Editor’s note: Hope you all had a restful and/or productive weekend. The following post is a guest post from fellow GTA (Greater Toronto Area) blogger, Graham Bell of Reverse the Crush. I really enjoyed reading about his experience and how he provided a key takeaway from each lesson he learned with respect to starting a business and failing.
Is there anything to be gained from starting a business and failing? That’s the question I propose as you decide on whether or not to continue reading this article. And, in my own experience, the answer is so emphatically
YES!
For the record, I’m not just blowing smoke here like a lot of other freelancers out there seemingly do. Most have started a freelance business, yeah. But how many have legitimate experience attempting to start a product/event company?
It’s easy to look around as an aspiring writer and see all of the entrepreneurial job postings out there and proceed to alter your writing to fit that mould. But that’s just not me!
Back in 2010-2011, I started what was supposed to be a clothing company called Dapper & Debonair. I know, pretty superb name, right?
I also started a lifestyle blog called dapperlifestyle to go along side it. And on top of that, an annual event called Toronto Art Saves was created in order to reach out and engage with our target market. The concept was to promote and work with up-and-coming artists.
Are you starting to see any cracks in the plan yet?
Try to start three businesses instead of one and see how well you execute.
However, I did have the help of 2 other partners. But, if I’m being honest, it was more like one and a half partners. One of them was quite fond of the idea of entrepreneurship, but didn’t take too kindly to actually working.
The good news is that I learned a lot! I always reflect back to the quote from one of my favourite movies ever, Blow, which is the story of an American drug dealer during the 1970’s.
“Danbury wasn’t a prison, it was a crime school. I went in with a Bachelor of marijuana, came out with a Doctorate of cocaine.” – George Jung
Because that’s how I feel about starting and failing. I went in trying to start a clothing company and came out with a Doctorate on how to blog. Well, sort of. It at least led me straight to what I should’ve been doing all along. And what I learned from failure cannot be taught in school.

It also gave me real experience with events and writing a business plan. Here are four other things l learned from starting a business and failing.
Start Small
My partners and I over zealously thought we could start a clothing company, hold down a lifestyle blog, and host an annual event at the same time. And even though it’s true that they are all related, each deserved more attention.
By failing to start small, we aimlessly let our focus fly out of control. The execution was just not there.
For example, we originally started with the intention to be a tee-shirt company and started the blog to help build hype. But I basically have OCD. I got so into blogging that I started pushing the actual products to the side to continue promoting the site.
In my defense though, I was primarily the marketing and branding guy, so you could argue I was just doing my job. However, the lack of focus on just one business diminished the productivity of all three.
Takeaway: Start small and stay laser-focused on producing the best quality rather than getting carried away. Build your product before trying to market it.
Choose Partners Wisely
This one should have an asterisk beside it because of its extreme importance. It’s also a difficult point for most because a lot of small businesses are started by family and friends.
But I urge you to take extra consideration before entering into a business with someone just because they happen to be a friend or relative. You have to avoid partnering with a person that has the “eventually” mantra.
There must be a better reason because it’s not always going to be fun. There are difficult conversations to be had and crucial decisions to be made.
You need to make sure your partner wants to be successful as badly as you do. They need to show that they have something to bring to the table. A skill opposite yours is obviously best.
I and the good partner learned this the hard way and lost what we thought was a friend in the process.
Takeaway: Before signing the dotted line or opening a joint business account with someone, do your due diligence! What skills do they bring to the table and what is their intended motive to becoming an entrepreneur?
Ask for the Sale
One of the great reasons for starting a business is that you get to give back. Yet you can’t let that detract you from the real purpose, which is to make money.
Probably the biggest regret I have with the company is not putting up the products we made for sale. During the course of Dapper & Debonair’s short lifespan, we actually produced 2 products: A bottle opener and some neat looking rocks glasses. I still use both products to this day.
Unfortunately though, we literally gave them away as thank you gifts during the two Toronto Art Saves events. This decision still irks me to this day. In my opinion, the giveaway cheapened and depleted the perceived value of the products. In fact, I think guests would have appreciated them even more with a price tag attached.
Takeaway: Don’t be hesitant to ask for the sale. Your hard work and effort are worth something.
Go All In or Don’t Go In
I’m not much of a believer in plan B’s. Why even start something if you don’t think it’s possible in the first place?
Sure, I do agree it makes sense to work a part time job while you get the business up and running. The bills aren’t going to pay themselves. But you have to be absolutely dedicated and believe that the company will succeed.
I really don’t think any of us fully bought into what we were doing. Granted, we were fresh out of school and attempting to start a business in one of the most difficult industries that exist. Still though, that’s not a valid excuse.
Regrettably, we were hesitant to put what little money we each had on the line. And that turned out to be a big mistake because it impacted our execution and ability to gain trust with potential customers.
Takeaway: Go in head first with a whatever it takes attitude. Most importantly, enjoy the process!
Final Thoughts
Hopefully, I didn’t scare you away from starting your own business, but facts are facts. Starting a business is challenging. On the other hand, it can be energizing.
I now operate as a Sole-Proprietor partially because of my past experiences. However, if I was to ever start another product/event company, these are a few components that I would pay a hefty amount of attention towards.
About the Author
Graham Bell is the Owner | Blogger of Reverse the Crush, a website about eluding the 9 to 5 in favour of more time and freedom. Graham worked in the financial industry for nearly 4 years but recently quit to pursue more meaningful work. He now works from home as a blogger, investor, and is an aspiring freelance writer. You can follow him on Twitter: @reversethecrush
I really loved this post, we seem to have similar patterns to our life. I too have had a few start ups fail. I now blog, freelance write and have a VA gig too. I’m still currently working in financial services but looking to earn my time back and quit the 9-5 within the next two years. It’s good to know someone has managed it!
Thanks for reading & commenting David!
It’s always good to hear of others seeking financial independence as well. It’s great that you have also have a time frame attached to your goal. Hope everything goes well with the freelance writing and blog. Thanks again!
I love this post. I was actually there through the whole process of dapper and debonair as a bystander watching. It’s nice to hear about it summed up in a post. It’s great advice to about needing passionate focus on fewer things. And not to partner with people just because they’re friends. Great post!
Thanks for commenting Derek!
I’m glad you agree with the advice because you were someone that watching and sometimes helped with the process. All you do is just learn from the mistakes and move on. Thanks again!
Thanks for commenting Derek!
I’m glad you agree with the advice because you were someone that was watching and sometimes helped with the process. All you do is just learn from the mistakes and move on. Thanks again!
Excellent suggestions for someone looking to start a small business.
Thanks for commenting Nabeel! Glad you liked the suggestions 🙂
I agree with so many things you said, first about taking on too much at first. Too many people have big plans but don’t ease into things. It reminds me of people who want to lose weight and plan this massive overhaul in their life but it’s too hard to manage. Secondly, working with people, That one can be super tricky. There is always someone it seems who has to be pulled up by the bootstraps constantly.
Hi Tonya,
Thanks for taking the time to read and comment! Sounds like you’ve had a similar entrepreneurial experience. Hopefully it worked out or you learned from it in the end. And that’s such a good comparison! People that try to lose weight by taking the quicker routes often end up finding it too difficult to keep the weight off afterwards. And you definitely need to be careful about who you work with. Glad you enjoyed and thanks again 🙂
A very inspirational post for aspiring entrepreneurs! Being a business student, this article has cleared up a few things for me as well. I’ll be sharing this post with my friends and classmates for sure!
Hi James,
I’m glad to hear you found the post to be inspirational and that it helped make things more clear. I hope your classmates find value in the article as well. Good luck with business school and in your future endeavours!