Hot Seat: The Startup CEO Guidebook

Hot Seat: The Startup CEO Guidebook

by Dan Shapiro


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The most mysterious role at a startup is that of the CEO. What exactly does the CEO do, anyway? Hot Seat: The Startup CEO Guidebook pulls back the curtain on the executive suite. This may be the title held by Jobs, Gates, and Zuckerberg, but it’s also the title held by thousands of overconfident wantrepreneurs with starry eyes and little hope of success. This book is about what separates the successes from those who fall flat.

Author Dan Shapiro, founder and CEO of Sparkbuy Inc (acquired by Google, where he now works) shares the directions, trials, tribulations, and strategies of the startup CEO—the ways startups are born, live, and die, as told from the view at the top.

This book is divided into five sections:

  • Founding covers the moment from the first idea of the business up until the incorporation and financing.
  • Funding, one of the earliest and most difficult challenges, explores many strategies in depth.
  • Leadership helps you come up with a strategy, create a culture, and navigate the pitfalls as you build your executive team.
  • Management covers how to argue with your team, when to play the CEO card, and how to manage your board.
  • Endgame explores how to finish your startup with grace and create the best outcome for everyone involved.

Product Details

ISBN-13: 9781449360733
Publisher: O'Reilly Media, Incorporated
Publication date: 05/22/2015
Pages: 322
Sales rank: 870,493
Product dimensions: 6.00(w) x 8.90(h) x 0.90(d)

About the Author

Dan Shapiro is the CEO and cofounder of Glowforge, a startup that's creating the first 3D laser printer. Dan's also the primary turtle wrangler at Robot Turtles, LLC, a company created when he accidentally launched the bestselling boardgame in Kickstarter history. Dan spent the previous two years leading a Google subsidiary that operates comparison shopping products. Shapiro landed at Google when they bought his previous company, comparison shopping website Sparkbuy. Before Sparkbuy, Shapiro was founder and CEO of Photobucket Inc. (formerly Ontela).

Dan's been featured on NPR, the Wall Street Journal, and on the front page of the New York Times. His game, Robot Turtles, can be purchased everywhere from Target to MOMA. He is a mentor for the Founder's Institute, 500 Startups, and Techstars. He has been awarded eleven US patents, and received his B.S. in Engineering from Harvey Mudd College.

Table of Contents

Preface ix

Part 1 Founding 1

1 The Virtues of an Early Bankruptcy 3

2 The Cofounder Dilemma 11

3 Deciding on the Dream 19

4 Sharing Shares 27

5 Vesting Is a Hack 37

6 Spending Money 43

7 Conclusion 47

Part II Funding 49

8 The Fun of Funding 51

9 Don't Ask for Introductions 53

10 The Standard Pitch Deck 57

11 The Nonstandard Pitch Deck 75

12 Business Plans 79

13 The Pyramid Pitch 81

14 Pitching Twitter; Pitching Hoverboards 85

15 Why Taxi Drivers Don't Take Venture Capital 87

16 Angels and Demons 95

17 The Lead Investor 107

18 Winning at Crowdfunding 113

19 Miscellaneous Financing Sources 125

20 How Much You're Worth 131

21 How Much You Need 133

22 Notes or Priced? 135

23 Conclusion 141

Part III Leadership 143

24 The Six Things You Cannot Delegate 145

25 Repeat Your Strategy 155

26 Contrarian Segmentation 159

27 Hypocrisy Is a Symptom of Values 165

28 Impostor 167

29 A Drummer for Spinal Tap 173

30 Your Company Culture Is a Meaningless Platitude 179

31 Creating Culture 185

32 Conclusion 187

Part IV Management 189

33 How to Make Your Company Half as Effective 191

34 The CEO Card 197

35 Building a Sublime Organization 201

36 The Lies of Big-Company Life 219

37 14 Answers That Will Save You 100 Hours 225

38 The Board of Directors: Your Peers, Your Obligation, Your Bosses 231

39 Conclusion 237

Part V Endgame 239

40 Of Course This Company's for Sale 241

41 Why to Sell 243

42 There Are Three Exits-Remember, the Nearest Exit May Be Behind You 249

43 Obligations Before Negotiations 255

44 Negotiations 263

45 Exiting with Grace 269

46 Sparkbuy's Story 271

47 Conclusion 287

Acknowledgments 289

Index 291

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