Five surprising lessons from starting a business in my 50’s

Updated to Business, Life on December 27, 2022.

“With the sheer number of baby-boomers now approaching retirement age, the era of the olderpreneur” is upon us.” Financial Times

When I was a kid people retired at 60 – 65 if they didn’t like golf.

When you get old, you retire. This was an irrefutable fact of life like moss grows on the North side of trees and striped shirts make you look fat.

I didn’t listen.

Somewhere around the age of 53 I hoisted my entrepreneurial flag one more time and launched a new start-up. It all started with an itch I couldn’t scratch and wanting to build a solution others would want.

Unlike 80% of start-ups, mine has a happy ending.

Today my small team serves clients in five countries, the business is profitable, we have no investors, no debt and it returns a nice income.

This is the story of why I did it, what I did, what to avoid and how it turned out.

But, I’m getting ahead of myself. Let’s start with the back-story.

Starting a business – I’ve been bitten before.

I’ve been bitten by the entrepreneurial bug a number of times before. My first foray into business began as a river guide on the glacier-fed rivers in Western Canada under the tutelage of my older brother, Dan. Like a puffer fish, we would balloon from a core team of 4 in the winter months to some 35 guides, office staff, drivers and swampers for 5 hectic sweat-soaked summer months.

It was a lesson in chaos theory and last-minute planning.

After we sold that business I joined three partners to start what is now called Antarctic – Logistics. We had a monopoly on Antarctic tourism to the interior of the continent. Of course, in Antarctica, you could sell hot dogs and have a monopoly.

Of course, in Antarctica, you could sell hot dogs and have a monopoly.

We didn’t have money or wealthy investors, so the whole operation (including buying two airplanes) was done using a clever accounting concept called unearned revenue. This pseudo financing works great if you deliver everything you promise—not so good if you’re shut down by nasty weather or have aircraft turned back mid-flight by the Chilean military.

But, that’s all for another blog post.

Returning home to finish my MBA, I made rent with a string of start-ups, including a haphazard construction company, selling advertising and some random consulting in the tourism industry.

For the last two decades, I’ve chased contracts for corporate training and public speaking.

And then I had a big idea.

Then I had an idea

I’d been writing a blog for two years and, like most bloggers who’ve dipped their keyboard into publishing online, I wanted more traffic. I thought if I could share my blog on social media I should be able to attract new followers, more traffic and, ultimately, new business.

Somehow I thought my start-up business would satisfy my curiosity

So I hired a virtual assistant in the Philippines to pull excerpts from my blog and turn them into social media updates. At the time it was de rigueur to hire VA’s overseas. So that’s what I did.

And it worked. Sort of.

The concept proved out – my traffic was up and I was spending a lot less time promoting my blog. But coordinating the work of someone overseas in their time zone, with their schedule (including “disappearances” because of health issues or a cousin’s wedding) was time-consuming and frustrating.

“Business opportunities are like buses, there’s always another one coming.” Richard Branson

In the rafting business, our most successful trips were created because first, we wanted to do the trips. I thought I could apply the same thinking with my nascent blog service.

In the parlance of start-ups: if I had an itch that needed scratching maybe other people did as well.

That’s when I asked the fateful question that would lead to launching my new business: What if I turned my little solution into a start-up business?

Who else wants this?

At some point that first year I was leading a one-day boot camp for public speakers. Despite my complete lack of market research (mistake #45, if you’re keeping track) this seemed like the perfect opportunity to test my new business idea.

At the last minute, I wrote up a very rough description of my new service. I even included a space (for the more motivated folks) to add your credit card information.

I set the price at $197 per month. This was anything but a sophisticated calculation: over $200 seemed like too much and I guessed I wouldn’t be making money at anything less.

Four years later, we are still using the same price.

I didn’t have a name for the new service, but because I imagined we would sort of be rescuing blogs, I called it SOS (as in Save Our Ship). A year later I force-fed the acronym “Save Our Social” into the name SOS. It was pretty corny and for obvious reasons useless for marketing, but for the next three years it was called SOS.

