Going All In With Your Start Up

Bold Kiln | OperatorVC
Pen | Bold Kiln Press
4 min readJul 28, 2014

Being an entrepreneur is much like playing poker. The rules of the games are the same and so are the chances of being rewarded. While I can draw parallels on the everyday entrepreneurship endeavor with the practical ploys in poker, today I’m going to focus on the big question that every entrepreneur with a ‘winning idea’ has to ask him/herself at some point — Do I Go All-in?

Recently I found myself once again at this very junction — asking myself the question — Do I Go All In with what has been my baby for the past 2 years? Sure, I’ve been growing it steadily while I have been working elsewhere, but is that what I want to do even at this junction? Is this finally the moment that I’ve been waiting for — to stop working for others and burning the midnight oil for my little bundle of joy?

It took a little soul-searching and a lot of contemplation, but I think I’ve made up my mind and know what the right move for me is. Let me walk you through the process that should help you decide for yourself what works best for you.

Learn All That You Can

As you stare at the pair of Kings you hold in your hand pre-flop and decide to go for the big call, you don’t know if the table cards will open up in your favor or not.

Letting the hand play out before you make your big call is not a bad thing. Playing it slow has many advantages, the chief of which is that you get to learn quite a lot more before you bet all that you have.

The risk with going all in early, on the other hand, is that you’re stuck with the base knowledge that you start with along with learning on your own as time passes — whether from successes or failures.

Moonlighting with your business while you work a job, lets you learn a lot more about the operational end of the role than you do going it on your own. What I learnt working for one year at a startup would have taken me at least 3 years to learn had I decided to take up my venture full time early last year. Today, I know I made the right decision at that point to let my enterprise take its time to grow into its own.

Weigh Your Options

When is the right time then to make the call?

There is no universal answer to this question and don’t believe anyone who tells you otherwise. The answer varies depending on various factors that you need to evaluate. What I’ve found is that while I may go for a quick draw decision sometimes, at times like these you need to take a step back and carefully consider the options.

The main question is — do you even have a choice at this point? Will you miss the opportunity to cash in on what seems like a winning hand if you don’t back it with all the chips you have?

If not all the cards are on the table yet, you can always opt to wait and watch as things develop. Either play along or up the ante slightly so your profits are higher in the end.

Build Your Image

A strong table image in a game of poker can not only win you the odd hand and get you through a bad hand, but it can also swing other players into making large calls that you want them to. The credibility that your entity and you have in your industry or market, draw a direct parallel to this ‘table image’.

Building up a portfolio of work and clientele while you work a job or moonlight, lets you hit the ground running. Your credibility, and that of the services you offer, makes the big difference between building a trustworthy brand that gets you your ideal customers and compromising with clientele that you only take up because the big fish won’t bite.

No matter what your plan of execution is, make sure that by the time you decide to push all your chips into the center of the table, you have at least a few people who will follow suit because of the image that you have carefully built up to this point. After all, what’s the point of going all in when all you get is the change that is already on the table?

At the end of it all, the call needs to be yours. After all, you’re the only one who knows what cards you’re holding.

Do you plan on Going All In? Let me know!

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Bold Kiln | OperatorVC
Pen | Bold Kiln Press

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