The Day Everything Fell Apart

The darkest hours of being a founder

I woke up drenched in sweat at my parents’ house.

My breathing was shallow, and my heart was pounding so hard I could feel it throughout my entire body.

For months, we’d been deep in the M&A process, working day and night to sell our startup, e-bot7, to a U.S. company.

Dozens of lawyers were involved. Hundreds of pages were under negotiation. Every detail became a battleground between conflicting interests.

The entire company: 130 people and five years of hard work was on the line.

At the same time, my body was beginning to give out. I’d been suffering from chronic headaches and I couldn’t sleep more than four hours a night. I was thinner than ever before. It felt like my body had forgotten how to recover and each day, my energy dropped even lower. I was caught in a downward spiral I couldn’t escape.

On top of that, I started to worry these headaches weren’t normal anymore.

They didn’t feel like typical tension or stress headaches. They felt like something deeper, like actual pain inside my head.

What if this was something serious?

Suddenly, my phone rang and pulled me out of my thoughts.

It was my co-founder. He said he had a bad feeling that the sale of our company might fall through.

At that point, we had been deep in negotiations for over four months. The deal was nearly done.

We both always had a good instinct for these things, so I immediately went on high alert.

My thoughts started spiraling. I kept asking myself: Was it a mistake to turn down the funding round and go all-in on the sale?

Were we too naive to think the acquisition would actually happen?

Should we have taken the $25m from the American investor instead?

Just a few months earlier, we were actively looking for new investors.

After more than 100 rejections and dozens of calls and meetings, we finally found a U.S. investor willing to put $25 million as an investment into our company. That would have given us 18 months of financial runway and room to keep scaling.

But right in the middle of those negotiations, we received a message from an Israeli contact we’d met years ago at a Berlin conference. He’d hosted multiple events in our space and was now consulting for the U.S. company.

In his email he got straight to the point and he simply said:

Would you be interested in meeting the CEO?

We were already familiar with the company from several client projects and had always seen them as an innovative, forward-thinking company.

At the time, they were publicly listed on the NASDAQ, employed around 1,500 people, and were recognized as a market leader in live chat and AI-powered customer service.

We were flattered. No company had ever shown serious acquisition interest in us before. Especially not as big and not from the U.S. Also, we were excited to meet the CEO, who had built the company over the past 20 years.

After many conversations of their C-Level and deep reflections, we decided to go with the acquisition instead of another funding round.

Even though our company seemed to be in good shape and was growing, the idea of financial freedom, of letting go of the daily stress and constant uncertainty was simply too tempting. Also, we would have become the biggest company for AI-powered Customer Service in the world.

When we informed the U.S. investor about our decision, he understood but pulled out immediately.

From that moment on, we had no choice: we had to bet everything on the sale.

By the time my Co-Founder called me, we only had about six weeks of financial runway left.

We were burning through tons of money and desperately needed funds to pay our 130 employees to keep the business alive.

For five years, we’d worked day and night. Countless hours at our desks, endless customer calls, stressful funding rounds.

Now it all seemed to be crumbling.

Then something dramatically happened: The U.S. company had suddenly changed the initial deal, drastically.

Under the new structure, we wouldn’t even have been able to cover the taxes on the sale. The shares came with a mandatory one-year holding period, yet we were expected to pay taxes on the full reported value regardless of whether the stock went up, down, or became worthless.

Also, our investors would’ve never agreed to that.

Many of them hadn’t wanted us to sell in the first place.

I was in shock. We had worked so long and hard for this moment and now it might all be over.

I tried to stay calm, to slow my breathing.

Over the past few weeks, I had done everything I could to find balance. Meditation, healthy eating, daily exercise.

But in that moment, none of it mattered. The feeling of disappointment and anger was overwhelming.

I walked downstairs, sat at the table, and tried to eat a few bites of breakfast.

But I couldn’t. The anxiety sat like a rock in my stomach so heavy, I couldn’t swallow a single bite.

Still, I tried to act normal when my dad came down to join me.

I didn’t want to burden him more.

Just a few days earlier, my mother had passed away after a long battle with cancer.

We had taken care of her at home until the very end.

I still remember the moment clearly.

I was on a call with an investor when I got a heavy, sinking feeling.

After the call, I closed my laptop and walked downstairs into the living room.

My brother had flown in from Amsterdam a few days earlier and was already standing by her bedside.

My older sister, who lived just 20 minutes away, had arrived a few hours before.

We all had the same feeling, that it might happen that day.

So we stood by her side and witnessed her take her last breath.

Our dog Amy started howling at the exact moment it happened.

I’ll never forget that moment for the rest of my life.

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