(Originally appeared on my LinkedIn.)
When my grandmother would ask me what I wanted to be when I grew up as a young child my typical reply was "CEO". I've always fancied myself a business person, dating back to my pre-teen years when I created a lawn mowing business and a leaf raking operation that cornered the neighborhood market, a candy-selling enterprise that locked down a majority of market share in my middle school and, years later, a beloved sneaker boutique in Austin and experiential marketing agency that counted both South by Southwest and ESPN X Games as clients.
But, in the last two years, since co-founding Localeur and serving as its CEO, I've really learned what running a business and being a leader is about. We were named the Best New Startup in Austin in 2013 and we've received praise from the likes of The Today Show, Forbes and TIME along the way as the creators of one of America's best travel apps, but we've also had our share of bumps in the road and near death events. We went nearly two years averaging less than six weeks of money in the bank on average, often went weeks without compensation, I nearly went into personal bankruptcy while maxing my credit cards and blowing through tens of thousands in savings and liquidated stock options, eviction notices and unpaid bill cycles mounted, the hiring and letting go of employees happened, not to mention constantly dealing with routine failed VC pitches, broken promises from inexperienced investors and being copied by highly-resourced competitors like Google and Foursquare.
But here we are, nearly 30 months since starting the business, and we're experiencing our best growth ever, having grown more than 700% since December, we've partnered with companies like Uber and HotelTonight along the way, we have secured investments from leaders of some of America's most notable companies including Facebook and JPMorganChase, and we're now serving thousands of travelers on a daily basis from around the world including the 16 major U.S. cities we serve up recommendations on the best places to eat, drink and play exclusively from locals today. I'm not yet ready to consider myself successful nor our business, but it's very clear that we're well on our way outperforming the early years of growth our main competitor, Yelp, experienced in the mid-2000s with millions more in funding and far more experienced leadership. Part of our growth as a business has been a reflection of my personal growth as a CEO, and I want to share a little bit about how I've become a better leader.
What I've learned over the past few years is that there's no single thing that can make you successful as a business leader. Having what it takes to become an entrepreneur or a CEO in tech is no different. Instead, it's a collection of attributes and experiences that shape you into a business leader more so than the existence of a single quality or "it" factor.
However, if there was a single characteristic I believe may help someone along the path of becoming a leader in their chosen field, business especially, it would be the constant desire to improve and learn. There's no better example of this than surrounding yourself with people who can teach you new things and share new perspectives; often times that means getting a mentor, hiring people smarter than yourself and building a board of directors. Another way to surround yourself with smart people and create new opportunities to improve and learn is to read. Whether you're a Kindle owner or you buy those hardback things in bookshops, as I do, reading books is a sure-fire way to enhance your ability to lead. Here are some of the books that have helped me become a CEO.
Getting There by Gillian Zoe Segal - This is a great simple read for anyone looking for inspiration to get started. With stories from everyone from Warren Buffett to Anderson Cooper and Rachel Zoe, you'll get a good mix of stories of early struggle and recent triumph that prove no one's journey to success is paved in advance.
Why We Can't Wait by Rev. Dr. Martin Luther King, Jr. - You can't drop the Doctor nor the Reverend from MLK's name because both are so important; both his education and his faith. As a CEO, you often need to be studied and to be believed. In this book, while jailed in Birmingham, he shares a letter to fellow clergy that may be the most important letter in American history. At a time when the Charleston tragedy show us how far we still have to go to heal America's racial wounds, MLK's book is an annual read for me to honor his legacy and study up on leadership at the highest, most culturally and morally significant of levels.
Zero to One by Peter Thiel - I learned a lot about the lonely path of being a tech CEO from this book. Excerpt: "People are scared of secrets because they are scared of being wrong. By definition, a secret hasn't been vetted by the mainstream. If your goal is to never make a mistake in your life, you shouldn't look for secrets. The prospect of being lonely but right - dedicating your life to something that no one else believes in - is already hard. The prospect of being lonely and wrong can be unbearable..."
The Obstacle is the Way by Ryan Holiday - This is a short and quick read that will go a long way in becoming a leader. I say that from experience. At one of my lowest points as CEO of Localeur, I read this book and was instantly recharged and feeling good about our prospects as a company during one of our most challenging times so far.
How Google Works by Eric Schmidt and Jonathan Rosenberg - Whether you're reading books about the inner workings of Google, like this one, or Apple, or some other behemoth company, you're going to pick up at least one or two new weapons for your arsenal as a leader. I surely did.
Things a Little Bird Told Me by Biz Stone - A lot of people stumble into leadership and I liked this book a lot because while Biz was always a creative person, this book chronicles his journey from that of a artsy/designer type into a true business leader. I can relate to this somewhat having majored in communications in college rather than business, and having started my career as a speechwriter rather than an engineer or business consultant like many in tech.
Good to Great by Jim Collins - Out of all the essential business books of the last 20 to 30 years, this one is probably #1. This is the kind of book every executive should read on their journey to becoming a CEO and the kind of book every CEO should read bi-annually to stay sharp as a leader.
Lean In by Sheryl Sandberg - This isn't a PC pick; this book is truly revolutionary. Growing up with just a single mom in the house helped me understand the educational and professional sacrifices many women make, but this book helped me go a step further to realize the ways in which I, as a man, can do more to help women reach their potential as well. My first board member also happens to be a women, my mentor and former boss, Heather Brunner, and I wouldn't have had it any other way.
Startup CEO by Matt Blumberg - I'm not quite wrapped with this one, but already I've dog-eared about 40 pages of the book and made about 100 mental notes. This isn't one of those fluffy business books. This is a very thoughtful, insightful book with tons of guidance on the strategic and tactical elements of being a CEO.
The Hard Thing About Hard Things by Ben Horowitz - He's one of the biggest talkers in tech for a reason; the guy knows his shit. Being a CEO is lonely and it's hard. Ben pulls no punches in this book on his way to doling out some of the most helpful advice you'll ever get minus all the success bias many tech CEOs and VCs are known for.
Lucky or Smart by Bo Peabody - Long before I become a tech CEO, I was a kid in college trying to learn more about business without being a business major. Reading this book was one of the first big steps I took and I'm so thankful I did because it's since helped me to trust both my instinct and the smarter technical folks on our team at Localeur when big decisions had to be made.
Whatever it Takes by Paul Tough - Reading tech and business books can help you become a CEO but so can reading about leaders in other difficult fields. I'm not sure if there's a more challenging occupation than being an educator and this book shares the unique challenges Harlem Children's Zone founder Geoffrey Canada faced en route to building a program that has transformed education in one of America's toughest neighborhoods.
Confidence Men by Ron Suskind - Business and politics go together at times, and this is one of the best books I've read that shows the back-and-forth relationship the two have. Set during the financial crisis of 2008-09 with Wall Street's mismanagement and Obama's candidacy-then-presidency, you get the feeling this is the kind of book you learn from by remembering hard lessons in failure, poor judgment, networking and quick thinking.
The Dog Stars by Peter Heller - People who read fiction are more creative, and to be a CEO and leader is to think creatively about how to solve problems. The problems presented to the main character of this novel by Cormac McCarthy-esque author Peter Heller are ones that fellow business leaders will be intrigued by enough to view the solutions much like those found in business cases in Harvard Business Review, only in a much more post-apocalyptic setting.
1Q84 by Haruki Murakami - Probably the biggest outlier on the list because business and personal leadership aren't really topics you'll find in the book, but Murakami has a way of taking you through unique experiences in a way that is both unexpected, twisted and mind-bending. Basically, it's a book about being a founder / CEO without it being anything about business or industry. Just trust me.