Ground Zero: How Losing Everything Taught Me to Build Angel Investing Like a Startup
Two years ago I moved countries with two teenagers. I shut down or sold my businesses. Lost my network. Lost my status. Lost my team. Lost predictable income.
In my previous life I was known as a founder. Forbes 100 Europe alumni. Four startups. One exit. I had momentum. Reputation. A place in the ecosystem.
My podcast was top 3 on iTunes business category for three years straight. Hundreds of thousands of listeners. People stopped me on the street. I’d walk into events and feel that small electric charge of recognition - you know, when someone’s eyes light up because they know who you are before you say a word.
My ego? Let’s just say it was well-fed )
Then suddenly - none of that mattered. New country. New rules. No network. No shortcuts.
Nobody knew me. Nobody wanted to know me.
The Crash
Luxembourg didn’t care about my Russian startups or exits.
The first few months were brutal.
I felt like a victim. Like the world had taken everything from me and left me with nothing but two confused teenagers and a suitcase full of irrelevant achievements.
War. Geopolitics. Circumstances beyond my control forced me out.
I didn’t choose this. This was done to me.
I was angry. Grieving. And lost.
Here I was - Forbes-recognized founder, podcast host with hundreds of thousands of listeners, someone who’d built and exited companies - and I couldn’t even get a meeting with a local VC:
“We’ll keep you in mind.”
“Send us your LinkedIn.”
“We’re not hiring right now.”
You know what’s harder than starting from zero when you’re 18?
Starting from zero when you’re 40-something and you remember what it felt like to be somebody.
When you’ve tasted recognition and then you have to go back to being the person who asks for introductions. Who pitches herself. Who sits in the waiting room.
Going from “people know my name” to “nobody returns my emails” is a specific kind of humiliation.
And I spent months marinating in it.
Feeling sorry for myself. Refreshing LinkedIn. Wondering if I’d made a terrible mistake.
The Shift
And then one morning - I remember exactly where I was sitting. Kitchen table. Usual Luxembourgish rain outside. Coffee going cold.
I was reading Bible, and I hit this line:
“And we know that in all things God works for the good of those who love him.”
All things.
Not “the good things.” Not “the things that make sense.” Not “the things you chose.”
All things. ALL THINGS.
The war. The forced exit. The lost businesses. The teenagers ripped from their lives. The street recognition that evaporated. The podcast listeners who couldn’t follow me here. The network that didn’t transfer. The reputation that meant nothing.
All of it.
And I just sat there with that.
Because if I actually believed this - if I actually trusted that God was working for my good and not against me - then this wasn’t a tragedy.
This was a setup, ha.
Maybe I didn’t choose to leave Russia. But I could choose what I did with the blank page I’d been handed.
Maybe I didn’t choose to lose everything. But I could choose who I became when I rebuilt.
For the first time in months, I felt something shift.
Not from grief to joy - that would come much later.
From victim to participant.
I stopped asking “why did this happen to me?”
I started asking: “what is this making possible that wasn’t possible before?”
And weirdly - thrillingly - I realized:
I have no idea. And that’s the most exciting thing that’s happened to me in years.
A blank page. A new country. No one watching. No one judging. No expectations.
God had just handed me permission to start over.
Not as punishment.
As gift.
The Choice
I chose to move to the other side of the table.
I’ve always wanted to become an investor - to support founders building meaningful companies. Being around and empowering startups excites me. It always has!
I could have tried to rebuild another startup. Could have networked my way into a founder-in-residence role. Could have played it safe.
Instead, I did something that felt uncomfortably vulnerable: I went back to school.
Venture fundamentals school. Venture Syndicate building school later.
Literally sitting in classes, taking notes, asking questions that probably sounded stupid to people who’d been investing for years.
What’s the real difference between a lead and a follower in a round?
How do you spot real GTM conviction vs. BS?
Why are venture studio spinouts often traps? (spoiler: yeah, really)
How do you valuate startup properly?
No reputation to protect. No ego to perform. No one in that classroom knew I’d built companies before. No one knew I used to be somebody.
It was strangely freeing.
For the first time since I was 18, I could be a beginner again.
