Learn From My Biggest Business Failures

With a few successes mixed in

Photo by Pawel Janiak on Unsplash

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Some of My Biggest Business Mistakes (and a Few Surprises)

Recently, Morgan wrote a great post on some of her mistakes in business. I loved it, and wanted to share some blunders I have made along the way. I also wanted to share a few things I got right, because I think there’s a trend there.

That Time I Wrecked My 500,000 View Website

By the start of 2015, my website’s traffic was at an all-time high. Traffic for 2014 had topped half a million, and traffic in Jan of 2015 topped 50,000. So I was on pace to hit 600,000 or so in 2015. I decided it was time to get serious about my website and its ability to drive leads to my business.

I started researching all the ways to improve your website. I switched to ‘dedicated’ hosting. I learned about how plugins and scripts could slow down the load time of your website. I deleted a bunch of crap and got my website’s load time down to a blazing 3 tenths of a second.

Then I found the article that changed everything. It said that Google would rank your website higher if it was listed as http://yourwebsite.com instead of http://www.yourwebsite.com. Apparently, removing the www improved your search rankings. And as luck would have it, this was a very easy switch to make, right in the Wordpress dashboard!

So I made the switch, right around the time that I switched to ‘dedicated’ hosting.

Then I watched in shock as my traffic began to fall. A lot.

At first, I assumed it was something to do with the hosting. Years later I would learn that the advice on removing the www only applied to NEW websites. When I did it on my existing website, I unwittingly broke every search link on the website.

Yeah. I went back and checked, and sure enough, the traffic losses were all coming from search engines. And since search engines were almost 80% of my traffic at the time, well you can imagine what happened. The 500,000 views in 2014 went down every year till 2023, when views were up marginally, and rose again slightly last year. To 25,000.

To be fair, traffic would have likely fallen anyway even if I hadn’t botched my site, as user behavior was changing, but it wouldn’t have been nearly as large of a drop.

I Sabotaged My Book’s Presales

This is another instance of trying to do my own research and listening to the ‘experts’ and it backfired. My book came out in 2013, and I had all of 2012 to help market the book and prepare to launch.

Then, as now, Bestseller lists were pivotal to a book’s success, especially at launch. This meant there are, and were, a lot of competing theories on how to maximize your chances of making the Bestseller lists. A key component was increasing your sales rank as much as possible on Amazon. Especially at launch.

So how did presales affect sales rank on Amazon? I researched, and the ‘experts’ said that all presales would count as books sold on launch day. For example, let’s say you presold 500 copies of your book. On launch day, Amazon would count those as 500 copies sold ON LAUNCH DAY. So presales are a great way to ensure you have a high sales rank at launch, so the experts said.

So that’s what I did, starting a year before my book launched, I went all-in on presales. All my speaking in 2012 required that the event organizers buy books for attendees. It worked great, and by the end of the year I had presold a couple thousand copies.

Then I learned….Amazon actually counts presales as they come in. Which I kinda guessed because I noticed the sales rank going up a bit throughout the year.

But what’s worse…when my book launched in march of 2013, Amazon didn’t have enough books in stock to sell! The book sold out after a day or so, and for the first WEEK (launch week!!), Amazon was sold out.

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Photo by paolo candelo on Unsplash

I Wasted WAY Too Much Time and Energy Judging My Performance Against Others

In many ways, social media is performance art. Especially in professional circles. Years ago, a friend added me to a private Facebook group they had created of friends and peers that focused on business travel. The goal of the group was to bring together frequent business travelers to share tips and advice on how to navigate the experience.

At first, the group was great. Members freely shared their best tips on travel, the best luggage, how to book flights, rides and everything more efficiently. But over time, the group devolved into a stream of humblebrags about free upgrades, dealing with clients that want to pay double your rate, etc etc etc gag.

Let’s be honest: When your business hits a slow stretch and all you see on social media us updates from your peers about how they are (supposedly) conquering the world, it leads you to question what you are doing wrong.

Several years ago I reached this point. I was doing all I could, but I just couldn’t match the endless prosperity that seemed to be raining down on everyone but me.

I reached out to a couple of peers who I trusted to tell me what was really happening. I asked them both how in the world they were making it and what in the world was I doing wrong?

The first one told me his wife had a career as a realtor, and that’s how they were paying the bills. Another told me that she was keeping afloat due to a military pension. Both told me the same thing: Much of the content I saw on social media bragging about success was manufactured. The guy that who was speaking at events all the time? His dad owned his ad agency and was floating him cause he wasn’t being paid to speak. The ‘highly successful’ marketing expert with 200,000 followers on Twitter was working life insurance on the side and his wife was paying the bills.

This taught me to stop worrying about what others did or did not do with their work. It taught me to run my own race and to work on what I can control. Comparing myself against someone else is pointless because that person operates under a completely different set of assets and liabilities than I do. And I am only seeing their highlights, while being painfully aware of all my shortcomings.

So Many Offers With No Takers

Morgan talked a lot about her spending weeks and months developing courses and offerings that never sold. I’ve had the same thing happen so often. One problem I’ve consistently ran into is rushing an offer out of desperation moreso than market need. Cash is slow so let’s throw out a Black Friday offer. Did this multiple times on my consulting services, think I sold one package. Which helped me, and the client, but that’s a decent chunk of promotional time over multiple years for say $500 or so.

