What Steve Jobs never told you about entrepreneurship

It’s a tough pill to swallow – being an entrepreneur. Calling the shots and taking the brickbats of failure, the author with 15 years of startup wisdom in his stride has an imaginary conversation with the Apple cofounder. And it was time call out the oft-ignored niggles of that journey…
1.1k CLAPS

Your time is limited, so don’t waste it living someone else’s life.”

Imagine a large Steve Jobs portrait in a dark tiny office with the quote staring back.

As thus started a vexed monologue with Steve Jobs…

“Well... Steve that was the plan… and that’s what made me take the plunge in my late 30s to live life to the fullest. But what happened instead is - I am spamming probable clients and investors waiting for a reply in my inbox for a meeting.”

“Well, maybe entrepreneurship is a journey and not the end. But I feel so beat that I hope it ends soon, and it better well be. The rollercoaster ride I have been through in the past three years makes me realise that it ain’t as easy as your entrepreneurial quotes make it sound. I wonder why successful entrepreneurs don’t talk about dark realities in their journey...”

Steve Jobs

Self doubt

You tend to doubt things around you when things are not going the way you planned. That’s when you realise this thing ain’t as easy as you thought it would be in your head when you set out to achieve it. Doing your own thing will set you free. But you realise that it is an expensive price paid for freedom, you ultimately pay for it with uncertainty.

Reality hits you hard when you see your peers doing well in their corporate jobs and you think maybe the entrepreneurship plunge was overhyped and miscalculated. It sinks in further when you stop getting replies to your emails from people you have been working with earlier, in your corporate avatar. Guess that’s when you realise maybe people hung around because of the job title that your megacorp company provided, and now it is being stripped off. It’s you alone who has to ensure the person you meet finds value in meeting you. Eventually, the biggest disappointment might be not living up to your own potential.


The person who said, “too much smoking kills you,” never did enough sales follow-ups. Being stood up on a date with a crush is always a tough pill to swallow until you are stood up on a 5 am conference call with an investor who is in a different time zone.

It was amazing to see Captain America ready to fight with himself all day in the Avengers: Endgame, but that’s when you understand superheroes are just normal people with supernormal willpower to never give up. Sometimes you don’t need a hero to save you, but just yourself to push you to your limits to deliver. The best way to win is to keep pitching, it’s all about pitching at the right time.

Insufficient funds

It might be the untold truth; you may need to get funded to be taken seriously in the ecosystem. First-time entrepreneurs face this problem, they start out bootstrapping with enthusiasm to build out a perfect business but end up spending too much, too soon. An interesting aspect about building a startup is that the money you assume will suffice until the time you get funding is never enough.

Building your business is like boxing - unless you don’t get punched enough, you won’t become a champion. And if you think you are hitting below par, take a loan, banks will make sure you are always on your toes, making money. There is nothing sweeter than making profits before you expand. Getting funding isn’t equal to winning a lottery ticket. The more frugal you are with your money, the more confidence you will gain from the community.


“Persistence” is the most underrated word that we do not hear often enough from successful entrepreneurs or in random discussions at startup conferences. Because the reality is “passion” or just loving what you are doing is not enough to make a successful business. You need the fire of persistence to make it big! Why? Well, because it isn’t easy to build a business, a lot can happen in the process. To sustain it takes a lot out of you. You might be surprised that the thing you loved doing just for fun isn’t fun anymore because the business took the fun out of it.

Passion is usually overrated while persistence is a bigger requirement than passion in building a successful venture. But any entrepreneur 12 months into the business, not making the projected revenue, would tell you passion isn’t the fuel that is helping them drive business, it is persistence that makes it happen.

Bad decisions

In building a business, you find yourself in many tough situations where too much time and money is wasted before realising what is broken, and how it can be fixed. While growing a business, it isn’t important to be right all the time, but it is important how quickly you can right your wrong when you see it.

Often the business is stuck between the difficult choice of letting go or changing the path. More often than not entrepreneurs tend to stick around with a broken model even when they know it isn’t going anywhere because it is difficult to put their hands up and say that this isn’t working. Sometimes letting go can be the bravest thing you can do and sometimes pivoting your business model can save it. Statistically, bad decisions are only the second biggest reason for failure, the first is indecisiveness. Always try to be ahead of the curve or be the reason for it.

In the end, every story is unique, and you are only working towards making sure yours is remembered. When you are building something impactful, it takes time. It’s a long dark lonely journey with the tough realities surrounding it. You need to take one step at a time forward and try not going backward.

“The people who are crazy enough to think they can change the world are the ones who do.” Guess, Steve Jobs knew this to be true that you have to change the game and others will follow.

(Disclaimer: The views and opinions expressed in this article are those of the author and do not necessarily reflect the views of YourStory.)

(Edited by Suruchi Kapur- Gomes)