Being An Authentic Entrepreneur

May 1, 2016

by Ravi Raman

Up until January 2015, I was either a child, a student, an employee or a traveler.

Zeroing in on the times when I was earning a paycheck, I always relied on someone else setting the rules of engagement, defining how work was to be done and gratefully accepted the paycheck (and bonuses, and stock grants) I would be handed every now and then.

My list of jobs has included: lifeguard at my high school, hawking my class notes to other students for $20 a class (legally!), working in the accounting department of a global airline (in midtown Manhattan), setting up offshore funds for uber-wealthy people at Merrill Lynch and finally, for almost 14 years: strategizing, creating and dreaming up the future in a variety of product planning, product management and marketing roles at Microsoft.

In all of the above cases, someone else handed me a paycheck. Then, I left it all behind and backpacked the world with my wife for over a year, during which time I had zero income.

Since 2015, things have been different. I’ve been doing my own thing. I thought I would fit right into the masses of entrepreneurs out there. What I’ve discovered is very different.

My Entrepreneurial Journey

I like to call myself an entrepreneur and have plugged myself into the startup culture where I currently live and online. I attend networking events, Startup “Weeks”, open houses at various “accelerators” and gobble up everything I can read online about the topic.

Unfortunately, I don’t fit in.

Most of the entrepreneurs I’m meeting and reading (with a few exceptions) pretend to be bigger than they are. They thrive on the idea of where they are going (building something big) not where they are (a kid with a crazy idea). I feel like an outcast, happily toiling as a small business, in a world that is craving “big.”

I like to call myself an entrepreneur, though, according to Seth Godin, I don’t qualify to be part of the entrepreneurial club.

Entrepreneurs, so says Seth, are building businesses that sustain without their direct engagement. I, on the other hand, work for every dollar. In Seth’s terms, I would be something different. I would be a freelancer. While I don’t get paid per hour, I provide a service (Executive and Career Coaching) and get paid for results. I have (intentionally) not automated or scaled my business yet, to ensure that clients get the best results, am flexible to their unique needs and that I maximize my own learning.

I love Seth, but I don’t sit well the freelancer label. More on why in a second. First, I want to talk about entrepreneurship.

The Secret Dream

It’s en vogue to be an entrepreneur and now is a great time to become one. It’s never been easier. There are a ton of problems that are worth solving and technology makes it easier than ever to apply your brain to any one of those issues from wherever you choose to live.

When I worked in corporate offices, I secretly dreamed of becoming an entrepreneur.

If you are like me and spent most of your adult life working in the tech industry; you probably think being an entrepreneur means running a “startup,” which equates to the glamour of appearing (and being) “super busy” (there are few things I hate as much as people who proclaim to be “busy”) working in a cool loft space, hob-knobbing with Angels and VCs on your way to becoming your next Uber or Slack, or perhaps just selling to one of the five horsemen (Facebook, Google, Amazon, Apple, Microsoft).

My entrepreneurial journey is nothing like this and contains no desire for it to be like this. I started my business because I was called to do it. I saw a massive problem (outwardly successful people being stuck and miserable in their jobs) figured out the solution (coaching), applied the solution first to myself and finally noticed that there was a massive shortage of this solution being offered to a particular group of folks (technology professionals).

From the get go, I have wanted to keep my business small, more like a cottage business than a factory, to make sure that it was something I really wanted to dedicate my life to (after a year in business, the answer is yes). By being small, I could build the type of business I wanted, in a way that works for me, and ensure that I could provide a great experience and powerful results for clients. My vision was first to focus on being a craftsman, not being something big, akin to a factory.


With this “start small, be a craftsman” ethos, I’ve had the chance to experience the joy that comes from feeling like I’ve actually earned every dollar that comes in (and since I offer a money-back guarantee, this raises the stakes!). I’ve learned in a way that never could have had I joined someone else’s business to practice my craft or just provided services to my old employer (as so many freelancers do that leave a corporate position).

Unfortunately, I don’t hear a lot of people talking about the value of being small and embracing the craftsman and cottage business ethos.

Freelancer is a tainted word, but shouldn’t be. Entrepreneurial types seem to look down on the freelancer as if they are selling themselves short and not dreaming big enough. It is as if the freelancer is scared to do more and be more. It’s the myth that freelancer = hourly worker = bad.

This couldn’t be further from the truth.

A freelancer has everything hanging out on the line. They are the ultimate hustler. They are working and earning what they get and maximizing the learning potential. Freelancers may choose to scale their time down the road by building products and services (as I plan to do), but first, they hone their craft.

Build your work of art, then build the machine and system to replicate. Not the other way around.

However, freelancer – to me anyway – has a stigma, so I don’t describe myself as one. I identify as an entrepreneur since that is the term society understands. More clearly, I am a coach. Deep inside, I feel I am craftsman – though I don’t say that to people or they would think I’m a master wood worker and I barely know how to use a saw.

It’s too easy to hide behind the label of “running a business” and “managing a big team.” This is just posturing to make it seem like there is an army behind you when really it’s just you (with perhaps a few others). I’ve noticed this trend in engaging with some other professionals in my coaching industry, who talk about their “firm” and their “client base” and their “institute” they have created to train others in doing what they do.

The names of their companies conjure up images of some grand building with Ionic columns and gargoyles at the front door. In reality, they are freelancers who both coach and train, with no physical location and a few administrative support staff paid part-time.

Why not be proud of being small instead of pretending to be huge?

Warren Buffet

I spent most of the day yesterday watching Warren Buffett and Charlie Munger drop knowledge bombs on 20,000 rapid fans during the 2016 Berkshire Hathaway annual meeting. You can check out my learning from their meeting here.

It amazes me that the two greatest investors on the planet are able to run their business so simply. They are proud to be small, have low overhead and make deals swiftly. They have a website that is super old school and have zero posturing in everything they do.

If two of the wealthiest (and most respected) people on the planet can “get by” by flaunting their small-ness (like a craftsman), why don’t more entrepreneurs take this approach?


There is a beauty and power in being small and honing your craft. If you are an entrepreneur and are flying solo or with a skeleton crew, don’t pretend to be bigger than you are. Be the craftsman you are and be proud about it.

Dream big but keep your feet firmly planted in the earthy soil.

On the other hand, if you are scaling up because you feel to or think that being successful equates to being big, it’s time to gut-check yourself. If you need to be big to accomplish your dreams, by all means go for it, but make sure you are doing it for the right reasons. There is no use in pretending you are a massive business – or trying to build one – just to please others.

You can’t be authentic if you are pretending to be big. The world craves and rewards authenticity, and there is noone as authentic to your world as you. So go be you in all your glory, and see what happens. That’s what excactly what I’m doing and it’s working out just fine.

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