How to Start a Business at 50+: 7 Inspirational Entrepreneurs Share Their Experience

Senior entrepreneurs interview

Mark Zuckerberg founded Facebook at 19. Steve Jobs started Apple at 21. Elon Musk co-founded the web software company Zip2 at 24 –– seems that the whole world belongs to the youngest. Is it possible to succeed later in life, for example, if you’re 50? Or have you already missed your boat?

We all heard and saw those stories of recent college graduates starting a billion-dollar businesses out of their garages. That’s a sweet Hollywood-stereotyped fairytale, which sells well and makes even 30-year-olds feel that their time has gone. In fact, such stories don’t happen that often and many successful entrepreneurs started much later in life.

Vera Wang began to design her famous wedding dresses when she was 39. Ray Kroc was 52 when he opened his first McDonald’s franchise. Fauja Singh, a marathon runner, ran his first marathon when he turned 90. And this list goes on and on.

It seems that building your dream life at the age of 50 requires lots of courage and determination. But if we look at the situation from a different angle, the fifties are a perfect time for self-development. Kids have grown up, you have a certain professional experience and financial background, and you still feel youthful and energetic. Why not cherish something for yourself?

We talked to several people over 50 who have started successful projects at an older age. They shared their experiences and useful tips, and shed light on what building your business later in life looks like.

We thank everybody who contributed to this article:

Some inspiring (and unexpected) statistics

Before you dive in, let’s look at some statistics about the way age may influence future success in business. Benjamin Jones, a professor of strategy at the Kellogg School, has suggested an answer to the question “How old should an entrepreneur be to become successful?”

His research showed that, contrary to popular thinking, the best entrepreneurs tend to be middle-aged. The average founder of the fastest-growing tech company was 45 at the time of its founding. Furthermore, a given 50-year-old entrepreneur is nearly twice as likely to have a runaway success as a 30-year-old.

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Here’s an interactive tool, in which you can compare the ages of entrepreneurs to see who is more likely to found a successful startup. Source: Kellogg Insight

Why does this happen? The explanation may be as follows: older people have had decades to build the business and develop leadership skills that help their projects succeed. And while they may be less into certain consumer trends, they may know quite a bit more about other business opportunities.

Sounds promising, right? The experiences our interviewees shared with us just confirm the results of this study. Let’s see what traps and pitfalls they had to face on their way to building their own businesses.

P.S. We didn’t mean to invite women-only participants –– it happened by chance 🙃

How old were you when you became an entrepreneur? What made you decide to start a business?

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

I created my Instagram blog when I was 69. My aim was to help women get rid of their fear of aging. At the same time, I became a popular ageless model –– the media even called me a local Maye Musk. In half a year I started cooperating with advertising agencies.

Lisa B.
Lisa B.

owner of cheese & milk store

My husband and I moved to another city when we were 52. Our kids live in the capital, so we decided that there was nothing to keep us in our hometown. When we were 56, we opened a small store. We specialize in cheese, but also sell meat, milk, and other products. Having a business allows us to earn a living while being retired.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

I became an entrepreneur and founded my dance school when I was 63. I was inspired by the idea of teaching my peers to dance and move beautifully and correctly. In ordinary dance schools, they often feel out of place and sometimes can’t keep up with the younger students. My school is meant for people in their 50-60, that’s what makes my project unique.

Jacqueline Van Der Laan
Jacqueline Van Der Laan

owner of Jacky's Garden

I was 49. At the right time, I was introduced to the owner of the location where I started my restaurant. I fell in love with the venue and location! In 3 days I had my concept, and finances ready.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

I started working for myself in 2009 when my second daughter was born. Maternity leave is suitable for working remotely with texts. In 2012 I became a co-owner of a magazine, and in 2022 when I was 50 I joined the Moscow Business Association. Now I’m planning to develop two business directions: PR and video production.

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

When I was 53 I decided to change my career and enrolled in the Fashion Institute of the local Architectural Academy (I already had two degrees). I specialized in fashion design. Later I transferred to the USA and graduated from Fashion Style Institute. I was moved by the desire to fulfill the dream of youth and turn my hobby into a career.

What was the most challenging thing when you started a business? What difficulties do you have to cope with now?

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

I had been an entrepreneur earlier and I was familiar with the peculiarities of running your own business. But it was a completely different experience, a new sphere, new game rules. I had to create and run social media profiles, especially Instagram –– that’s the hallmark of a stylist. Also, it was necessary to make a statement, speak in public, and arrange the photoshoots. The technical part was the most challenging. But I managed to overcome it successfully and had my first clients and projects. Currently, I’m USA-based and work both online and offline.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

At the beginning of my entrepreneurial path, it was difficult to combine work and family duties. Sometimes I worked as an employee at other companies but always tried to make time for my personal projects. Nowadays everybody is having a really tough time. My most challenging task today is to diversify more into movies and start earning money in the field of feature films and commercial shooting. I’ve already succeeded but I’m still thriving for the better.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

The difficulties I faced at the beginning of my entrepreneurial career are still relevant. Women of my generation do not tend to dance –– they’re more into child-rearing and gardening. So I have some trouble finding my students, but the result is worth it! It turns out that dancing perfectly fits other hobbies (laughs).

