Pre-Internet Entrepreneurs: Cornelius Vanderbilt

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Cornelius Vanderbilt


Entrepreneurs and industry leaders face steep learning curves. That’s part of what makes startup enterprises so thrilling for those engaged in them. Climbing that curve is even more thrilling when you can get paid for it, though—a fact the world’s top entrepreneurs knew long before the days of venture capital and billion-dollar tech companies.

The Lesson: Get Paid to Learn

Cornelius Vanderbilt’s father ran a moderately successful ferry company in the New York City area, and Cornelius himself started working on his father’s boat at a young age. He started his career in the sail and steamboat business—which is where he made his first fortune—being paid to learn the ropes, and he took that mentality with him as he moved along.

Soon after starting his own business with his own boat, the young Vanderbilt was hired to help manage a larger and more established ferry company that travelled non-competing routes in the same area. He kept his own company going and growing while earning a nice salary at someone else’s company, figuring out how to form and implement the successful business and legal strategies necessary for larger enterprises.

When he finally left his position as a manager for the other ferry company, Vanderbilt’s own company had grown tremendously due to the knowledge he had acquired. His profits allowed him to expand and make other investments, building one of the first great fortunes of the 19th century.

The Action: Find the Experts Who Will Pay for Your Training

We don’t all have a father in the steamboat industry, but that doesn’t mean there aren’t people willing to pay for you to learn about your business—especially if you’re willing to provide dedicated and honest labor in return.

Seek out businesses in your niche, or closely related niches, who don’t directly compete with you. If you’re not quite ready to start your own company, find anyone who does what you’d like to be doing in five or ten years. Get hired, offer what knowledge and services you can on a freelance basis, or otherwise make yourself an asset. Get them to pay you for the value you can create, and learn everything you can from your work.

The knowledge and the relationships will pay long-term dividends.


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