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15 important lessons in entrepreneurship

Anecdotes from a decade as a small business owner
The entrepreneurial spirit is a strong one. The idea that anybody from any background can start a business is very moving. We have unlimited access to free knowledge and resources on the smartphones in our pockets at all times. You can register a DBA for $30, apply for an EIN, open a small business checking account, and apply to accept credit cards all within one hour, starting a business has never been easier.
I have met countless aspiring business owners in my lifetime and I think that it is fair to say that the biggest barrier to entrepreneurship is a mental one. I would argue that not all business owners are entrepreneurs. I owned a business for 2 years before some massive changes in the way I saw the world sparked the entrepreneurial spirit in me. The Oxford dictionary definition of entrepreneur is:
“a person who organizes and operates a business or businesses, taking on greater than normal financial risks in order to do so.”
I believe that there is almost a hierarchy of business ownership:

Aspiring Entrepreneurs

People who have loose sets of plans and either wait for the ‘perfect moment’ or ‘financial stability’ before starting a business. From my experience there is no perfect moment and financial stability is rarely something you can clearly define or feel.

Business Owners

Common examples are gig economy workers and independent contractors although it can also refer to people who own small stores, side businesses, moonlighters, hairdressers, artists accepting commissions, or anything else where the owner brings in an income. These are people who may attempt to be their own boss to put food on the table. The business may not always be something that they can rely on full-time, and it is usually not scalable, nor does it attract investors.


An entrepreneur will risk everything they have to realize their vision or goals. Entrepreneurs won’t retire at age 25 if Google acquires them, they’ll take the money and risk it on their next venture. They put everything into what they do even if their friends and family don’t understand it. When I think entrepreneurship, I think passion and persistence, even to the point of being stubborn.
It takes a unique personality type to start a business. Entrepreneurship is a high risk, stressful, and overwhelming endeavor. Ask any entrepreneur for advice, and they'll have no shortage of anecdotes and warnings - it is nearly impossible to anticipate the obscure problems they're going to run into as a result of wearing so many different hats at once. The word entrepreneur is often glamorized but it’s not inherently a glamorous direction.


Nearly a decade ago I started my first business. As a kid, my father was a salesman. He put on a suit and tie every day before heading into a stereotypical office building. On a few occasions I had the opportunity to visit my father at work alongside my brother. We would trick or treat there on Halloween with the other kids and argue with the girls about whether it was “bring your kid to work day" or “bring your daughter to work day”.
All things considered; my father was reasonably successful. I came from a family of wholesome values, we always had food on the table, everybody gathered for birthday parties, and I remember my father driving a different SUV each year. For better or worse, he was my role model and as such - I glorified the idea of an office job.
I took my first office job at 18 years old and it happened to be as a debt collector. Not exactly something you grow up thinking that you will become - but it was a desk job and that felt good. I share the same name as my father so I used his engraved name placard on my desk. Fast forward a few short years and I was running a collection agency for my employers at the time. Once they reached a certain level of success, they delegated a ridiculous amount of work to me and I'm actually very grateful for that. One day, it hit me.
“The vendors, the brokers, the associates... They all know and trust me. I understand the inner workings of this business better than the owners of the company. Why do the people who don't even show up or know what happens here all make so much more than I do?”

...and so, it began.

This part is scary. If you're an entrepreneur who left a decent paying job to start your own business, you will know the self-doubt that comes with it. One day you may feel on top of the world, you have momentum, things are happening. The next morning you wake up and realize you have no idea what you're doing, and you just signed a 3-year lease costing more than your apartment does. You're burning through your savings (or potentially a loan) at a ridiculous rate and you need to make things happen - fast.
It doesn't necessarily help that your friends and family don't understand the business. They may not understand why you would take a risk like that. They certainly don't understand what it's like to lay in bed - too anxious to fall asleep - just for the alarm clock to remind you that it's time to leave the house, completely sleep deprived. You registered a corporation - now you have some sort of accounting or legal obligations. You might not be sure what they are, so you mark down a reminder to find an attorney and an accountant.
When you do find that attorney, they ask you a loaded question:
⚖“Why would you start a business without consulting an attorney?"
😳 I thought I knew the business inside and out...
When you find an accountant, they ask you something similar:
📉“Why didn't you draft up a business plan and map out your expenses? You realize how much of your income needs to be set aside for taxes, don't you?”
😨 Am I going to end up homeless?
Your experience may be significantly different than mine, but what I've just described is fairly representative of what my peers at the time (small debt collection agency owners) went through. Many of us were naïve. Many of the people that we've worked for in the past were incompetent.

