The Impossible Work Of The Founder-CEO


Jonathan Gan
Founder & CEO


A tech-startup with a spectacular aura: innovative, disruptive, industry leading, successfully fund-raised, cool offices, great reputation, working with highly intelligent and creative people and as the founder you have the independence and freedom to fulfill your own dreams. They name successful start-ups after mythical creatures because the thing that makes them special is a type of magic that you can’t earn or buy.

Everyone has ideas, some good, some not. Some of the ideas are marvelous and revolutionary and yet, 97% of all the tech start-ups will fail and from the remaining 3% which can be defined as a success — only a handful will become big companies, while the rest will do a small/medium exit. Why is this? Most start-ups all have the same components, smart people, great ideas and a hunger to succeed, yet only a few go on to make a mark on the world. What sets them apart? It’s something you can’t see or quantify. Yes, there are principles that all successful start-ups incorporated on their way to success, but there is no set formula that you can use in order to succeed.

One of my favourite diagrams to describe the start-up journey is the Start-up Curve by Paul Graham.

The Startup Curve graph; by Paul Graham,

The Startup Curve graph; by Paul Graham,

The amazing initial enthusiasm that carry away the entrepreneurs, the diving into the trough of sorrow when the start-up is fighting constantly to find its’ way in the market, up to the golden point when the start-up hits the Product-Market-Fit and begins to scale.

But this graph is also misleading, almost a lie, as it’s totally out of scale. The reality is that the first stage, before reality sets in can take from a few days up to few weeks, no more than that. Then the time scale in the trough of sorrow, well… that can take a few years and might feel like an eternity. Like a thirsty and hungry person who is lost in the middle of the desert, without a map or compass, who can only see the horizon in the same shape and distance, every single day — the only powers that give them the strength to continue are faith and determination.

The feeling I had when I invented Whichit a few years ago was spectacular. A period full of energy, enthusiasm, creativity and pure initiative — aiming to change the way marketers interact with their audience. It’s been 4 years since I founded Whichit, relocating from Israel Startup Nation to Great Britain alongside my two Co-Founders, Yarden and Galit. A long and hard journey that taught me one main thing about tech start-ups: It’s not about the idea, but it’s all about the execution of the founding team, over a period of time.

Even today, after few years of running our start-up, with rich experience in the Trough of Sorrow, we are still holding the faith and belief of the idea. We can feel and see it in every aspect of the business — from the support and care from our investors, who joined us on this long journey, our business partners who recognize the unique and innovative value we are bringing to market, the successful commercial activities with our clients who are growing by the week and last but not least, our team: technically “employees”, but practically they are the soul of the start-up and keep on fighting even in the darkest hours; a team you want by your side when you’re building a tech start-up.

Being a Founder-CEO of a hi-tech start-up is a bitch (excuse my French). Long hours, hard work, working under constant uncertainty, great responsibility, constant concerns. As a Founder-CEO you are overloaded at every single moment, dealing with millions of tasks that cross every aspect in the business world no matter what your background is, while you have few resources. Every day is a challenge that becomes a struggle, getting “Nos” on a regular basis and still trying to continue like nothing happened. To be the Founder-CEO of a hi-tech start-up is doing the impossible every single day.

I was fortunate to have two super talented Co-Founders. Yarden, our CTO, covering all technology aspects of the business. From taking the concept and the initial definitions to full production. Even though when we began he didn’t have full knowledge and experience of several technologies and code languages, he was able to learn and perform with almost a vertical learning curve, with extraordinary talent and improvisation to achieve our product goals.

Galit, out Creative Director, is the master talent of the company. Basically, every single pixel in Whichit: it’s her design. From the creative language, the commercial campaigns, marketing and sales materials, website, blog and social channels, up to the full definition of the products, the user experience and interface. Thanks to her talent and creativity, we won the ‘Start-up of the Year’ from Facebook in 2015.

As we already know, talent is very important but not enough. The core team never stops surprising me with their dedication and hard work, sometimes with sacrifices of very late nights, working during weekends and holidays. Constantly communicating around work to execute our plans successfully. Getting into the small details and putting their care and personal touch in every corner of the product, services and piece of work, putting their soul into the tech.

The WBS Of The Founder-CEO

I had the chance to look back, reviewed all the disciplines I was involved with in the past few years of running my tech start-up. The millions of tasks spread across every domain and industry exists in the startup and business worlds. I don’t think there is a better school or degree that can teach you what can be learnt in a single year as a Founder-CEO of a hi-tech start-up.