I could ask dumb questions. I could admit I didn’t know things. I could learn without performing.
You know what’s liberating about losing everything?
You stop worrying about looking stupid. Because you've already lost what you were afraid of losing.
The Realization That Changed Everything
Here’s what surprised me most:
Early-stage angel investing feels exactly like starting a company.
And yet - founders are taught to be systematic. Investors are expected to wing it.
Think about it:
When you build a startup, you’re told to:
Define your ICP with precision
Build repeatable sales processes
Track metrics religiously
Create systems that scale without you
But when you become an angel investor?
The advice is: “follow your gut,” “pattern match,” “invest in people you believe in.”
Which is just... vibes masquerading as strategy.
Most new angels I meet struggle with the same things:
No reliable dealflow (just random intros from friends)
No structured way to filter opportunities (every deck feels urgent)
Fear of making the wrong first bets (paralysis by analysis)
Everything takes too long (90-minute deep dives into mediocre deals)
Every startup feels like a brand-new puzzle (no transferable learning)
I was doing all of this too.
At the beginning, each deck took me 90+ minutes to process.
I’d read every slide. Click every link. Stalk every founder on LinkedIn. Second-guess myself for days.
Now? 3-5 minutes for a first pass.
Not because I’m smarter.
Because I stopped relying on intuition and started building rules. And, Gooosh, I love systems and I love rules.
The System I’m Building: AngelOS
I started treating angel investing like I’d treat building an operating system.
Not a course. Not an info product. An actual operating system for making investment decisions.
Here’s what I mean:
The main goal:
Invest on data, not vibes
Cut bad deals fast
Don’t drown in inbound
Document every decision
Save time
Make it repeatable
Automate
I call it AngelOS. It has five core modules - and this is what you, my fellow angels, should be doing to make your investing journey easier:
1) Deal Sourcing Mashine
The system that collects inbound startups.
What it does:
Pulls startups from LinkedIn, demo days, accelerators, email lists, warm intros
Deduplicates (same startup from 3 different sources? Merged)
Enriches data: website, founders, contacts, country, stage, traction signals
Queues them for review
Logic: Parsing → Dedup → Enrichment → Queue
This alone cut my “where did I see this deck?” confusion by 80%.
2) ICP/Thesis Filter (First Pass)
In 30-60 seconds I answer:
Geography: Europe? US? Asia?
Sector: AI? B2B? SaaS? Climate Tech?
Stage: Pre-seed? Series A?
Traction: Revenue? Users? Waitlist?
Check size: €25K-€250K range?
Round strategy: Leading? Following? Bridge?
Any specific requirements? Impact startups? Sustainability? Founder pedigree? Backed by big names?
Output:
Fit / No Fit / Unclear
Short reason why
What data is missing
If it’s “No Fit” → archived with reason logged and follow up with the founder.
If it’s “Fit” → goes to the next level - Red Flags Engine.
This is what I’m packaging as the First Filter Kit - the exact checklist I use for every deck.
3) Red Flags Engine
This is where I tag risks.
Here’s the thing: there aren’t that many real red flags. Maybe 15-20 patterns that consistently predict failure and which are particularly important for us, angels.
Examples:
Stagnant growth (3 quarters flat)
Unclear ICP (selling to “everyone”)
Unclear GTM strategy (currently founder-led sales, with a sudden, unjustified step-change implied)
Grant-driven (revenue is just Horizon grants)
Etc, etc
What the engine does:
Assigns tags based on deck + data
Generates 2-3 specific questions to send to the founder
Logs the pattern for future reference
This is what feeds my Red Flag content - every post I wrote is a pattern I spotted in real deals that week.
4) Decision Brief Template
An auto-generated 1-pager for every startup that makes it through filters.
Contains:
Why interesting (2-3 bullets)
Why pass (3 specific reasons)
Key risks
Missing data
Questions for founder
Scorecard (see below)
Next step (pass / follow-up / committee review)
5) The Scorecard
I evaluate every startup on 10 signals, scored 0-3:
Founder-market fit - do they have unfair advantage here?
Team composition and experience - is the team well-rounded?
Distribution insight - do they know something about GTM others don’t?
