Vote: Who's the Greatest Rainmaker Ever? Second round matchups include Sam Walton vs. Ray Kroc. Who's going to come out on top?

By Matthew McCreary

Entrepreneur/Getty

Something about March brings out all the best rivalries . . . and we're not talking about the basketball teams for Duke and North Carolina. No, we mean business rivals like Steve Jobs and Michael Dell, Mark Zuckerberg and Jack Dorsey or even Mr. Monopoly vs. Scrooge McDuck.

While the NCAA is in the process of crowning a national champion, we want to know who you think is the world's greatest entrepreneur.

You've already surprised us by voting out big names like Bill Gates and Evan Spiegel in the first round. But who is going to survive round two? Now, it's time to pick your favorite men, women and fictional characters of business and push them into the Sweet 16.

Vote for each matchup below by 4 pm ET on Thursday, March 30 to make your voice heard. Check the site on Friday, March 31 to see who survived and advanced to the Sweet 16 of the Entrepreneur Bracket Madness Challenge.

Vote for your favorite entrepreneurs in other categories here!

Bracket Groups: Innovators | Creators | Moguls & Mentors

Matthew McCreary

Entrepreneur Staff

Associate Editor, Contributed Content

Matthew McCreary is the associate editor for contributed content at Entrepreneur.com.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business News

FedEx Board Member Selected as New Postmaster General

Former Waste Management CEO David Steiner has been selected as the country's 76th Postmaster General.

Business News

Warren Buffett Says to Forget About 10,000 Hours of Practice — If You Want to Master Something, Do This Instead

At the 2025 Berkshire Hathaway shareholders meeting, the "Oracle of Omaha" described the systematic approach to success that has worked so well for him over his storied career.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Business News

Klarna Is Hiring Customer Service Agents After AI Couldn't Cut It on Calls, According to the Company's CEO

Klarna released an AI chatbot and implemented an AI-induced hiring freeze last year.

Buying / Investing in Business

Former Zillow Execs Target $1.3T Market

Co-ownership is creating big opportunities for entrepreneurs.

Growing a Business

Here's How Scaling a Business Really Works (It's Not What You Think)

Scaling isn't just about growth. It's about reinvention.