The WBS Of The Founder-CEO [   see full picture   ]

The WBS Of The Founder-CEO [see full picture]

I created this Founder-CEO WBS (Work Breakdown Structure) diagram, which contains every domain and Scope Of Work (SOW) I personally dealt with, while running my tech start-up, Whichit. There are three levels of involvement I’m defining for each scope of work:

  1. Full — From definition and planning to delivery and full execution of the scope of work.

  2. Partial— Taking active part in the task execution, together with colleagues or a service provider.

  3. Shell— The action(s) taken was one or more of the following, while the actual task was created and delivered by someone else: planning, defining, managing, controlling, reviewing, mentoring, guiding.

As Founder-CEO of a hi-tech start-up, you will find yourself dealing with ALL of these components, while your level of involvement in each of them in the beginning of your start-up will be entirely on you, the more progress you make and the more team members you have, the level of your involvement will decrease, still everything depends on you. You may not have the professionalism, or you may not like a lot of these tasks (who likes to deal with GDPR or creating a company’s manual?!?), but like it or not, the execution of your tech start-up is dependent on each and every one of these small parts.

The T-Model In Professionalism

As you can imagine, it’s impossible to be an expert in every single discipline in the industry, nevertheless having the time to deal and manage everything together. The following model I created represents the variety of domains (horizontal) in the tech start-up world and the level of professionalism in each aspect (vertical). While the middle point is YOUR core professional domain, the more you move away from the center, the less professional YOU are in these domains.

The T-Model in professionalism is personal and will be different for each person. The goal of using it is to better understand where your strengths and weaknesses are in terms of knowledge, understanding and professionalism in each aspect of the start-up world. As an output, it will enable you to concentrate on working with your core specialties and expertise, while having others cover the specialties you are weak in.

The T-Model in Professionalism

The T-Model in Professionalism

As I mentioned before, EXECUTION is the key ability in a tech start-up. Not the idea itself, nor the tech, not the market and for sure not how much money the start-up has raised.

In its first years, until it becomes a stable company, a tech start-up IS NOT based on the traditional business models of T&M (Time and Materials) nor Bricks and Mortar, but more as an ongoing project, with a general direction and goal that is represented in a heuristic concept and with low resources to none.

Execution is defined as the ability to carry out a plan, order, or course of action. In simple words for the Founder-CEO of a hi-tech start-up, it is your ability to:

  1. Understand the start-up’s current situation.

  2. Measure your direction and distance to the main goal.

  3. Recognize the gaps and up-coming challenges.

  4. Translate gaps and challenges to tasks and prioritize.

  5. Act.

  6. Repeat. Every single day.

Good luck with doing the impossible possible and may the force be with you.


Whichit is an interactive commercial content platform that enables marketers and advertisers to increase user engagement, open new revenue streams & gain user-related insight. The company has an innovative technology that profiles users based on their preferences and uses machine learning to provide bespoke commercial incentives in real time.

The company is working with top agencies and brands and based in central London.

Our Story; From Startup Nation to Great Britain


Jonathan Gan
Founder & CEO


It’s been four years since we landed in London. Three young professional Israeli entrepreneurs, with a big idea and nothing else. Four years we worked every day, fighting to survive in the startup juggle, searching in the dark to find the golden cup in the local market. Sometimes we see it, even holding it for a while, enjoying those small victories in the endless and cruel start-up journey, and then going back to work, putting our full energy in our venture, with the belief that one day we’ll enjoy the fruits of our labour. In a nutshell, this is our story.

Don’t Worry, Everything Will Be Fine

As an Israeli I can say that this is one of the most used slogans. It would be an understatement to say that it is not one of the smartest. You’ll quickly find yourself in a situation in a wise man would never dare enter. But on the other hand, from my point of view, it is one of the chromosomes that an entrepreneur must have — to dare.

At Tel-Aviv airport with just a trolley, waiting for the flight to London, April 2014

At Tel-Aviv airport with just a trolley, waiting for the flight to London, April 2014

We started with a bunch of guys, a lot of help and support from friends, working to develop a crazy idea I had. With a basic version that looks like… well… basic and just few months into the project we won the Sirius Programme of the UKTI. A UK government program that choose around 60 startups worldwide, offering them to relocate to the UK and develop their startup in the local market, with a small grant, a 3 months accelerator program and an office for a year. You, just need to leave your home, your family, your friends, your network and build your start-up in a new market. The rest is up to you.

