Not Everything Goes Smoothly: Ryan Shares Some Crazy Failures

In 7+ years of freelancing, I’ve done a lot of things that seemed promising at the time… but then never really panned out like I thought they would.

For example:

A friend and client of mine was starting a new business with some partners. They wanted to create a website that would provide high quality videos on a variety of business topics.

They wanted to create an online “video magazine,” so they planned to provide the videos free, then monetize the site with advertising.

Anyway, my friend asked if I would be willing to be their resident copywriting expert.

I had some reservations, but they’d already taped some well-known experts, including Michael Port and Dave Lakhani. I figured if these experts were on board, then I ought to be, too.

So a few months later I flew to New York City to be videotaped and share my expertise about direct response copywriting.

I spent the day in front of a camera, in an apartment over a busy street, sometimes taking two or three takes to get a particular clip right.

The videos turned out really well. I was impressed. And I was looking forward to this new business rolling out.

Unfortunately, the new business never really took off.

I’m not sure what happened, but I wouldn’t be surprised if the company was underfunded, or perhaps the partners got into an argument and went their separate ways.

For me, it was yet another “learning experience” — an investment in time and money that never brought any kind of return.

More recently, I partnered with a friend and business acquaintance. I wrote a couple sales letters for him under an agreement that granted me a percentage of sales.

The first sales letter did really well, converting as high as 12.10% at one point.

The second sales letter did okay. It sold the product, but the advertising was expensive. With just one product on the front end, the offer wasn’t profitable and hovered close to break-even.

Anyway, my friend never paid me any commissions on the first letter, and it seemed to me that he never put much energy into growing either business.

To be fair, I didn’t put much effort in either after I finished the sales letters. What can I say? I cut my losses when I don’t get paid.

Want more examples?

  • When I was still employed, I borrowed money from my employer to get a fly fishing ebook written by a ghost writer. I wrote the sales copy and sold it on ClickBank, but the ebook never sold enough to recoup my costs.

I could probably fill a small book with all the things I’ve tried that haven’t worked out.

And yet in spite of all the failures and false starts in my past, there have been plenty of things that have worked out well for me.

So if you’re discouraged right now, just remember that success is a winding road that’s littered with the cast-offs of your work.

Some months are messier than others. ;-)

Just continue to refine your skills… improve your discernment… and try new things.

Eventually, you’ll get there.

-Ryan M. Healy

P.S. Success comes easier when you know How to Write (and Persuade) Better than your competition. Advertising legend Drayton Bird packs a lifetime of lessons into three videos you can get here:

Ryan M. Healy

Ryan Healy is a financial copywriter and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like,, and

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