Table of Contents
Chapter 1 Someone Else Was Supposed to Write This Book 1
The American Dream 2
The Future of Jobs-And Making Money 5
Escaping the Matrix 6
Chapter 2 The Brooklyn Grinder 9
Is Angel Investing Gambling? 9
The Sequoia Scout Program's Secret Origin 10
I Used To Dream About This Life 11
"Pass on What You Have Learned"-Yoda 13
No Gamble, No Future 14
For The Real Outsiders 15
Chapter 3 What is Angel Investing? 17
Angel Investing 101 17
Product/Market Fit and Exits 18
No Risk, No Reward 18
"You Only Have to Be Right Once."-Mark Cuban 19
Angel Investing vs. Boring Investing 21
A Typical Angel Investor Scenario 23
What's The Downside? 26
Chapter 4 Is Angel Investing For You? 27
Money, Time, Network, and Expertise 27
Dealing With Wild Cards 28
Chapter 5 Do You Need to Be in Silicon Valley to Be a Great Angel Investor? 31
Chapter 6 What's So Special About Silicon Valley? 33
Silicon Valley is the Center of the Universe 33
Location, Location, Location 35
Second Place is First Loser 36
Life in the Fast Lane 37
Network Effect 38
Literal Moonshots 40
Chapter 7 Startup Funding Rounds Explained 43
Is This an Angel Round or a Seed Round? 43
Sweat Equity 44
Bootstrapping 45
Friends and Family 46
Self-Funding 47
Incubator Funding 49
Seed/Angel Funding 50
Bridge Round, A.K.A. Seed Plus 51
Series A 54
Series B, C, D, E, F, and Mezzanine Rounds 55
Chapter 8 How to Be an Angel Investor with Little or No Money 57
Cap Table Basics 57
Five Ways to Get on a Cap Table 58
Shareholder Motivations 59
Other People's Money 62
Secondary Sales 63
Broke Angels 64
Founding vs. Funding 65
Chapter 9 The Pros and Cons of Advising 67
You've Gotta Start Somewhere 68
Opportunity Costs 68
My First Advisor Check 71
Saving Up 72
DYN-O-Mite! 73
Collision Course 74
Three Out of Four Ain't Bad 78
Chapter 10 Going Straight from College to Angels Investing 79
The Sucker at the Table 79
The Future is All around Us 81
Chapter 11 How to Hack Angel Investing: Syndicates 83
The Easiest Way to Become an Angel 83
Angel Syndicates 84
The Benefits of Syndicates 88
Chapter 12 Month One: Your First Ten Syndicate Deals 91
Picking the Syndicate Deals to Join 91
How to Act in a Syndicate 95
Write Deal Memos 96
Jedi Poker 97
Angel: It's Not Just a Job 99
My Biggest Miss: Twitter 99
Chapter 13 Month Two: Thirty Days of Angel and Founder Meetings 101
Building Your Network 101
Meet Twelve Angels 102
Meet Twenty-Five Founders 105
Getting Good at Saying No 106
Chapter 14 My Best and Worst Pitch Meetings 109
Pitch Overload 109
The Best and Worst Investors I've Pitched 110
Chapter 15 What to do before a Pitch Meeting 115
Hint It's Not Just a Google Search 115
Chapter 16 What to do during a Pitch Meeting 117
One Hour Minimum 117
Give Them Your Full Attention 118
Bring Pen and Paper 119
Activate Silent Mode 120
Coffee Shops Are a Last Resort 120
The Best Interview Questions Are the Ones You Didn't Write 121
Never Say Yes Or No During a Pitch 122
Chapter 17 How to pick a Billion-Dollar Founder 123
The Billion-Dollar Question 123
Filtering Your Deal Flow 123
Finding Businesses That Can Scale 126
Overcoming Blind Spots 128
Limit Signaling To Founders, Not Ideas or Markets 129
Chapter 18 The Four Founder Questions 131
A Thousand First Dates 131
How to Ask Questions 133
Question Zero 134
What Have We Learned? 140
Chapter 19 Going Deeper 143
The Next Five Questions You Should Ask 143
Tactical Questions 146
My Burn Rate Party Trick 149
Personal Questions 150
Chapter 20 Founder or Fraud? 153
Going the Distance 153
Key Founder Traits 156
It's No Secret 158
Silent but Deadly Or Silent and Dead 158
Chapter 21 Evaluating the Deal 161
Timing 161
Pro Rata 164
Valuation 165
Chapter 22 Why Angels should write Deal Memes 169
The Best Way to Improve Your Selection Process 169
The Greatest Deal Memo Ever Written 171
The Pied Piper of Startups 172
Keep Calm and Carry On 174
Chapter 23 The Perfect Way to Decline a Deal 177
Fifty Ways to Leave Your Founder 177
You Want the Truth? 178
Incubator Fatigue 181
Say "Not Yet" Instead of "No" 182
Chapter 24 Due Diligence Checklists 185
Reducing Your Risk 185
Playing Startup Detective 186
Crossing the Line 190
It Gets Worse 191
It Gets Much Worse 192
The Appearance of Impropriety is Impropriety 195
Chapter 25 Your First Yes 197
It Gets Real 197
Chapter 26 How Founders Should Treat Their Angels 201
Both Sides of the Table 201
What Angels are Going Through 202
How to Communicate with Angels 204
Loyalty 205
Jason Calacanis Does Not Eat Shit 206
Chapter 27 There is Nothing More Important Than Monthly Updates 211
Signs of Life 211
No News Isn't Good News 212
The Opposite of Monthly Updates 213
Replying to Monthly Updates 217
Chapter 28 Your Disastrous Second Year as an Angel Investor 219
Losing Streak 219
Doubling Down 221
A Bridge to Nowhere 221
Pivot Or Persevere? 225
Chapter 29 Keep Your Head Up 227
Light at the End of the Funnel 227
Panic is Contagious 229
Don't Speak for Your Portfolio Companies 231
Bankroll Management 233
Starting is Easy, Finishing is Hard 234
Learning from Failure 235
Chapter 30 Exits: Greater Companies are Bought, Not Sold 237
How You Get Paid 237
Secondary Shares 239
M&A All Day 241
Little Birds and Big Vultures 242
Smart and Gets Things Done 244
Everybody Wants You 245
Chapter 31 Finding Your Groove 249
What's Your Strategy? 249
Some Angels Bet on Founders 251
Some Angels Want to Solve a Problem 257
Some Angels Bet On Delight 264
Some Angels Bet On Markets 265
Chapter 32 Where Does Your Angel Story End? 267
You Return Less than You Invested 269
You Return What You Invested 270
You Return Two to Five Times What You Invested 271
You Return More Than Five to One Hundred Times What You Invested 271
Acknowledgments 273
