The Good, Bad, And Ugly Of Being An Entrepreneur

Y’all know I keep it 100 over here. Today I’d like to talk a little about the good, bad, and ugly of my current entrepreneurial journey. Too many folks write only about the good, but that is limited in its instruction and inspiration. It’s the bad and ugly of the entrepreneurial process to which most people relate and from which they have useful takeaways.

To steal a line of gallows humor from one of my advisors, “It’s always darkest before it’s pitch black.” That is some dark ass humor, but it’s true; at least in my experience. What the joke doesn’t say though, is if you keep working and maintain a positive attitude, eventually, the sun does shine.

I suppose what is good, bad, and ugly is subjective, but here’s my assessment of my situation.

The Ugly

A while ago I wrote about how I was using Groupon to increase product and brand awareness of my biz by getting exposed to the fifty million subscribers on the Groupon platform. The hope was it would also have at least a temporary positive effect on cash flows, and help with acquiring new users and customers who would come back and order without a Groupon voucher.

Well, so much for my plans. The whole Groupon thing completely blew up in my face.

I sold $30,000 worth of vouchers in two months. The economics of the Groupon deals are such that they make you cut your prices in half, then split the sale amount with you. So, unless you are marking up your product 4x, you lose money every time someone redeems a voucher.

I was excited we were selling so many vouchers, about 700, but I became alarmed when I noticed they were being redeemed at an extremely high rate (probably due to the holidays), which was causing pressure on cash flows. Thankfully, I was paying attention and a few days before Black Friday, I stopped the Groupon deal. If I hadn’t done so, I would be out of business today.

Let me repeat that. If I hadn’t stopped the Groupon deal before Black Friday, my business, the one I put all my blood, sweat, and tears into the last few years, would be shut down today.

Why, you ask?

Thanks to the Groupon deal I now owe the printer a fair amount of money. I’m extremely lucky they believe in me and the product and are working with me while I pay off the balance I owe, which is even more painful because January and February are traditionally slow as people take a break from holiday spending, and all the Groupon vouchers sold didn’t expire until the end of February. So while sales were slow, I was watching the outstanding balance increase and couldn’t do much about it.

Thankfully, sales are normalizing, the money-losing Groupon voucher redemptions have stopped, and I’m paying down the balance.

Oh, and the extra Groupon customer acquisition thing is a myth. So far, despite many people promising to do so, only one Groupon customer has come back and made a purchase for which they paid the normal price. After going through this very stressful journey, I wish I had decided to incorporate other methods into my business that would’ve helped me build brand awareness instead of using Groupon. My friend told me that I should’ve had some custom pins made so that I could hand them out to people in my local community as well as to professional businessmen and women at business events and tradeshows. I guess building a business is a system of trial and error and you need to be able to figure these issues out if you want to become successful. I hope that things start to normalize now. If things do normalize a little more, I’m going to take my friend’s advice and start looking into the little ways I could start improving the awareness of my brand, such as look into sites you’re able to view if you click here or search around for similar physical marketing services.

The Bad

Since I owe the printer so much money, I haven’t been paying myself for the last few months, as every dollar I’ve made has gone to reduce the balance with them. As you can imagine, this has caused a lot of financial and emotional pressure, if there wasn’t so much financial pressure I would have looked into honoring some of the prints using a brother pocketjet thermal printer or something similar.

To earn a few extra bucks, I started Uber driving last week, but, unfortunately, where I live is not a city of early adopters, so I have to drive thirty miles to Green Bay to pick up Uber fares. One of my friends encouraged me to apply to be an Uber driver because he also does it in his spare time. The job is flexible and can be rewarding, especially if you’re working in the right areas. Thankfully, he was able to tell me everything I’d need in order to start a career driving for Uber. He said it was essential that I had my own vehicle that I could use and that I would also have to look at taking out some insurance to allow me to take people to their desired destinations. He told me to Get Uber insurance quotes online because it might work out cheaper. After doing all that, I was finally ready to start my new career.

I also created a profile on Upwork to pick up consulting gigs.

The Good

And now for some potentially good news. The end of next month I will be featured in a major national magazine in a section focused on people who make career changes. And this summer, I will appear on a TV show, which, due to a crazy-penal confidentiality clause, I can’t discuss.

So there’s that.

But I’ve written before about how great PR doesn’t always translate to sales. And I don’t believe in silver bullets. But lord knows I could use one now.

And, if I’m lucky, the sun will soon emerge from this shitty, pitch-black place in which I find myself. And it will do so shining brighter, hotter, and more persistently than ever.

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Feature image credit: Thiago Rodrigues dos Santos Clint Eastwood in the good the bad and the ugly


  1. Aw, James I am so sorry to hear about what happened with Groupin, but does sound like you have a plan and sending some good vibes your way now for only the best now.

  2. Great post. Cash flow struggles are real. Hang in there! You’ve got a great product and a solid vision. The best is yet to come!

  3. Ugh James!!!! This is not cool at all. I cannot believe that about Groupon!! Thank God you were paying attention!! I love how honest you are here as I’m sure SO many people can learn from it. I’m totally exciting to find out about this national magazine and super secret TV exposure. Keep up the hustle James – you have a great product that WILL succeed.
    I’m also needing to get back to you on #train4life 🙂

  4. Great post – thanks for sharing the real deal of what goes on behind the scenes. Clawing your way through seeing your dream become a reality. Hang in there! 🙂

  5. So sorry, James. It’s sucks because you’re such a go-getter with a great product. I know the bigger exposure helps. I will keep you in my prayers. Best of luck to you.

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