Photo by Quino Al on Unsplash

Lessons I have Learn From Working For A Few Failed Startups

And Why I Will Work For A Startup Again

Cobus Greyling
5 min readJun 14, 2022



When you have worked for a few failed startups, you start to recognise the signs early on, and you instinctively know when to jump ship.

A startup needs to be lean and mean…money must be spent on the right things. Feast can very quickly turn into famine…in time of abundance store up for what might lie ahead.

Naval said, “the world is an efficient place”…the world will work perfectly fine without me or a particular product. A startup needs an exceptional product, supported by exceptional people to make itself relevant in the world.


Hiring needs to be astute and particular, many startups off-board people just to survive. Especially when a startup receives funding, and people is crucial for growth, the right fit for each task is of utmost importance. Each person needs to play a key role in moving the product or service forward in a very specific way.

Great demand is placed on employees of a startup, you need to be a believer, contributing to greater good, going the extra mile. You need a special kind of person working for a startup. There are too many good people that will never work for a startup again based on previous bad experiences.

And many people working for a startup hope for exponential growth at some stage, and benefitting from that. Which sadly, in many cases never come.

Product versus Service

Product or Service? A service is hard to leverage…having a group of people and selling their hours is tough and very linear.

Having a product on the other hand allows for leverage, a team focussing on a single product can lead to significant growth.

The product must not have underlying licensed software or components. Too many companies use white-label software. White-label software is software that is purchased by a company from a service provider and rebranded as its own. This is a shortcut to market, but there are two problems…

Firstly, the startup has no intrinsic value in terms of its product! The only value it can yield is customers and revenue from those customers. But from a software perspective, there is no own product.

The startup is at the behest and mercy of the service provider…if the service provider up the licensing cost, the startup needs to absorb it, or past that cost on to the user.

The burden of sales, support, marketing, etc, sits with the startup. This is a business model many large service providers follow, having business partners. Many of the business partners are also dependant on services.


There is nothing wrong with pivoting the product focus, functionality, etc. But the product vision must be crisp, shared and reviewed often.

A product owners must be relentless in their pursuit of excellence. The whole startup needs to act in the best interest of the product. This expunges politics and rivalries.

The startup exists because of their product and customers. First, do right by the customer.


Too many startups are dependant on one or two large customers. And thát one or two customers devours all the resources and efforts of the startup. Should they cease to be a customer, that spells the end of the endeavour.

Diversity in customers is key, selling software as a service, at a lower cost to many users is ideal. That is a model that can scale immensely. Democratising access to complex solutions and technologies creates real value.

Table Stakes & Differentiators

Naval once said, escape competition with authenticity. Look where the competition is not, and dominate there. A new field has no to very low table stakes. Achieving differentiation is much more achievable. As a market or technology grows, and there are more entrants, their products grow in functionality, and this in turn leads to higher table stakes.

Entering a market late, means facing high table stakes and a steep hill to climb only to reach parity. Then differentiation needs to be achieved, and market share captured. All while the competitors are also improving their offering and raising the bar.

Why I Will Work For A Startup Again

The singular focus and drive of being involved in a startup does not exist in a corporate environment. Corporates are looking to incubators, internal hackathons and more to foster a startup culture. But changing the DNA of an enterprise or corporate is hard.

There is something particularly satisfying to building something, to contribute to a product which add value to the people and organisations.

This quote from sums it up perfectly…

The master in the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his information and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence at whatever he does, leaving others to decide whether he is working or playing. To him he’s always doing both. ”

― James A. Michener



Cobus Greyling

I explore and write about all things at the intersection of AI & language; LLMs/NLP/NLU, Chat/Voicebots, CCAI.