Be a Startup Superstar: Ignite Your Career Working at a Tech Startup

By Steven Kahan

Find a job and quickly climb the ranks at a tech startup, even if you’re not a techie.

Are you underemployed or struggling to find a fulfilling career? Stuck on a low rung of the corporate ladder and don’t see a way up anytime soon? You’re not alone. Like many recent college grads and people who feel stuck in their corporate jobs, you’ve probably never considered working for a technology company that’s just starting out, especially if you’re not a tech whiz. That doesn’t matter. Tech startups are desperate for talent and creativity in all kinds of fields from people with leadership skills and new ideas—people like you!

If you’re looking to turn your general business know-how into a wildly successful career, Be a Startup Superstar is your guide. Yes, you can love your work, feel energized by your role, and earn the income of your dreams. Author Steven Mark Kahan left his safe corporate job to join his first tech startup, and since then he has helped seven startup companies sell or go public (meaning early employees usually score big). In this breakthrough book, Steve shows you how to:

• Look for five key traits when choosing a tech startup
• Get hired at a tech startup with your existing degree, skills, and experience
• Develop the leadership attributes and entrepreneurial mindset that can launch you to the top
• Make better decisions and get better outcomes in the tech startup world and beyond

Be a Startup Superstar provides the expert insider guidance you need to ignite your career by joining the tech startup revolution.

• Language: English
• Publisher: Wiley
• Release date: Nov 26, 2019
• ISBN: 9781119660712

Book preview

Foreword

What Are You Waiting For? It’s Time to Change the World!

I had been eagerly awaiting my first day at an enormous and very famous Wall Street investment bank. I had hit the big time! Through a family connection, I had landed an entry‐level position as my first job after college. Sure, I would be starting at the ground floor, but I was confident that I had the chops to succeed and move my way up the corporate ladder. I was super excited that morning as I introduced myself to my new manager, a grizzled Wall Street veteran.

However, with one simple action upon meeting me, the manager seemed to delight in crushing my enthusiasm. With his power move, my morning went from the wide‐eyed, first‐day excitement and dreams of a promising career, to imagining mind‐numbing drudgery for the next four decades. Did this guy, who must have seen hundreds of eager, fresh graduates just like me over the years, do this to everyone?

Before I was introduced to my new colleagues, before I knew what my initial role would be, heck, before I was even told where to pee, I was shown how to use the time clock. A time clock! Like you see in movies when they depict old‐time factories. The manager smirked as he gave me my very own punch card with my name on it within 10 minutes of the first day of my career. I was told I had to punch in when I arrived in the morning, again when I went to lunch, when I returned from lunch, and finally when I left in the evening.

A time clock? Really? Did they not trust me? Yikes, I thought, what have I gotten myself into? At that moment, I knew I had to plot my exit from the Fortune 500 company world of work.

It wasn't long before I became the sixth employee of an economic consulting company. What a fantastic career move that was. This was an environment where I was able to carve out my own path based on how my skills and interests aligned with the company's goals.

At the age of 26, I moved to Tokyo to start the company's Japan office. I went from literally punching a time clock at a massive corporation to being the sole employee of my start‐up company outside the home office. Soon I was doing business at a high level and making a difference. And I was having an absolute blast! The fact that I was located 6,500 miles away from the management team, plus the 12‐hour time difference, meant I was working when the rest of the team back in New York was asleep. And this meant that I had total and complete autonomy. I couldn't have been happier.

What a remarkable difference between the drudgery of my work as a tiny part of an enormous Fortune 500 company compared to my new work as a huge part of a small entrepreneurial venture. The lessons I learned about myself and what matters in my life have led me to continue chasing that start‐up culture to this day.

Now, I serve as an advisor to select emerging companies that are working to transform their industries by delivering disruptive products and services. My advisory clients include HubSpot, a company I started working with in 2007 when they had a handful of customers and fewer than 10 employees. I helped the HubSpot team grow the company to more than 60,000 customers in 90 countries, and more than $500 million in annual revenue. My current portfolio of advisory clients in the start‐up world also includes Mynd, Expertfile, YayPay, SlapFive, and InstaViser. I'm also a Go‐To‐Market Limited Partner at Stage 2 Capital, a venture capital firm that invests in start‐up companies.

