Everyone Is Asking Someone Else for Money

On Capital, Status, and the Humility of the Ask

There is a particular expression founders get when they realize you are a venture capitalist.  A certain twinkle in the eye. A spark of life. You can see the calculation unfold, the gears turning and grinding away, as they look for a calculated plan of attack.

The eyes quickly sharpen and then dilate. Whatever conversation was just happening has abruptly come to a halt. Somewhere a microscopic pitch deck on a lightly smashed smartphone screen is being prepped just for your enjoyment. Until a bigger, more important fish swims by, that is.

And so it begins… Sometimes gently. More often than not, with all the subtlety of a brick being thrown through the window of a moving vehicle.

Sometimes they ask what I invest in, wait for the answer, then pitch me something completely unrelated that they have rehearsed countless times anyway.

Sometimes I am eating, aggressively chowing down on finger foods that I’m somehow never able to truly enjoy. Other times I am already engaged in conversation with someone else, while the ravenous turkey buzzards circle me as if I were a rapidly decaying corpse in an otherwise barren desert. Oftentimes I am clearly attempting to leave, scanning the room for some sort of divine, deus ex machina escape plan. These distinctions have not always proved decisive.

In my peculiar line of work, I’ve been pitched in hallways, conference rooms, hotel lobbies, private dinners, loud parties, quiet corners, crowded elevators, parking lots, public transportation, even romantic date nights with my poor, understanding wife. You name it. Even during conversations that had absolutely nothing to do with venture capital until the other person discovered what I did for a living.

Well, it’s part of the job; I suppose I did sign up for all this.

More accurately, it is part of going anywhere while possessing a LinkedIn profile that contains the words “venture capital.”

Startup founders obviously need money to help them achieve their dream of building that longshot company from scratch. Investors are supposed to have capital to allocate, watchfully on the lookout for people to allocate it to.

Conferences gather both groups inside large buildings, provide them with lanyards, ply them with alcohol, feed them tasty food they can never quite find time to eat, and bless them with almost nowhere comfortable to sit, all while acting surprised when everybody begins hunting one another.

Apparently this is networking. I imagine it as the worst episode of Planet Earth, David Attenborough calmly narrating as founders and investors circle the canapé table, each pretending not to stalk the other.

Some founders are brilliant at this little song and dance.

They introduce themselves like normal human beings. They ask questions. They listen to the answers. They seamlessly slip in a mention of what they are building so organically you don’t even realize you’re being asked for anything.

More often than not, they flounder and flop. Some spectacularly. 

They appear to have robotically memorized a sequence of generic buzzwords in a particular order and will suffer some sort of catastrophic internal failure if interrupted before reaching the final slide.

Others speak for several minutes without pausing, making eye contact, breathing, or even showing any visible interest in whether the person is still standing in front of them or showing any signs of life at all for that matter.

I have also heard downright disastrous, confusing, puzzling, bizarre pitches. That too comes with the territory!

Pitches that seemed to become less coherent with every additional attempt to clear things up or answer easy questions.

Pitches where the founder insisted there was no competition, which is usually either very good news or extremely bad news. It’s nearly always the latter of the two.

Pitches built around a market so enormous that the company would only need to capture 0.000001 percent of humanity, including several remote tribes and possibly the research team living in Antarctica, to produce a respectable return for their investors.

You know the ones. (Well, I guess that depends on who is actually reading this. Say hello in the comments!)

Perhaps you’ve given a pitch like this before. Or received one! Maybe even both…Want to know the truly scary bit?

The pitch does not always end when the conversation does either. It could somehow find a way to follow you around after the event is long over.

There is the email sent ten minutes after the nonconsensual meeting. The second email harking back to the first dreaded email. The LinkedIn message checking whether the emails have been arriving. The casual status update that is not really relevant or an update so much as another attempt to restart a conversation that both parties may remember very differently.

A polite rejection can be treated as feedback. That feedback can also be treated as an objection.

The objection can be treated as the final obstacle standing between the founder and a glorious future in which I admit I was wrong, beg forgiveness, and personally carry their company toward a billion-dollar valuation on my weary, overburdened VC shoulders.

This can be extremely tiring.

There. I said it. Is it controversial to say that? I have no idea.

Being approached as a source of capital before being approached as a fellow person is strange. Every conversation acquires a second and third layer.

Is this person talking to me because they find me interesting?

Do we actually have something in common?

Did they laugh because the joke was funny?

Was the joke funny?

Or did they notice the investor badge and decide that my painfully average observations deserved their fullest possible attention?

Most likely, it’s some unholy combination of all of the above. 

Business relationships are inherently transactional. I’m fairly certain that if I ever went to business school, that’s the thing they would drill into my head on that very first day.

