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Massive Entrepreneurial Fails.

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Fall seven times. Stand up eight.
Japanese Proverb

I’ve been thinking that our followers oftentimes think we are somehow “lucky” in business or smarter than they are. So, this week, I asked my awesome friends to share a fail, disaster, or total miss from their businesses. And, to let us know if there was a lesson or some good that came from it.

I’m totally teasing with the title. These aren’t “Massive Fails“. My point is to show that at the time they probably felt like it, but you can see that every single one was or is just a step on the path to more awesome things.

I hope you enjoy this post. If so, please comment and share!

Brian T. Edmondson

When it comes to getting “lucky” in business (or anything else in life) I always think back to one of my favorite quotes from the Roman philosopher Seneca who said, “Luck is what happens when preparation meets opportunity.” Even those who win the lottery had to actually go out and buy a ticket and realize that they were taking a gamble and ran the risk of (certainly) losing money.

Lucky for those of us in business (no pun intended), the chances of success are much higher than hitting PowerBall, but we should realize that there is no guarantee of success and most likely we’ll have to lose a lot before we find a winner. Whether running a new paid advertising campaign, launching a new product, etc. we’ll have to test several different headlines, copy, audiences, etc. and fail quite a few times before we find a winner. For most people who fail in business it’s not because they aren’t lucky enough or smart enough, it’s because they just didn’t persevere long enough before they could succeed. It’s the classic Acres of Diamonds story.

I could give endless examples of where I’ve failed and continue to fail, but the key is I embrace the concept of failing fast and failing forward. A big example of what many people would consider to be a big failure was when I declared personal bankruptcy at the age of 25 while pursuing my dreams of building an online business. A traumatic experience no doubt, but I came out of that experience a better person in so many ways.

Just recently I sank around $1,000 into a Facebook ad campaign to promote a product and didn’t make one single sale. Losing $1,000 and having a big crush to my ego (I’m supposed to be a marketing “guru” right?) wasn’t pleasant, but the lessons learned on what worked and didn’t work were priceless.

Don’t be fooled by anybody that tells you that starting an online business and making money online is easy and doesn’t take hard work, dedication, and sometimes, yes… a little bit of luck.

Karon Thackston

I have had numerous fails during my 20 years of owning Every time I’ve made a mess of things, I’ve learned something – even if it was to never, EVER do _____ again.

One of the biggest mistakes I made (and one of the hardest to get over) was not outsourcing. In my mind, outsourcing was an expense that I could not afford early on. I thought I needed to do as much as possible myself to save money. Here’s how that worked for far too many years…

I’d need to set up a new funnel (or do some other techy thing, or install and configure some funky plugin, or whatever). I’d spend hours trying to learn how to do what I needed, digging around the ‘Net for free tips and whatnot. Then, I’d fail at my first 3 or 4 attempts. It finally dawned on me that I was losing money hand over fist by not outsourcing.

When I realized how much I could have been making in the 5-7 hours I struggled and did not even accomplish what I wanted, I was shocked. All the while, I could have paid a pro to setup the {whatever God-awful, techy thing you think of} and it would have taken them only minutes because they do this sort of thing all day, every day. I wasted time (when I could have been making hundreds of dollars) in order to save $50 or $75.

I head slapped myself and began looking for help the same day I had this realization. Not only did it free me up to make more, it also alleviated a LOT of stress.

Lou Bortone
“The Godfather of Video”

Share a fail? There are too many to keep track of! As entrepreneur, the only profession with a worse “failure rate” is baseball, where you only have to hit the ball 3 out of 10 times to be a superstar.

In fact, there are definitely times when I’m only batting 3 for 10 when it comes to promotions, selling products or selling coaching. Fortunately, those 3 “hits” are usually enough to run a successful business, and the “public” rarely knows, nor cares, about the 7 ideas that flopped.

I remember one embarrassing “dry spell” when I was participating in a “selling” program with a highly regarded “guru.” Our mission was to make 50 sales calls and close as many as possible, using their “foolproof” sales script. I made dozens of calls and was literally zero for 50. Nada. The big, fat goose egg. Epic failure. Not. One. Sale. 🙁

The lesson: Sales “scripts” are not for everyone, and some selling “systems” simply don’t work for introverts or less assertive personalities. I was a square peg trying to fit into a round hole. But once I dumped their “foolproof” script and put my own personality into client conversations, everything changed for the better. Skip the script. Follow your gut. You do you!

Angela Wills
Digital Business Coach

A total miss happened very early on for me. I was DESPERATE to leave my afternoon-shift factory job and I wanted to be gone in a flash. The ONLY thing on my mind was getting out of there. There is so much to a business than replacing one income for the next, which I was able to do by taking on Virtual Assistant clients.

