7 Lessons on Starting a Business After 50
From entrepreneurs who’ve done it
The chance to get equal education and benefits regardless of background and family privilege; owning an amazing vacation property in Tampa; doing what you love and getting a 6-figure salary for it…When we think of it, all those dreams boil down to the deepest and biggest of American dreams: becoming an entrepreneur.
If you’re over 50, it may feel like you’re late for the entrepreneurship party reserved for Millennials and GenZ. But there’s nothing further from the truth.
According to official statistics, 54% of America’s small business owners are over 50 years of age. Out of those, 33% are 50–59, and 17% are 60–69 years of age.
Moreover, business owners over 50 are also considered twice as likely to succeed in starting a business compared to 30-somethings. (All that life experience doesn’t go poof on you, right?)
If you’ve been working someone else’s American Dream for most of your life and think you’re too old to start your own business, think again.
Here’s how the lessons and insights from entrepreneurs who started their business after fifty will help launch yours.
1.Figure out your retirement finances
Starting a business is always about mapping your budget and evaluating costs. But when you start a business after fifty, your business startup costs will be irrevocably bound to your retirement savings.
Kathy Kristof is an entrepreneur who started her online business at age 58. One of the first things she recommends in order to escape your finances going poof on you right when you need them most is comparing your retirement plan to your business plan.
“Your first order of business is to figure out if you have enough [funds] assuming that you never make another dime AND spend whatever your maximum budget is for your business,” Kathy says.
And what about online businesses? You may have heard about the cost-saving benefits of opening an online business compared to a local business. But like school-teacher-gone-blogger Janice Wald reminds us (and yes, you CAN become a blogger after 50), “It takes money to make money”.
Success tip: Don’t assume that just because your business is online, it will fund itself. Depending on your niche, you will need to invest in marketing, SEO, indispensable business tools, and/or e-commerce platforms to nail those precious first and ongoing customers. Importantly, you need to figure out how much those business startup costs will draw out of your retirement fund (if anything), and how that will influence your future finances. The best way is to create a business plan or financial model of your business.
2.Identify a need in the market
Think of some famous brands and services — from Campbell’s Soup to Facebook to Macy’s. Each one became a household name because it became deeply associated with a unique service or product this brand excelled at.
Today’s market is already overflowing to the brim with generalized goods. If you plan to add to that heap, unless you’re opening a franchise, it may drain your finances and bring little results. On the other hand, niche products (think handmade goods, unique gifts, and products targeted to specific audiences and ages) are the “it” of today’s small business.
Dawn LaFontaine is a 56-year-old, former stay-at-home mom and creator of whimsical cardboard box playhouses for cats that she called “Cat in the Box”. The reason for Dawn’s success is that she had a “Eureka moment” and made the leap of faith despite gaps in business and tech experience.
“Don’t think you have to know everything first. This is an agile, ever-changing world, and the longer you wait, the more things shift around you. You’ll never be able to see mile 26 of the marathon from the starting gate, so don’t try. You’ll figure things out as you go.”
Success tip: When your product fills a niche need, it’s more likely to feature organically both in SEO results and on social media — today’s ‘word of mouth’. As a result, you will need to invest less in paid ads, marketing, and promotion. Good ideas to brainstorm are products that you find lacking in the market (something you’d like to have but can’t find), products for specific age groups or categories of people (e.g.: new moms, retirees, empty nesters, etc.)
3. (Re)use and revisit your life experiences
Another great option for starting a business after 50 is to find an area that you’ve gained expertise in throughout your life. In other words, monetize your lifelong career, hobby, or skills.
When Paul A. Dillon retired from the Chicago office of the McGladrey accounting firm in 2006 on the eve of his 61st birthday, he fully “reinvented” himself by launching a business concept devoted to helping veterans who want to start their own business.
As former U.S. Army Reserve 1st Lieutenant and Vietnam War veteran, Paul went on to create the concept for a business incubator in Chicago specifically for veterans.
Surprisingly, drawing on his own life experience was not Paul’s first choice.
“I started out thinking that I was going to provide project management and business development services to companies in the service industry,” Paul says. “But, that didn’t work out. I had to “pivot” several times before I found a niche that worked.”
Success tip: See how Paul started with rather a generalized business idea? It’s only when he drew on his life experiences and adjusted his business to address a particular category of customers (veterans) that he could relate to and vice-versa, that his business took off.
4.Get a free business mentor
We think of mentors as someone young people get to find their way in life. Someone over 50 coaching a 20-something. In reality, a mentor is essentially your guide at any stage of life when you want to try something new and can’t afford the mistakes.
