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11 Things I Wish I’d Known Before Starting a Business After 50

11 Things I Wish I’d Known Before Starting a Business After 50
Margaret Manning

Building Sixty and Me has been an incredible journey. In many ways, the company achieved “success” in the first year. We built a community of 50,000 women over 60, were featured on CNN and Facebook’s business page and launched 2 products. But, in other ways, we are just at the very beginning of our journey. I didn’t fully anticipate the number of pivots that we would need to make in the first year, or, frankly speaking, the amount of work that it would take to get us to profitability.

While our mission is far from being reached, I wanted to take a few minutes to look back and provide some advice to older entrepreneurs who are just be getting started. After all, I learned a lot of lessons the hard way! Here are the 11 things that I wish I’d known before starting Sixty and Me.

There is No Such Thing as an Overnight Success

Contrary to what you might read on sites like TechCrunch, there is no such thing as an overnight success. Starting a company is a long, hard process. When I started Sixty and Me, I had a 12-month plan for building a profitable business. Now, 18 months later, I can only sit back and laugh at my naiveté.

If you’re starting a new business, keep your expectations in check. Building a successful company will almost certainly take 3 years or longer. This is one of the many reasons that it’s so important to have a mission that you believe in. Without passion, you won’t be able to go the distance. This is especially important for older entrepreneurs, who may feel pressure to achieve success quickly.

Don’t Try to Please Everyone

I have a deep respect for the women in the Sixty and Me community. Over the last couple of years, I have had the privilege of talking to hundreds of them and they are among the most passionate, intelligent and kind people I have ever met. At the same time, in any group with 10,000’s of people, there are always going to be a few bad apples.

I remember the first time that I received a negative piece of feedback from one of our community members. For the life of me, I can’t even remember what the message was about, but, it was filled with ALL caps, incomplete thoughts and profanity. At the time, I was devastated. I had just spent 6 months, pouring my heart into the community, writing articles, interviewing experts, and, genuinely trying to help. I hadn’t even started showing ads on my website, so, I was effectively working as a volunteer.

Looking back, I’m not sure why this one email hurt me so much. Perhaps I just wasn’t used to receiving negative feedback. Or, maybe I just felt like everyone should appreciate the amount of work that I was putting in for free. Now, on the rare occasion that I receive unjustified negativity in my inbox, I delete it without a second thought.

As an entrepreneur, you are going to receive your fair share of negative feedback. It’s just a part of the process. Like Sixty and Me, the great majority of the people that you encounter will be friendly and reasonable. Just remember that you can’t please everyone. In fact, if you try to please everyone, you will almost certainly end up pleasing no-one. Remember your mission and forget the haters.

Don’t Worry About Your Age – If Anything, It’s an Advantage

When I told my younger colleagues that I was quitting my corporate job to start Sixty and Me, their responses ranged from mild amusement to outright shock. Aging stereotypes are so entrenched in our culture that the idea of a 65 year old women starting a company just doesn’t add up for some people.  As I have built Sixty and Me, I have discovered that, if anything, my age is advantage. With 30+ years corporate experience, I am able to avoid many of the “rookie mistakes” that I have seen younger entrepreneurs make. In addition, I am able to use my network to reach potential partners, customers and mentors.

According to, there is good reason for older entrepreneurs to see their age as an asset, not a liability.  They report that “…people older than 55 are almost twice as likely to start successful companies as people in their twenties and early thirties.” So, if you’re concerned about being “too old” to start a business, you may want to take a deeper look at the statistics. The numbers, as well as my own experience with Sixty and Me, indicate that older entrepreneurs hold all the cards.

Passion is a Necessary, but not Sufficient, Condition for Success

One of the most common business truisms is “Do what you love and the money will follow.” If only it were that easy! As I wrote, in a previous article, doing what you love is just the beginning. In order to build a successful business, you need to find the intersection point between what you love and what the world needs.

As I discovered the hard way, while building Sixty and Me, passion is mostly important because it keeps you going for long enough to build a product that your community really wants. If I didn’t believe that I was changing the world by helping women over 60 to live happy, healthy and financially secure lives, I would have quit a long time ago.

One of the great things about being an older entrepreneur is that you have had a lifetime to get to know yourself and develop your passions. Now is the time to share your unique mission with the world!

Own Your Audience by Building Your List as Soon as Possible

Sixty and Me started out as a community on Facebook. One of the reasons that we were able to grow so quickly was that other businesses undervalued the over-60 demographic. As a result, our posts faced less competition in our members’ news feeds. Over the course of 2013, the situation changed dramatically.

As Facebook switched its focus from growth to monetization, communities like Sixty and Me were stuck in the middle. While our community members continued to send me messages, asking why they weren’t seeing our posts, our reach continued to drop. As a result, I learned the hard way that the only way to truly “own” your customer relationships is to have your own list.

In the second half of 2013, we spend a lot of energy, moving as many people from Facebook to our Aweber newsletter as possible. In the course of just a few months, we managed to build our list from nothing to 5,000 subscribers. Facebook is still an important part of our strategy, but, I wish that I had started the process of building our list much earlier!

Build Systems that Allow You to Outsource Without Sacrificing Quality

When I started Sixty and Me, I wanted the company to be as lean as possible. This meant keeping the team small, without sacrificing growth. As a result, I was left with a somewhat uncomfortable choice (at least given my mindset at the time.) My partners and I could work more and sleep less, or, I could take the risk of hiring freelancers.

