This roller-coaster called “Entrepreneurship”: what I learned so far


I recently started a business while in a corporate job. It has not been easy. I change my mind on certain issues sometimes several times a day, and have been wrong about assumptions more often than I am right. I believe this journey represents a microcosm of the rollercoaster that is entrepreneurship.

This is my collection of key learnings along way…

The Idea

I was at a restaurant for dinner with a large group of friends. Everything that could go wrong did go wrong. The waiter was that guy who tries to memorize everyone’s orders without a notepad, but who inevitably gets a few orders wrong because he bites off more than he can chew. I counted 4 orders he got wrong with us – Great start. The waiter was nowhere to be found when we wanted more drinks. Then the bill – Huge frustration; the bill was the length of a Roman scroll, we had to designate a Chartered Accountant to do the maths and assign everyone their allotment. Everyone paid, but somehow the bill was R200 short. The strange thing – this has happened to me almost every time I go out to a restaurant in a large group. Extremely frustrating experience. But why is this “okay”? Why is it still the case in the 21st century? Why do people just accept it?

So we came up with an idea. What if there was an App that had all the restaurants in your city loaded. You go to the restaurant, scan the QR code on the table, and the App signs you into that table at that restaurant and allocates you a waiter. The App then contains the full menu of the restaurant, showing you anonymized data of other people’s orders so that you can see the most popular meals, and you can see what meals are usually paired with drinks. You can place your order through the App, and customize your order as you choose. Perhaps you can even push a button on the App to send a Push notification to the waiter’s phone and call them to your table. What about the bill? Simply split it on the App. No maths needed, no frustrations.

So I got excited, thinking this idea is going to change the world. We developed a prototype. This prototype exhibited approximately 7 features of what this App would do. I was ready – Ready to meet restaurants and pitch to them before building the full product.

Exciting times were about to begin… Jordan jumping in

‘The MVP’ Realization

Our first big meeting – A pitch to the owner of Rocomamas; Brian Altriche. Who knows how we got something so high stakes so early. In some ways failing spectacularly is more useful than failing forgetfully. And fail we did. The pitch was just wrong. We were selling all 7 amazing features that this App would bring thinking that was what a client wanted to hear. Brian responded with a simple question: “Who is your client?” I was confused by this, thinking maybe Brian had lost concentration, and proceeded to repeat the entire pitch again, in which I focussed on the exciting features. Brian’s response was the same: “Who is your client, and what problem are you solving?” At this point I realized I had not answered his question at all. Talking about the features of a product does not demonstrate the value of the product. He needed a succinct, thoughtful answer stating who will be paying for the product, and what key solution the product presents. At the time, I was so taken aback by everything that I didn’t have the right answer. Failed spectacularly, and learnt something very important: Use a prototype to demonstrate the most important feature; use the pitch to discuss the main problem being solved, the single solution that will solve it, and have a business model ready.

In essence, I realized that we need to keep it simple, focus on Minimum Viable Product, and overwhelming someone with information does not equal a sale.  

‘This is my Client’ Realization

25 Meetings later. No jokes, no exaggerations. Twenty five. No success. Restaurants mostly liked the idea; they were just terrified by the logistical changes that would go into accommodating the App. Many restaurants said they were keen until they fell off the face of the earth and “ghosted” me as soon as the meetings were done. I thought maybe the 46th restaurant will love it and that will be a true entrepreneurship success story of persistence.

However one day I met someone who owns a catering company who provides the canteens for corporates and everything changed. He told me, if the App was simply a food ordering app it would work amazingly for him. If an employee could view the canteen menu from their desk, and place order, and collect when ready – he would pay for that. This was the first time someone told me they would pay for my product. I felt excited tingles, but I also felt that “canteens aren’t as sexy as restaurants”. After I came to my senses I realized, maybe the product isn’t ready for restaurants, and maybe we could solve a very real problem in corporates of bypassing lunch time queues at the canteens – saving people time and productivity.

If someone will pay for the product that solves a real problem they have, that is the client. Simple, but very important.