Lisa B.
Lisa B.

owner of cheese & milk store

I know everything about cheese –– for more than 20 years I’ve been working as a salesperson. That’s why the most challenging part of building a business was to find a suitable location. The assortment may be great, but if the location is bad, no one knows about the store. Also, it was difficult to find reliable suppliers. Due to sanctions, it’s impossible to purchase some products, and for us, it’s important that our clients have a choice.

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

The most challenging part was coping with Instagram technologies. I bought two 8-week courses for bloggers, mastered copywriting, and photo and video creation skills, and learned the basics of Internet marketing. As a model, I attended a school for 50+ models where we learned about the secrets of posing and various defile techniques.

Jacqueline Van Der Laan
Jacqueline Van Der Laan

owner of Jacky's Garden

To start your business in Thailand is not easy: there are a lot of rules and regulations to follow. I did not choose the easiest time to open a restaurant –– Covid made it even harder.

Do you think age is an obstacle to starting a business? Justify your answer

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

Age can’t be an obstacle! A person is either capable of doing something or not. If you are such a type, you will do your best even if you’re 60, and if you’re not, your thirties won’t help. Moreover, I already have an experience of overcoming hard times – and, as people say, if you did it once, you can do it again.

Lisa B.
Lisa B.

owner of cheese & milk store

Age is a plus –– your professional and life experience help to avoid many mistakes. Also, as an adult, you take a sober look at things and don’t romanticize entrepreneurship. You don’t go ahead of yourself and carefully study every next step.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

On the contrary, age is your advantage when it comes to building a career or entrepreneurship. Surely, there are certain issues when it comes to communication with younger colleagues –– they live in a digital world and think differently. But we always try to find common ground, and if it doesn’t happen, we quietly part ways. It is very important to find your soulmates among clients, employees, or business partners.

Megan S.
Megan S.

private counselor

Age is not a determining factor. There are other issues to consider: the existence or non-existence of dependents (burdening factor), the additional source of income, etc. These factors may ease or, otherwise, hinder the start of your business. Age can be an advantage in case you study a lot and get rid of false beliefs.

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

To me, age doesn’t matter at all. The most important thing is the purpose of your business. Why do you start? What can you give to people? My mission is to inspire women to lead a health-saving lifestyle and be active even in the “third age”.

Tell us about your business failures. What lessons did you learn from them?

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

I owned a business before –– I was producing and selling kitchen furniture. Surely, there were ups and downs, and it was a real school of life. My most valuable lesson is that you need to do the thing you are passionate about and try to delve into the tiniest details of the process. No matter what field you are engaged in, each of them has its processes and business structure –– including style and fashion sphere.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

I had unsuccessful attempts to start a journal with three co-founders –– each of them was trying to grab the biggest piece of the pie. The conclusion is that you can only have one business partner who has the same worldview, interests, and values.

Lisa B.
Lisa B.

owner of cheese & milk store

I was trying to start a business while being employed, but it was impossible to play a double game. Your project requires complete immersion, and if you don’t have enough time you’ll face difficulties very soon.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

It wasn’t easy to go public and offer my services. I managed to cope with that. But I still have something to improve like the ability to never give up, persistence, confidence, and self-belief –– nowadays these skills are extremely relevant.

They say it takes a certain type of personality to become an entrepreneur. Do you agree? What qualities do you need to possess to run a successful business?

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

Every person, who can take responsibility for the result, is able to start a successful business. You shouldn’t be afraid of getting out of your comfort zone and developing new skills at any age.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

It is easy to start a business, but when it comes to getting real results, it requires a lot of perseverance, diligence, and self-confidence. The ability to never give up, fail and learn to fail, analyze your experience, and find inspiring environments are the core qualities of a successful entrepreneur.

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

Sure, the entrepreneurial state of mind differs from the non-entrepreneurial one –– they are quick thinkers, with well-developed leadership qualities. These people are able to take responsibility and endure tragic blows. That’s why not every person can become an entrepreneur (for example, those with a “government employee” mindset).

What was your biggest fear when you started your project? How did you overcome it?

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

I’m always in the public eye, and in the beginning, it was really uncomfortable for me. It was hard to start and look for the first projects and clients –– the impostor syndrome bothered me, too. I had to master many related activities: photo posing, make-up skills, social media marketing, and many others. Add to this moving to a foreign country and the necessity to learn a foreign language. But you need to keep moving!

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

Like many other entrepreneurs, I was scared I wouldn’t get any clients. But gradually I managed to ensure a pool of regular customers. Some of them have been with us for years. Also, I spend a lot of time developing business relationships and joining both offline and online professional communities. It helps to promote my projects and find new clients, new partners, and friends.

