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A Practical Way to Get Rich . . . and Die Trying: A Memoir About Risking It All

A Practical Way to Get Rich . . . and Die Trying: A Memoir About Risking It All

by John Roa


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"A scathingly honest memoir of entrepreneurship's dark reality... I would advise every entrepreneur—or anyone who dreams of becoming one—to read this book."
—Eric Schurenberg - CEO, Fast Company and Inc.

A young tech entrepreneur's memoir of building his hugely successful company and the mental and physical price he paid for it

At the age of twenty-six, John Roa was an aspiring but struggling entrepreneur. He was broke, racking up debt, and ready to give up on his dream of being self-made. In a final effort, he founded the design firm ÄKTA, which quickly became one of the fastest growing startups in America, and just five years later, he sold it for a fortune to Salesforce, the largest company in San Francisco.

This is his account of rising from a self-described below-average student to becoming a poster boy for the successful young entrepreneur, while nearly destroying himself in the process. His journey is an absurd, twisting, and often comical story of talent, luck, rapidly changing technology, larger-than-life personalities, sex, gambling, and excessive alcohol and drug consumption—which ultimately took their toll, resulting in a spectacular burnout that he almost didn’t survive. As he healed in the aftermath, he began to question the ethos that had brought him to that dark place, and over time, came to realize how common these debilitating issues are in entrepreneurship, even if they are rarely discussed openly.

Rather than another glamorous rags-to-riches saga, A Practical Way to Get Rich . . . and Die Trying is a cautionary and deeply honest memoir about the price of success for ambitious young people, who are so often unprepared for the adversity, mental health issues, and abuse that can come along with “making it.” It also serves as the foundation for a campaign of honesty and vulnerability, in an industry that currently lacks both.

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Product Details

ISBN-13: 9781984881229
Publisher: Penguin Publishing Group
Publication date: 09/08/2020
Pages: 320
Sales rank: 1,130,521
Product dimensions: 5.90(w) x 8.90(h) x 1.20(d)

About the Author

John Roa is an entrepreneur, technologist, philanthropist, international business investor, and podcast host. In 2010, he founded innovation and design consultancy ÄKTA, which was acquired by Salesforce in 2015. He now runs the investment group Roa Ventures and nonprofit organization Digital Hope. He lives in New York City.