In entrepreneurship, a mentor will speed up your learning process and will help you avoid a lot of pitfalls. As someone experienced and equipped in business, a business mentor or coach will save you time, finances, and peace of mind. A business mentor can be younger than you, as long as you’re both comfortable and involved in the learning process. In fact, a younger mentor will teach you a lot about modern business.
Right before turning 50, Colleen Kochannek got thrown into entrepreneurship unexpectedly and with no digital experience to boot. Today a successful online business owner, she knows the importance of starting off the right foot and finding guidance.
“SCORE [is] a great organization part of the Small Business Administration offering [volunteer mentorship] services,” Colleen says. “You can also find business coaches and mentors online. Ask in Facebook Groups you participate in. Referrals are often your best bet.”
Success tip: Getting a professional business mentor doesn’t have to cost you a lot — or in fact, any — money. Organizations like SCORE and online business communities are a great way to connect, learn, and network with other business owners for free.
5.Network before you launch
The most successful startups are those that first build a network and then launch. Unfortunately, most business owners do the opposite: they get their product out and think the audience will come. When that doesn’t work out, they get frustrated.
If you’re just planning to start a business and are in the brainstorming stages, now is your best time to start reaching out to everyone you know. And yes, everyone means everyone.
Harvard graduate Kelly Christiano worked for Corporate America for most of her life before launching her own consulting firm. She knows a thing or two about not only having a large contact base but productively drawing on it.
“Don’t be afraid to reach out to former colleagues, old friends, and contacts even if you haven’t been in touch for years,” Kelly says. “Most people love to help and provide their advice. You’d also be surprised how many of these connections can lead to real business opportunities.”
Success tip: You’ve probably heard of the 6 degrees of separation rule. The one that demonstrates how you can reach any person in the world (think literally any celebrity) through six “friends of friends”.
Whenever you think of it as irrelevant or uncomfortable to contact someone you’ve been out of touch with, just remember that they can be the missing piece of the puzzle for your business. Online business communities can also be a fantastic help in building a support network.
6.Ask family and friends for digital help
Let’s be honest. As a new business owner over fifty, you’ll feel a lot more challenged in launching a business, especially an online one, than a GenZ who’s had an iPad hanging in their crib. More often than not, you’ll also feel rather embarrassed to ask your family for help in digital matters. Don’t be!
Anna Boccia is a 61-year-old retired florist who recently launched her own handcrafted artistry shop on Etsy. Her secret to starting that e-commerce business and sailing around digital and tech challenges, moreover in pandemic times? Not being afraid to ask her family for help.
“My daughter runs a boutique PR firm, and she has been an amazing resource in establishing my business,” Anna says. “My sons-in-law are great photographers, and they’ve helped me with my product shots. I was always nervous about asking for him because everyone is so busy, but I found when I made the ask, the people around me were happy to help.”
Success tip: As a small business owner over 50, you may have the privilege most younger business owners don’t: that of a supportive family. Even if your family doesn’t include professional photographers or marketers, they know things about social media that will make you go “wow”. And if your adult kids are busy, try school-age or teenage grandkids or family members! They will love helping you out with social media, and you’ll get the benefit of fun family time.
7.Hire out any ‘tech stuff’ you don’t want to learn
In running a business after 50, you’ll stumble upon a lot of “tech stuff” that will be nearly impossible to avoid. But that doesn’t mean getting your business up and running is rocket science.
Colleen Kochannek advises to separate essential tasks you’ll need to do yourself vs. things you can delegate.
“Learn the basics. [If needed], pay someone to teach you the tech systems you do need to know,” she says. “[But] hire out any ‘tech stuff’ you don’t want to learn. Fiverr and Upwork are good places to start. You [can] also hire people from these sites to teach you how to do specific tasks.”
Success tip: For a small business, things you need to do yourself are usually client and team communication (e.g. business phone system like MightyCall), and collaboration tools for startups with a remote team (e.g. Trello). Also, knowing the basics of Customer Relationship Management as well as social media management (e.g. Hootsuite) will be a huge bonus. On the other hand, things like PR and even getting your website set up can be outsourced to freelancers.
Last but not least…
Entrepreneurship in your 50s is not only possible — it will give new meaning to your life.
Instead of a time that may seem dull or boring, you can make your retirement a time when that American dream you once had will finally come true and bring you deep joy.
The only catch to becoming a business owner in your 50s?
As Kathy Kristof puts it, “Be prepared to work like back in your 20s!”
Bilingual pianist & business journalist. Writing about the Human Experience.