I quit my job and moved into my business role but the total miss became evident about four months later when I was basically tied to my desk morning, noon and night. I had quit my job to be home for my son, to create a life I loved and to love what I did and I had none of it. The only thing I’d done was trade one boss for about 15 (or up to 25 at times) and I was so stressed out, overwhelmed, overworked and just could not even see or think straight. It was a serious problem!

I fixed it, of course, and it’s now eleven years later and I make it my mission to NOT see others get caught and stuck in the same trap as I did. I now live with the kind of freedom that lets me do what I want, when I want and where I want.

That did not just happen. It had to be designed. It had to be thought about, planned about, worked on and tested until it became a reality. And I love that. I love that we CAN create exactly what we want, if we get really clear on what that is.

Kelly McCausey

I have tried a lot of things in my business that didn’t work over the years. I’m willing to fail, even spectacularly, even publicly, if it means I’m stretching and growing and have the chance to love people and make money. That means I could tell you any number of stories 😉

Like the time I decided to tackle the whole launch formula thing.

I was selling an array of products easily and profitably but a lot of smart heads said I should have a ‘signature product’ that sells for a higher price. So I retired a lot of individual products, went into my virtual work shed to create a really big product with modules galore. Then I studied the process of having a big launch. I planned out videos and emails and crafted the best sales page I could imagine – which wasn’t easy because the product was now sooo big I didn’t know what to say about it. I reached out for affiliate support – which did not come in droves.

The launch week arrived, everything was ready. Freebies every day, new videos every day, awesome follow up planned. And pfffffzzzffffzz.

I made sales. About $10,000 in total. Hurray? Not really. For all the time and effort, it didn’t increase my overall sales. My expectations were that all this extra hoopla and the big course price, together would create at least $25,000 at launch and keep making me big chunks of cash for a long time to come. That isn’t what happened. Turns out, it’s not simple to sell expensive products that include everything but the kitchen sink.

I dropped it. I don’t sell it anymore. I GIVE it to my coaching clients to support them in whatever area they’re needing extra information in.

In some ways I don’t regret giving it a try because I had to know. In another, private, deep down in my heart way – I wish I hadn’t done any of it. It sucks to fail.

I took my lessons from it though. I rock at creating, marketing and selling smaller products that meet very specific needs. I am in my genius zone with I deliver group coaching programs and challenges. I keep my focus on these things and continue to love people and make money.

Candice L. Davis
Author Coach

Every time I’m asked about a business failure, the same story pops into my mind. It was the kind of painful moment that lays a groove in your brain so you never forget it. Four years ago, my business partners and I put weeks into building our first digital product, an online course to help people write, publish, and market their nonfiction books. We were proud of the course, and we invited some of the experts we knew personally to become affiliates for our big launch day.

They had the audience. They had the engagement. They sold nothing. In fact, they did little or nothing to promote the $1500 product.

The problem: We’d reached out to experts who’d never been involved in affiliate marketing, had no idea what it entailed, and didn’t really have an interest in promoting affiliate products. They were lovely people who wanted to do us a favor, but a post or two on their Facebook business pages didn’t move the needle for us. Our affiliates didn’t know what they were doing–and neither did we.

The lesson: It’s a lot easier to work with experienced affiliates for a big promotion, but if you’re just introducing your affiliates to the concept, it’s wiser not to rely heavily on them for your marketing efforts. (It seems like common sense now, but we were caught up in the excitement of building something new!) Make the effort to get the newbie affiliates’ buy-in, and make sure they have all the information they need to do a great job as an affiliate. A few months later, we did just that, and we enjoyed our first multi-five-figure day with one webinar for a single affiliate.

Terry and his DogsTerry Dean

Well, this is a toughie, because I have so many failures and mistakes. Where should I start?

Here’s a good one. I had a flash of brilliance. It was an incredible idea that was going to make a fortune.

Create a step-by-step marketing course designed specifically for local business owners. Perfect. They all need this. I disappear into my man cave and work on this for 6 months. It was a masterpiece. Over 300 pages packed with A-B-C instructions, checklists, worksheets, and more. The crowd cheers, “He is finally done and ready to launch this game changer.”

Launch. Silence. A few sales trickle in, but nothing like the stampede that was expected.

Six months down the drain. What was my mistake? No one identifies themselves as a local business owners.

Local business owner is too general. They’re dentists, chiropractors, CPAs, physical therapists, gym owners, martial arts dojos, restaurateurs etc.

I was able to make the project profitable by editing the product and sales copy to dentists. Then going after that specific audience.

But this miserable failure has an even better silver lining to it. Around half of my one-on-one coaching clients sell B2B in these exact types of niche markets. A portion of their success has been built upon my failure.

The big takeaways here are to do your research before running with a big product idea. What are people currently buying? What do they want to buy? What solutions are they searching for?

Everyone wants a custom solution just for them…even if the answer is 95% the same as other related markets. Becoming more specialized is a way to set yourself apart.

