100 days of a startup

Notes on what it took and how it has been!

Fear.

We as a species survive, thanks to fear. But when its about creation and not survival, Fear is the biggest stumble block. I believe that overcoming fear has been the most challenging part at PickYourTrail. What adds to the woe is that, Fear is multi-dimensional. It transforms itself to suit the occasion.

The Idea Phase

This is when the fear of failure strikes you. I find it odd that the fear of failure is proportional to how successful you have been at your workplace. Despite the reasonable success at work, convincing oneself that the idea is worth the shot is a herculean task.

When you get the courage to bounce off ideas, some of the feedback you receive compounds the fear. “Isn’t this similar to abc?” “What is your revenue model” “How will you build this without a tech co-founder?”. Valid from the questioner’s POV. But the impact it can have on a fledgling entrepreneur is humongous.

The Plunge Phase

When you decide to take the plunge — fear transforms itself into cash. The EMIs, student loans, perceived change in lifestyle et al.

With a steady inflow of cash, letting go of something that you have strived hard for can be painful.

Compounding factor: Social peer pressure.

Finding your Feet Phase

Its like those video games. As you near the finish, the villain becomes stronger. Just when you have laid the other demons to rest and started to focus on your idea, the mother of all fears strikes you. I like to call this, the fear of the Unknown.

Fear of the unknown — is the biggest and toughest of them all. Much of this fear is “fictional” and not factual. That’s what makes it difficult to conquer.

All it takes is a streak of bad days, persistent delays in shipping products out or a new kid on the block with great PR. Though you know that it was not going to be easy, the fear of the unknown raises fundamental questions and pushes you back to the starting point. And what happens when you start a video game all over? Yup, you end up fighting all the fears from scratch. The saving grace is that you get better with practise. Still, the Fear of unknown takes time to conquer, because there are potentially an infinite number of unknown unknowns.

How do you overcome these fears?

The two most important things for me have been

— Support Systems

— Simply5

Strong Support Networks

As with most things, support for an entrepreneur starts at home. I have been fortunate to have a wonderful set of Friends and Family (FnF). They have been my goto for emotional support and uplift. The most comforting words in your deepest moments of despair come from these folks. Their unflinching hope and belief in you is the right dose of adrenaline needed to keep you going.

The next and perhaps the most difficult support to find would be that of a Mentor. While FnF help you with the much needed emotional support, the Mentor helps you wade through the professional mess. You spend most of the early days at a startup firefighting and getting your hands dirty. It can sometimes be difficult to keep your focus on the larger picture. This is where a good solid mentor helps! A good Mentor asks the right questions, down plays your demons and leverages his/her experience to guide you.

The last one is the dark horse. Easy to overlook, but if done well, can add great value — The support from fellow Entrepreneurs. Just as the mentor, finding the right set of entrepreneurs to open up to and bounce ideas could be difficult. But if you are active in the circuit, attend a few events etc, you end up bumping into a few of them. And who knows? You might end up starting up something with some of them someday!

The second tool that has worked well for me in running the show is nothing but 5 simples sentences. I like to call them Simply5!

Simply5

1. One step at a time. Celebrate small wins.
2. Arrogance is suicidal. Grunt work needs to be done.
3. Criticism is not the same as cynicism. Embrace critics, ignore cynics.
4. Failures are part of the journey. Don’t be too harsh on yourself.
5. Scale is relative, perseverance isn’t. Overnight success takes years.

The last 100 days have been an amazing roller coaster of emotions and an experience that in hindsight, was worth the plunge!

Bonus read

In case you managed to reach till here, find below a few articles that I have read, re-read and re-re-read over the course of this journey.

1. Slow ideas: A brilliant long form on why some innovations spread fast, and what it takes to make others faster.
2. Stop Worrying About Making the Right Decision: A good read on why emotions matter when we make decisions.
3. The abundance of slowness: Great read on why being busy is not the best thing to be.
4. Scott Adams’ Secret of Success: Failure — if you like the comic, you would love this as well!
5. The meanings of life: The heaviest of the lot. Raises a lot of pertinent questions. Love the plural in the title!
6. How to tell your story to investors: Prepping for the future. Again, a different view on what works when you try to raise money.
7. Do things that don’t scale: A lot of what’s in this article might apply and some may not, but the fun is in figuring out what works and what doesn’t. Btw, this also happens to be that seminal article by Paul Graham (YC Co-Founder)