How the first investment round almost killed us
A raw story about rejection, pressure, and doing whatever it takes to survive
Dear readers,
I hope you’re having a great week.
After finally finding our CTO and co-founder, we knew it was time to go out and raise our first round of funding.
What happened next? Let’s just say: it nearly broke us.
You can read the full (and brutally honest) story in this week’s article.
Best,
Xaver
P.S. I’m working on the ultimate fundraising online course, sharing how I attracted some of the world’s best investors like EQT and signed over $40M in funding through various companies. Want early access? Join the waitlist here.
Missed my last story? Check it out here.
We had never really fundraised before.
The only investment we had received up to that point came from the accelerator Wayra $100,000, of which only 50% was actual cash.
The rest was tied up in services like office space and advisors.
In truth, we had no idea how to raise money.
The first thing we did was simple: figure out how much we actually needed.
I opened a basic Excel sheet and started calculating.
We needed to hire three developers on top of our CTO.
At the time, both of us were still living with our parents, so covering basic living expenses was also a priority.
We estimated roughly $50,000 per person, enough to rent our own apartment and have a little runway.
The money had to last 12 to 18 months.
We knew from other founders how time-consuming and painful the fundraising process could be.
So we planned accordingly.
Next, we built a basic pitch deck.
We had no clue what we were doing, so we Googled:
“What slides does a pitch deck need?”
The usual slides came up:
Problem, Solution, Market, Business Model, Competition, Team, Ask.
We drafted something quickly and iterated until it felt halfway decent.
We started reaching out to investors we had met at events.
Some founder friends gave us warm intros.
The first calls actually felt promising: I shared our vision, explained the product, and they seemed genuinely excited.
But after we hung up… silence.
Days passed.
Weeks passed.
Nothing.
No replies. No feedback. Just… ghosting.
It was a punch in the gut.
A sign that something wasn’t working.
So we went back to the drawing board.
Asked other people for feedback on our deck. Rehearsed the pitch with founders who had been through it, made improvements and kept going.
We reached out to new investors.
The conversations shifted slightly, but the outcomes didn’t.
At least this time we got actual rejections:
“The market is too crowded.”
“We’re seeing too many chatbot startups.”
“How will you compete with Microsoft or IBM?”
They had a point.
We weren’t the first in the market.
Far from it.
By the time we started fundraising, chatbot startups were everywhere. Investors had seen pitch after pitch. Some smiled politely. Others didn’t bother to hide their skepticism.
When we said we were raising $700,000, a few actually laughed, some quietly, some not.
There were mornings I didn’t even want to open my inbox.
By then, I had racked up more than 40 or 50 rejections.
I couldn’t help but ask myself…Am I just wasting my time?
Every conversation felt identical.
Same questions.
Same doubts.
Same endings.
It was like living Groundhog Day. Stuck in a loop I couldn’t break.
It was time we changed direction.
Instead of chasing VCs, we turned to angel investors.
We applied to angel networks. Many had websites showing investor faces but no names.
So we got creative.
We used Google reverse image search to identify the people behind the photos, then connected with them on LinkedIn.
It worked and we saved thousands in membership fees.
We also started pitching at events and startup competitions.
Slowly, it started working.
We got in front of more investors.
Some only wanted to write €10K checks. Some wasted our time completely.
But a few actually committed.
Then, out of nowhere, we got a call from Main Incubator, the corporate VC arm of Commerzbank.
One of their analysts had seen us at a pitch event and wanted to meet.
On paper, they were a perfect fit. They invested in early-stage startups and looked for innovation they could bring into the bank, similar to how Wayra had introduced us to O2 Germany as a customer.
After a few calls and a board meeting in front of Commerzbank executives, they committed: $300,000.
Finally, we had a serious lead investor on board.
And we knew this could change everything.
With that validation in hand, we went back to the investors we had previously spoken to and told them:
“The round is nearly full.”
In truth, we still had $400,000 left to raise.
But FOMO did the heavy lifting.
Suddenly, the former CEOs of Microsoft Germany and Cisco Germany wanted in.
We were beyond excited.
For us, it was a turning point.
Their involvement gave us instant credibility and the rest followed.
Other investors didn’t ask many questions.
They simply followed their lead.
We negotiated the term sheet with Main Incubator, worked through the shareholder agreement and started preparing for the notary signing.
The whole fundraising process had already taken over six months, but we didn’t care the round was finally coming together.
Then, the day before signing, the unthinkable happened.
The Microsoft and Cisco investors pulled out.
No explanation. Just:
“We’re out.”
Our hearts sank.
Those two names had brought legitimacy to the round.
We feared others might back out too, thinking something must be wrong.
So we made a move.
We called each investor personally and said:
“Those two stepped out but everyone else is still in.
You’re still in too, right?”
Surprisingly, everyone stayed.
One investor even increased their commitment to cover the gap.
Two weeks later, we signed the deal.
We were emotionally drained.
Mentally exhausted.
But we didn’t care.
We finally had the money.
And we felt like we’d earned every cent of it.
Interested what happened next? Go to next article here.
Roller coaster ride! You earned every cent of it.