Five minutes, that was the time it took to make the decision. We are moving! In just a couple of months we sold the car, the motorcycle, ended our apartment leases. We packed the whole house into boxes and stored it all in a long-term warehouse. Bought tickets on a low-cost flight and went to the airport with just a trolley and five boxes to be sent in a week’s time. Don’t Worry, everything will be fine.

The British Paradox

A business card. The basic information that represents you and your business. A small piece of paper that every business person has. It took four and a half months to get one in the UK.

In order to have a business card, you need to have a normal local phone number so people can contact you. In order to have a normal UK phone number you need to have a contract with one of the telecom suppliers. In order to have a contract with one of them, you need to have a local UK bank account. In order to have a UK bank account you MUST HAVE a local home address, with the original council tax set to your name. But in order to rent a flat in the UK you MUST HAVE a bank account. But in order to have a bank account, you must have an address… I call it the “British Paradox”.

That was one simple example, out of many, that represents the basic most simple and obvious things in life for a local resident, are a struggle for the foreign person, like us. Add that to the life of the entrepreneur and you just start to imagine the number of hurdles we needed, and sometimes still need, to overcome on a regular basis. Sometimes people, mainly in potential investor meetings, asking me why it took us a few years to get to where we are, like building a start-up and in a foreign country should be in the blink of an eye … I always hold myself from explaining all the reasons, because if you never ran a marathon with no end point in the middle of the desert and with no water, you’ll never understand the feeling of an entrepreneur.

The Team is Everything

That’s what every investor will tell you, that’s what every entrepreneur will testify. And I can say the same. Most of the start-ups that failed, the core team was the main reason. Whether it was an internal dispute, the team wasn’t strong enough or not fit to the role. The core team is the heart of the start-up’s success.

Galit (Creative Director); Yarden (CTO); Jonathan (CEO)

Galit (Creative Director); Yarden (CTO); Jonathan (CEO)

Throughout the years, many employees passed through our company. We always kept our team small, professional and highly motivated, in order to keep the company, lean, effective and efficient. But the core team was always there. Each of us have our own specialty, and our own individual personality. Together, we complemented each other and bolstered our strength.

Along the way, I noticed that we literally taught ourselves almost everything we know today in the start-up world and in our industry. Yes, each of us have rich experience and knowledge in our domains from past roles, and all of us are holding advanced degrees from top universities. Yet, just with a crazy idea on a power-point, we found ourselves dealing with new technologies, new markets, new materials, new tools, a new country, a new network, new everything. We challenge ourselves to learn on the go; planning, building, trying, testing, failing and then again… and again… and again…

A start-up is not about the idea, its all about the execution and execution is made by the team.

Small Victories Its All You Need

Building a B2B technology start-up from scratch it’s like the David and Goliath story, but this time there are a lot of them and you’re more like a baby-David. Trying to go through the massive corporate doors, proving your product in a competitive market where big tech companies dominate the market and thousands more are jumping from all over, trying to bite the cake, and then the long and clumsy sales cycle. While all this time you’re looking to survive your basic existence with investment and trying to manage hundreds of administration and operational tasks to keep the machine going on. You and just a several team members.

But it doesn’t mean you can’t enjoy the small victories along the way. Those are actually the most important, as they are the light-bits for the entrepreneur. The orange peel trail in a long and bumpy road. Those small victories reflect that you’re on the right path. Indicate that you’re still alive.


Whichit. Startup Introduction 2017


A year after we landed in London, we won the ‘Start-up of the Year EMEA’ by Facebook, later on the year we won the People’s Choice Award at Pitch@Palace by the Duke of York and we won the Innovate UK R&D Funding Award with a £250k grand to develop one of our algorithms.

As we were determined and consistent with the concept of the idea, playing with the product definition, testing different angles and messages to the target market, we have been able to hit the golden point of the start-up — the Product-Market-Fit. From that point the target market started to convert and became clients, the conversations became deals and revenue and the search mode turned to growth.

It was like in the Matrix movie, when Neo saw the Matrix. We then knew and saw the perfect formula. What we need to do, how and where. It’s not the end goal and no champagne will be open just yet. We still have a long ride in front of us and the odds are still against us, like any other tech start-up. But we have been able to overcome another step on the way to the cockpit, enjoying the small victories along the way.

To be continued…

Whichit is an interactive commercial content platform that enables marketers and advertisers to increase user engagement, open new revenue streams & gain user-related insight. The company has an innovative technology that profiles users based on their preferences and uses machine learning to provide bespoke commercial incentives in real time.

The company is working with top agencies and brands and based in central London.