Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

by Jason Calacanis


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One of Silicon Valley’s most successful angel investors shares his rules for investing in startups.

There are two ways to make money in startups: create something valuable—or invest in the people that are creating valuable things.

Over the past twenty-five years, Jason Calacanis has made a fortune investing in creators, spotting and helping build and fund a number of successful technology startups—investments that have earned him tens of millions of dollars. Now, in this enlightening guide that is sure to become the bible for twenty-first century investors, Calacanis takes potential angels step-by-step through his proven method of creating massive wealth: startups.

As Calacanis makes clear, you can get rich—even if you came from humble beginnings (his dad was a bartender, his mom a nurse), didn’t go to the right schools, and weren’t a top student. The trick is learning how angel investors think. Calacanis takes you inside the minds of these successful moneymen, helping you understand how they prioritize and make the decisions that have resulted in phenomenal profits. He guides you step by step through the process, revealing how leading investors evaluate new ventures, calculating the risks and rewards, and explains how the best startups leverage relationships with angel investors for the best results.

Whether you’re an aspiring investor or a budding entrepreneur, Angel will inspire and educate you on all the ins of outs. Buckle up for a wild ride into the world of angel investing!

Product Details

ISBN-13: 9780062560704
Publisher: HarperCollins Publishers
Publication date: 07/18/2017
Pages: 288
Sales rank: 459,043
Product dimensions: 5.90(w) x 9.10(h) x 1.20(d)

About the Author

Jason Calacanis is a technology entrepreneur, angel investor, and the host of the popular weekly podcast This Week in Startups. The founder of a series of conferences that bring entrepreneurs together with potential investors, he was a “scout” for top-tier Silicon Valley venture capital firm Sequoia Capital and frequently appears in the media. He lives in San Francisco, California.

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

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Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 5 out of 5 based on 0 ratings. 1 reviews.
SueM821 More than 1 year ago
This book is a road map – a constructive way to alternative investments that have heretofore have been a mystery to most. Jason Calacanis is right, there is a lot of untapped, pent up money that is looking for other investment avenues. Moreover, the book give guidelines on how the investor can really get involved. The money invested become more than an abstract, the money is a vehicle for investing in PEOPLE, PRIDE, INGENUITY AND HARD WORK. You worked hard for your money, now constructively help other hard workers.