One day you wake up and realize you are not in love with your startup and partner anymore

Chen Feldman
Apr 27, 2018 · 9 min read

One day I woke up and like any other morning, I started the walk to the innovation space I work at and bought myself coffee and something healthy to eat.

But something felt different that day, I still didn’t realize what that feeling was but I understood that my point of view on Guiderr (my startup) changed.

All the passion I went to sleep with every night and woke up with every morning, decreased significantly.

Suddenly, ideas and co-operations I worked on to take the startup forward seemed less relevant or less interesting.

Suddenly ,my partner impressed me less than before.

I tried to ignore that feeling because sometimes, after going to sleep and letting things settle down, they disappear or become less intense.

But I kept waking up that week with the same feeling. Nothing has changed.

On the contrary, the opposite happened and the feeling became sharper.

At that moment I understood that after 2 years of working around the clock with a lot of passion and effort, my love story with Guiderr and my partner, had ended.

Usually I am the kind of person who makes a decision with a lot of logic and analyzing behind the scenes.

I think of the advantages and disadvantages of each parameter before making the decision.

But this time it was different, I just knew that this decision was right for me.

It was like things started to connect in my head slowly until they came out as one clear insight.

Shit! What should I do now? We have just started a pivot to the chatbot field in the last two months! Potential investors and co-operations started to be more interested in us (even that is not enough) and it is even becoming more interesting from the technological and development side than before.

How will my partner and the team react? What will happen to all the code I wrote and the effort I spent?

What will my family and friends think? Did I fail? Did I waste all this time?

Those were only part of the thoughts that were running inside my head at that moment and I did not have an answer to all of them.

But, one thing was sure, I decided without wanting to decide, it was almost like someone else decided for me.

Maybe some of you know this, but when you have a startup and you meet some friends and family, they always ask : “How’s it going with your startup?”, so I couldn’t hide it too much time.

To some of them I said everything is as usual and to some that I’m considering leaving but haven’t decided yet (even though I knew i did).

So what now? How do you notify your partner?

The short answer: During a calm moment of the day and in the most gentle way you can.

The long answer: You think very well in advance how to phrase your decision in a way that will let him understand it without too many question marks. Being honest as you can be.

Try to show that you are still around and are not disappearing, you can still help, consult and even join some future meetings until things become more stable.

Break apart a partnership is a lot like a divorce (luckily enough I have no experience with that).

There are people who get hurt here and might change course due to your decision. There are kids (product, team and potential partners) who demand attention and want to keep growing in a smooth way without screwing their character after their parents broke up in a bad way.

Here, it is very important to avoid thinking only logically and technically, try to also think about what it’s like to be in your partner’s shoes at this moment. How would you react if you were in his position? What would you expect that would make you feel more calmer about the whole change?

Nothing is perfect but it is important to try.

At the end of the day, you do have appreciation for one another and a history of working together with common targets.

Another thing is that Israel is a small country where almost everyone knows everyone through 1–2 people and you really want to avoid bad mouthing each other and creating bad karma that will eventually reach different people.

So here we are, I updated my partner and we started with all the technical stuff of what to do now. Will he continue with the company by himself? Do I get a share? What share? Do I continue being involved in some way?

Those and more are very sensitive issues which can explode and become trouble in a second if not handled delicately and correctly.

During this process it’s most important that everyone stay down to earth and not escalate disagreements irrationally.

* I won’t go deeper into these processes since they are still in process.

Ok, so I made a decision, I gave notice to my partner… now what??

When you build a startup and you don’t join one that already offers salaries and has raised funds, you are more involved and your decisions carry a lot more weight from day one.

But from the other side, when you build something from scratch you can find yourself without any income for a very long time and no one can guarantee that that will change in the near future. In my case we started with 2 steps, in the first 6 months I worked all weekends, woke up early each morning and worked until late at night. After that I decided to quit my job and worked full-time on Guiderr without a salary or guarantee of success.

The problem is that you always feel that the seed investment is right around the corner and after a couple of months it doesn’t happen. But after a couple of months you get that round around the corner feeling again.

