9 Months of a Startup Journey: What I Learned When I Chose to Stop

We stopped the startup after a 9-month sprint. It is never easy to make decisions like this when there is a lot of emotion involved, but like in poker, you have to look at the cards you hold, how many chips are left in the stack, and decide what the right move is at that point in time.

How it started

Nine months ago I decided to build a startup. The decision was not simple, especially after 10 months earlier I founded a services company in Singapore that generates nice profits. But I felt it was the right time, the stars aligned.

It took me a few months to finish existing projects, almost freeze the Singapore activity, and focus on building the startup. I built a strategy, timelines, and a clear work plan, including a predefined Stop-Loss button.

Ideation stage

I started with a structured process:

• 5 main problems to test

• Shallow and deep market research

• Conversations with friends in the industry, professionals, investors, and anyone who could contribute

After two months we reached the critical decision between two main problems.

Validation stage

Talks with dozens of potential customers and professionals, and warming up investors in the background, led to a decision: we go with the problem we know in depth, one that has real customer need, and investors showed interest.

The first fundraising attempt

The initial thesis was simple: a basic deck, a familiar and deep market, clear customer need. We decided to “test the waters” with friendly funds that invest in a strong team, that is what we believed at the time.

The idea was to do a few weeks of open conversations, get feedback, then go out to the “real round”, and maybe by chance raise without really intending to.

We did not get the surprise check, but it was not part of the plan anyway.

The turning point at RSA, San Francisco

We flew to the other side of the world to RSA in San Francisco, the biggest cyber conference. The goal was to do deep and technical competitive research. We researched and learned about 15 companies of all sizes, public companies, growth companies, and of course startups. An important point: the advantage at a conference like RSA is that most companies send their product people and also very technical folks, and you can get a lot of interesting, useful, and current information about what the company is working on. Information you will not get on the company website, and you will definitely not get a demo just for market research.

The conclusion was clear: we were behind on time-to-market for the problem we wanted to solve, and we needed to pivot. The most important insight was to understand what not to do. Most companies “got addicted” to a certain style of cyber solutions and struggled to think outside the box.

Preparing for the real fundraising round

At that point we thought the pivot was not significant, which in hindsight was not really true, but it did require more market research in the competitive direction and wider validation. We started serious preparations.

The playbook we built

Investment thesis:

• An Israeli fund that will believe in us as a team, Seed funds mostly invest in the team

• A US fund that will understand the technical depth and join the round

• Willingness from 10 potential customers on the problem definition

Preparation:

• Build a sharp deck with clear messages

• Bring on a designer or product lead for consistent design

• Search for and find a third technical co-founder

• Run an investment process by geography

• Prioritize investors and warm and cold intros to relevant funds

• Precise scheduling of meetings

• Clear start and end dates

Supporting team:

• Advisors who are friends in the field for feedback along the way

• A storytelling friend

• Friends in funds

• Founder friends

• Friends with connections to potential customers

• Professional friends in the domain

Lesson: keep the pace while moving and update the messaging all the way through.

Results

After 20+ meetings with funds from Israel, the US, and Singapore, not including second, third, and fourth meetings, dozens of meetings with potential customers, hundreds of hours of work, flights to the other side of the world, and many late nights, the moment arrived to decide what to do with the cards we had.

8 key takeaways from the fundraising process

1. Geography matters. Funds are less open to founders who are in different countries, especially Israeli funds.

2. The scale challenge. Funds were not convinced how we could rise above the current noise of companies advancing with solutions in the space.

3. The thesis needs to follow trends. Israeli cyber funds wanted to see a narrower solution on one hand, but on the other hand most did not want to bet on the team and preferred to see that other funds were moving in this direction before they take the risk on a thesis that is not yet aligned with trends.

4. US funds demand more. US funds understood our defense approach and where we were going, but they do not usually invest on a deck only, unless there is a very strong relationship or founders who sold a company. They mostly like to see a prototype and potential customers reacting to it, then they invest.

5. Singapore funds are cautious in cyber. Singapore funds do not like to invest big money in cyber because they lack deep understanding. They prefer to do it with a fund experienced in cyber, and they prefer to invest when there is a prototype and a few potential customers.

6. Response times vary. Some funds respond very fast, and some will never get back and just disappear.

7. Feedback is not always real. Not every piece of feedback you get from a fund is what they really think, sometimes they just do not feel comfortable saying the truth.

8. Military background matters in Israel. Israeli funds have a bias toward alumni of tech units, and they prioritize them over proven business experience.

The inflection point - Right After Black Hat Las Vegas

At that point I understood I had to make a move that would change the path, to collect more chips instead of losing a few more. My partner thought completely differently. That was the inflection point.

It pushed me to press the pedal and ask hard questions:

• Even with the professional and personal friendship, is this the right partnership for success

• Are we in the same agreements we had when we started the journey

• How much have the gaps widened

Nothing is perfect. Like I once heard, “perfect does not exist.” But this was the moment to put emotions aside and imagine how it will look when there are employees with families behind them, customers who committed and believe, investors who want to see success. The pressure will only grow, and the gaps will expand.

The right thing was to stop now and look forward.

Conclusion

Every day in the last 9 months I learned something new. I do not regret it for a second.

No matter how many times I think I have done something, I always know that when I go into a new adventure with new variables, different timing, and different locations, it will be a different story with new challenges.

This journey taught me that sometimes stopping in time is the most significant decision. Not every journey ends with the success we planned, but every journey teaches us something important about ourselves, about the market, and about what it takes to succeed the next time.

Thank you to all the VCs who gave us the opportunity and shared your time and feedback, to the friends who believed and supported, and to my family, especially my wife, who always has my back and supports me with any risk I take. This is not trivial, and I do not take it for granted.