Over the years, all of this taught me the value of failure. I think failure is only a negative if it leads to you quitting. And even that can be a positive if it forces you to pivot in a direction that leads to something better. But typically there is a key lesson in each failure that can be taken refined an improved upon in your next attempt.

Here’s Some Successes

One of the common themes through many of my mistakes over the years has been forcing something without giving it the time it needed.

On the other hand, often my successes are a product of spending plenty of time to develop a solid plan and execution.

Here’s an example that goes back to my attempt to get a book deal for Think Like a Rock Star. In 2011, I began to start pitching publishers on the book idea. One of the things that attracted publishers was my social media presence. And they noticed that I was posting my presentation files on Slideshare, and that they were getting a few hundred views or so. That proved there was interest in the concept, in their eyes.

This gave me an idea. What if I gave a talk, and shared my slides on Slideshare and promoted it before, during and after the talk? This could increase views on Slideshare, and I could use those higher numbers to help sell publishers on the support for the ideas in the book.

I had a talk planned in Atlanta for the fall of 2011. All throughout the Summer I promoted the talk on my blog, on my accounts on Twitter, Facebook, everywhere.

That ensured that I had a standing-room-only crowd for the session. Then before the talk began, I posted the slides on Slideshare, and pointed everyone to the URL for the slides. I even scheduled tweets to go out during my talk, promoting the slides on Slideshare. Then when the talk ended, the last slide reminded everyone to find the slides on Slideshare.

All of this worked wonderfully. The tweets for the slides going out DURING the talk were a big hit, and the slides were so popular they got featured on the frontpage of Slideshare later that day, due to all the sharing happening on Twitter.

When the smoke cleared, the slide ended up with over 50,000 views on Slideshare! This gave me credible evidence I could (and did!) show publishers that my idea had an audience.

But it all happened due to months of planning.

Another time, I created a $30,000 revenue stream on a complete whim. In 2008 and 2009 I attended and spoke at South By Southwest. It was an absolutely amazing experience both times, and I got to spend a ton of time meeting all these wonderful people I had previously only known online.

But each time, I got home and totaled up the expenses and realized damn…that was a helluva lot of money to not get any business out of it! We were talking probably $4-5k in total expenses for both years, with no direct business from either trip.

2010 rolled around, and I simply could not justify going back, so I stayed home that year. I had begrudgingly convinced myself I wouldn’t be going to SxSW in 2011 either.

Then in January of 2011, I started seeing all the updates from my friends who were going. The more I thought about it the madder I got that I couldn’t afford to go.

At the time, I was doing Blogchat every Sunday night on Twitter, and had just started taking sponsors a few weeks earlier.

I had a crazy idea. What if I tried to do a live version of Blogchat at SxSW? I could sell sponsorships to cover the event and my expenses. Hey what’s the worst that could happen? There’s no interest and I end up staying at home. And I’m doing that anyway.

So I wrote up a blog post in a few minutes, said I wanted to do a live Blogchat at SxSW, and if you wanted to sponsor the event, let me know.

I sold the main sponsorship within 30 minutes. I was stunned. Dell later came on as a sponsor as well. I had no idea this would work, let alone so amazingly well. The sponsorships I sold gave me enough to cover my expenses for a week in Austin, plus a little spending money.

Here’s the kicker: Flying into Austin for the event, I had a short layover in Houston. There, I met a conference organizer I knew who was also heading to SxSW. I told him I was doing a live Blogchat at SxSW, he loved the idea, and we agreed to a deal to have me do a live Blogchat at his event in the fall. The deal was made at the gate waiting to board a flight to Austin. I ended up doing about 5 more live Blogchats at conferences over the next year.

All over an idea that was launched on a whim. But it shows that there was always a way to monetize Blogchat in a live setting, I had just never explored it. There could also be a way to monetize your content that you aren’t considering.

The two key lessons I have learned is to not give up, and to give an idea a long enough runway to get off the ground. If I had demanded quick results from Substack in terms of subscribers and revenue, I would have left here after the first couple of months. It’s still a slog, but slow and steady growth is still growth. And much of what I am doing differently here on Substack with Backstage Pass came as lessons learned from the last 10-12 years of trying to get a newsletter off the ground.

The problem I have run into in the past, and I know many of you can relate, is getting in a pinch and needing to quickly develop a new revenue stream. It leads to forcing growth, which rarely works. It leaves you frustrated and can lead to a cycle where you start and stop new streams over and over again. Never giving any of them the time they need to mature and become profitable.

So what’s your biggest business mistake? Do you relate to any of these? What about your successes? I’d love to hear those as well, drop a comment, please!

Oh and

Neela 🌶️

will be here Thursday. Did I bury the lede there, or what? :)

Mack

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Backstage Pass teaches you how to better connect with your customers, readers, clients, or donors. The lessons shared here draw on my experience over the last 20 years building customer engagement strategies for companies like Adobe, Dell, Club Med, Ingersoll-Rand, and countless others. I give you real-world research, examples and tactics that show you how to create customer engagement efforts that drive real business growth.