‘No Opportune Time’ Realization

All the while this was happening, I was still in a job – A comfortable, well paying, prestigious company, corporate job. I was “happy” there. Well, as happy as someone can be when they unapologetically long for Fridays, and dread Mondays. I was waiting for the right moment to leave corporate and pursue my business fulltime. However, I realized something very important: There is no such thing as the opportune time. There will always be a bonus around the corner, it will always be close to payday, there will always be another expense you want to get out of the way. If we have a business idea that we want to pursue, we have to pursue it while that entrepreneurial fire is burning at its strongest. That moment, for me, was end of 2016, when I had a prototype and some tangible interest from my target market. I went all-in on 28 December 2016.

I believed in the potential of the business, and when you truly want something to fulfil its potential, you may have to go all-in.


‘The York Zucchi Meeting: The in-person-sale’ Realization

A month passed, the pension fund started fading rapidly, 55 sales cold emails later, I realized that this was going to be much more difficult than I thought. The catering company that told me they were interested were just starting out, and couldn’t afford extra costs at this time, so that was a big blow to my hopes. A lack of email response from the other companies I pursued was an even bigger blow. I began thinking, is it possible I’ve completely misread the situation and maybe this product won’t work in canteens or restaurants? Existential crisis #673 (aka the life of an entrepreneur).

Concerned, stressed and somewhat bewildered, I organized a coffee meeting with York Zucchi to get some advice. I was excited for this meeting, as I had heard a lot about him, watched some of his interviews, and admired his journey until now.

After taking the time to understand the product and the proposed business model, York had simple, yet priceless advice for me – Approach the 10 highest value potential clients.   Go into their stores, speak to their staff, wait there until someone listens to you, and get their honest opinion on your business. The only way to know if a business is viable, is if the clients you really want and need would pay for it. Ofcourse, your product may not be right for them right now, but getting the real target market’s view is crucial, and they may be ready to take a risk. The purpose of pursuing the highest value clients is to understand if this business can actually make money at scale, and if it can be something to revolve your life around.

Very fortunately, I went to a nearby office canteen, asked the kitchen manager who her boss’s boss’s boss is, and she started dialling the phone and handed me over to her. Just like that, I had a sales pitch over the phone to the right person. Fortunately I then got an in-person meeting with one of the major catering companies in the country. The meeting went excellently, we agreed we would learn the value of this together with a pilot in one of their canteens. That was ideal case scenario, and would have never happened if not for York’s advice.

Key learning: Before taking the plunge, chat directly to a good sample size of the biggest possible clients you’re after – If they’re in, you’re onto something.

‘The Pilot’ Realization

I was excited, nervous and anxious about the pilot. It was finally happening. The success or failure of this business could hinge on this month. I learnt during this pilot the importance of minimum viable product – from a staff training perspective, and from the perspective of positioning the product to the userbase. If the pilot wasn’t simple for everyone to understand and simple to use, it would have never worked. Another massive learning was the extent to which things can go wrong in a pilot; hence, again, the importance of a pilot. For example, I would have never thought that when an order is placed, the kitchen staff should be alerted of this order with a continuous sound until the order is accepted. It may sound absolutely simple and essential, but I just assumed the staff would be permanently looking at the order screen – How naïve. The beauty of a pilot is a safe environment to test assumptions, learn, make mistakes, change things, improve, and build a product that solves real problems. I would not replace that opportunity for anything.

Fortunately, the pilot went really well (all things considered), and the catering company signed on for rollout across their corporate units. I can’t express in words the joy at finalizing that process – To know that an idea is now a reality; bliss. However, the hard work; the real hard work, only begins after the contract is signed.

The Now

We have been operational for 8 months, have 4 corporates loaded, and have had over 1300 transactions through the App thus far. I had hoped we would be much further ahead than we are, but patience is something that I have to be patient for. We have learnt that assumptions and reality are very different. We have learnt that a combination of patience, drive, mad conviction, and resilience form a cocktail of the most important attributes of an entrepreneur. We have learnt that App awareness is one thing, but App adoption and engagement is an entirely different challenge.

We have learnt that learning is something we will always be learning.

That is the beauty of the entrepreneurial journey. It’s crazy, but isn’t that how life should be?


Jordan lecturing


Jordan Stephanou can be reached on or if you are interested in his solutions for your canteen or restaurant, go to


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