Read an Excerpt

I'm excited to share this story with you. I'm also quite petrified, as I'm about to tell strangers all about my crazy life, wildest proclivities, and darkest secrets.
Well, too late now. So much for being a private person.
At the age of twenty-six, I was dead broke and ready to give up on my life goal of being an entrepreneur. At twenty-nine, I was a millionaire and running one of the fastest-growing companies in America. Two years later, I sold my company and my mind was ruined.
To you, my story may be entertaining, motivational, demotivational, funny, unbelievable, familiar, sad, or absurd. That depends on your perspective. All I can promise you is that it's honest: a true account of how one young man navigated his way through the painful yet powerful lessons of success. It's the type of story I wish I could have read half a lifetime ago as I prepared for my own entrepreneurial journey, rather than yet another whitewashed, bullshit memoir about what reaching the top in business supposedly looks like.
I've always thought of myself as a pretty normal guy. I grew up in the Midwest with three siblings and a loving family. We didn't have a ton of money, but we did have a golden retriever and presents under the Christmas tree. Having my life defined by high-stakes entrepreneurship wasn't exactly my plan. I had never met another entrepreneur in my youth, and, frankly, didn't even know there was a term for people like me, who love hustling, doing deals, solving problems, and taking risks. I dove down that rabbit hole, and what happened next was anything but normal.
For better or worse, society today is defined by tech entrepreneurship. Technology has changed how we communicate, find love, travel down the street, stay in touch with friends, and battle disease. No other industry produces more billionaires and billion-dollar returns. It's virtually the only industry in which anyone with a good idea can go on to change the fabric of the world in a matter of years and become incomprehensibly wealthy.
It's the modern-day gold rush-except that the prospectors of the 1850s knew that when they went west, they likely weren't coming back, at least not with their physical and emotional health intact. Today, we prefer to keep that possibility a secret. No one wants to talk about the price we entrepreneurs pay in the pursuit.
Entrepreneurship is a wide-ranging topic. God bless the ambitious individuals who set up a hot dog stand or take over a small family business, though they aren't my focus in this memoir. My subject is those who go for glory, and are willing to leave limbs on the field in their pursuit. The maniacs who trade safety, sanity, and sensibilities for a shot at becoming rich and even famous. Or, for a chance to permanently change the world.
That's the lens that formed the foundation for this book, that made me ask: What really makes an entrepreneur? What separates us from normal people? Are we really as crazy as we seem? Or is it the current culture of entrepreneurship that forces us to do crazy things to succeed? And finally, what did I really learn from the journey?
This is a raw, behind-the-scenes look at my path to prosperity at a tender age, with all of its flaws and absurdity. Other successful entrepreneurs' stories will differ from mine, but based on numerous private conversations with my self-starting brethren, the core themes of what I experienced are far more common than you may think.
Winning in this game isn't necessarily clean, dignified, or healthy, and that must be accepted and acknowledged. My biggest issue with the narrative of success today is that in business, we are pressured to always look strong and godly, even during difficult periods. This quickly becomes a toxic model that aspiring entrepreneurs are forced to emulate, and then when they struggle, which is inevitable, they are led to believe they are the only ones doing so, or that they are somehow doing it wrong because everyone else makes it look so easy and graceful. In every single business memoir I've read, the author somehow makes even the worst aspects of the job sound aspirational.
I believe we could benefit from illuminating the realities of this closely guarded world. Rather than the never-ending books and films that have been carefully manipulated to perpetuate dangerous myths about business and success, I think there should be a candid discussion of some hard truths. Let's talk about why entrepreneurs have 60 percent more mental health issues than the general public, or why the suicide rate among youth in Silicon Valley is four times the national average. Let's talk about the culture that encourages us to risk everything in the pursuit of success, and whether that is the right attitude.
The predominant culture in startups today doesn't even try to disguise itself. "Move fast and break things" is the mantra of the startup founder. "Fake it 'til you make it" is our rallying cry. "Do whatever it takes to succeed" is the unspoken golden rule. "No pain, no gain" is motivating only until you consider how toxic that guidance is. Entrepreneurs are incentivized to put personal wellness aside, manipulate the truth, take outsized risk, and cheat where necessary in order to win.
The worst part of this mindset is we also lie to ourselves. We become so accustomed to our perceived worlds that they can become a new reality. We end up believing our own bullshit, further blurring the lines between what is real and not. We exist in a perpetual reality distortion field. This delusion makes us isolate ourselves, ignore warning signs, build on artificial confidence, and push ourselves and the people around us too far. And if things go bad, we are suddenly confronted with the mountain of decisions we shouldn't have made and lies we must face, and only then do we become aware of the consequences.
Imagine being told there is a pot of gold atop a huge mountain in front of you. Even though you can't see the summit, you think to yourself, I bet I can climb that. You take no consideration of safety or risk. No gear. No net. Just start climbing. That is entrepreneurship in a nutshell.
This mentality defined my rise to the top and fall to the bottom. While I'm ultimately proud of what I accomplished, there is also a lot to be said about what I learned, the downsides of my lifestyle, and what I would have done differently. Until recently, I never allowed myself to be honest about those things, because I felt an obligation to play the part and not show vulnerability publicly. When asked about my experiences in an interview or onstage at a conference, I would perpetuate the same heroic narratives that everyone else does in business. Often I'd be speaking to young, impressionable people, and I believed this made me sound smart and strong.
I would play the role of the impervious young CEO they all wanted to see. I would hide my humanity and struggles. I refused to show any sign of what I perceived as weakness. I wanted people to aspire to be me. I suppose I still do, but for different reasons. I've chosen to no longer perpetuate the superhero myths of entrepreneurship.
Instead, I now want to embark on a campaign of vulnerability and honesty, in an industry that currently lacks both. What you're about to read is the beginning of that journey, and I hope it makes this book feel a little bit more approachable than others in the genre. I didn't create a well-known, billion-dollar company. I am not famous. I didn't have anyone backing me. I'm just a guy from a suburb in Detroit who fell upward through the world of startups.
The idea of baring my soul to the world is, I admit, unnerving. I worry about the damage it could do to my reputation and relationships-at least from anyone who wants to judge me for my behavior when I was making too much money at too young an age. Or for what it feels like to have a drug- and sex-fueled bender you almost don't wake up from. Or for some of the vile ways mental illness takes hold of your mind as you try to handle the stress and pressure of running a tech company with lightning-fast growth. There were many times I almost buried this book in the ground, but I stopped myself from doing so because of the important discourse I hope it can foster. In order to facilitate those discussions, I've chosen to lead by example. That is why you're now reading this.
This is a true story based on my best recollections over three decades of my life. In some instances, I had to compress or rearrange events to facilitate the narrative. Because hundreds of people involved in my story were innocent bystanders, I've taken certain liberties by changing some names and recreated dialogue to protect their privacy. Others don't deserve that courtesy.
A Practical Way to Get Rich . . . and Die Trying
1 | Vegas (2014)
The maid at the door looked horrified.
I could think of three potential reasons as to why: First, I probably looked like a strung out pirate, staring at her through one twitching, deeply bloodshot eye, the light from the hallway making it far too hard to open the other.
Second, it could have been the smear of dried blood across my stomach. Seemingly, I hoped, from the blistered, fresh tattoo on my forearm, which I had just now noticed.
Third, and most likely, was that I had answered the door stark naked. Despite her best effort, she stared down at my old boy with a sickened look, as if there were a crocodile attached to it, and then probably reconsidered her choice of employment.
This is Vegas. She's seen worse, I thought.
Our eyes remained locked for a few more moments before I shut the door without a word. I felt my way to the Wynn's plush curtains and ripped them open, which sent the midday light flooding into the room. The sun was a knife to the center of my brain, amplifying the pounding in my temples and the toxic feeling in my chest. My mouth tasted evil.
I pondered this bizarre wasteland that had become my all-too-frequent playground of choice. My detachment. I then noticed what looked like the frosted ghost of someone's ass on the window. The two girls in the bed behind me explained that. I suddenly had a flashback to the prior night's hedonistic chaos, to our bodies smashing against that window-the only thing between us and a five-hundred-foot drop-thinking to myself, I wonder how strong this glass is?, and not being terribly concerned with the answer. There were worse ways to go, I figured.
They laid snoring in a naked tangle on top of the covers, a mess of hair, tattoos, and dried sweat. I couldn't tell you a single thing about them. If I was supposed to feel anything at that moment, I didn't.
I considered the mayhem of the room and then saw the bedside clock, which revealed that I was dangerously close to missing my flight-for the third day in a row. Through fogged vision, I threw my clothes haphazardly into an expensive leather bag, rubbing a tiny pile of cocaine that was left on the table across my gums. As it turned out, I accidentally took one of the girl's dresses with me. I also left behind an $18,000 watch and three shoes.
Back to Chicago. Back to work. Back to my life of organized chaos overlaid with a thick patina of professionalism. Back to my throne as the thirty-year-old CEO of one of the fastest-growing companies in America.
Twelve hours later I was in the back of an ambulance. I knew I was dying.

