Chapter 1
Use the Tech Start-Up Boom to Zoom

A start-up is "the largest group of rebels, rule-breakers, and unconventional thinkers that you can find to create breakthrough change in the world."

-Chris Kane, co-founder and CEO of Munchmoney

Picture this: a lecture hall crammed with students in their last semester. The professor asks for a show of hands-who is planning on applying to a Fortune 500 company, or a top five tech giant? A sea of hands rises. A start-up? Merely a smattering. This was the scene that my friend, Josiah Sternfeld, professor at the McCombs School of Business at the University of Texas at Austin, described to me.

I was surprised. I'd spent my entire career working for a string of tech start-ups, making millions of dollars, countless friends, and indelible memories in the process. It seemed nonsensical to me that so few business school students had considered start-ups, while at the same time so many young companies found themselves in talent droughts. With so many unemployed and underemployed young people, I tried to imagine why so few had raised their hands to apply for a job at a start-up in tech. Maybe because so many are carrying student loan debt, they fear it would be too risky to work for a company with no track record.

But I had to wonder if all those eager undergrads gunning for the Fortune 500 gigs ended up employed. I thought not-as my friend discovered, everyone wants to work for these companies. The big corporates have the name, the prestige, they offer stability, and, because they receive so many applications, they can afford to be highly selective.

I did some research, and, as I suspected, many of the "Big Company or Bust" grads weren't enjoying smooth success in the professional world. Fourteen percent of young adults with bachelor's degrees (or higher),1 and 43% are underemployed, according to a report by the labor analytics firm Burning Glass Technologies.2 So, what's happening here? Why are so many bright, energetic, and creative young people having trouble finding gainful work? Why is it so many recent grads send out hundreds of applications that yield little more than an interview or two?

I read more articles and found out that many of these once-hopeful grads become resigned, defeated, and end up taking jobs in the service sector and living with their parents, licking their wounds before making a charge at an MBA. Or, like me when I first got out of college, they fall into some dead-end, miserable job, and wait for the day they can quit.

If this scenario sounds familiar, if the person I'm describing is you, take heart. It doesn't have to be like this. I once was in your predicament, and I found a way out and never looked back. You have other options. Lots of them. Today, you can find massive opportunities in technology start-ups, and you don't have to be a techie.

The Unprecedented Opportunity in Tech Start-Ups

First, let's examine what a start-up even is. According to the US Small Business Administration, a start-up is a firm that's less than one year old. That, however, provides a poor picture of what actually defines a start-up. My friend Doug Erwin, chairman and principal of RedHouse Associates and a serial tech entrepreneur, offers a more instructive definition. According to him, start-up is a stage. He says, "A company is still in the start-up stage if it operates like it's the last frontier for outlaws, a world where nonconformists can live and create and sell their ideas."

Who doesn't want to be involved in that? At a start-up, you get to play the rough riding rebel on the run, the freewheeling upstart pestering the lumbering, flat-footed law. If you go to work for any of the Fortune 500 or Big Tech, you become one of those bumbling lawmen-a cog, punching in to pass the days pushing papers in a daze.

"Sure," you say, "this sounds great. But how do I get in?" Well, the good news is, start-ups are proliferating at an unprecedented pace. According to the Global Entrepreneurship Monitor, worldwide, three new start-ups open every second. That comes out to 100 million a year.3 In 2017, in the US alone, entrepreneurs created 404,000 new start-ups.4

The growth in start-ups, and the potential for upward mobility, is particularly strong in the technology sector where I have spent my career. My first tech start-up experience began more than 30 years ago-long before the boom. If anything, that sector is an even more lucrative opportunity now, as new technology permeates every aspect of our world-how we work, communicate, travel, eat, exercise, buy things, manage our health, move money around, consume entertainment, and even interact with our pets.

Naturally, the tech sector has become one of the largest components of the US economy. According to CompTIA's Cyberstates 2019 report, nearly 503,000 tech businesses were operating in the US in 2018, marking six consecutive years of growth. Fueled by small, emerging tech businesses, employment in the US technology sector reached 11.8 million workers in 2018, increasing by an average of 200,000 new jobs every year since 2010.5 The tech boom is on, and there's a massive opportunity to reap the rewards for anyone who is willing to rise to the challenge.

This is particularly true now, with an extremely high amount of capital flowing into tech start-ups that shows no signs of stopping. From 2016 through the first half of 2018, 44,000 start-up businesses received more than $282 billion in funding. Forty-one percent of them, nearly half, were technology companies.6

However, life is not all rosy in the start-up world. The market is saturated with ideas and products, so in order to succeed, tech start-ups need a lot more than money. They need a unique and valuable product or service, a solid business plan, intelligent advertising, effective management, and high customer retention. Of course, you can't just go out and buy any of these things, which means that tech start-ups primarily need one thing to succeed: strong teams of people.

According to a 2018 survey of tech start-up CEOs, 66% said the number-one issue keeping them up at night is "hiring good people." Not acquiring customers, not revenue growth, not raising more money.7 While this may seem counterintuitive, it's actually obvious-a company can only go as far as the people who run it will take it.

In the same survey, 60% of CEOs said it was harder to recruit talent in 2018 than it was in 2017. So, finding the right talent is a problem, and it's getting worse. Add that to the fact that 45% of tech start-up CEOs expected to hire 6 to 20 employees in the following year, with 13% saying they expected to hire more than 51 employees in the next year, and you get a talent drought.

Now, you might think that all these jobs tech companies are looking to fill are for software developers and coders. Not so. They need employees in sales, marketing, operations, finance, design, and HR, to name a few.

Why is it so hard for start-ups to find good people? A large part of the problem comes from the monomaniac focus recent graduates have on working for the big companies. Even though tech start-ups offer a huge number of benefits (discussed later in the chapter), they still have to compete with the established giants. In the areas with the largest concentration of tech companies, like New York and the San Francisco Bay area, leviathans like Google, Facebook, and Apple swallow up most of the talent. Everywhere else, the Fortune 500 and locally based incumbent giants send representatives to schools for job fairs where they can sniff out and recruit the talent they need. You'll never see a start-up at a school's job fair. They can't spare the manpower or the cash from the all-hands-on-deck needs of their day-to-day operations. Often, start-ups need to hire people who can work remotely. But can you imagine a start-up in Silicon Valley or Seattle sending a team to Lawrence, Kansas, and a thousand other small towns with big schools to hunt for talent? They can't.

That means that start-up companies are desperate for smart, self-motivated, creative, hardworking, visionary people who want to share their talents in an innovative workplace that's buzzing with energy and opportunity. And they're not just looking for techies. They need people of all types and levels of experience-artsy, techy, young and old, experienced and green, in-person and remote.

Note that I didn't say start-up companies are just looking for "talented people with Ivy League MBAs and prestigious connections." Today's most valuable large companies (such as Apple, Amazon, Airbnb, or Uber) not so long ago were start-ups with humble beginnings. Their initial teams didn't come in with Harvard MBAs and years of experience in corporate jobs. In fact, it's likely that involving leaders with traditional business backgrounds would have impeded these companies' abilities to grow.

Today's start-ups have big ideas, they're well-funded, and they need people who can join the team and help to bring...