Taking The Leap: Don't Just Be A Wannabepreneur

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Taking The Leap: Don't Just Be A Wannabepreneur


Chances are, if you're reading this article, you are either involved in a startup already, or looking to be involved in one.

This article is for the folks in the latter category, the "wannabepreneurs".  The ones that have always wanted to be entrepreneurs, but haven't quite gotten around to it.  The folks still slogging it away in BigCo land waiting for the "right" entrepreneurial opportunity to come along.

Here's my advice:  Stop Waiting!

If you've got a passion for startups, you need to be in a startup.  Either run with the best idea you have and start your own thing (even if the idea sort of sucks), or join the best people you know that are already doing something.  Just get out of the daily slog that is most big businesses.  Scratch that itch. 

Be an entrepreneur, not a wannabepreneur.

Here are a few quick points to help convince you:

1.  You're probably overestimating the risk of leaving that BigCo job.  Chances are, that sort of job (or something awfully similar) will be there a year from now if things go miserably.

2.  Though nothing compares to doing your own thing, joining a startup team is not bad either.  It's a great way to dip your toes in the water.  Often, half the battle is just getting out of your comfort zone and being around startup people.

3.  Regardless of what your risk tolerance is, you can likely still find opportunities that are more entrepreneurial than what you're doing now.  There are startups with really high risk, with nothing but a dream and a developer (or two) all the way to startups that have raised several rounds of funding and are on the IPO path.  You should be able to find a startup that meets your risk profile.

4.  Unless you have some compelling evidence that things are going to get easier later to do something more entrepreneurial, chances are, they're not (going to get easier).  So, if the question is when, not if, then ask yourself "why not sooner, rather than later?"

5.  For those that are thinking: "Yeah, this is all easy for you to say, you're not walking in my shoes", I say this:  You're right.  If you truly don't have the situation or circumstances to take the leap, that's ok.  I just implore you to at least think about it and decide for yourself whether your obstacles are real or perceived.

I'll close with a quote that's been on my list of favorites for a while:

"Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable." -Sydney Harris


Posted by Dharmesh Shah on Mon, Jun 09, 2008


I come from back ground where most of the people I know are in working middle class. Not challenging status quo was norm there. I always did otherwise and I ended up achieving multitude of things that people have discounted I never will because I do not have that sort of background. For entrepreneur
1. If you are generating revenue for your employer, then you will for your self too.
2. Never try to find perfect idea/thought to start your business or startup. Try it and if you are doing it for first time you will learn many things anyway though business is not success.
3. Taking risk that is still overrated. It is not that risky if you are already working for BigCo because you can get in a year if you are not comfortable those high adrenaline zone.
4. I motivate myself by looking at lots of other successful entrepreneur and freedom that will fetch me to implement my thoughts. It burns me from inside if I can not achieve that freedom to implement my thoughts.
5. Ask and you will receive. :-)

posted on Monday, June 09, 2008 at 2:31 PM by i-Iconoclast

May I add another quote...
"He who is afraid of making mistakes is afraid to succeed." - not sure, this quote was in a frame next to my dad's bed

posted on Monday, June 09, 2008 at 2:38 PM by todd g

Your post is inspiring and reminds me of Napoleon Bonaparte's quip, "A leader is a dealer in hope!".
Entrepreneurs are drivers of hope, they have to be!

posted on Monday, June 09, 2008 at 2:55 PM by Carlos Hernandez

Excellent post, and thanks for sharing. As one who is firmly entrenched in the start-up world, I know that it is scary, exhilarating and ultimately, worth it. For those who haven't taken the leap yet, my advice is to save enough money to get you through the first six months of your idea. That should be enough to prove it out and to get you out of the BigCo thinking.

posted on Monday, June 09, 2008 at 4:19 PM by Josh Asbury

Great post. I agree with the people who've responded. I recall a quote from Dan Kennedy, "Every successful achievment begins with decision. Most unsuccessful lives are conspicuously absent of decision."
Moving out of your comfort zone is uncomfortable, especially for those of us who have spent tons of energy, heartache, and time trying to build careers that never seem to go anywhere. If your heart isn't in the right place with your work, I've found the misery of staying in that job worse than the fear of doing something new.

posted on Monday, June 09, 2008 at 7:26 PM by Jesse Boland - Entrepreneurial Team Building

Years ago, when I was contemplating starting my own internet marketing consulting biz, a friend of mine told me, "Leap and the net will appear."
While I needed a little help in taking that leap (was fired from my job), he was absolutely right.
To that allow me to add, once you start moving in the direction you feel you should go, positive things will amazingly, even miraculously, begin to move toward you. I think it's not unlike Newton's first law, the Law of Motion: An object in motion stays in motion. An object at rest stays at rest.
Nothing can begin to move toward you if you don't first move toward it. It takes faith and courage, but it works.
Since taking that fateful leap, I not only ran and sold my own business, but was co-founder in another startup, co-authored a book and became somewhat recognized as a thought leader in the field of business blogging. None of that would have happened had I never taken the leap.
So, just do it! Jump!