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

I was scared that no one would be interested in my project. I doubted its value and uniqueness. But my subscribers convinced me that I inspire them and give hope for an elegant and healthy maturity.

According to you, is it possible to make big money with your own business after 50? Can you define what “big money” means for you?

Jacqueline Van Der Laan
Jacqueline Van Der Laan

owner of Jacky's Garden

In the restaurant business, it is hard to make big money due to margins and costs –– no matter how old you are. I don’t seek money –– I just need a good quality of life and a solid financial backup.

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

I think it’s possible. If you know your strengths, what you love to do, and what people are ready to pay for, you’ll get stunning results. But my project is not for money –– it gives me inspiration. I would do it even if I didn’t get paid for my job. When you’re 72, “big money” is not a necessity.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

“Big” or “small” money is a relative figure. I like the word “enough”: I should have enough money to eat high-quality food, wear nice clothes, take care of myself, develop my skills, and travel. Someone may dream of a personal yacht on Caribbean islands, but I’m not one of them.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

When we analyze the experience of McDonald’s and KFC’s founders, we see that everything is possible. In Russia, Beeline’s founder also started the business at an older age and developed it into a large project. As for me, at my current state, I’d like to earn about 7500–15000$/month, with a monthly business turnover of 75000$+. In the field of cinema, if you are a director and producer, the income can many times exceed the budget of the production. Now I’m going towards my goal.

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

It depends on the professional field and the scale of your own desires, ideas, and opportunities. The age of 50 in the USA is considered very young, so there are no obstacles to pursuing your financial goals. To me, “big money” is the figure that is enough to cover all my needs and dreams, something that gives me freedom.

Do you face ageism when running your business? In which areas?

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

Sometimes there’s a misunderstanding of processes with our younger colleagues or clients, but this is manageable. Age is not a determining factor –– the cultural and intellectual level of a person, their interests, beliefs, and desires are more important.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

Quite the contrary! My age is my advantage. When women see me, 68-years-old, dancing and looking good, they understand that they can do the same in their fifties, or even sixties. As for me, I go to ordinary dance schools, where I learn to dance with my grandchildren’s peers. My age doesn’t matter to them at all. Neither does it to me. (smiles).

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

I didn’t. When I was 70, I was invited to host TEDx Talks in Minsk on the topic “Why I’m not afraid to grow old”. 580 000 people around the world watched this video on the official TEDx channel.

Lisa B.
Lisa B.

owner of cheese & milk store

When you are over 50, it is harder to get employed, even if you are an expert. Starting your own business is a chance to avoid ageism –– it allows you to earn money without the necessity of proving to others that you haven’t lost your grip.

What helps you overcome challenges and continue doing your thing?

Lisa B.
Lisa B.

owner of cheese & milk store

The dream of my own house, prosperous retirement, and financial independence from my children.

Tatiana Konnova
Tatiana Konnova

founder of “Age of Dance” school

The understanding that it’s impossible to avoid failures when running a business. I love this quote from Churchill quote: “Success is not final, failure is not fatal: it is the courage to continue that counts.” Successful people really inspire me, it’s great that there are many of them in this world!

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

There are two things that help me: the responsibility for my daughters and the desire to fulfill my dreams. The elder is 26, but she still needs my support, and the little one is only 13 –– there are so many things for her to learn to find her way. And my dreams are connected with the field of cinema. If you don’t rely on government funding and make movies using your own and sponsors’ money, it is quite possible to find your niche.

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

When you grow old, you get rid of the dependence on other people’s opinions. You aren’t afraid to lose, because you understand that it’s not the end of the world. You look at the failures from the height of your age, with humor, or even irony. Now you can do anything you want!

What advice would you give to those who decided to become an entrepreneur at an older age?

Olga Shatyko
Olga Shatyko

blogger, model 70+, TED speaker, “Health-saving lifestyle” project

Start a business only if you are ready for risks, responsibility, and temporary difficulties.

Jacqueline Van Der Laan
Jacqueline Van Der Laan

owner of Jacky's Garden

Follow your heart but also be realistic. At any age, it’s hard to start a business –– you shouldn’t expect a relaxed life. Start your project if you are passionate about it and believe in yourself and what you do.

Mariia Darskaia
Mariia Darskaia

founder of DAR Media PR agency and film company DAR-film

As Confucius said, “Choose a job you love, and you will never have to work a day in your life.”

Elena Lashko
Elena Lashko

fashion stylist, online/offline styling courses, “Beautiful age” project

If you have a passion, try to turn it into a source of income. Start with a little, don’t invest too much money in your project –– try to “play” business. But it’s not a recommendation, just thinking out loud.

What to read about starting a business later in life

Here are some useful blogs and articles to consider when building your business after 50.

Articles

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