Chase the vision, not the money; the money will end up following you.”Tony Hsieh, Zappos CEO

I remember at the end of my workshop pulling out my flyers and doing a little dog and pony show to pitch my idea. It was the first time anyone had heard of my service and I was nervous.

Here’s the shocker – one third of the audience signed up!

I’d like to say it was an Ed Sullivan-introducing-the-Beatles moment. It wasn’t. In the end, I don’t think any of them actually started their account, but it was good validation (and more than a little motivating).

Time to grow up

Within a few months I had a handful of clients, and two trusting souls (both lived close to where I live) doing the writing. The system was admittedly simple.

Clients would subscribe, once a week we would read their blog and then turn it into daily updates on Facebook, LinkedIn, Twitter and Google+. They got more exposure to new readers and we would save them hundreds of hours of time.

A note about our service: Since then our service delivery model has become a lot more sophisticated, but the basic premise of reading and sharing the blog on social media remains. And even though our main promise is to take the social media monkey off their back, our clients enjoy a very healthy monthly increase in traffic to their blog.

I was still balancing my time with speaking (my main income) and delivering all-day seminars, so work on SOS was relegated to evenings and the occasional weekend. Once in a while I would get inspired and spend a day doing a makeover on the guts of the system or some extra marketing.

In the first two years I think I was working on SOS about 10 hours a week.

The surprising thing about SOS is it was profitable in the first month and has been ever since. There’s lots of evidence that the majority of start-ups fail – often the problem being solved isn’t big enough for people to care about it.

“Cool idea… but it’s not that big an issue for me to find sustainably sourced wooden sunglasses.” Melanie Curtin,

I knew our solution was valuable. The challenge was to commit to promoting just one solution.

Some clients simply wanted to get social media off their hands, others were all about blog traffic and bigger email lists. We still struggle to find the perfect value proposition that works for every one.

How we’re doing today

I’m writing this article in August 2018 and we’re still a tiny, but profitable company that employs 9 contractors. While our sales are low six-figures, our gross profit margin continues to hover around 30%, we have no debt, no investors to pay and continue to grow at 10-15% per year.

With any start-up, self-doubt can be your constant companion

I’ve taken businesses to the multi-million revenue level before and it’s very exciting. Lots of drama, late night calls, emergency meetings and sudden windfalls. BlogWorks (as we are now called) is different.

BlogWorks is more like a steady train that keeps on chugging – I like it that way. I can comfortably leave for weeks at a time (I’ll be in Nepal building a school and trekking for the month of November) and all will be fine.

Of course, it wasn’t like that in the beginning. And there’s been many times when I’ve thought about cashing out. Maybe, I still do.

At some point, there was a switch between a struggling, hand-to-mouth business to one that does chug along. That’s a sweet moment.

And I made a lot of mistakes along the way.

Mistakes we call lessons

“Success means you’re going to have better problems.” – Bo Burlingham, Small Giants

Some of my mistakes were easy to fix; others were more painful and took longer to back out of. In retrospect, they all seem very avoidable – even dumb.

We tried lots of marketing ideas – most didn’t work

In the spirit of sharing and we all get smarter the more we know, here’s an hors d’oeuvre serving of my goof-ups:

  • I’ve spent thousands on Facebook advertising and got minimal results. Always the optimist, I repeatedly convinced myself thinking there was a better way. So far there hasn’t been.
  • After paying two different consulting firms to replace the name “SOS” I came up with BlogWorks on my own. Not their fault—I didn’t know what I wanted and it was probably premature to hire experts before I had my act together.
  • It took me two months to back out of a profit-sharing deal that I hadn’t thought through in the first place. In the end it all worked out, but it was an uncomfortable exercise in honesty and sticking to what I knew was right.
  • In a rush of excited anticipation, I hired two salespeople and after only two months and zero sales had to let them both go. The lesson here was if you don’t know how to do the work (like cold call sales), don’t try to outsource it.

Keeping the faith

Starting a new business is one thing. There’s a lot of adrenaline flowing when you’re gathering a team, designing your products and getting your first sales. I still remember logging into my bank account and, for the first time, seeing deposits that didn’t involve me flying somewhere and standing in front of an audience.

