The term “startup” has been romanticized in the age of overnight tech billionaire and glitzy magazine covers. It evokes the memory of ping pong tables, perpetual rounds of funding, and steadily rising charts. However, speak to those who have in fact created a business from the ground up and you’ll hear an entirely different tale.
At Quotenestify, we are well aware that there is no such thing as a polished press release that is going to bring wisdom to an entrepreneur. It’s in the muddy, unvarnished confessions of the foundations who made it out of the trenches. Constructing something from nothing demands more than everyman’s share of irrational optimism, more than everyman’s share of pain-thriving, more than everyman’s share of redefinition of failure.
The following are some of the best quotes from amazing founders that embody the tumultuous, fearsome and exhilarating nature of the startup journey.
1. Reid Hoffman: The Need for the Leap
The definition of an entrepreneur is someone who takes the plunge and builds a plane.
— Reid Hoffman
The Context:
Legendary VC Reid Hoffman has heard thousands of business pitches. This is a quote he used to make to account for the distinct way that startups are founded versus corporate work.
The Philosophy in Practice:
In normal company working, one wouldn’t jump until the plane is completed, tested, and insured. This is not something that startups have. When you wait for your product to be flawless or you believe you have no risk at all, the market will have gone on without you. Entrepreneurship is a super scary business, as Hoffman said. Sure, you need to be willing to believe in the vision, you need to step out of the safety of the ground and act on trust that the pressure of the imminent ground will force you to understand how flight works before you hit the ground.
2. This is a discussion about the “F” word and how it is being redefined in Sara Blakely’s mind.
My dad would push us to fail, and ask us what we failed at that week if we didn’t, he would be disappointed. He did that at a young age and it made me think of failure as not the end, it’s not failing to try.
— Sara Blakely
The Context:
Sara Blakely was the youngest self-made billionaire, having founded Spanx, before she became a door-to-door fax machine salesperson. She was constantly rejected. This idea for her undergarment company was laughed out of the room by several factories.
The Philosophy in Practice:
In most of our lives we have been taught that failure is a permanent stain on our record and is a cause for shame. Blakely’s philosophy is that it is a great measure of effort when you fail. Don’t be too cautious if you’re not failing every now and then. A prototype that fails, or a pitch that goes down, is not a setback in the startup world, it’s just another data point. Founders are able to take the risks that make real innovation possible and to make the rapid iterations that liberate them from the fear of failing to get it right the first time.
3. The psychological toll was the impetus behind this book.This book is driven by the psychological toll.
I was like a baby, as a startup CEO I got up every two hours crying,” he said.
— Ben Horowitz
The Context:
Ben Horowitz is a co-founder of Andreessen Horowitz, one of the most successful VC firms. Prior to that, he guided his software firm, Opsware, through the dot-com bubble, almost losing his company several times and ultimately selling it for $1.6 billion.
The Philosophy in Practice:
The quote breaks the veil of the glamorous CEO by employing dark humor. For society, the founder is the fearless visionary whose bold steps take him/her towards success. Horowitz affirms the tremendous psychological toll of leadership. Being in charge of investor money, employee lives, and your own life is agonizing stress. It is essential to recognise this “Struggle” (Horowitz’s term) It brings up for isolated founders the idea that being afraid and panicked is not a weakness; it’s just part of the job.
4. The Power of the Differentiator (Steve Jobs)
Perseverance is a factor that I believe is responsible for about half the difference between the successful entrepreneurs and non-successful ones, says I.
— Steve Jobs
The Context:
Steve Jobs was interviewed in 1995 about some tips for those wishing to start a business. He was also at the time a former member of his own company (Apple) and attempting to keep his next company (NeXT) alive. He was well-familiar with the toil of the hustle.
It is important to have a philosophy in practice.
It’s easy to claim that startup success is about having the genius of the intellect or the perfect timing of the market. Those things are helpful, but Jobs knew the road of entrepreneurship was so arduous that any sane person would give up. Thus, the ones who rise are the ones who will not die. But the one trait that sets the good ones apart is perseverance in the form of steadfast determination and persistence. That’s being able to take a big hit on a Tuesday and still come back on Wednesday to pitch a new client.
The myth and the reality of the Startup.
When deciding to embark on a business, it’s essential to temper expectations in reality.
| The Common Myth | The Startup Reality |
|---|---|
| The Trajectory: A straight line towards the sky and right.The Trajectory: A rollercoaster – extreme highs, near death valleys. | |
| The Goal: To launch a “Minimum Viable Product” with embarrassment and then make changes based on feedback. | |
| The Lifestyle: Unpredictable hours, constant putting out of fires, and heavy responsibility. | |
| The Secret Sauce: A brilliant, never before seen idea. |
Starting up a business is not an easy task. It is an exercise in going against the grain of accepted logic and taking a chance on failure in front of the audience. As these quotations show, though, if you can survive the free fall, reinterpret the failures, and outlast the pain, it’s the adventure of a lifetime to build your own plane as you fall to Earth.