Be a Startup Superstar is the book I wish I had when I was in college and considering a career in business. It's a deep dive into start‐up culture and includes wonderful stories about what life is like on the inside of successful, high‐growth organizations. I found myself nodding in understanding and appreciation on each page.

This is no academic tome written by somebody who simply studies what others do. Steve Kahan is a highly successful entrepreneur himself. He's been in a number of successful start‐up ventures and has also been in the trenches in the huge‐company world. Steve delivers valuable insights on every page. He's your personal mentor as he guides you through the start‐up world.

The stories you read in these pages show you how to be successful working at a start‐up. In my experience, there is a huge difference in how to approach work at a mega‐corporation versus a start‐up, and Steve tells you exactly how to navigate those differences. In a big company, politics rule. Pleasing the boss is often more important than serving the customer. In the start‐up world, the opposite is true: Success comes from what you do to grow the business, not from what you do to serve the egos of the muckety‐mucks with big titles. Steve uses real‐world examples to point out those differences so you can navigate your career with skill.

Start‐up companies represent an enormous opportunity for smart self‐starters. And these entrepreneurial ventures are always on the lookout for talent, for people like you. CEOs tell me all the time that the most difficult part of their job is finding the passionate people who will make a difference in their companies.

If you want to work for a company where everybody at the cocktail party will recognize the name on your business card, this is not the book for you. If you want somebody else to tell you what to do at work, look elsewhere. However, if you're eager to have fun, make a difference, and change the world, read on! We're counting on you.

— David Meerman Scott, entrepreneur, business growth strategist, and bestselling author of 11 books, including Fanocracy and The New Rules of Marketing and PR www.DavidMeermanScott.com @DMScott

Introduction

Life is no brief candle to me. It is a sort of splendid torch which I have got a hold of for the moment, and I want to make it burn as brightly as possible before handing it on to future generations.

—George Bernard Shaw, playwright

I invite you to imagine you and I are meeting for a dinner appointment. It's a warm evening and we are seated at an outdoor rooftop restaurant overlooking a bright, big city. As the sun sinks into a soft orange glow, and the lights from the buildings illuminate the deepening blue of the streets below, we talk about your college experience. Your face lights up as you tell me about the recognition you received; the camaraderie you experienced with professors, classmates, and friends who challenged your thinking. You express a longing for the structure of the educational framework where success surely comes to those who work hard.

And then our conversation shifts to your current job situation.

You inhale deeply. During college, you had imagined so much success and income in your future, but here you are, full of knowledge and ready to put it to use, ready to prove yourself—but you're stuck. You're stuck in a job where advancement seems long and far away, and your life lacks the richness you desire and expect. You think about your peers, and while there are a few lucky ones who already seem rich and happy (according to their social media posts, anyway), you and most others are still getting by, trying to mitigate risk due to those aforementioned student loans you can no longer defer. You're hoping for a big break or a lucky streak, or a mentor to take an interest in you and help you to navigate through this career conundrum in which you and other young professionals are caught.

I am that mentor, and I'm taking an interest in you. This book provides the insider perspective of a mentor who has been in your exact situation and found a way forward, not just to a great job, but to a great career and massive success, both financial and personal. I want to help you discover your own path to becoming a brave leader in a world that you might have previously overlooked or written off as too risky: the tech startup world.

While working for a startup might seem riskier than working for a large corporation, the potential rewards far outweigh the risks. And, if you're smart, you can mitigate the risk. I will show you where the opportunities lie, how to take advantage of them, and how to choose a start‐up with the best chance for success—whether you're aiming for a tech or nontech role.

Have you ever felt stuck in your job? Have you wondered how you will ever reach the level of success you imagined for yourself? You're not alone. In 2019, amid a robust economy and low unemployment, college graduates struggled to get hired. Upon graduation, 75% didn't have a job lined up at all. It took the average college graduate almost eight months to find a job—all against a backdrop where the average student loan debt was $41,810. Add to that the fact that in the same year, only 31% of employees in the US and Canada felt engaged at work, and I believe this means we have a serious epidemic on our hands.

