I did not start writing on Substack to speak to founders.
Founders already have no shortage of advice, encouragement, podcasts, frameworks, and pitch coaches telling them how exceptional they are supposed to be.
I am here for angel investors. Especially newer or part time angels navigating one of the most asymmetric asset classes available. When angel investing is done with discipline, it has historically outperformed public markets, private equity, and venture funds by a substantial margin. When it is done casually, it quietly destroys capital.
My goal here is simple. To help angels make fewer avoidable mistakes by being more honest about how we evaluate founders.
Because most angels think they are judging substance. In reality, many are responding to performance.
The uncomfortable truth about charisma
If you listened to most startup folklore, you would assume the best founders are magnetic. Visionary. Effortlessly articulate. Able to make uncertainty sound like inevitability.
Those founders raise money easily.
They do not always build enduring companies.
Over time, I have become increasingly skeptical of charisma. Not hostile to it. Just cautious. Charisma is a tool. In the wrong hands, it is camouflage.
Some of the strongest founders I have backed are unimpressive in meetings. They are calm. Analytical. Occasionally awkward. Often boring. They do not perform confidence. They demonstrate understanding.
That pattern shows up too consistently to ignore.
The founder trait that actually matters most
If I had to reduce founder quality to one core attribute, it would be obsession with the customer.
Not passion for the product. Not belief in the mission. Obsession with the customer.
Founders who truly understand their users can explain friction points precisely. They know where value leaks. They know where behavior contradicts stated intent. They talk about complaints with more energy than compliments.
This matters because customer obsession forces reality into the conversation. It limits self deception. It anchors decisions to evidence rather than narrative.
Everything else matters too, but it compounds off this.
Why angels misread “great communication”
Here is where angels routinely get it wrong.
Many founders described as “great communicators” are simply great sellers. They are fluent. Polished. Always certain. Rarely silent.
That is not clarity of thought. That is momentum.
I pay close attention to whether a founder can say, “I don’t know,” without collapsing. Not as a rhetorical flourish. As a genuine admission.
One of the most revealing questions I ask is deliberately awkward:
“What part of running this business are you going to be bad at?”
Founders who have never asked themselves this tend to bluff. Founders who have thought deeply about it answer cleanly. They know their limits. They know where they need help. They already understand the shape of the risk.
As angels, we should reward that honesty rather than penalize it.
Angels & Unicorns
"Are You Ready For The Yes? What Every Founder Needs To Know Before The Wire Hits Their Account" - Read the first chapter FREE here.
Pushback is a feature, not a bug
There is another signal angels often misinterpret.
Pushback.
Occasionally I will suggest something that would not work, purely to see what happens next. Strong founders push back. Calmly. With reasoning. Sometimes with data. Sometimes with instinct they can explain.
Weaker founders agree.
Yes people are dangerous. They optimize for approval rather than outcomes. They mistake alignment for competence.
If a founder never challenges you, that is not respect. It is avoidance.
The red flags angels should stop ignoring
There are very few instant disqualifiers, but the ones that exist are not subtle.
Being caught in a lie, however small.
Market sizing that relies on “everyone will buy this.”
Casual references to trillion dollar markets without grounding.
Inability to talk at a high level about financial forecasts.
Confidence that is never punctured by uncertainty.
Angels do not need founders to be finance experts. We do need them to understand the basic financial logic of their own business. If a founder cannot explain how money flows through the model, risk is being outsourced to optimism.
A simple self-assessment for angel investors
This is the part most angels skip.
If you are investing your own capital, ask yourself honestly:
Am I drawn to insight, or to confidence?
Do I confuse a fluent pitch with clarity of thought?
Do I reward certainty, or intellectual honesty?
When a founder pushes back on me, do I respect it or resent it?
Do I probe customer understanding, or settle for vision?
Am I disciplined about what I look for, or reacting to how a meeting made me feel?
Founders are not the only ones performing in the room. Investors are too. The quality of your judgment is shaped by the quality of your questions.
A closing reality check
Charisma wins rooms. Substance builds companies.
Angel investing rewards the ability to sit through boredom, uncertainty, and incomplete information without reaching for comforting narratives. That skill matters more than most people admit.
If this framing made you uncomfortable, that is probably useful information.
Which founder trait do you think angel investors overweight the most?
And which one do you think they systematically undervalue?
Most founders spend 6-9 months fundraising. Half that time is wasted pitching investors who were never going to say yes, or taking money from angels who kill their Series A fundability.
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In my experience founders who deeply cared about solving the problems of their users and actually wanted to spend time outside the building with them was critical. But so rare as most are idea focused and just want to make it real first before interacting with the world.
One additional trait that I’ve also found important is a track record of grit. Founders who have had previous successes and failures always get my attention as that lived experience is pure gold.
Sometimes I’ve just invested to make sure I have a seat at the table on the next venture that I know they will undertake.
My viewpoint reading this is from both a founder and an investor.
From the founder side — I've sat in enough pitches to know the pressure to perform confidence. Early on with Mindora, I caught myself optimising for how things sounded rather than what we'd actually learned. The shift came when I started leading with what wasn't working. Counterintuitively those conversations went better.
From the investor side — your "What part of running this business are you going to be bad at?" question is one I'm stealing. The bluffers reveal themselves instantly. The best founders I've backed answered that question before I asked it.
One pattern I'd add…founders who talk about their customers' complaints with more energy than their product features. That's the obsession you're describing. It's hard to fake and easy to spot once you know what to look for.