As older entrepreneurs, we have a lifetime of experiences and skills to draw on. This can be a blessing and a curse. On the one hand, we can often accomplish tasks quickly, without having to bring in outside help. On the other hand, we are often reluctant to outsource tasks, especially if there is a perceived risk of a lower quality result.

Now I realize that hiring freelancers is only risky if you don’t take the time to build systems. As Michael Gerber discusses in his book, The E-Myth, thinking about your business as a franchise can help you to have the best of both worlds. By breaking down your business into a series of repeatable systems, you will have the confidence to outsource repetitive tasks without risking quality.

The hardest part of this process is giving yourself permission to slow down and fully document how your business should work. In my experience, entrepreneurs are “results driven” – they feel good when a new article is posted, a new product is launched or a new contact is made. The important thing to remember is that, while creating systems takes time, it is the only way to build a truly scalable business in the long-term.

Start Selling Something as Soon as You Can

I resisted charging for my services for a long time after founding the company. I told myself that I didn’t want to “scare away” my community by asking them to pay for something. I worried about whether I had the knowledge or the skills to build a product that people would actually pay for. Now, I realize that these were just excuses to hide my own insecurities. The truth is that I was scared of failure and rejection. Putting a product into the market takes guts. So, for almost a year, I continued to add value to the community without asking for anything in return.

Now, I realize that this was a mistake for two reasons. First, by delaying the release of my first products, I held back useful information that would have helped my community members to be successful. Second, like every person who puts value into the world, I deserved to be compensated for my work.

My advice to new entrepreneurs is to get your first products to market quickly. Whether or not you find success the first time out of the gate is not the most important thing. What matters is getting used to the process of launching, collecting feedback, refining and re-launching.

Don’t Aim for “Perfection”: Launch > Learn > Refine > Launch

Some of my reasons for not launching products in my first year were emotional; as I mentioned before, I was genuinely concerned about how my products would be received. As the same time, I struggled with more rational concerns. I worried that my products simply weren’t ready for the market. My videos could always be better, my marketing texts could always be sharper and my list could always be bigger.

Looking back, I now realize that I wasted months of valuable time, trying to make my products “perfect.” When you work for a large company for most of your career, as many older entrepreneurs have, you get used to taking your time with product launches. “Unlearning” your corporate rhythm is one of the hardest, and most important, steps that entrepreneurs, especially older entrepreneurs, need to take.

I now know that, instead of aiming for perfection, I should have focused on a more iterative process of launch > learn > refine > launch. This would have allowed me to avoid wasting time on content that people didn’t want, while focusing on the features that they really needed.

Celebrate the Milestones, but, Don’t Expect them to “Change Everything”

Entrepreneurs have a habit of continuously looking to the next milestone for salvation and I was no exception. I remember thinking, “If I could only get featured by Facebook… that would change everything.” Sixty and Me was featured on Facebook and, even though I made some great contacts, very little changed. Then, I thought, “As soon as I release my first product… everything will be easier.” It wasn’t.




You will have hundreds of milestones on the path to startup success. What I realize now is that it is important to celebrate these important events, without putting too much weight on them. While you may look back and see pivotal moments in your business, they are almost certainly not going to be the ones that you planned for.

So, plan for the next milestone, but, focus on your long-term vision. Your mission will sustain you much more completely than any tactical success.

Build Systems that Allow You to Scale Relationship Building

When I started Sixty and Me, I made it a point to greet every new member of the community individually. I also answered every single email personally, even when the volume approached 50 messages per day.  I still try to connect with as many people as I can, but, I have also come to understand the importance of automation in managing my business.

About 6 months ago, I moved all of my customer relationship management, including my newsletter list, to Infusionsoft. This amazing service allows me to keep track of all of my contacts, set up interest-based marketing campaigns and handle transactional requests, such as lost passwords.

Quite honestly, Infusionsoft is at the center of everything that I do with Sixty and Me. My only wish is that I had moved to a service like Infusionsoft earlier. Not only did it help me to scale my relationship building, but, it also forced me to take my product development to the next level.

Don’t Quit Your Day Job Until You Have to!

In order to work on Sixty and Me full time, I made the difficult decision to leave my corporate job behind. I made this choice, in part, based on the false belief that my path to profitability would be short and relatively simple. Boy was I wrong! After about 6 months, I realized that, while Sixty and Me was growing fast, I would need to supplement my income or get another full time job.

Fortunately, I was able to find enough consulting work to be able to continue to run Sixty and Me, without going back to corporate. In my case, everything worked out ok. However, if you are considering leaving your job to start a company, I would advise you to be extremely careful. Sometimes the best decision is to continue to work at your company, while you build your side business. This will give you plenty of “runway” to launch before you have to start thinking about how to pay your bills.

This is especially important for people in their 50s and 60s as getting back into the workforce may be challenging if your startup doesn’t meet your expectations. So, think twice before jumping in feet-first.

Starting a company is one of the most fulfilling, frustrating, empowering, life-consuming activities that you can undertake. The only valid analogy that I can find, and it’s not a perfect one, is raising a child. You sit up at night, thinking about how to make your business successful. You nurture and feed it. You take pride in its accomplishments and monitor its health obsessively.

If you are just getting started, I hope you find the advice in this article useful. If you are further down the path to startup success, please share your insights with us in the comments.

What do you wish that you had known when you started your company? What advice would you give to the other members of our community who may be starting a company for the first time? Please join the discussion and “like” and share this article to keep the conversation going.

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