posted on Monday, June 09, 2008 at 9:26 PM by Paul Chaney

Great post Dharmesh. You have instigated the already burning desire in me. Cheers!

posted on Monday, June 09, 2008 at 10:06 PM by Sharat Thakur

As usual, Dharmesh, a cogent and useful post. I especially like the quote at the end, as it exhorts the "git 'er done" attitude that all would-be-successful entrepreneurs need to embrace to make it work over time. Thanks!

posted on Tuesday, June 10, 2008 at 11:48 AM by Anthony Kuhn

Just what I needed this morning. Being someone that just took the leap 1 month ago, I left my job and have 6 months savings to try and get things going.My confidence shaky somedays, somedays it is off the charts as I KNOW what I am doing is going to be successful.
But a point that is missing and I believe to be the hardest to cope with is friends and family. It is difficult to explain what and why you are doing your thing.Paving your own road. You may get frustrated at their lack of vision.
I'm seeing firsthand how relationships can get strained when times get tough(budgeting).Sadly I have had to make the one statement that I feel I was forced to make. 'If you do not 100% support me now, do not expect to be with me when I become successful'....

posted on Tuesday, June 10, 2008 at 2:25 PM by TJ

Very nice blog..

posted on Wednesday, June 11, 2008 at 1:43 AM by Govind Kadaba

<P>I have this on the wall immediately behind the computer I am sitting at now:
<P>"The Man who makes no mistakes does not usually make anything."
<P>Its a print from an original old fashioned hand-driven printing press from Blists Hill, in the Iron-Bridge gorge in the UK - where the industrial revolution was born.
<P>The saying is valid. Everyone makes mistakes. That is OK, its what you do, how you react to those mistakes that sorts the achievers from the might-have-beens.

posted on Wednesday, June 11, 2008 at 6:07 AM by Stephen Kellett

Bah, its a lovely blog - If only there were some hints as to which tags work so that when you post it actually comes out OK, rather than the mess that is my previous posting (or a preview function).

posted on Wednesday, June 11, 2008 at 6:09 AM by Stephen Kellett

A big company can offer not much more than a job when you peel back the layers of big company benefits and lofty titles while a start up offers a career.
The people you meet along the way will provide countless career opportunities offering a level of job security far greater than any big company could ever offer.
It's easy to see the benefits of working for a start up when you talk to those who have been involved with one yet those who have not seem to be in the dark with respect to the actual pro's of being involved with a start up. Some think it's all about the equity (definitely a nice piece of the puzzle) when there is a host of other benefits from being involved with a company destined to change the world, or at the very least make a good product/idea/service better.

posted on Wednesday, June 11, 2008 at 12:34 PM by Joe Sharron

There are lots of in-between options as well. If you've got a great new idea, it doesn't hurt to have two jobs for a while with your startup being stealthy. We accomplished a great deal of research this way and gathered an incredible amount of feedback. Get your friends opinions about the company - and if its yours, research research research! Leap!!!

posted on Wednesday, June 11, 2008 at 1:02 PM by John Stack

I agree with John Stack that working the regular job and getting things in place for the startup is a great way to go.
However a point will come where you need to truly dedicate yourself to the new startup and you will need to part ways with an employer.
If you truly have the entrepreneurial spirit you will never be happy until you at least give it a shot.
Trust me ;)

posted on Thursday, June 12, 2008 at 1:22 AM by Raymond Angel

Great post Dharmesh. I'm with the majority here that believes that its best to stay working until a plan or prototype of some sort is ready. There's an inflection point on the risk curve where money and readiness can be optimized without wasting too much time. Not to mention while you're at the job you're around like minded engineers, biz folks, etc who you can bounce ideas and gather feedback while still operating in stealth mode.
I'm eager to read your advice on initial funding. Some founders have funds to bootstrap while other have a more dire need and look to seed investors like YCombinator. Even if you have say $50k allocated from your bootstrap funds would it be more advantageous to work with seed money, or stretch your bootstrap funds until you have a full product with users (and gasp.. revenue), then pitch to angels or VCs.

posted on Thursday, June 12, 2008 at 1:51 AM by Joe A

You know while talking about starting business would be great beause at least I am talking. But from my experience, I would rather start anything however small and rediculous may be and start building my "business acumen."
Though idea is very important but to start something and then keep it rolling gives really many other things to look at that you may not realize when placing plan together for business. I would just summarize, "Just Do It!".
I have seen amazing difference in my approach within a year of starting something. Please notice that I did not put it as great idea to start with. I just started and then I stumbled upon so many other thoughts and business ideas that soared my confidence even higher because I know I can earn for myself. Deja Vu!

posted on Thursday, June 12, 2008 at 6:27 PM by Manish Gajjar

Dharmesh, Great post and very useful, i have added some additional thoughts regarding this here's the gist of it:
Basically the fear of taking that leap stems from a low self belief, so for budding entrepreneurs who want to take that step: They should try to conquer their belief in themselves and confidence and they will be able to make that first step and quit that BigCorp.