This epidemic is not new. It nearly infected me.

Many years ago, after graduating college and landing my first job processing claims in a large bureaucratic corporation, I realized that the traditional safe path from school to climbing the corporate ladder was not only high risk for my career, it almost felt like a death trap.

I dared to question my plan and ask myself, What if I could earn a great living and love the work I do?

Even though I had no skills or experience in technology, I left my boring, low‐paying analog job and went to work for a tech start‐up, and it afforded opportunities that would have never been available to me had I remained in a traditional corporate environment.

Since then, I have spent more than 30 years building my career within the tech start‐up world. From my first start‐up job as marketing representative at Database Design to my current role as CMO of Thycotic, I have been blessed to work for seven tech start‐ups. All six of my prior employers have either successfully sold or have gone public, generating more than $3 billion in shareholder value. I've had the privilege of working with hundreds of amazingly talented start‐up entrepreneurs. I've learned about how they think, what they do, and the attitudes they hold that have helped them achieve extraordinary success.

My mission, and the purpose of this book, is to offer the underemployed, college‐educated young person a way out of the death trap. If this is you, keep reading, because I'm about to reveal some of the massive opportunities available in tech start‐ups today, even if you aren't a techie. This book arms you with the knowledge of how to choose the right start‐up, and how to succeed once you get hired.

If you carry a huge student loan debt, the reality is that you can't afford not to work for a start‐up. At a big corporation, pay is limited to incremental annual raises according to the company's well‐entrenched salary policies. On the other hand, in working for a start‐up, the big payoff comes through stock options. Often, a start‐up will offer you a relatively modest starting salary and an opportunity to own a piece of the pie for yourself. This could lead to extremely high compensation later on, assuming the company grows and eventually has a successful exit. I experienced this six times as of this writing, and it's worked out very well, like millions of dollars well.

Working for a start‐up won't just help your bank statement—it will also help you grow professionally at a quicker pace than would be possible at a large corporation. Most start‐ups don't hire with a set idea of your potential or career path. It's the perfect environment to try on different roles and find your zone of genius, and then move up quickly from there. You can come in at an entry‐level position and end up working on big, world‐changing projects alongside the founders where your contributions can be seen and noted. At the right start‐up, you can quickly stand out and gain more responsibilities and opportunities to advance, both in your position of authority and compensation.

Finding exceptional opportunities is only the beginning—you need to be ready to seize them. This book provides you with the seven traits of successful start‐up entrepreneurs—how they act and the attitudes they share in common—and how you can develop and practice the art of leadership until these traits become a part of your own success story.

Be a Startup Superstar is divided into two parts. I recommend that you read the book in its entirety from start to finish, and then go back and reread and dog‐ear the pages you need the most at any given time.

In Part I, I explain the opportunity: tech start‐ups need new and exciting talent of all kinds. Beyond tech skills, these companies seek people with all kinds of talents and creativity who have bold ideas and the leadership skills to bring them to fruition. Of course, the best opportunities often come with a side of risk. Most start‐ups fail, so to give the reader the best chances for success, Part I wraps up with a chapter on the five key traits to look for when selecting a tech start‐up before you apply for a job.

In Part II, I share the seven keys to the C‐suite, which include dozens of golden nuggets about what you need to do to ignite your career in the start‐up world, and how they are vastly different from the traditional corporate norms. You can begin to practice these leadership attributes and entrepreneurial mind‐sets that can propel you to the top and keep you there. These are the traits they don't teach you in college or in on‐the‐job training by a corporation's learning and development team. These are the lost leadership skills that will help you break out from the pack and rise to the top. They will turn your potential for success into reality. They will help you learn the lessons that will empower you to make better decisions and get better outcomes in work and in life itself.

In short, forget climbing the corporate ladder; I'm going to show you how to rocket past every rung and land in the C‐suite in record time. Never before has there been a greater opportunity to rise to the top at great speed. Now is the time to go for it.

Part I

The Best Opportunities Are in Start‐Ups

Tech start‐ups are popping up all over and they need talent—desperately. You don't have to be a techie nerd to succeed in a tech firm. These companies need all kinds of talent and creativity from people with bold ideas and the leadership skills to bring them to fruition.

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