And even painful failures can be a stepping stone to greater success.

Note from Nik: If you’re an intermediate to advanced marketer and you sell your own products – be sure to check out Terry’s My Marketing Mentor Program

Nicole Dean
Awesome Human, Author, Business Consultant, etc.
From here!

Well you already know my motto. “You don’t have to be perfect to be profitable’. (You can even tell from this image circa 2012.)

God knows that I’m not. I manage to screw things up often enough to prove that. 😉

My biggest failures and what I learned.

I would say my biggest failures over the years always come from (lack of) confidence and (lots of) fear.

I’m scared to do something and I don’t take action and I miss my window of opportunity. (You have no idea how often this happens.)

I WISH I had more failures, but I have the opposite problem. I don’t have enough. Because I do the things that I know are safe and easy. Which isn’t always a bad thing in my position. But it sometimes is.

I mean, I do preach to my coaching clients and we brainstorm what would be “fun, easy, and profitable”.

And that’s true. That’s where I like to spend 90% of my time.

But… sometimes a good stretch is needed as well. 🙂

Along the same lines, I’ve oftentimes been scared to let go of something so I hold onto too many things and I dilute my energy.

I’ve failed to let go of tons of stuff, even though every year, I commit to doing it.

Every year, I make a list of websites that I need to sell or give away.

Every year, I think how much easier my life would be if I would just do it.

But I don’t do it. This mistake has literally cost me hundreds of thousands of dollars – simply because I’m not 100% focusing enough on my ‘money’ projects.

The funny thing is that, if I looked at my business and my life as if I were my own coaching client, I’d kick my butt!

I would never let one of my coaching clients hang on to this much baggage. It’s not practical and it’s certainly not the most profitable plan.

It’s not even that I really spend TIME on most of the “extra” stuff. It’s just a mental drain and sucks my soul. (Not to be toooo dramatic or anything. lol!)

I keep justifying that the extra websites and projects are just “sitting there making money” – which is true for a lot of them. But, how much risk and wasted mental energy do I really need in my life?

If I were to let them go and focus on my Focal Point – the profit that I would get from that would so squash the small amounts that some of those small sites bring in every month.

Over the years I have worked hard at simplifying, but it’s still not enough. 

1. No more junk mail. (I’ve eliminated most of my junk mail.)

2. No more telemarketers (we turned off the ringer on the home phone years ago).

3. I’m dumping all unnecessary things – even if it only involves a few minutes per month.

4. Heck, I even had laser hair removal on my legs so I don’t have to waste time shaving anymore. lol. (Too much information? Probably.)

It’s time to file this away for good and to put my chronic overwhelm from mental clutter to rest.

Lesson learned. All things come with a price. Even good things. I don’t need this much “stuff” in my life or in my head.

My Epic Fail. 

But if I were to say one EPIC fail that I had, it would actually be a co-epic fail with my friend, Kelly McCausey who shared above.

We host Beachpreneurs Conference / Workshop events.

And, because we are smart, we rely on experts. So, for our hotel event, because there’s so much risk, we used an Event Coordinator.

That was a smart move.

But we still ended up with miscommunication between us and the hotel, which cost us money – and a LOT of stress.

Kelly read the contract. (And at this point she’d already hosted a few events, so she was pretty knowledgable.)

I read the contract. (I used to write Bank Manuals for a living so I know how to pick apart words!)

The Event Coordinator read the contract. (And this is what she does for a living.)

We all misunderstood one word.

It was a costly word.

The result from this mistake?

Since then, Kelly has become pretty freaking smart in negotiating with hotels for events. Both for us and for her own events. It was also a great test of our partnership AND our friendship (not really) AND we learned some things about communication AND in stress management (really). lol.

Thankfully we have a great hotel now for our Beachpreneurs events. And we love going back every year. (Join us!)

Talk to me.

1. Do you have a failure that you would like to share? And a lesson learned?

2. Did one of my friends’ posts resonate with you?

3. Do you suffer from mental chaos? What are you doing about it?

As always, I would love to hear your thoughts on the matter.

Nicole Dean

PS. If you like this post – share it and check out my friends’ sites. That’ll make me happy! 🙂 Appreciate you!

I appreciate shares and I adore comments! Please share your thoughts.

  • Bo

    Karon Thackston’s story definitely resonates with me at this time. I know I need to start outsourcing, but have many fears around it: don’t want to spend the money, what if I don’t have enough work every month for a VA, what if the person I outsource to does a terrible job (I have hired for one-off stuff before and sometimes the communication isn’t clear enough and I end up redoing it anyway, plus paying for it).
    Need. To. Do. This.
    Great article, thanks.

    • Nicole

      That is such a common issue, Bo. You’re not alone. I used to teach an outsourcing course. I can definitely chat about it more here, too. Watch for that. <3

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