posted on Saturday, June 14, 2008 at 10:27 AM by Ismail

Great post Dharmesh. Its tough taking the leap to becoming an entrepreneur , especially if there is a certain security (financially speaking) attached to working for a large corporation.
But like Wayne Gretzky says: "You miss 100% of the shots you never take".

posted on Saturday, June 14, 2008 at 10:05 PM by Shaon Diwakar

Thanks a lot Dharmesh for rekindling my dreams...Let me mail back to you after a year with some good news..

posted on Sunday, June 15, 2008 at 10:06 AM by illiyaz Mohammad

"Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable." How true!

posted on Monday, June 16, 2008 at 11:06 AM by RahulDesai

I had been the rackmount server industry, and I got a slogan that I always believe, and want to share with you. "IT TAKES MONTHS TO FIND A CUSTOMER, BUT .... SECONDS TO LOSE ONE."

posted on Tuesday, June 17, 2008 at 11:43 AM by John Wu

Great quote.
I would also add another point.
6)You don't let your friends or family tell you what to eat, when to sleep, how to dress. So why are you letting a stranger tell you what to do 8 hours a day of your life? Take control of that 1/3 of your day, be your own boss.

posted on Thursday, June 19, 2008 at 11:28 AM by patrick

I'd love to! I've got the idea(s), the talent to code them up, and the passion to stick to it and crank it out.
But know what else I've got? A wife, a mortgage, and 2 kids.
Seriously, I really would love to make the leap to a startup, and have been wracking my brains on how to do it. But so far everything has failed. I tried hacking on the side at night, but wasn't able to get very far.
So, it's not quite as simple a decision as you think for many people, Dharmesh. A lot of people can't afford it.
Here's a challenge: I'd love to hear how you'd do it if you were in my situation. Wanna bite?
Thanks for the great blog!

posted on Monday, June 23, 2008 at 3:41 PM by DAR

It is a great blog Dharmesh, I have just completed my graduation from IIT Roorkee, India. I have a job as a Field Engineer at Schlumberger Asia, which is into oil field services,paying me $90000 p/a. But I feel I wont be happy because I have always been an entrepreneur. So I have made up my mind that tomorrow I will mail to my company HR telling them that I am not joining them,these days I am working at a start up in the net domain, but by the next week I will start my own business in health foods.I guess it is better to take the plunge at 23 than 25 or 27. Thanks for a great blog which has made my decision all the more firm, now I need to convince my family.

posted on Sunday, June 29, 2008 at 5:51 AM by Satya Vyas

Forceful post and great comments! 
A naive observation though -- if everyone wanted to work for him/herself, wouldn't there be one-person-armies everywhere? Since that's not to be, there have to be some (smart, appropriate) people who are willing to work for others in a professional manner. 

posted on Monday, June 30, 2008 at 8:49 AM by Kedar Mhaswade

I can relate to your comments DAR. I also have a wife, 2 kids and a mortgage. Unlike you however I could not code if my life depended on it and I am short on ideas.  
However I have been involved in 4 tech startups over the last 12 years and I know how to take a new technology, even if it is not quite ready for prime time and find customers for it. Which is not a bad skill to have when starting a company.  
My problem has been coming up with the "killer idea". So time creeps by as I wait for this light bulb to go on over my head - unfortunately, the killer idea never comes. 
So a month ago I grew tired of waiting. 
I have set a deadline to come up with 5 ideas. When this deadline arrives in 2 weeks, I will move forward with what I hope to be the best of the five. I will keep the day job due to the aforementioned obligations. 
The downside to this approach is that I may spend time on the wrong idea, which will produce no tangible results yet cost me in terms of opportunity and time spent away from the family. And time is a big issue as this project will be after the 9-6 job. 
On the upside, I hope this process will inspire me to create something new and successful. And who knows, while the first idea may not be the right one, it may be a steeping stone to the right opportunity. 

posted on Friday, July 04, 2008 at 1:34 PM by Tim Blacker

A famous aphorism from Mark Twain sums it up nicely: 
“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” 
Here are a few more practical tips: 
Know where to find resources to help you along: You can find plenty of very bright and talented low-cost developers around the world these days to jump start your ideas. I have successfully built, and helped built several successful SaaS products in the last few years using this approach, and have several in the pipeline currently. The best part of this approach is that you can build quick prototypes for potential investor(s) and/or potential customer(s) before going all the way. This especially makes sense for startup companies with limited budget and resources.This pays great dividends if you can build a trustworthy team. 
Know the lingo of the domain: You may have a great idea, but limited expertise or exposure in that domain. I have personally experienced this when an unexpected question makes you look like a fool. 
Know what your main idea is: You might think what you want to build, but then again you might not. There is too much information out there to distract you from your main interest.  

posted on Sunday, July 13, 2008 at 10:20 PM by Austin James

Fantastic post with some fantastic comments. You made a good point about waiting for the perfect idea. Truth is - any idea you actually execute will take many shapes as you cross through different phases. The world's greatest ideas usually didn't start so great. Just go for it. 

posted on Tuesday, September 16, 2008 at 4:58 PM by InvestmentPlayground

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