Speed/shipping - are they moving fast or stuck in planning?
Traction vs burn - efficiency, not just growth
Market depth - is there real budget for this problem?
Product/technology viability - is the core offering innovative, protected?
Defensibility path - what stops copycats in 3 months?
Round dynamics - who else is in? Who’s leading? Terms clean?
Cap Table structure - is it clean and investor-friendly?
Threshold: ≥20 points (out of 30) to move forward.
Below 20? Pass with documented reason
Want the full Thesis/ICP Filter, Red Flag Full Engine, and access to my bi-weekly Investment Committee meetings? Upgrade now and get them instantly.
Why I’m Building This in Public
I’m not teaching theory.
I’m documenting the system I’m building for myself.
Every Red Flag post? That’s a pattern I just tagged in 3 deals that week.
Every dealflow drop? Those are startups that scored ≥20 on my system and I want other angels to see.
Every breakdown? That’s me stress-testing my filters by explaining them out loud.
Right now I’m obsessing over:
How to build a systematic way to angel invest from scratch.
One that:
Helps you filter deals quickly (without feeling like you’re being lazy)
Avoids obvious traps (before you wire the money)
Creates repeatable decisions (so you’re not starting over every time)
Builds conviction instead of anxiety (because you know why you’re saying yes)
Compounds learning over time (every deal makes you sharper)
This is what I’m building:
Investment Committee calls → Live group reviews of real startups. We run them through AngelOS together. Share what we see. Build pattern recognition collectively. You learn 10x faster when you see how other investors think.
Curated dealflow with transparent criteria → I’m not sending you every deck that lands in my inbox. I’m showing you the ones that scored ≥20 on my system - and explaining exactly why they made the cut and what red flags I’m watching.
Public toolkits → The Thesis/ICP Filter Kit. The Red Flag Guide. The Decision Brief template. Everything I’m using internally, you can use too. Improve it. Tell me what I’m missing.
Community of systematic angels → I’m gathering people who are tired of investing on vibes. Who want to move from random bets to structured decision-making. Who believe that angel investing should be treated like building a company: with rigor, collaboration, and documentation.
The Two-Year Mark
It’s been two years since I moved to Luxembourg.
Two years since I lost everything and had to start over.
I now run TK Capital, an angel syndicate (just launched in February)
I coach founders at Fit4Start through Luxinnovation.
I’m a scout at HustleFund, and a fellow investor at AngelSchool.
I’m still learning. Still asking questions. Still going to venture school.
But I’m doing it systematically.
And here’s what I know now that I didn’t know two years ago:
Losing everything gave me permission to rebuild correctly.
Not the way angel investing is “supposed to be done.”
Not copying what worked for someone else in 2015.
But building the infrastructure that early-stage investing actually needs:
An operating system. Not a course. Not vibes. A system.
One that works whether you’re writing your first $25K check or your fiftieth $250K check.
If You’re Building From Zero Too
If you’re an early-stage angel (or preparing to become one)...
If you’re tired of making gut-feel decisions and hoping you’re right...
If you want to move from random bets to structured investing...
I’d love to compare notes.
I’m having conversations right now with a small group of people who are building their own investing frameworks from scratch. Who are already investing. Or planning to invest. Sound like you? Message me!
I’m sharing everything I’m learning in my Angel Investor Signals newsletter:
ICP/Thesis Filter - the exact screening questions + market filters I use before first calls (€250 value)
Red Flags Engine - my fast-kill heuristics for weak deals (€300 value)
AngelOS Build-in-Public - how my sourcing, scoring and syndicate OS evolves (€200 value)
Dealflow Machine: startups I’m Reviewing + Scorecards - live deal analysis (€400 value)
Dealflow Diaries - lessons from LP calls, misses and mistakes
(€150 value)Bi-Weekly Investment Committee Calls (24/year)
(€600 value - €25 per session equivalent)
Total value: €1,900+
Your price: €99 / year
Let’s build this together.
- Taisiya
amazing story. im similar but a founder right now. i was wondering how does someoen get in touch with you legit? r u using a platform like anglelist?
Good story. Inspiring. Thank you.