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3 Billionaire Entrepreneurs Who Started in Their 50s

We talk a lot about 20-something-year-olds who have started successful businesses and become multimillionaires, but what about the successful entrepreneurs who are over 50 years old (and beyond!) who have created super significant businesses?!

They matter too!

In this post, we’re going to talk about 3 inspiring successful entrepreneurs over 50 and a lot of the things they did so that you, regardless of your age, can get any business off the ground.

Let’s get into it.

3 Successful Entrepreneurs Who Started in Their 50s

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Successful Entrepreneur Over 50 #1: Julie Wainwright of The RealReal

Julie Wainwright founded The RealReal in her mid 50s.

She was actually employed as the CEO of 7 different companies before finally deciding to start her own!

I love that.

One of the companies she ran (, a website that sold household pet supplies) actually failed when they ran out of money during the DotCom bubble! But in 2011, she was actually bored of all the CEO jobs and finally decided to make the leap and started her own company

Go Julie.

(PS, if you’re curious what a CEO does, check out my day in the life of a CEO here.)

So how did Julie get the idea for The RealReal and what is it?

She started out with three criteria:

  • She wanted to create an ecommerce company
  • She wanted to create something that couldn’t be knocked off by dropshipping or Amazon or Ebay
  • She wanted to sell to a huge market

Julie got the inspiration for the perfect niche when one of her friends told her that she frequently bought second hand luxury goods at high end boutiques stores. After doing some research, Julie realized that this is a multi billion dollar industry!!

I had no clue.

The second-hand luxury market checked off her boxes, so The RealReal was born.

In the early days of The RealReal, she started it from her home with just a couple of employees, and her vision was to create a marketplace where sellers could authenticate and sell pre-owned luxury brands like Chanel, Hermes, and Louis Vuitton.

Even though she was in the CEO chair for decades, she wasn’t afraid to get her hands dirty! She drove around in a U-Haul truck, picked up packages from sellers’ homes, and answered customer service calls herself.

In the first year The RealReal did $10 million in sales — that’s so impressive! — and in 2019 she took the company public.

Now, it’s been over 10 years since she opened the doors and today the business is worth over 1 billion dollars!

What are some lessons that we can learn from Julie?

  • Find a niche where you can easily win. Everyone is doing dropshipping or affiliate marketing (at least the get rich quick scammers are) but what’s an area that you’re excited about and think no one else could copy you?
  • Be humble. Julie had been a CEO for 7 different companies, but she was still out there doing deliveries herself! That’s something I always encourage everyone who’s starting a business, including myself: do the dishes. Don’t just assume you can outsource everything. Try to actually understand it first, then start hiring people for those roles.
  • When you’re older, you have resources. If you’re younger, your disadvantage is that you don’t have resources. But for Julie, she probably has the advantage of experience, savings, a deeper network, more knowledge on how to hire, etc. So think about what you can leverage, regardless of your age.

Successful Entrepreneur Over 50: Bernie Marcus of The Home Depot

This is the story about how Bernie Marcus co-founded The Home Depot after getting fired at 50.

Bernie grew up in a tough neighborhood and he wanted to become a doctor, but his family couldn’t afford the tuition for medical school so he worked as a pharmacist at a drugstore instead. But, he eventually realized that he was more excited about the retailing side of the business so he transitioned to working retail at a cosmetics company.

I like this guy.

He ended up working his way up the corporate ladder and eventually became the CEO of the Handy Dan home improvement company — but not for long because he got fired along with his future co-founder, Arthur Blank, during a corporate restructuring of Handy Dan’s parent company.

So what did Bernie do?

He probably complained a little bit, like anyone would do, but instead of dwelling on it, he saw it as an opportunity to FINALLY start his own home improvement company!

This happened a lot during the pandemic. I heard of a lot of people who were forced to start businesses and do things they’d never done before — and it worked out for them! Sometimes limitations or being forced into these kinds of things helps you take the leap on something you otherwise may not have done when you were comfortable.

