Introduction to Shadow Entrepreneur

Follow my exact execution for my startup, get billion-dollar ideas and learn how to go from zero to hero in entrepreneurship.


Welcome to Shadow Entrepreneur!
A newsletter that brings you the best entrepreneurial education out there and gives you the inside scoop on how startups work. (Plus I’ll be sharing all the amazing opportunities and ideas that I have for free so someone out there can make millions from it)

Why did I start this?

Why I started ‘Shadow Entrepreneur’ or ‘Shadow Ajay’ is because early in my career and entrepreneurial journey, I found that 99% of my learning came from shadowing more successful people than myself. They may not have everything figured out but they had at least some value being a few steps ahead of me. Now I’m not claiming to be the best entrepreneur in the world but if you’re early in your journey, then you’ll find a lot of value in seeing what I do day to day/week to week.

Who am I?

I’m just an entrepreneur who is starting again from ground zero for a new company called EveryAfter (though I am toying around with various ideas). However, I have started quite a few companies that I’ll share over the coming months. I started with Doppler (AI for universities) in 2013 which raised some capital and then built companies till Perlin & Tradeflow which we raised over $50M in venture funding (from the likes of Enterprise Singapore, 500 Startups, Bitmain etc.) where we were building solutions alongside the International Chamber of Commerce. I’ve had the pleasure of working alongside partners, co-founders and employees who had decades more experience than me and now I feel that it’s time to pass that information on. Though transparently I’m still working towards my first exit, IPO or liquidity event as a founder - but hopefully my many mistakes and successes can help you get to where I am and you can also follow me as I work towards that goal.

Who is this for?

Anyone who wants to be or is an entrepreneur that wants to see how it’s done from the inside. I’ll be as transparent as a possibly can be as we grow my company from pre-seed all the way to an IPO/Exit. I’ll share the hard times, good times and also the pivots so you can see why we made certain decisions.

What is this?

A lot of the inspiration for this comes from Shaan Puri where he launched a similar style newsletter and provides amazing value where he builds in public.

Each newsletter will have 3 main components:

  • A weekly summary of what I did and what I was thinking. In essence, having it such that you were sitting right beside me

  • 1 to 2 amazing startup ideas or opportunities that I’m seeing right now. I’ve thought up hundreds of ideas and tested over 60 and formed companies around 8. It’s important to have an experimental/scientific approach around testing and launching ideas. However, I’m now very much focused on my current startup and so I want at least someone to pursue these ideas.

  • A framework/concept that is super important for starting companies. I’ll dive deep into a specific concept that might be relevant for the work I did that week or just, in general, a great info piece.


My personal goal is to have a content piece out weekly and we’ll start with a free newsletter that will come out each week. From there, I might start introducing podcast-style audio clips & other things such as a potentially paid tier to get more involved. We’ll figure it out as a community - what we feel is best to go forward.

Regardless of what happens, I’ll ensure that this will be free for 2021 and have 50+ content pieces by the end of the year.

Till next time,