My assumptions were incorrect

The piece of the puzzle that many of us were missing is that our employers tended to come from wealthy backgrounds. I had a hard-earned $8,000 set aside for start-up money in my personal savings account. It felt like a lot. My employer, the one who started the agency I was running before branching off on my own, had $20,000 in seed money from his father. He lived with his parents. They had a family accountant, a family attorney - and connections. I merely had the money I was able to save from my bonus checks, all while living the most boring existence you could imagine.
I made more than just a few mistakes, but I've come to learn something about myself. I don't learn properly without making my own mistakes. I think a lot of entrepreneurs share this trait. If I had consulted with an attorney and an accountant before starting my agency, it may never have become a reality. The careless risk that I took by running headfirst towards my goal without checking to see what was in the way, is, in fact, how I found any level of success. The crazy part is that I wouldn't recommend that method to anybody else. I don't know that I could even count all of the careless decisions I made when I started my business, but I am trying to do my part today, by sharing my experiences and mistakes with other aspiring agency owners.
There's something ironic about that. I didn't listen to any of the advice that anybody gave me. I made my own mistakes on my own terms and I think that was incredibly important. At the same time, if I could go back to the beginning of my entrepreneurship journey, knowing what I know now, I have no doubt in my mind that I would find an exponentially greater level of success.

15 important lessons I’ve learned as an entrepreneur

I have to admit that I only know this quote because of The Office.
You miss 100% of the shots you don’t take
There is no ‘proper time’ to start a business. You will never feel 100% ready.
The entrepreneurial spirit can be learned or acquired; you don’t need to be born with it. You do however need to try. I think of it as a mindset which is easier for some people than others to tap into, but it stems from passion and ambition.
You can only learn so much from tutorials, self-help, motivational quotes. People tend to get stuck in that ‘preparing’ phase because reading a book about entrepreneurship feels like you’re doing work toward becoming an entrepreneur, but it produces no tangible progress and it teaches you more slowly than action does.
Nobody will do it for you. You can’t count on a mentor and if you find a mentor, consider yourself very lucky. Other entrepreneurs are busy doing what they do and when someone is an expert in an industry, their inboxes are going to be flooded. If you are fortunate enough to have a true mentor, they will only continue to act that part as long as you’re making true progress, trying your hardest, acting on their advice, and respecting their time.
You can’t do it part way. Entrepreneurship requires sacrifice and it is often thankless and demoralizing. There will be ups and downs. Don’t expect the ups without the sacrifice, don’t let the downs kill your spirit, and realize that it’s never ‘all for nothing’. Every negative experience you have is a teachable moment.
Be patient. Success won’t find you overnight. In fact, you will likely lose money and sleep for a while before you do find any level of success. When you earn success, it will be worth it. You will feel accomplished and it will feel well earned.
Don’t compare your beginning to someone else’s middle. The obstacles that some people overcome to get to where they are isn’t always apparent. No two stories are exactly alike. You do yourself a huge disservice when you start comparing, especially if it demotivates you.
You will often feel imposter syndrome. You will feel like your success isn’t rightfully earned once you start to find it. You will think you’re inferior to your peers. That is something that you need to realize is very normal. Be humble but don’t doubt yourself. Don’t ever think you’re not worthy or that you aren’t meant to find success.
Take every opportunity you can to learn from the mistakes of others, but really understand the mistakes. Something that is a mistake to one person, may not be a mistake for someone else. Each business is unique as are the entrepreneurs. Absorb relevant information like a sponge.
Network nonstop. You never know where your big break will come from. It may be completely unrelated to the industry that you are operating in. People who network find more opportunities. People who don’t network outside of their industry get stuck in echo-chambers. Those who do network meet more diverse people and have more diverse opportunities.
Don’t regret the path that leads you to success. I can look at my past and identify tens of thousands of dollars that I might as well have flushed down the toilet for all it’s done me. I can’t be bitter about the house I didn’t buy with that money because realistically, that money bought me invaluable knowledge. It just took some distance from the mistake to realize it.
Anybody can be an industry leader. As cliché as it is, you need to think outside of the box. If you only ever follow someone else’s business model, you’ll never surpass your peers who do the same thing. That will result in leaving too much up to luck. Always try to look at your business, your goals, and the way you think from different perspectives. Question the industry standards, find a way to make your business unique.
Don’t believe everything you read. Not even this. As an expert in an industry, I can confirm that there is a lot of misinformation available to the public about that industry and it is written as ‘fact’. Real life, firsthand experience is the only reliable way to learn without misinformation.
Always act with integrity. Integrity is ‘doing the right thing even when nobody is looking’. Cutting corners or acting in bad faith will always catch up with you. More valuable than your business is your reputation. A failing business can be restructured or redirected. A person who has damaged their reputation may never recover from that and as a result, opportunities will pass them by. Your name is your biggest asset, treat it with respect by treating others with respect.

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