I am not shocked or offended by this revelation. Nobody attends a venture conference purely for the architecture, the coffee, the vibes, the potential friendship, or the opportunity to stand beneath hideous fluorescent lights and discuss software infrastructure with hundreds of exhausted, travel-weary strangers.

We are all there because we need something.

Founders need investors. Investors need founders. Sponsors need our contact information.

Conference organizers need another eight hundred euros for access to a dinner happening behind a curtain approximately twelve and a half feet away.

Well, look what we have here… A functioning ecosystem!

Still, there is a peculiar feeling that comes from being treated like a walking wallet with opinions attached. It hardens even the softest, most charitable and well-meaning hearts. Repetition makes detachment easy. Eventually, you stop hearing a person ask for help and start hearing the opening lines of another transaction.

So naturally I started to make jokes about it as I am wont to do. A small step toward retaining my own sanity.

Many, if not most, investors partake in this rite of passage. Jokes and humor sustain us.

We trade stories about the worst pitches, the strangest approaches, the wildly inappropriate moments, the people who refused to accept that a conversation had ended, or perhaps refused to accept that it had never really begun. Tales of awful manners or downright refusals to accept thoughtful, well-intentioned feedback we went out of our way to provide.

Some of the stories are incredibly funny. These are some of my favorite conversations with fellow investors where we compare battle scars and war stories.

Founders under pressure, surrounded by infinite competitors, investors, countdown clocks, burn rates, and the spooky, panic-inducing knowledge that their team needs to get paid whether the next fundraising round closes or not, sometimes behave with the social grace of a panicked raccoon trapped inside a gourmet kitchen.

And you know what? I empathize with them wholeheartedly.

In fact, both things can be true at once.

Some founders are earnest and nervous, while some are calmer and frighteningly well-prepared.

Some are panicked, arrogant, rude, or a bit too drunk after taking advantage of the open bar to quell the nerves.

Some are desperate, obnoxious, and conceited at the same time, one of the more impressive and confounding psychological achievements available to our species.

Some are simply just bad at pitching, or lacking the silver-tongued gene.

On the other side of the coin, some investors are simply assholes. Cruelly deriding and lording over the plebeian tech serfs beneath them, enjoying the lofty perch they reside on.

Unfortunately, the longer I spent on the investor side of these conversations, the easier it became to forget that these types exist.

At first, I thought I was merely laughing at the absurdity of bad pitches or unpleasant interactions with overeager founders.

The timing or the language. The delusions of grandeur. The TAM larger than all of Earth’s total economic output.

The total absence of self-awareness.

The strange little theater of someone smugly yet sweatily pretending not to need something while very obviously needing it more than almost anything else in the world.

But the stories changed after enough retellings.

Or maybe I did.

The founders slowly disappeared from the story and became typecast into neat little archetypes.

The desperate one or the delusional one or the annoying one or the belligerent one.

Another pitch. Another request. Another human being approaching me with an incomplete idea and the misplaced belief that I might be able to help.

Somewhere along the way, I stopped merely making jokes about their behavior.

I’m ashamed to admit that I began enjoying what the behavior suggested about me.

That people needed my attention. Or that my opinion carried some sort of outsized weight.

That I belonged on one side of the table and they belonged on the other. That their nervousness said something about their abilities, while my ability to remain stoic and calm said something flattering about my own abilities.It did, of course, but only because I was not the one asking for money.

At least, not at that particular point in time.

A More Expensive Kind of Begging

Of course, venture capitalists do not live permanently on the comfortable side of this seemingly one-sided arrangement, although I must admit that would be nice.

We spend a downright impressive amount of time complaining about founders asking us for money, considering that asking other people for money is also a rather important part of our own line of work.

Founders raise rounds, and venture capitalists raise funds.

The terminology is different enough to preserve everyone’s dignity, but the underlying activity remains eerily similar.

A founder presents a company that barely exists and explains why it will eventually become extremely valuable. A venture capitalist presents a collection of companies, some of which may not exist yet, and explains why they will eventually become extremely valuable, based on a hunch.

One arrives with a product, or an MVP, or a half-functioning MVP held together by caffeine, cigarettes, and the goodwill of a criminally underpaid engineer.

The other brings a thesis, a pipeline, a portfolio construction model, several graphs climbing heroically toward the upper-right corner of the screen, and a team slide featuring the cheesiest team photos you’ve ever seen. 

Both are asking someone to ignore the large empty spaces where evidence will hopefully appear later and picture a future in which that money will multiply by unreasonable amounts.