Table of Contents

Introduction xi

1 Vegas (2014) 1

Part 1 The Pledge

2 Motor City 5

3 Doug and the Guitar 7

4 Vince and the Computer 10

5 Onsite Operations 14

6 Ascension 17

7 Expansion 22

8 Connivance 26

9 Hustle 28

10 Heading West 30

11 Isaac the Designer 32

12 WiredLabs 36

13 Kalamazoo 38

14 Down Again 41

15 End of Academia 46

16 Europe 50

17 The Big Break 52

18 Varsoft Technologies 56

19 Transformation 61

20 Preparation 64

21 Fountainhead 69

22 Kevin Lerash 74

23 Vosges 78

24 The Proposal 82

25 The Pitch 84

26 Bankrolled 89

27 Topgolf 91

28 In Business 96

Part 2 The Turn

29 The Genius Misfits 103

30 The First Day 107

31 The Show 110

32 Execution 114

33 Excelerate 117

34 Growing Up 119

35 Newton's Cradle 123

36 The Impostor 125

37 The Bros 128

38 Moving On Up 134

39 The Battle 139

40 The War 142

41 Spider-Man 145

42 The Big Fish 149

43 Agencies 154

44 The Warden 158

45 The Show 165

46 Maximus 168

47 Grow, Baby, Grow 173

48 The Promised Land 178

49 Growth Rate 183

50 The Inca Trail 185

51 The Grandmaster 187

52 The Bells 190

53 The Desert 191

54 The Gala 196

55 Fueled 203

56 The Thesis 211

57 Printing Money 214

Part 3 The Prestige

58 Machina 221

59 The Empty Chair 224

60 Nouveau 226

61 The Catamaran 229

62 The Demons 232

63 The Takeover 236

64 The Plume 239

65 Icarus 242

66 The Crash 245

67 The Light 248

68 Pot of Gold 251

69 Concrete Boxes 255

70 The Messiah 258

71 Double Barrel 261

72 Four-Thirds 267

73 The Florida Man 270

74 The Road Show 273

75 The Hawks 277

76 The Dream 281

77 On Sale 284

78 Magnum Opus 287

79 The Final Day 290

80 Fin 292

Afterword 297

Acknowledgments 301

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