One Big Reason Small Online Businesses Fail

See the big mistake I made with one of my online businesses and see how you can avoid it.

Today I wanted to share one of my online business failures.

You’ll see how one simple mistake derailed a pretty solid business idea.

And it’s a mistake I’ve seen my clients and many online business owners make.

You’ll want to read it to avoid making the same mistake in your business.

Here’s how it started…

The Business Idea

In 2015, I created a local job listing website called JobsWinona.

The website was a dashboard where local job seekers could find a running list of job openings and links to many non-local, niche job sites.

I discovered the opportunity while working with a local employment agency client.

Three things told me it was an opportunity I should pursue:

  1. Search traffic. I noticed that terms like “jobs in winona mn” were getting 1,900+ searches per month on Google at the time.

  2. Existing market. I counted all the ads in the local newspapers’ help wanted section and did some simple math. I don’t remember the exact numbers, but there were 20 or more listings on average each week. I learned the newspaper charged over $100 per listing (20 x $100 = a solid side income stream).

  3. Paying customers. I had some inside information about one local employer spending over $100K annually advertising their job openings.

It was a pretty safe bet that I could make a decent amount of money by offering online listings to employers and putting them in front of Google traffic.

Plus, I could upsell employers on other services like Facebook or Google ads to help them get even more eyeballs on their listings.

It was a slam dunk.

The Big Mistake

The website was bringing in some revenue.

  • I earned a few small listings here and there.

  • I earned a few cents per click via an affiliate partnership with Indeed and similar sites.

  • And JobsWinona was partly responsible for a lucrative consulting gig working with the employer who, coincidentally, was the one I told you about earlier that was spending $100k on advertising.

Nice, but the revenue was nowhere near as profitable as it could’ve been.

I made the mistake of relying exclusively on the website to do the selling for me.

I thought employers would visit my site, see my offer and jump at the opportunity to buy a listing or an ad.

A few did but not as many as I would’ve had if I had just picked up the phone and called companies to introduce myself and the business.

And it wasn’t just sales I missed out on.

By not picking up the phone. I also missed valuable feedback.

By talking to my potential customers, I would hear their objections and maybe even discover other problems I could help solve.

This would’ve helped me find more opportunities and to fine-tune my offers.


I eventually gave up because I told myself I wasn’t making enough to justify all the time and money I put into the project (another mistake).

And ended up selling the website on Flippa for $500 (AND another mistake).

Every once in a while, I still kick myself for messing this one up.

Live and learn.

The Big Takeaway

If you're building a business online, don't make the same mistake I and many other online business owners make.

Talk to your customers.

Even though it is an Internet business, you are still dealing with actual people.

Sure, at some point, your web pages can become like robo salespeople selling for you 24-7 (which is one of the reasons I fell in love with internet marketing in the first place).

You must talk to real people to get feedback on your offer and fine-tune your messaging on those web pages (especially in a B2B niche like this).

Talk to your customers.

  • Pick up the phone and call.

  • Ask to meet on Zoom.

  • Meet for coffee.

  • Whatever.

You’ll learn a lot.

Music Lesson

Speaking of failure…

One area of my life where I learned a lot about failure was as a performing singer-songwriter.

I failed over and over and over. And most of the time, I was doing it in front of people who were pissed that I wasn’t playing more Journey (true story).

The worst part is that the margin for error for failure was much slimmer.

Because it’s not as easy to be profitable when the product you sell, music, is free.

In fact, Some people would get pissy with me if I asked if they wanted to buy a CD. “Can’t I just hear it on YouTube for free?”

I tried many things to grow an audience and make money.

I had a few things work and was able to break even most months. But it was challenging to make a profit, especially when you have three young kids and a teary-eyed wife asking if I have any money for this month's mortgage (another true story).

But its all good.

The great thing about the struggle, though, was that it made marketing and selling other products much simpler for me.

In fact, I used to do this in my pitches to potential Google Ads clients.

Something like…

“If I can market and sell a product (music) that nobody wants to pay for, I can easily sell your product/service, which I can see 10,000 people a month are searching and paying for.”

So, as a hat tip to musicians making it work and as a lesson to the rest of us that what doesn’t kill you, makes you stronger, here’s an episode of my Music Melting Pot podcast that features songs by singer-songwriters telling all about the highs and lows of being a musician.

Listen now…

Pssst… sorry if this is annoying BUT click the button below to listen on Mixcloud if you do not have a Spotify Premium account and want to hear the full versions of the songs.

Thank you for reading and see you next time.



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