• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
CommentaryBernie Sanders

Dear Bernie Sanders, Sorry I’m The Problem With America

By
Rob May
Rob May
Down Arrow Button Icon
By
Rob May
Rob May
Down Arrow Button Icon
February 22, 2016, 12:26 PM ET

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.

About the Author
By Rob May
See full bioRight Arrow Button Icon

Latest in Commentary

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Commentary

crowell
CommentaryRetirement
Retirees are facing a $345,000 bill they never saw coming — and most aren’t prepared
By Andrew CrowellApril 14, 2026
1 day ago
AI agents are acting like employees, but company structures still treat them like software
CommentaryOkta
AI agents are acting like employees, but company structures still treat them like software
By Dan MountstephenApril 13, 2026
2 days ago
trump
CommentaryWhite House
The futility of Trump’s grandiose personal branding of public assets, from ballrooms and bills to ships and planes
By Jeffrey Sonnenfeld and Steven TianApril 13, 2026
2 days ago
mueller
CommentaryEntrepreneurship
I grew up in a family of entrepreneurs. Here’s what I had to unlearn to build a $1 billion business
By Samuel MuellerApril 12, 2026
3 days ago
boomer
CommentaryLongevity
America is not ready for its own longevity crisis — and 2026 is the wake-up call
By Aimee DeCamillo and Diane TyApril 12, 2026
3 days ago
layoff
CommentaryManagement
The middle manager cuts saving you millions today will cost you everything in 2028
By Kristien TurnerApril 12, 2026
3 days ago

Most Popular

Billionaire philanthropist MacKenzie Scott has donated again—a week after gifting millions to a college, she's just given $70 million to Meals on Wheels America
Success
Billionaire philanthropist MacKenzie Scott has donated again—a week after gifting millions to a college, she's just given $70 million to Meals on Wheels America
By Fortune EditorsApril 13, 2026
2 days ago
Retirees are facing a $345,000 bill they never saw coming — and most aren't prepared
Commentary
Retirees are facing a $345,000 bill they never saw coming — and most aren't prepared
By Fortune EditorsApril 14, 2026
1 day ago
He was coding at 12 like Elon Musk and became one of Google’s youngest-ever CMOs—but now says Gen Z is better off ice skating than learning to code
Success
He was coding at 12 like Elon Musk and became one of Google’s youngest-ever CMOs—but now says Gen Z is better off ice skating than learning to code
By Fortune EditorsApril 14, 2026
1 day ago
Anthropic is facing a wave of user backlash over reports of performance issues with its Claude AI chatbot
AI
Anthropic is facing a wave of user backlash over reports of performance issues with its Claude AI chatbot
By Fortune EditorsApril 14, 2026
1 day ago
Current price of gold as of April 13, 2026
Personal Finance
Current price of gold as of April 13, 2026
By Fortune EditorsApril 13, 2026
2 days ago
Current price of oil as of April 14, 2026
Personal Finance
Current price of oil as of April 14, 2026
By Fortune EditorsApril 14, 2026
22 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.