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Start a Business After 50 — Advice from YouTube Star Lou Reyes

Why should you start a business after 50? 

Lou Reyes, founder and face of Over50tv and Side Hustle Rules on YouTube, shares his online business insights in this episode of the Online Business Expert Series.

Over50tv offers career advice to people who are over 50. 

Side Hustle Rules is a new channel that provides tips on how to start a side hustle, which Lou firmly believes is the best way to start your online business now — begin with something small and build it up. 

I’ve gotten to know Lou during the time that I’ve been active on YouTube. He’s been an incredible supporter of my channel, and I was excited to interview him! 

He has great tips for anyone who wants to get into the online space and start a business after 50.

And he has a surprising story to tell about how he got his start as an entrepreneur.

Screenshot of Pamela Wilson and Lou Reyes as they talk about why you should start a business after 50.

From aspiring “gangster” to successful entrepreneur

Lou grew up in a housing project in Cleveland, Ohio, which he says wasn’t a great environment.

One day he made a decision — he was going to make some money. Like a lot of kids, he looked at what people around him were doing, and decided to follow suit.

What he saw was people selling drugs. Lou decided he’d do it, too — but do it better.

So he went to his school library and read every book about gangsters and drug dealers he could get his hands on.

He quickly realized that line of work doesn’t end well. 

Lou shifted his focus to business, and never looked back.

“…it started by my desire to get out of a poor situation, to transform my existence, my life. And I went from that to deciding that I’m going to go ahead and become a self-employed person. 

“So then I started reading every book I could about business. That’s how I got to where I’m at today — reading all the time to understand how to get to where I wanted to go.”

Lou Reyes talks about his entrepreneurial journey.

Lou started out in business in his mid-20s with a cleaning service. 

From there he moved on to graphic design. He wasn’t making enough money, and realized he needed to advertise. 

He created a newsletter, started selling ads and his newsletter grew into a chain of 17 publications across the US.

He built the newsletter into a business-to-business magazine, then created a successful trade show business, which he later sold. Now he’s growing his online business on YouTube. 

Lou uses every experience and piece of knowledge he’s gained over the years and combines it with his curiosity and interest in meeting people.

Start a business after 50 with one built-in advantage

One of the great things about being 50 or better is that you’re “bilingual.” You “speak” analog and digital. That gives anyone who wants to start a business after 50 a unique perspective on the online space.

“I think you can use it to your advantage, there’s no question. … We have the advantage of when the internet really started, when everything was launching, we saw it in its infancy.”

Lou created his Over50tv YouTube channel as a way to reach a lot of people. He prefers to start something small and build other businesses around it. 

He knows paying attention to your audience so you get to know what they want and need helps you create the best content marketing

Lou loves YouTube’s analytics tools. It’s one reason he recommends YouTube over other social platforms.

As he examined his analytics for Over50tv, he saw an unmet need — people wanting to learn how to start a business after 50.

“…on Over50tv, anything that talked about starting a side business always got a lot of views. I said, okay, let’s start this other channel. I use the experience that I have starting businesses to help more people.”

Start a business — after 50 or before

Lou knew his experience could provide a solution. Side Hustle Rules was born.

He’s excited about Side Hustle Rules. It’s designed to help people who want to start a business at any age. Starting a small side business is part of his entrepreneurial philosophy.

“I’m always looking at not just what we can do today, but what we can add on to that to help make it strong and build a nice structure.”

He plans to expand his business by building a production studio, which will enable him to create content more efficiently — a key to his online business growth.

Lou’s experience in print shows him the advantages of running an online business.

In the past, he’d only know if an issue of his magazine was successful when the advertisers got a response. To increase revenue, circulation had to increase — along with expenses. 

Digital is different, in response time and the way content is produced. 

By looking at analytics, it’s possible to see immediately what an audience likes, and to monetize content according to audience demand. 

“…it’s an exciting time right now. No time is better than right now. Anybody, anyone, at any age can make money on social media, if they’re just willing to learn.”

I asked Lou what advice he’d give to someone who’s considering video — especially if they’re a little intimidated by going on camera. 

What he said was simple and powerful.

“If you have a solution, don’t worry about how you come across. I mean, who cares? But just be sincere.”

Lou freely admits he cringes when he looks back at his early videos, so this advice is from someone who’s done it.

3 great pieces of advice to help you start your online business now

Having a solution to a problem is a great foundation for you to start your online business now.

Sincerity helps you connect with people. 

Listen. To your audience’s desires, and to people who can help you start your online business now.

And don’t worry about age. 

A chance meeting in a grocery store helped Lou establish Over50tv. He discovered the person he was talking with had a YouTube channel.

“…he was a young dude, a young guy who introduced me to other young people. And I would go to sit with about four or five of them. And we would just share ideas. One day one of those young people said to me … ‘I gotta be honest. When I saw you, I never thought that somebody who looked like you would be interested in YouTube.’” 

Screenshot of Lou Reyes saying you should celebrate your experience and not be intimidated by anything - start your online business now.

Lou acknowledges that some people will be intimidated by asking someone much younger for advice. But one of the smartest things you can do when you start a business after 50 is to never feel intimidated.

Use your experience to boost your confidence — and never talk down to anyone. 

And always be curious.

Want to start a business after 50 but not sure where to begin?

Lou’s advice is to find a mentor — someone who’s experienced the ups and downs in online business. 

He sees some people on YouTube who have successful channels, but in his opinion, a lot of it is luck.

Luck isn’t a replacement for the hard-earned experience a great mentor can share.

“Find somebody who’s got that experience, that’ll help you. …There are many times in our life as an entrepreneur where we’re down, where we have no money, where our bank account is empty, where our friends are few and far between…

“And we need somebody who can connect with us and give us advice, the suggestions that we need, the things that we need to hear that no one else will tell us. So find a mentor.”

No regrets later — start your online business now

Lou wants to encourage you to start your online business now. You don’t want to look back in two or three years and ask yourself why you didn’t start sooner.

Now is the perfect time!

You can find Lou at Over50tv and Side Hustle Rules on YouTube.

Thanks to Lou Reyes for sharing his experience and advice on online business!

Pamela Wilson

Pamela Wilson is the Chief Marketing Officer at DCS. She’s the creator of the Offer Accelerator Program. Learn more about Pamela’s content marketing books, and read reviews of the tools used to run this site.
Pamela Wilson coaches people in midlife to build profitable online businesses
I’m Pamela Wilson

In 2010, at the age of 45, I started this site and grew it into a business that offers freedom, flexibility — and consistent revenue.


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