How to Start a Business After 50 in Seven Steps

The American Dream — how exactly do we define it? Is it the chance to get equal education and benefits regardless of background and family privilege? To own that amazing vacation property in Tampa? To do what you love and get a 7-figure salary for it? When we think of it, all those things only 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.

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, according to statistics.

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.

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, SideHussl, 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.”

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 digital 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 and go for it

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 market 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 starting 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 that eventually became Bunker Labs. Surprisingly, however, 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. 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 the business concept to address a particular category of customers (veterans) that he could relate to and vice-versa, that his idea 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.

Right before turning 50, Colleen Kochannek got thrown into entrepreneurship unexpectedly and with no digital experience to boot. Today a successful online business owner coaching other “typewriter generation” aspiring entrepreneurs at The Scrappy Frontier, she knows the importance of finding early guidance.

“SCORE [is] a great organization part of the Small Business Administration offering [volunteer mentorship] services. You can also find business coaches and mentors online. Ask in Facebook Groups you participate in. Referrals are often your best bet.”

Success tip: A business mentor can be younger than you — don’t let this intimidate you! A younger mentor will teach you a lot about modern business and share their enthusiasm balanced by your wisdom. 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 getting involved with IGI Enterprises. 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. 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.

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 Makani 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. 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 some “tech stuff” that will be impossible to avoid. But that doesn’t mean you have to become a tech guru to become a successful entrepreneur.

To achieve harmony in your workday, 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. [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.”

Here’s an example of the digital essentials you’ll need to start a business:

  • Business phone number — for communicating with clients from a business number as opposed to a personal cell number, which looks unprofessional, you will need a business phone number. We suggest a business phone system like MightyCall,targeted specifically at small business needs.
  • Business website — essential for getting your online business out into the world. Building a website is totally simple with DIY website builders.
  • Customer Relationship Management (CRM) platform — for managing your client base. This can be a simple platform that’s already integrated into your business phone like MightyCall’s or a bigger CRM platform like Hubspot for when you have many clients.
  • Accounting and financial software — accounting software like this will save you a lot of money on an accountant.
  • Social media tools — tools like Hootsuite for instantly publishing your news on several social media platforms save time on publishing social updates to multiple platforms simultaneously and scheduling posts in advance.
  • PR tools — Reaching out to journalists and getting the word out about your business is useful and free on platforms like HARO which connect small business owners to journalists and B2B blogs that can spread the word about their business.

Success tip: For a small business, things you need to do yourself are usually client communication and team communication. Also, knowing the basics of CRM tools, as well as social media will be a huge bonus. 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.

There’s only one catch. As Kathy Kristof puts it, “Be prepared to work like back in your 20s!”

Want to learn more about savings as a small business owner? Complement this guide with our out-of-this-world fast, mobile, and budget-friendly phone system for small business. We’ll help your team talk anytime, anywhere, and about anything, at a stunning price.

Take a look at MightyCall’s business phone features or learn more about VoIP!



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