Four Horsemen of the Investor Apocalypse

Contempt That Destroys Investor–Entrepreneur Relationships

Contempt is one of the Four Horseman of the Apocalypse. Once it shows up, it is the end of a relationship.

Contempt doesn’t look like shouting. It is mostly passive aggressive. It masquerades as “patience” that overlays growing frustration.

In a previous post, we talked about how an entrepreneur can have contempt for the investor, and in this post, we look at ways investors can have contempt for the entrepreneur.

Contempt Is Passive-Aggressive, Not Overt

The investor/entrepreneur relationship has a striking asymmetry to it. Investors can appear to have all the “power,” as the entrepreneur must ask for money and make changes to respond to investor requests. It is very easy for “experienced” investors to get caught in the trap of thinking they have “insight” and “experience” that the entrepreneur lacks.

There are two elements to this: first, the investor quickly sees issues, based on their experience, where the entrepreneur needs some help or additional work. Second, there is an inherent feeling of control and power where the entrepreneur is supplicating at the feet of the investor looking for money.

Maybe an Underlying Psychology about Angel Investors: Impostor Syndrome?

Anybody (who is not sociopathic) has that tiny voice somewhere inside saying “you are not good enough.” Investors are not immune to this, and in fact, it is heightened.

“Successful” people often earn their wealth through hard work and determination. But there is always a good bit of luck. Being at the right time and the right place with the right skill set occurs when you are hardworking and industrious, but there is always the luck part.

Would someone else, with the same opportunity, done much better? Absolutely.

Impostor syndrome has plenty of well-established coping mechanisms, not the least of which is braggadocio and inflating the person’s actual contribution. The person with impostor syndrome often tells themselves a counteracting narrative – you convince yourself that you were, indeed, that good “back in the day.” Unchecked, impostor syndrome comes out in arrogance as a way to cover up and compensate impostor syndrome.

This is not to say that every angel investor falls into this trap, but it has been known to happen.

More Psychology: Angel Investing is Inevitable Failure

Let’s just say that angel investing is not known for its high returns. There are outsize returns of 100X or more, and these get a lot of press. But, inevitably, angel investing will break your heart more times than not.

An angel makes an investment based on their “belief” that the company will succeed. It is really a suspension of belief, as the angel wants to believe that the entrepreneur will be successful.

However, with the track record of 1 in 10 or 1 in 20 investments carrying the day with an outsized return, the whole angel game has far more loser bets than winners.

When your spouse reminds you of how excited you were at the beginning and now the company is failing, there can be immense pressure to try to get the company into the winner column. This same dynamic happens when the general partner of the venture firm has the inevitable call with the limited partners.

Nobody likes to admit that they have been wrong. Sometimes, the investor feels duped or misled, but often they red flags were there at the beginning but you invested anyway wanting to “beat the odds.”

Impostor Syndrome turning into Contempt

Angel investors (as well as their VC counterparts) have all kinds of pressure. They can be the internal psychological motivations, such as impostor syndrome, which can be every bit as overwhelming as watching every investment go down the tube.

These pressures can lead an investor to take out their frustrations on the entrepreneur.

When an investor moves into passive-aggressive contempt, the founder immediately senses it. Communication breaks down, but not because of arguments — because of silence.
The founder stops sharing problems. They sanitize updates. They start performing competence instead of demonstrating progress.

That performance reinforces the investor’s bias: “They’re not being honest.” The investor pulls back further. The founder becomes defensive. The loop closes.

Eventually, the investor isn’t an ally anymore — they’re an observer waiting for validation that they were right to give up.

How It Starts

Contempt usually begins with disappointment. Maybe the founder missed a target or stumbled in a presentation. The investor loses confidence but doesn’t say it outright. Instead, they go through the motions of engagement — board meetings, feedback sessions, check-ins — but their tone changes.

They start asking rhetorical questions instead of real ones. They use “guidance” as a way to signal superiority. They stop trying to understand how the founder thinks and instead start judging from the outside.

It’s a small shift, but it’s fatal. Once you’ve stopped trying to understand, you’ve stopped being a partner.

How to Fix It: Understanding Before Judgment

The solution isn’t to “be nicer.” Sugarcoated feedback and HR-style empathy just add another layer of passive aggression. Founders see through it instantly.

The only way out of contempt is to understand before you evaluate.

1. Ask Real Questions

Not “How are things going?” — that’s filler. Ask questions that reveal how the founder thinks:

• “What assumptions led you to this decision?”
• “What tradeoffs did you see when you picked this path?”
• “If this goes wrong, what’s your fallback?”

These questions aren’t about catching mistakes — they’re about exposing reasoning. When a founder sees that you’re genuinely trying to understand, they respond with honesty instead of defensiveness.

2. Explain How You Think

Don’t hide behind authority. If you disagree, explain your framework:

• “Here’s what I’ve seen in other companies at this stage.”
• “I’m worried about burn rate because it kills optionality later.”
• “This looks risky to me because I’ve seen how X tends to unfold.”

When founders can see how you think, not just what you think, they can calibrate against it. That’s respect in action — not tone, not politeness, but transparency.

3. Stop Performing Support

If you’ve lost confidence in a founder, say it directly. Don’t disguise it in polite detachment.
“I’m concerned about how decisions are being made, and I want to understand before I decide whether to stay engaged.”

That’s uncomfortable, but it’s real. And real conversation can rebuild trust. Passive support cannot.

4. Own Your Biases

Every investor has blind spots. Maybe you favor founders who sound like you, or who use familiar jargon. Maybe you overreact to confidence or polish. If you don’t check those instincts, they quietly turn into contempt for people who don’t fit your mold.

Awareness isn’t weakness — it’s professionalism. You can’t fix contempt you refuse to acknowledge.

The Difference Between Judgment and Understanding

Judgment is easy. It’s fast, clean, and feels smart.
Understanding takes effort. It requires humility — the willingness to admit that the other person might see something you don’t.

Most investors think they’re providing “accountability” when they’re really just asserting dominance. Real accountability means helping a founder see the consequences of their decisions and giving them the context to make better ones. That can’t happen through passive-aggressive detachment.

What Real Respect Looks Like

Respect doesn’t sound like flattery. It sounds like focus.
It’s when both sides are willing to be blunt without being cruel. It’s when questions are asked to learn, not to corner. It’s when the investor stays engaged even when frustrated — because they care more about the outcome than about being right.

Respect isn’t politeness. It’s clarity. It’s taking the founder seriously enough to challenge them directly, and taking yourself seriously enough to listen.

The Investor Founders Remember

Founders remember which investors helped them think better, not which ones lectured them.
They remember who engaged when things got messy, not who disappeared behind “supportive” silence.

Be the investor who actually understands before judging.
Not the one who hides behind polished contempt.

Contempt doesn’t just end relationships — it erases value.
Understanding builds it.