I wrote a book about startups, and I’m not even a founder!

Uttara Shekar
6 min readFeb 14, 2022

I wanted structure, representation, and more.

A year and a half ago, I decided to write a book on how to build startups. I had been working at Amazon for about 6 years at the time, and existential questions like, “Is this it?” and “Am I happy with this job and lifestyle?” popped up regularly in my head. The answers were never too clear, but I could see the light of aspiration shine towards building something of my own someday.

As we all know, technology-based businesses are thriving in today’s digital age. Employees working in the tech industry can see the countless new startups being built from scratch with very little initial capital. Bootstrapping of a business can be done in as little as thirty minutes for some of us.

To learn more about how I’d go about starting a business, I started reading books about startups. Books like Lean Startup, $100 Startup, and Founders at Work are considered the most popular in this space, and so naturally I started with them. I eventually went on to skim through multiple other books like Blitzscaling, Zero to One and The Startup Owner’s Manual. These books are well written, and explain the idea of building in a lean manner and innovating to achieve success. I gained important startup-building tips from these books that, I’m sure, will help me when I decide to make the leap.

But there was something gnawing at the back of my mind after I was done reading these books. Something bothered me about them, and I took some time to understand the reasons. Those reasons eventually compelled me to write my own book about startups — The Startup Leap.

1. I wanted a structured approach.

Everyone knows that startups are chaotic, especially for first-time founders. I am that sort of a person who would want to know the first three or four things that I should focus on when I’m in the initial stages, and where that journey will lead me from there on. I know that many of my colleagues are like me too.

I want to be armed with specific knowledge about the phase of the journey I’m currently on. I want to be able to navigate into a single resource to understand what I can do better about the challenge I’m currently facing.

The existing startup books, while helpful, hardly offered that structure. While I could understand the general approach of building startups, I am not the sort of person who would read four books or twenty blog posts while I’m trying to solve a time-critical business problem to understand the best possible solution. Frankly, no one is. I wanted a single go-to resource that would lay out the journey for me at a high level and allow me to navigate from there as I pleased. I missed that structure in the existing startup books.

2. I wanted an unbiased perspective.

The popular startup books out there have been written by founders. They speak about their journey and their challenges, and how they overcame them. Many of them also give examples of other businesses. But I found that they would lay stress upon certain problems more than others.

Some considered marketing and sales of the product the biggest challenge while some others considered finding the perfect co-founder the hardest part. Their books, which were based on their personal experiences, were also skewed toward whatever they considered the biggest challenge.

In my book, I had the advantage that I could look at these challenges from an unbiased, third-person perspective. I noted down every challenge that the founders that I interviewed faced, but didn’t give any of them more importance than the others. Of course, I did mention it as a common problem if more than 60% of my founders faced it.

Every founder's journey is going to be different, but it definitely helps to be aware of ALL the shit that could hit the fan and learn how to navigate them, instead of just being aware of the select few that the founders-who-wrote-books-about-it lay more stress upon.

3. I wanted specific questions answered.

As an employee in the tech industry, I’ll admit — I have a good life. A good job, a comfortable lifestyle, not too much work-related stress, and decent work hours. Although I know I’d love to build my own startup, the process of starting intimidates me.

Before I wrote this book, I had countless questions about the startup journey — I wanted to know how my life would change, how much time I would get with my friends and family once I start, how can I build enough of a cushion to at least give my family similar comforts when I’m in the initial phases, how can I arm myself with enough knowledge while I’m still a salaried employee so that I am better prepared for when I don’t get regular paychecks, and so on.

Most of the books I read did not really get into any of these questions — they weren’t directed toward employees in the tech industry. On the other hand, my book speaks to people like me — employees in the industry who are looking to make the leap but who are also too apprehensive to do so because they don’t know how to do it “safely”. I provide some safe and tried-and-tested ways to make the “leap,” which really means “a handful of baby steps in the right direction”.

4. I wanted to hear from founders with diverse backgrounds.

The well-known startup books do not bring up how different the startup building experience can be for founders of different cultural backgrounds, genders, or communities. Some people may argue that a book on how to build startups does not really need to include such perspectives, but unfortunately, the real world doesn’t work like that.

It’s important to acknowledge the challenges that people from minority groups may face when they start building their businesses from scratch. Unconscious bias toward women-led or minority-led companies is a reality that cannot just be ignored. In my book, I’ve written about the challenges of several women founders who come from different cultural backgrounds who faced such challenges and came out strong. As an aspiring woman founder myself, I learned valuable lessons on how to be an effective founder even though I belong to a minority group.

5. I wanted to know what founders missed learning about in the existing startup books.

Most founders I spoke to said they have read the popular startup books out there. As someone who had started off reading these books too, I knew there were pieces to the puzzle that were missing. At the time, I couldn’t put a finger on it. I wanted to understand what today’s founders would have appreciated knowing before-hand that they didn’t learn from these books. I got so many interesting answers that I created a whole chapter on it!

The existing startup books talk about grit and how to stay motivated, but many of them do not get into the emotional roller-coaster ride that founders unknowingly sign up for when they begin their journey. I don’t want to give out spoilers, so I won’t get into it here— but “The Startup Catch” is one of the most loved chapters of my book, so you may want to read that.

6. I wanted a book that was published in the last five years.

Many of the most popular startup books were published between 2011 and 2014. But I’d say the world and technology have advanced considerably since 2014. Starting a business can be as easy as clicking a few buttons on a computer today. Frankly, I don’t even know what it was like in 2014 but I can say that it probably wasn’t this easy.

I wanted to learn about new founders who made it big in today’s world. I wanted to understand how different their challenges were from the Amazons and the Microsofts, and what tools and technologies they used to navigate through them. Fortunately, most founder stories in my book are from today’s businesses, many of which are still thriving to this day.

If you liked this article, you may want to read “Startup building — why first-time founders need structure” to learn more about my book.

Uttara Shekar Khedekar is a software engineer at Amazon. She is also the author of “The Startup Leap: Finding Structure in the Chaotic Journey of Startup Building”. At the time of writing this post, Uttara wants you to read her book and leave a nice review for it on Amazon and Goodreads. She promises to send you virtual blessings and hugs if you do so.

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Uttara Shekar

Author of “The Startup Leap: Finding Structure in the Chaotic Journey of Startup Building”. I write for fun and code for money. [Website — www.uttarashekar.com]