Startup Opportunism – Watch Out For The Double-Edged Sword

TL;DR – Opportunities present themselves quite often, sometimes ones that sound very appealing and “sexy”, however, a smart entrepreneur needs to carefully review the risk/reward before entertaining one: Size of the prize, potential defocus, chances of success, long-term effect (negative/positive and net effect), etc.

*preamble – don’t confuse experimentalism with opportunism. Those are two different things. I reckon experimentation is KEY to success (and fun).

Opportunism probably also, but here’s what I have to say about it:


I’ve been an entrepreneur for a good 7-8 years now. Not always a successful one, not even “a successful” one yet, some would say.

But one thing that I learned was that many ideas sound great in theory, however, they tend to take your eyes off of the prize more often than not.

As a Newyorker (those of you who ever lived in New York would immediately recognize the reference), my most immediate association with an opportunistic startup entrepreneur is a mouse: trying to find the thinnest sliver or crack in the wall to come in and cause mayhem. Not even sure what that mayhem is, and what dangers await for “trespassers”, but we’re almost instinctively drawn to it, perhaps because we need to succeed very quickly, in an almost abnormal way.

So many competitions, accelerator programs, launch pads, showcases, incubators, partners that have an agenda, crazy clients that are waving the cleavage of a busty cheque.

All are temptations, possibly great ideas, but also – potential distractions, sometimes detrimental.


I wrote a piece about why startup founders/leaders need to establish a presence in their target market before they even have a product, as early as they can conceive it.

This might not be a plan, but it’s at the very least the foundation of a strategy – first, be there, then plan, then execute and course correct as you go.

But sometimes, you have all of those different opportunities: “we like your company, how about you join our program for 8 weeks? we’re great because x,y,z and you’ll likely get a,b,c” or “we think you have a great offering, perhaps we can partner and you can build something for us for free so we can try and resell or whatever”.

I’m not saying you should say no to these opportunities. I’m assuming if you’re past seed funding, you ought to have some type of plan and strategy.

Opportunism is very important as a part of our dynamic mindset – we can’t afford to ignore those that are indeed potentially huge breakthroughs, and it’s not unheard of.

Personally I almost never say no to an opportunity right off the bat. I listen, if I’m curious I’ll study it, and then I follow the protocol below, to make a decision:

  • Try getting the best estimation of the size of the prize. Ballparks are also helpful.
  • Assess the gap between what is in your wheelhouse currently (or in progress), and how far off is this opportunity, if we chose to take on it., efforts wise. This refers to every single aspect of your business: on tech, staff (skills/knowhow), product, support, etc.
  • What does failure mean? is this a hail mary, or can you allow yourself to experiment and not die (figuratively)
  • What other benefits do you get from this? big name signed? reputation? brand recognition? the more the better, of course
  • Ask around. Do you know people who tried or experienced this or anything similar? personal experience is super helpful.
  • And finally – trust your gut, as well. Sometimes after having quantified and contemplated, an opportunity can also be a personal bet. You feel it inside you. If you do, I say go for it. If we can’t trust our entrepreneurial instincts, after having factored in everything “rational”, then we’re in the wrong game. If you have partners, try to agree and achieve consensus, it would make the choice much easier and less regrettable – also, when everyone is fully engaged, it makes it much easier to succeed.

Strategy and opportunity are like Ying and Yang: seemingly opposing forces that have to co-exist to create harmony and balance.

We have to embrace and exercise both all the time – but we also need to be very mindful of ramifications of breaking that balance.


Don’t be a mouse. Think hard before you decide to enter the “apartment”, and if you decide to do so, GOOD LUCK!


P.S. the photo represents me experimenting in flying out to meet a potential partner. It didn’t go through.


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