Confessions of an Entrepreneur

3 entrepreneurs reveal the stuff-ups they'll never forget

Image via Stocksy

Perhaps the saying should be, “to err is entrepreneurial.” Here, three entrepreneurs reveal their biggest, face-palm-inducing stuff-ups. 


What’s lamer than a crappy photo of Nebraska? Having to pay US$8000 in copyright infringement penalties for it. At my company The Contents Factory, we write thousands of blog posts every year for our clients and agency partners and although we try to catch everything, occasionally a mistake sneaks by us. On this occasion one of our writers published a blog post to a client’s site about finding great deals in Omaha, Nebraska (complete with an altogether underwhelming photo of the city, which may or may not have been taken by a drunken college student with a camera phone in 2005). More than three months after the post went live, the client got an email from an attorney who deals with one thing only: image copyright infringement. Fortunately our lawyer was able to negotiate a settlement – we ended up paying US$3000 instead of the original US$8000 in copyright infringement penalties. But it was the equivalent of several months’ rent at the office, or holiday bonuses for our staff. All for an image published on a website we could prove via Google Analytics that fewer than 100 people read. It was our fault but I’ll never make that costly mistake again.

Kari DePhillips, co-founder The Contents Factory


Our business The Real Estate Style, offers a service where we go into houses that are up for sale and style them to attract buyers. Well, we once did a job – against our better judgment – that was a mortgage repossession. The house had already been left to fester by the previous owners, who were being forced to sell it. I had a terrible gut feeling yet STILL didn’t request payment upfront (can you guess where this is going?). After the auction we went to collect the furniture and artwork, to find a AU$7000 painting, a AU$2000 rug and, randomly, two cushions had been stolen overnight. But this isn’t the only – or worst – time this has happened. One Saturday morning we got a call from an estate agent just hours before the auction, saying the house had been cleared out overnight and was now 100 per cent empty. What did we learn? To always have good insurance; writing down everything you put into a house and keeping receipts! And to never ignore a bad gut feeling – if it smells bad, it generally is!

Sara and Amy Chamberlain of The Real Estate Stylist and The Artwork Stylist


When I started my web development company Dotnet with business partner [and] friend Antonio, I thought that between the two of us we were not only the best marketers on the planet, but also the best at design… the best at accounting… the best at sales… the best at everything. And that we didn’t need anyone else. Whenever anyone rang to speak to these various departments – which were made up of he and I – we would put them on hold and simply pass the same phone over to each other. I’m pretty certain most clients noticed that each time they called it was the same two voices pretending to be other people. Since then, the biggest lesson we learned was – you can’t be all things to all people. The sooner you admit there are things you don’t know, the sooner you can employ the right staff to fill these skillsets, and the smoother your business will run.

Flavio Faccin, founder of Dotnet Webdesign


Do you have an entrepreneurial confession to share? Comment below – we’d love to hear from you!

This is an excerpt from Issue 23 of the Collective, grab a copy to read the full article. 

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