If you follow me and know my story, I used to be what people would classify as “dumb.”
I had little knowledge and was pretty ignorant and naive about pretty much everything.
I often had trouble understanding new concepts or would lose focus easily when reading a slightly lengthy article online.
In short I had no notable skills whatsoever.
This was a few years back (yes I’m a slow learner too).
I was so sick and tired about my lack of knowledge and skills that one day I decided “that’s enough” and I must do something about this or what’s the point in living?
So I went on a “knowledge acquisition spree” and haven’t looked back since. I started to devour any and every book I could get my hands on.
As though being “dumb” alone wasn’t bad enough, it seems I was also dealt the “poor” card in life.
Due to this I spent a lot of time reading books on business, finance and entrepreneurship in the hope of acquiring the knowledge that could perhaps one day build a comfortable life for me and my family.
I started slow and it took me awhile to get through a book.
But over time I found I got better at grasping key concepts and more excitingly I found there were recurring patterns that came up frequently across different sources!
Okay without further ado, here’s what I’ve got so far:
1. Start With Why
Simon Sinek in his book Start With Why explains the reason why great companies like Apple are so successful.
Apple doesn’t start with the what or the how.
Otherwise a sales pitch from them would sound like this: “we make great computers (the what). They’re beautifully designed, simple to use and user friendly (the why). Want to buy one?”
Instead in everything Apple does it sounds more like this: “in everything we do, we believe in challenging the status quo, we believe in thinking differently (the why). The way we challenge the status quo is by making our products beautifully designed, simple to use and user friendly (the how). We just happen to make great computers (the what). Want to buy one?”
See the difference? One feels like just about any sales pitch whereas the other feels authentic and genuine.
What is your why? Do you have a clear mission, values and vision?
I wrote more about this powerful idea in The Golden Circle.
2. Be Relentlessly Resourceful
I learnt this from Paul Graham, and it’s stuck with me ever since.
He distilled being a good startup founder down to two words: relentlessly resourceful.
The opposite quality of this he calls: hapless.
Most dictionaries say hapless means unlucky. But the dictionaries are not doing a very good job. A team that outplays its opponents but loses because of a bad decision by the referee could be called unlucky, but not hapless. Hapless implies passivity. To be hapless is to be battered by circumstances—to let the world have its way with you, instead of having your way with the world.
It means when obstacles come your way as they inevitably will, you don’t just immediately pack your bags and fold.
Instead you never give up and use your creativity to find a way no matter what – whether it be going under, going around or going over the obstacle.
It’s the difference between being passive vs being proactive.
3. Don’t Be Afraid to Take Calculated Risks

Some risks are stupid. Like betting your house at the roulette table.
But every entrepreneur at some point will have to take some risk in order to succeed.
As the saying goes “high risk high return, low risk low return, no risk no return.”
The main thing with taking risks is they should be calculated risks. You measure the downside and see if it’s commensurate with the potential upside and whether that suits your risk appetite, profile and tolerance.
4. Belief in Yourself and Your Vision
Further to point #1 about starting with why, you now have a clear mission and vision.
But do you yourself believe in it no matter what?
This may be one of the hardest parts of being a successful entrepreneur. Most new ventures fail, so starting a new business is a daunting proposition to say the least.
There will be plenty of times where you begin to doubt yourself and wonder if you made the right decision to invest your savings or quit your job in order to pursue this path.
It is during these times your belief in yourself will be tested the most. This is a test you must pass if you want to join the “Gilded Halls of the Successful Entrepreneur.”
After all if you don’t even believe in yourself, why should your customers believe in what you’re selling?
5. Patience is a Virtue
As they say, “all good things take time.” It is no different with starting a business.
Just like how a plant cannot grow to become a tree in a week or month, why would you expect your business to grow at that rate?
I wonder how many businesses were this close to succeeding but failed right before they succeeded simply because the founder wasn’t patient enough to see it through.

6. Don’t be Afraid of Failure
We are all human so we are all afraid of failure to some degree.
But have you ever been so afraid of failing at something that you didn’t even dare to start in the first place?
This is equivalent to shooting yourself in the foot, also known as failure by default.
I wonder how many businesses or million dollar ideas throughout the history of mankind have just never seen the light of day because the person with the idea never faced his fears and never took the plunge.
7. Intense Self-Discipline
You can be as well intentioned as you want but good intention that doesn’t lead to disciplined focused action is useless.
Many people want to improve themselves.
Many people want to eat healthier, exercise more, read more or start a business.
But wanting something alone and doing nothing is pretty much worthless otherwise we would all be pretty/handsome billionaires living in Waikiki.
This is so important so let me put it another way. All good intention without discipline will lead to New Year’s Resolutions and nothing more.
I see self-discipline as a form of “Governance of Self.”
What this means is you do what you know is the right thing even when no one is looking or forcing you to.
As an entrepreneur there will be many days you don’t feel like getting up in the morning, or dealing with a difficult client or dealing with an innumerable number of difficult situations.
The human tendency is to delay and procrastinate on things we don’t feel like doing and this is where successful entrepreneurs have to be self-disciplined.
Question time
What do you think of my list? I plan to add more to this list in the future as I’m sure there are many more ingredients that make a successful entrepreneur.
If you have any ideas/experiences to add, please leave a message in the comments.
Would love to hear your input.
Until next time.
Godspeed,
Tony Lee Jacobs
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