I found myself in a situation that is called “The gambler fallacy”. In short, this details a situation in which you think that one more try and 17 red will land on the roulette and you’ll win! You feel you spent a lot of time until now and your chances have increased , but that’s not necessarily true.

At some point (two months ago) I realized that I have to find some source of income. I still believed in our product and the direction we were headed, but I needed some money in order to survive the next couple of months.

The meaning of this decision is not simple, it means:

  1. Less time to work on your startup
  2. Investors and potential co-operations ask if you’re “All-In” and you’re faced with trying to explain to them that you took a step back in order to produce a bit of income since you cannot get it from them
  3. A risk that might kill the startup

In another post I might give more details on the deep and long process I did to figure out how I could quickly generate income from 2 work days a week that would be enough to cover my monthly expenses.

But in the meantime I will just tell about the final decision itself.

I realized that only through freelance programming jobs I’ll be able to succeed achieving my current financial goals and still spend at least 3 days a week on Guiderr and this is what I did!

I started by getting clients from my immediate circle, I created a new website, a business card and the offers started to come (luckily).

Pretty fast , I got my first paying customer and the second one while learning a lot on many types of clients (another idea for a future post).

Suddenly ,after a year and a half without an income, I got some money I could put in the bank. The pressure and the uncertainty of when money will come immediately decreased.

I even enjoyed it, first time I got a check that I earned totally independently, an interesting new feeling and achievement.

Let’s get back to the decision on leaving the startup. Suddenly ,due to the freelance jobs I had soft ground to land on. Not the safest one, but in my world, safe enough.

I have to stop for a moment and make one point very clear.

If you decided to leave a startup or a company you have two options:

  1. Just leave and do everything you can from that moment to make it work
  2. Try to start preparing in advance for the transition, so that when you leave you’re better prepared and have more time and control to decide what to do next.

With the second option, you have less pressure to make fast decisions with an hourglass in staring you in front of your face. You decide the rhythm of your life and you can go after what you want and not what others want you to do for them.

Good! So we hurdled over the initial blow of leaving, now what?

To tell the truth, It is just the beginning and writing here is part of the understanding of the processes and letting stuff sink in and learning from them.

These days, I’m doing a freelance project (together with a friend who joined me and also recently left a startup. Kind of a support group for freelancers), I do a software podcast every two weeks that will be launched very soon and really enjoy everything and loving it.

I realize that I have just gotten off a rapid train ride, and am not in a hurry to take a new ride on a new train.

I want to feel again what’s it’s like to earn a monthly salary, how it is to work on diverse projects with diverse and different clients.

But to the people who know me, it is very clear that I do not ignore new ideas or thoughts.

I just decided that for the next couple of months I want to mainly listen around, discover new fields and meet people that can expose me to new ideas.

When the thing that will light me up again will arrive, I will use the tools I got from the startup experience and my judgment abilities and decide what to do.

To shortly summarize,

As I see it, even though my mindset was that I was building a startup for the long term and gave all I could, I found out on one sunny day that this was only one more milestone in my path through the entrepreneurial world and independent life of creating new things.

A world I am really attracted to and definitely see myself staying in and spending most of my time on.

This is the first post as part of a series of posts I plan to write on the process I went through (and went through me) and the insights I learned in my first journey to build a startup.

In the next post I will write on issues that people do not always enjoy mentioning and admitting: Failures and Mistakes.

Part of the journey contains a lot of those and people tend to avoid them. I believe that the ability to accept them ,learn from them and pass over them next time to be better, is an important skill that can be taken from here.

I will tell about some major mistakes I and we did as part of the journey from my point of view with the hope it will help others and save you time in your personal journey.

Thanks to all the people who read until here I hope you learned something new and I did not waste your time (:

* Special thanks to Yuval Margalit and Ardon Wesly for helping with the editing!

Chen Feldman

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I am a Tech entrepreneur and freelance developer based in Tel Aviv.Hosting a software podcast and curious about new technologies that can change people life's.