by Rob May, February 22, 2016
A tech CEO feels Berned.
I agree with Bernie Sanders. The economy is rigged. In fact, it’s what my father, who is very conservative, taught me about life. Some find it surprising because the general position of liberals seems to be that conservatives don’t realize, or won’t acknowledge, this rigged economy. But my dad’s advice to me time and time again was that the world was rigged and the only way I could make it was to work harder than the people who were in charge of the rigging.
A few years ago I was walking through Harvard Square when a woman holding flyers for Elizabeth Warren stepped in front of me. She asked if I thought the government should pay off student’s debts. I don’t think the government should, but, then again I never had student loans. No, it wasn’t because I was from a wealthy family. I never had student loans because I worked every semester I was in college, and during some summers, I worked two jobs. I did this because I thought the world was rigged against me.
I missed out on a lot, because I worked so much. I didn’t have the life like many of the college students I’ve hired in the last few years. They study what they love — philosophy, political science, art, regardless of whether or not they have good job prospects. They travel. Mostly they seem to go to Vietnam and Cambodia. They eat out a lot more than I did at their age. They know all the trendy restaurants and hot bars.
When I got out of college, I lived well below my means, saving $25,000 so I could start my first business. That business failed miserably. I ended up losing over $50,000 total. It took three years to pay off the credit card debt I wracked up.
Over the next decade, I started three more businesses. Two of which failed. For one of them, a video yellow pages product I built with a friend in 2007, I used to take my vacation days from my “real” job and go door to door, selling video listings to small businesses. I lost a lot of my own money, as my disposable income never went to travel or luxury goods of any kind. It went to business ideas.
I kept at it because I believe, much like Bernie, that the world was rigged against me. I spent every evening after my day job working on side projects, learning new skills, reading. I didn’t own a TV for a long time and, even to this day, I’ve never seen any of the classic shows people like to discuss: The Sopranos, Breaking Bad, Mad Men, Game Of Thrones. I was working while they were on.
When I finally had a company that was successful, the experience of running it was more stressful than you could ever imagine. I had to deal with some really rough things. There was the time when, on the day we were supposed to close our Series C funding round, the lead investor called and said they weren’t going to wire the money. We had six weeks of cash left, and now I had to figure out what to do. There was the time when two of my executives quit within 10 days of each other, making my board and employees all wonder what was going on, and if there was something detrimental going on at the company that I wasn’t telling them.
There was a board meeting where, I took so many rapid fire shots from board members that one of my executives told me afterwards that he would never want to be a CEO and go through something like that. There were things that I can’t write about publicly, but that, if you have ever run a company, you know what I’m talking about. It really sucks to be in charge sometimes.
Despite the strain that entrepreneurship put on my finances, my health, and my personal relationships, I kept at it because I wanted to be successful. And eventually, yes, I became a millionaire. It only took 15 years.
Along the way, I learned a lot. I created over 100 jobs. And in the end I helped build something useful for thousands of companies around the world. But when I hear Bernie speak, I feel like I’m the problem with America. I’m one of those millionaires he mentions who should pay more taxes. I’m the bad guy. I’m the white male who is only successful because everything was handed to me. I don’t deserve the money I made. All the things I sacrificed don’t matter. The additional stress I was under doesn’t matter. The risks I took don’t matter. According to Bernie, the world needs fewer people like me, and more people like the smart Yale student who majors in something useless, travels the world, and then graduates with $100,000 in debt that people like me should pay off via higher taxes.
Yes, the economy is rigged. Any economic structure will favor some at the expense of others. But the wonderful thing about America is that if you are willing to make the right sacrifices, you can achieve whatever you want. Unfortunately, we’ve come to believe that achievement should be easy. Changing that attitude is the first step towards making yourself more successful.
Rob May is the co-founder and CEO of Talla, a Massachusetts-based developer of an intelligent virtual assistant for recruiting teams.