More recently I’ve I become a student of productizing your business and turning a service company that nobody would want to invest in or (heaven forbid) buy, into a profit-making machine based on monthly subscription fees.

The best book on this concept is Built to Sell by John Warrillow (it’s a fable and quick read). His subsequent book Automatic Customer goes into more detail and provides tons of current examples of how to create a subscription-based business. I highly recommend both.

Keeping a business going is another thing.

That’s hard work. And many days I simply didn’t feel like it. Thanks to my speaking income and some good decisions in other businesses I knew my family would be taken care of. But, I didn’t want BlogWorks to be a little hobby – I really wanted to see how big I could take it.

From the start, I knew there were certain areas in the business I would enjoy, like tinkering with our product, training staff, designing marketing and talking with clients. It was all the areas I tried to fake that got me into trouble.

And that brings me to lessons learned…

Lessons learned

1. You can’t do it alone

For over 20 years I did very well as a corporate trainer and speaker. My income was mid six-figures for nine months work. And even though I had talented support staff, good systems and got paid silly money for one hour on stage, that model doesn’t scale.

If you get paid to speak, the only way to increase your revenues is to either raise your price (hard to do) or your volume (which means more hotels, taxis and airports and time away from home.)

The secret to our growth, if there is one, has always been people

With BlogWorks we grow with people.

The better the people I add to the team the more our revenues increase. Every time.

“We’re not in the coffee business serving people, we’re in the people business serving coffee”Howard Schultz, CEO Starbucks

The trick, I’ve learned, is to hire up, not laterally. It’s easy for me to hire people like me – people with lots of enthusiasm who love to brainstorm and start things. What I really needed were people better at customer relations and running systems and coordinating staff. I need people who can do what I’m not good at and do it every day.

That’s why I can’t do it alone.

2. Not every day is a Friday

Not every day is Friday.

You will have days that suck.

Clients complain, a delivery is missed, some mysterious online thingy stops doing its thingy.

It’s not fun, but it’s usually over by the dinner time.

In entrepreneur land, it’s helpful to know your darling will poop its bed once in a while and you have to clean it up. Even better is to surround yourself with great people who are ready and willing to stop the pooping before it happens.

“The problems you have you experience in your mind. The solutions to those problems lies in the same place” – Wayne Dyer

My rule is if we see a problem more than once, we need a new system.

3. Better systems lead to better success

Better systems equals better business

Even in your early start-up days you need good systems. In my definition, a system is routine you create once and then use over and over.

Our systems include: how to onboard a new client, create content, post content to social media, publish our blog and so on.

Each system is written up in a simple Google Doc called an SOP (Standard Operating Procedure). The trick (and this is worth the whole price of this article) is for the person who owns that job to edit the SOP, not me.

In other words, you might be tempted to think “Well, we never want to see THAT happen again, so I’ll stay up late tonight and craft this very tidy routine that so and so will dutifully follow.” Nope, won’t happen.

Until “so and so” creates the routine (with your guidance, of course), he/she will not be thinking, nor will they be as responsible as if they created it themselves. Trust me, this is gold.

“A business reliant on its owner is unsellable, so the owner becomes trapped in the business.” John Warrillow, Built to Sell.

As you grow your company, improve your systems. As soon as you start “winging it” or customizing your services you lose profit and time spent more precious time putting out fires.

4. You will want to quit

I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying. – Jeff Bezos, Amazon

At some point I started wishing it would all be easier—I wanted my Gladwell tipping point and to see new clients start rolling in. It didn’t happen.

Our biggest days have been 3 new clients, but many days rolled by with zero.

I’ll admit I’ve thought about quitting many times. “For cripes sake! I’m in my 50’s,” I’d think, “maybe I should just wrap this up and sell it to someone in their 30’s!” In those moments, I feel pretty alone—like all my efforts aren’t amounting to much.

Fortunately, I’ve discovered a secret button.

What’s your secret button?

When I push this button it’s like looking up and noticing the forest, instead of the trail I’ve been stumbling along. I feel hopeful.

