Nine Checks In: What Angel Investing Taught Me About Running My Own Company

I wrote my first angel check about a year after my exit. I thought I was doing it to "give back to the ecosystem." That was partially true. The more honest answer is that I missed the early-stage chaos and wanted a seat close to it without living inside it.

Nine investments later, here's my scorecard: two companies are performing well above where I invested, three are grinding along in that ambiguous middle zone where most startups actually live, two are effectively dead, and two are too early to call. If you know the math of angel investing, that's a normal distribution. Nobody who tells you they're batting .800 as an angel is telling you the whole story.

But the returns aren't the interesting part. The interesting part is what writing checks taught me about operating — because I've now sat on both sides of the table, and each side exposes the blind spots of the other.

Lesson one: the deal you talk yourself into is the one that burns you

Both of my zeros had the same signature. In each case, I had a reservation early — once about a founding team that had never worked together, once about a market that needed customer behavior to change before the product mattered. And in each case, I talked myself past the reservation because everything else looked great. Impressive founders. Clean decks. Warm intros from people I trusted.

Here's what I learned: as an angel, your first honest reaction is usually the diligence. Everything after that is often just you building a case for a decision you emotionally already made. The best investors I know don't have better information than me. They have better discipline about listening to their own initial discomfort.

The operating parallel is direct. Every bad senior hire I made as a CEO followed the same pattern — a flag in the first interview that I explained away because the resume was strong and I needed the role filled. Twenty years in, I'm convinced the skill isn't spotting the flag. Everyone spots the flag. The skill is refusing to negotiate with it.

Lesson two: invest in lines, not dots

I stole this framing from a VC I co-invested with, and it changed how I evaluate everything. A dot is a single data point — one great pitch, one strong quarter, one impressive demo. A line is trajectory: what did this founder say they'd do three months ago, and what actually happened?

My best-performing investment came from a founder I'd been having coffee with for almost a year before any round was open. Over four or five conversations, I watched him make claims and then hit them. Small ones — "we'll have the pilot signed by March," "we'll be at $40K MRR by summer." When he finally raised, the decision took me a day. I wasn't evaluating a pitch. I was extending a line I'd already watched him draw.

Flip that around and it becomes fundraising advice: if you're a founder planning to raise in twelve months, your raise starts now. Every update you send an investor between today and your round is a dot on the line they'll eventually judge you by. Founders who go dark for a year and then show up with a deck are asking investors to price a single dot. That's the most expensive way to raise money.

Lesson three: your check size is your permission slip, not your influence

Early on I made the classic operator-turned-angel mistake: I confused a $25K check with a mandate to advise. I sent one of my first founders long emails about pricing strategy. Unsolicited. Detailed. Almost certainly annoying.

He was gracious about it, but I eventually realized the dynamic I'd created: he started managing me instead of using me. His updates got vaguer. His asks disappeared. My "help" had turned a supporter into another stakeholder to handle.

Now my rule is simple: after I invest, I say one thing — "Here's what I'm actually useful for. Call me when one of those shows up." Then I shut up until they call. The founders who use me, use me hard, in bursts, on specific problems: a pricing decision, a term sheet review, a first sales hire. That's worth more than fifty unsolicited emails.

Running my own board seats taught me the same lesson from the other chair. The best board members I've had were low-frequency, high-amplitude. The worst were the opposite.

Lesson four: dead companies teach you the most, if the founder lets them

One of my two zeros ended with a founder who ran the shutdown like a professional: told investors early, returned the remaining capital — about 30 cents on the dollar — and wrote a genuinely useful post-mortem. The other went quiet for six months and I learned the company was dead from LinkedIn.

Guess which founder I'd back again tomorrow, sight unseen.

Angel investing is a repeated game played over decades in a small community. How you lose is part of your track record. The founder who returned 30 cents on the dollar cost me money and earned my next check at the same time. I don't think enough first-time founders understand that a well-run failure is a career asset.

What this costs and what it pays

For anyone considering angel investing off the back of an exit: budget real money for tuition. My first three checks were, in hindsight, payments for an education — I invested too fast, in things too far from what I understood, with too much confidence transferred from a domain where I'd earned it to one where I hadn't. The learning only compounded when I slowed down to two or three investments a year, inside the vertical I actually know, which for me is B2B SaaS.

And know what you're really buying. The financial returns, if they come, will take seven to ten years. What you get immediately is pattern exposure — a live feed of go-to-market experiments, pricing moves, and hiring mistakes across nine companies instead of one. I'm a better operator and a better board member because of it. That part paid off in year one.

If you've made angel investments: which check taught you the most — and was it a winner or a zero? I have a strong suspicion about which one it was for most of us.