“Not Investment Advice” is Scaling Judgment’s section where I reflect on my journey as an investor. A few months ago, I wrote about my first property investment. This time, it’s my first angel investment.
About a year ago, I wrote my first angel check to a company called Huskeys. I did not source the deal myself; I came across it through a syndicate I am part of. At the time, the company was still in stealth mode and raising its pre-seed round. At the beginning of September, it closed its series A. That prompted me to go back through my notes and write this short reflection on the deal.
Early-stage investing is largely a gamble. There’s no point in me reciting statistics on how many startups are born and die every year. The game isn’t about being right all the time. It’s about being right occasionally, when it matters.
My current mental model for assessing an early-stage company is built on five ideas, in no particular order: the market, the problem, the founders, the ecosystem, and customer feedback. If all five pass the common-sense test, there’s a chance we’re onto something.
The Market
“What I did in my youth is hundreds of times easier today. Technology breeds crime”. These are the words of Frank Abagnale Jr., the conman Leonardo DiCaprio played in Steven Spielberg’s 2002 classic “Catch Me if You Can”. The same words echo in my head today whenever I think back on this little bet.
Cybercrime has been around for a long time, arguably since the birth of the Internet, and it has followed the same trajectory: the more the Internet has grown and technology has advanced, the more ways bad guys have found to steal our money, and data, mess up with our systems, and make our lives harder. Maybe it’s just me, but every couple of months I get an email from one of the many services I’ve used over the years, telling me they’ve been hacked. They reassure me they’re still doing a great job and that none of my sensitive data was necessarily compromised.
But those emails may come to feel like a minor inconvenience compared with what lies ahead. This summer, AI agents being tested by OpenAI escaped their sandbox and spent days attacking Hugging Face's systems.
Who would have thought AI would bring new security challenges? If any schmuck can now vibe-code an app (one that’s easily hacked), a bad actor can use Claude Code to hack their way into ever more complex systems.
To cut a long story short, cybersecurity doesn’t look like a shrinking market. If anything, it stands to benefit, sadly, from the spread of AI. I could pull together plenty of data points to prove the thesis, but I won’t. It’s common sense.
The Problem (and the Fix)
Explaining the problem can get very technical, and I won’t pretend to understand all the ins and outs. I’m not a techie, after all. Put simply, most companies protect their websites and apps with a stack of tools sitting at the “edge” of their network, where outside traffic first arrives. The best known is the WAF, or Web Application Firewall, which filters traffic using fixed rules: it lets good visitors in and keeps bad ones out. That works well for simple websites with predictable traffic. Its more sophisticated cousin, WAAP (Web Application and API Protection), extends the same idea to the apps and APIs that power most of what we do on our phones.
The trouble is that WAF technology has been around for more than twenty years, and most large companies now run several of these tools side by side, each from a different vendor and each with its own rules. Nobody really knows how well the whole setup is working. Legitimate customers get blocked, attackers slip through, and security teams spend their days tuning rules by hand. AI makes all of this harder, because the question is no longer just “human or bot?” Some bots are customers. In layman’s terms, it’s a bloody mess.
Huskeys sits on top of whatever a company already has and acts as the brain: it measures what’s working, recommends what to change and makes the changes across every tool at once.
The Founders
Itai and Roy are not your average tech bros. Itai started coding at 13. Like most Israelis, he did his military service, and he put his talent to work hacking systems with AI. I haven’t met Roy, but Itai describes him as the best hacker he has ever seen at work.
While serving in Unit 8200, Israel’s signals intelligence and cyber unit, they began to see the weaknesses in existing cybersecurity systems first-hand, and decided to build a business around fixing them. Plenty of people start businesses because they see a problem, of course. What makes Itai and Roy different is their deep expertise, a sharp understanding of the problem, and the ecosystem around them. I also suspect their time in the army instilled a strong sense of discipline in both of them, and discipline is essential when building a company.
The Ecosystem
Many of the things we use everyday and that we take for granted were originally developed in the military, either by will or by accident. To name a few: the Internet, GPS, the microwave oven, and even the superglue.
In this sense, there is a bit of a track record when it comes to innovation and army people.
Furthermore, the guys are based out of Tel Aviv. Few people know, but technology and Tel Aviv go hand on hand, especially when it comes to cybersecurity the list of companies that started there is a long one.
Something I have observed is that an early-stage business has good chances of making it if there is an ecosystem around it. Look at any list of startups and a handful of cities such as San Francisco, New York, London, Paris, and Stockholm take the lion’s share, at least in the Western world.
Tel Aviv is also in there, which gives me confidence that this could actually work out. Why? An ecosystem means access to capital and to other founders and ex-founders, who bring hard-won experience of building startups.
To put it bluntly, it’s easier to build a successful tech startup where other startups already are than in the middle of nowhere.
The Customer’s feedback
One thing I think Itai and Roy did brilliantly was talk to lots of potential customers before they had a product ready, to really understand the problem and test a few ideas. It’s something I recommend to every early-stage founder I speak to: go out, talk to customers, then build the product together with them. It also gives you a list of warm leads that can turn into your first customers. Feedback from their early testers even made it into their pitch deck. I thought it was brilliant.
Looking back at my notes, after almost a year since my decision, I feel more confident in my original reasoning. Not because Huskeys has closed a Series A, though that’s encouraging of course, but because the reasons that made me write the cheque are still holding up.
The market is real, the problem is painful, the founders know their stuff, and they are building in an ecosystem that gives them access to talent, expertise and capital. That’s my framework, and so far I am right.
Now, a Series A is a nice milestone but it doesn’t mean the investment will pay off. There’s still a long way between raising money and building a valuable, sustainable business. Ask me over a beer.
But angel investing is about something else too. You’re making a decision with little information, trying to tell a promising opportunity apart from a convincing story.
I’ve learned a lot in the process, alsnot least that I genuinely enjoy connecting with people who are starting things and supporting them along the way.
If you’re building something and think I could add value, don’t be a stranger. Reach out.