From working at Handy Dan, Bernie had a deep understanding of retail and home improvement so he knew that the opportunity for his business to stand out was in their customer service. He knew that they could do it better.

How they started Home Depot

Bernie and Arthur had a HUGE vision for what The Home Depot could become. Their vision was to create a super home improvement store that offered the biggest selection of goods at the lowest prices with the best customer service.

Now remember, this is at a time when there were big-box stores like Kmart, Sears, and Mervyn’s. Opening up a massive hardware store wasn’t easy! So big dreams required a big team.

So Bernie and Arthur brought on two more co-founders to help build the company — Ken Langone, who was an investment banker and Pat Farrah who was merchandising genius — and they opened their first two Home Depot stores in Atlanta in 1979.

But they actually had a hard time getting customers in the door at first!!

And I love this. I think persistence and perseverance test how much you really want success.

So in an effort to get customers to come into the store, they did a promotional stunt where they handed out $1 bills to pedestrians and invited them to come to the store.

It didn’t work. Most people just kept the dollar.

But they focused on the basics: huge selection of products, really great prices, and amazing customer service. And slowly, they built up that loyal customer base and word of mouth began to spread.

So why did Home Depot succeed?

  • Make it convenient. They were the first ever one-stop-shop home improvement store in the country! Before, customers had to go to multiple places to get what they needed. So think about for your own business, how you can combine things to make it more convenient for your customers.
  • Their customer service staff was phenomenal. Instead of hiring regular people who weren’t handy, they hired craftspeople that could truly help customers out. Think about how you can offer top-quality service to your customers, and give it to them!
  • Start a business around what you’re interested in. What’s a magnet for you? Where are you actually being driven? Early on in his career, Bernie was interested in retail so he pursued it until it led him to starting Home Depot. He followed his interests.

Successful Entrepreneur Over 50 #3: Leo Goodwin of GEICO

Leo Goodwin and his wife started GEICO when they were 50 years old!!

A little background about Leo…

He was trained as an accountant but became an insurance salesman.

Alright. Both pretty boring jobs.

No offense to any accountants and insurance salespeople out there.

So how did Leo spot an incredible business opportunity?

He realized that there was a HUGE business in selling insurance to government employees.

Wait, hold on… Why?

Government employees have super stable, boring jobs that are very low risk, so the employees themselves are very low-risk to insure which to insurance companies means…

Cha-ching $$$!

The insurance options for government employees at the time weren’t great, so Leo and his wife created GEICO.

Which, I don’t know if you know this fun fact, stands for:

  • Government
  • Employees
  • Insurance
  • Company

Did y’all know that?!

In the early days of GEICO, the #1 goal was to reduce business costs in order to offer insurance at a lower price than their competitors.

This is something that I think is really powerful — knowing the unique thing about your business that it stands for. For GEICO it was simple: reducing their business costs so they could have the lowest price in the market.

In their first year, GEICO wrote about 3700 policies and had 12 employees — which is impressive for a new business. In 1940, after they had been losing money for several years, they finally turned their first profit. And 6 years after they opened their doors, Warren Buffet actually purchased the entire GEICO company!

To this day, it’s one of the top ways he’s made most of his money (over $41.6 billion from GEICO alone).

Interesting, right?

What are some lessons you can learn from Leo?

  • Find customers that aren’t getting marketed to. Where are customers being underserved in your niche? Maybe competitors are ignoring them or there’s an opportunity no one else can see. Think about how you can help those customers out.
  • You don’t have to be an expert. Who cares about your age. Who cares that you don’t have experience. Most of the greatest inventions happened by non-experts. People who don’t know what they can’t do are doing the impossible. So no matter your age, whether you’re 15 or 65 — start planting seeds and making stuff happen RIGHT NOW.

Who’s an older entrepreneur that you’re inspired by? Tell me in the comments down below.


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One response to “3 Billionaire Entrepreneurs Who Started in Their 50s”

May 10, 2022 at 8:07 am

GEICO fun facts! Inspiring read. Keep up the good work Noah ??

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