My button is to look at what’s working. It’s that simple.

We are doing a lot of things right! When I remind myself of what my team is doing, the solutions they create without ever involving me…it’s incredible!

My button isn’t a panacea—I still have work to get done. I get that. At the same time there’s something magical about a little business that chugs along day after day and delivers a valuable solution for our clients.

In that moment my perspective shifts from a struggling little start-up to something quite good, that’s getting better.

What’s your button?

5. Learn to say NO to the wrong clients

What you don’t do determines what you can do.” Tim Ferriss

Saying “No” to money is hard. And I freely admit that early on in our growth I was saying “Yes” to anyone with a blog and a credit card. That cost me.

Attracting clients who aren’t a good fit will cost you over time. This is true for any service business. The trick is to first understand who your ideal customer is.

As much as I was tempted to leap into new markets, like targeting lawyers (don’t respond to emails), realtors (blogs are too time sensitive), doctors (hopeless with email) our best results came from attracting more clients like our best clients.

Our most faithful clients are speakers, authors, consultants and coaches. Spinning our marketing wheels with blind forays into unknown markets wasted time and cost me money.

This is the toughest marketing lesson I’ve had to learn:

If your market is big enough, has the need and can afford your service, you always get the best results by expanding in the market you already know.

In addition to tapping into our best markets, I also decided from the very beginning to avoid customizing our service.

That was a huge decision. Especially because most new clients asked for some unique twist on our service “Can you also proofread my blog?” “Will you also do the SEO for my blog?” “Can you tweet twice on Mondays, and once on Tuesdays?”

Every time you customize your service you lose money. And in our case, customizing often meant that client left anyway.

This goes back to the lessons Warrillow teaches in Automatic Customer – if you want a subscription-based business to scale you have to stick to your knitting and resist the temptation to customize.

Nothing beats a better product

“I just keep making something I would want.” Jason Fried, co-founder, Basecamp.

At the end of the day, you’re only as good as your product. And you should be proud of your product.

Sure, you can have a snazzy website and offer 30 days free, but if your product sucks, so will sales. It’s as simple as that.

This simple truth has been proven over and over with BlogWorks—after all our efforts at marketing, nothing beat a referral from a client who loves what we do. It’s hard work to keep improving something already working, but it will pay off.

“Make every decision—even decisions about whether to expand the business, raise money, or promote someone—according to what’s best for your customers.” Derek Sivers

For the last three years, we’ve been introducing upgrades to our service about every six months. The result is a more complicated process.

At the same time, the results for our clients have improved and that’s turned into more referrals.

A great question to ask is “Is my product so good they can’t live without it?” If not, get back to the drawing board and make it better.

How we look today

“Timing, perseverance, and 10 years of trying will eventually make you look like an overnight success.” Biz Stone, co-founder of Twitter

Writing this article reminds me of how much water has gone under the bridge since the day I offered a half-baked idea to that unsuspecting audience. We aren’t a million dollar business – not even close – but we have a steady stable of clients and a dedicated team working hard to get it all done.

I’m proud of what we’ve created.

It hasn’t been easy promoting a service nobody’s heard of (“You do what?”)—I’ve lost count of how many times I’ve rewritten our sales copy. But our service works and we’re filling a need in the market.

And then there’s me.

I’m now sixty and while I consider myself a hard worker and eternally optimistic, I notice my energy for the business comes and goes depending on what job has to get done (or what the weather’s like outside.)

I’ve hired a software designer to build a back-end for our service and that interests me. And we’re trying new approaches to getting prospects into our sales funnel – that also interests me.

On the other hand, I notice I have less patience for anything not new, like fixing problems we’ve seen before or explaining the details of how to complete a task that I think should be obvious.

I’m not sure if BlogWorks will ever be much bigger than it is. That’s okay with me. Maybe someone will be attracted to the regular income and scoop it up – okay with me as well.

In the meantime, my goal is to have fun running a start-up (how long are we allowed to call a start-up that?), working with a great team and delivering a great service. And on days when the magic isn’t there and I’d rather be writing a 3,800-word blog post (like this one), well, that’s what I’ll do.