Day in EveryWay,We Get a Little Better 113

Chapter 13: Compensation 125

Chapter 14: Promoting 133

Chapter 15: Rewarding: “It’s the Little Things” That Matter 141

Chapter 16: Managing Remote Offices and Employees 147

Chapter 17: Firing: When It’s Not Working 153

Part Three: Execution 161

Chapter 18: Creating a Company Operating System 163

Chapter 19: Creating Your Operating Plan and Setting Goals 167

Chapter 20: Making Sure There’s Enough Money in the Bank 177

Chapter 21: The Good, the Bad, and the Ugly of Financing 185

Chapter 22: When and How to Raise Money 195

Chapter 23: Forecasting and Budgeting 201

Chapter 24: Collecting Data 209

Chapter 25: Managing in Tough Times 215

Chapter 26: Meeting Routines 223

Chapter 27: Driving Alignment 233

Chapter 28: Have You Learned Your Lesson? 239

Chapter 29: Going Global 247

Chapter 30: The Role of M&A 255

Chapter 31: Competition 265

Chapter 32: Failure 269

Part Four: Building and Leading a Board of Directors 277

Chapter 33: The Value of a Good Board 279

Chapter 34: Building Your Board 283

Chapter 35: Board Meeting Materials 293

Chapter 36: Running Effective Board Meetings 297

Chapter 37: Non–Board Meeting Time 305

Chapter 38: Decision Making and the Board 309

Chapter 39:Working with the Board on Your Compensation and Review 315

Chapter 40: Serving on Other Boards 321

Part Five: Managing Yourself So You Can Manage Others 329

Chapter 41: Creating a Personal Operating System 331

Chapter 42:Working with an Executive Assistant 339

Chapter 43:Working with a Coach 345

Chapter 44: The Importance of Peer Groups 351

Chapter 45: Staying Fresh 355

Chapter 46: Your Family 367

Chapter 47: Traveling 375

Chapter 48: Taking Stock of the Year 379

Part Six: Selling Your Company 385

Chapter 49: A Note on Exits 387

Chapter 50: Preparing Yourself for an Exit 391

Chapter 51: Preparing Your Company for an Exit 397

Chapter 52: The Sale Process 403

Chapter 53: Transition and Integration 415

Chapter 54: Thinking about Your Next Step 419

Conclusion 425

Bibliography 429

What’s Next? 433

Index 435

Matt Blumberg founded Return Path in 1999, grew it to 500 employees and $100 million in revenues, and sold it to Validity in 2019. Matt is chair of Path Forward, a nonprofit that helps mothers and caregivers reenter the workforce. He is creating his next startup and writing a companion volume to Startup CEO.

Being a startup CEO is a job like no other: it's difficult, risky, stressful and, in venture capitalist and long-time Return Path Board Member Fred Wilson's view, "lonely, heavy duty, and a thankless task." As a startup CEO, seeing things for the first time, you're likely to make mistakes, to fail, to get things wrong, and to feel like you don't have any control over outcomes.

Author Matt Blumberg has been there, and in Startup CEO: A Field Guide to Scaling Up Your Business, Second Edition he shares his experiences, mistakes, and lessons learned as he guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees in 2019. In the highly volatile internet world, Matt and his team managed the company through the dot-com crisis of 2000, 9/11, the financial meltdown of 2008, and through the successful sale to Validity in May 2019.

Startup CEO is not a memoir of Return Path's 20-year journey, but a thoughtful CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that they will likely face.

Organized into six parts—Storytelling, Building Human Capital, Execution, Leading a Board of Directors, Managing Yourself, and Selling Your Company—Matt guides you through the thorny, challenging situations you'll face and provides solutions. With this book as your guide, you'll discover:

• How to tell your story to your team, new hires, investors, and customers for better decisions, greater alignment, and speed
• How to balance your life and grow your company at the same time
• How to develop, lead, and leverage your board of directors

A new section covers selling your company. As a first-time CEO you'll probably sell your company only once, but buyers will have done multiple deals. How can you turn that to your advantage so that your company is bought, not sold?

Startup CEO is the field guide every CEO needs throughout the growth of their company.

PRAISE FOR STARTUP CEO

"One of the key principles of the Lean Startup movement is that entrepreneurship is management. In Startup CEO, Matt Blumberg provides a comprehensive guide to every facet of entrepreneurial management. An essential and practical guide for entrepreneurs everywhere."
—Eric Ries, author,The Lean Startup

"There's no silver bullet for building a great company. Startup CEO deciphers the challenging, complex, uncertain, and oftentimes lonely role of a first-time CEO without oversimplifying it."
—Ben Horowitz, cofounder and General Partner, Andreessen Horowitz

"I've been on Matt's board for more than a decade, and I've watched him develop into one of the finest CEOs I've had the pleasure to work with. With Startup CEO, Matt allows other entrepreneurs to profit from his years of experience and emulate his remarkable example."
—Fred Wilson, cofounder, Union Square Ventures

"There is the one-in-a-million company that catches lightning in a bottle and grows like a weed without care and feeding. For the rest of us, there's Startup CEO, the how-to manual for getting there the old-fashioned way. This book will be your coach, mentor, and advisor in any situation you or your company are likely to encounter."
—David Rosenblatt, CEO, 1stdibs

"Startup CEO is the definitive book for any CEO—first time or otherwise—of a high-growth company. While dozens of books have been written about starting businesses, it's time for entrepreneurs to focus on scaling them. Matt shows them how."
—Brad Feld, Managing Director, Foundry Group