Read this when the hard (fun) part comes.

There’s a certain draw to being an entrepreneur. An idea strikes you. You hustle and grind and eventually hit a wall. Through sheer determination and a little luck, you break through the wall and build a legacy that persists past your retirement. You’ve turned your vision into reality. You’ve made the world a better place all the while becoming a few dollars richer.

It’s an intoxicating story.  People want it. You want it. You take the mantle of entrepreneurship. But buyer beware: the hard part will come. You are not exempt from the process.

Go ahead and ring your bells, light your candles, and call out to God, but beware, because when He comes, he will put you on his anvil and beat you and beat you until he turns brass into pure gold.

Sant Keshavadas

You know what craziness is? We know everyone dies.

We know everyone will become old, their mind decays, their body loses its vigor. They will lose their hearing, they will lose their eyesight, and they will lose their mental acuity. But we never make the connection that this process will also happen to us.

I think something similar happens in entrepreneurship. You always hear stories of entrepreneurs who have doubted themselves only to find success on the brink of calling it quits. Or you hear of all the disasters entrepreneurs face that almost certainly spells the death of their company. But they prevailed. We think: yeah, disaster will strike, startup is hard, founders will doubt themselves. But not me. It’s going to be all rainbows and sunshine. It’s going to be smooth sailing for me.


Take a look at Paul Graham’s startup curve.


It’s the prototypical startup growth chart. Everyone goes through it. Here’s some examples:

AirBNB – People think airbnb was a overnight success. Balony. They struggled for two years before finally achieving product market fit. AirBnB was originally a company trying to provide overflow housing for conventions and festivals. Highly recommend watching the very entertaining and inspiring AirBnb story.

Slack – People think Slack, the newest billion dollar darling, was an overnight success. Wrong. The origins of slack actually began in 2009 as an internal communication tool developed by a gaming company, Tiny Speck. Fast forward a few years later, Tiny Speck fails, they lay off a significant portion of the company and re-formulate their chat tool into Slack.

Twitter – Originally a service to share podcasts which was made obsolete by Apple’s iTunes store.

Instagram – Originally a location-based check in service similar to Foursquare. The app was complicated and confusing. Eventually, they pivoted into an image sharing platform.

Ok, so you know the hard part will come. It always does, because it’s the real initiation into entrepreneurship. That’s right. I don’t think you become an entrepreneur when you ship your MVP or when you incorporate your company. Nor when you get your first business cards or a company email address. I think great entrepreneurs are made when they encounter their first crisis or moment of great doubt. It’s the feeling of the great abyss in your gut that threatens to swallow your entire existence. It’s your heart pounding so viscerally that you feel the palpitations induce a headache and you can’t think straight but you have to anyways.

But it’s also the fun part. It’s when the game begins and you are provided with opportunity to test your wits and discover what you’re made of. The hard part is the excitement of entrepreneurship. Because in reality, without the crisis and moments of doubt, entrepreneurship would be really boring. It wouldn’t be fulfilling. It wouldn’t be what you signed up for. Screw the smooth sailing. You want some waves baby.

With all this being said, the hard part is hard. Here’s are three concepts that might help you navigate “the trough of sorrow”.

  • Twitter’s original idea blew up instantly. They actually went through 3 or 4 more pivots before finally arriving at the product we recognize today. Tiny Speck blew threw millions of dollars of funding from some of the top VCs. They failed hard core. Great entrepreneurs don’t always make the right decision. But they will make their decision right. Given what you’ve done, how can you make the most of it? Every disaster is an invitation to reformulate your thinking, gather insight and recalibrate your push forward.
  • Ok, your traction sucks. Your retention is poor and your active user’s chart is sideways. But how fast are you learning? Because you should focus on your learning curve. How fast are you getting to where you need to be to make the traction curve better? Sometimes, product market fit is more like a step function than a continuous curve.
  • Find an emotional anchor. I have a playlist title “When the going gets hard”. Whenever I begin to doubt my ability. I go for a jog and listen to the playlist. I’ve anchored a certain mental-emotional state to this ritual. It reminds me of why I’m doing what I’m doing and to keep my eyes on the ball. Have a ritual that you can retreat to, recuperate, and come out fighting.

“Today is cruel, tomorrow will be worse, but the day after tomorrow will be beautiful. Most people stop tomorrow evening and never get to see the sun shine.”

Jack Ma

This is the hard part. Don’t give up.  This is where you make your glory. When you look back at this moment in 10 years, this will be your greatest war story. This is what makes you a bonafide entrepreneur.

This is where the game begins. Savor it.

Further reading:

How not to Die – Paul Graham, founder of Y Combinator

Startups don’t die, they commit suicide – Justin Kan, co-founder of and


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