Trust that we have noticed something other people missed. Accept that we possess the judgment to act on it. Believe that the market will remain open, the founders will remain sane, regulators will remain sufficiently distracted, and our carefully modeled returns will survive contact with the profoundly unmodeled chaos of our shared reality.

Then, ideally, they wire the money without too much additional thought or follow-up questions.

Investors often talk as though founders belong to a separate species called ‘Fundraisers,’ identifiable by haunted expressions, financial projections, copious amounts of trauma, and a sudden desire to reconnect with someone they met once at a forgettable side-event in Lisbon long ago.

Fund managers do the same damn thing.

We adapt the deck to our audience. We bring one part of the strategy forward and subtly move another back into the shadows from whence it came. We change our words or cadence or levels of excitement to match the potential LP, in the hope that it will nudge us ever-so-slightly closer toward that fateful check.

We study the person across from us, waiting for a nod, a question about one of the portfolio companies, or any small indication that they are still mentally present and have not slipped into the dissociative fugue-state haze that often occurs halfway through a fundraising presentation.

The waiting is the worst part. The most familiar and loathsome part of fundraising after sending over a deck or other fund materials.

You send the data room over and receive a polite reply explaining that the opportunity looks very interesting.

“Very interesting.”

What a magnificent little phrase that is, eh?

It offers warmth without commitment, attention without enthusiasm, and the possibility of another conversation without creating any legal, financial, or emotional obligation to ever speak ever again.

It can mean just about anything you want or don’t want it to.

A yes that has not yet been approved, or a no that has not yet found the courage to introduce itself. Maybe just an email opened by accident while someone was searching for a boarding pass or a six-digit login code.

There is no reliable way to know, so you wait while repeatedly muttering to yourself that you are not waiting. You convince yourself your professional future doesn’t hinge on the answer to that question.

By God, you have an entire company to run. Or a fund. Or at minimum, a very important, sleek-looking spreadsheet requiring your immediate and undivided attention.

You try as you may to carry on like a normal, emotionally stable adult who has not checked their inbox nine times since breakfast.

The delay can always be explained. The committee has not met. The family principal is traveling. The investment team is trapped inside an internal review involving scenario modeling, risk analysis, outside expert consultants, and one extremely wealthy eighty-three-year-old man who refuses to approve anything until his preferred tarot card reader returns from vacation.

Perhaps they are crushed beneath an avalanche of applications, and their system has fallen to pieces, utterly incapable of surviving the wrath of their inbound leads (I speak from experience here).

I have watched carefully constructed processes fall apart once enough people begin throwing decks, messages, introductions, reminders, updates, and friendly little nudges into the machinery.

There is always a process, and there is also usually someone else who needs to be consulted, even when the person consulting them has spent the previous six months presenting themselves as the sole ruler of a private financial empire.

Founders ask venture capitalists. Venture capitalists ask limited partners. Limited partners may answer to families, committees, boards, trustees, government mandates, consultants, beneficiaries, or another pool of capital sitting further upstream.

Eventually, that wealth chain becomes impossible to coherently follow.

You begin to suspect that most of the world’s money is controlled by seven people sitting inside a windowless room in Geneva, passing the same folder back and forth while the rest of us lowborn peasants pretend to possess autonomy and investment authority.

Well, everyone indeed answers to someone. That’s an objective truth.

The person who appeared enormously powerful over lunch may spend that same afternoon trying to persuade someone who barely remembers their name.

None of this came as some sort of grand revelation to me, though.

I already knew fundraising was an excruciating, torture-tactic of a game. I knew founders carried payroll, expectations, years of work, all while shouldering the deeply unpleasant possibility that none of it would survive the rigors of startup life. 

I have always tried to treat them as people first, even when the pitch was terrible or the timing bordered on criminal. Sadly, that empathy doesn’t make you forever immune despite your best intentions. 

There is some research behind this discomfort. Experiments on power and perspective-taking have found that power can make it harder to see a situation through someone else’s eyes, often without any conscious decision to stop caring.

Apparently, the room can begin rearranging your mind before you realize you have started believing it.

You can understand the hierarchy perfectly well and still enjoy your special, cozy place inside it. You can recognize another person’s vulnerability and become impatient with it anyway. You can know that status is temporary while quietly absorbing the way a room or event or person treats you.

No, raising capital did not teach me that founders were indeed human. That’s a bit obvious even for the not-so-sharp among us.

Raising capital did, however, show me how easily knowing something and consistently behaving as though you know it can drift further and further apart.

This neat, little lesson became harder to ignore as I moved through different kinds of financial rooms, attended different events and VC dinners, or sat through a bona fide litany of different LP pitches.

I have been in my fair share of rooms where venture capitalists are treated like rockstars or minor members of a royal family. Red carpets and flower petals gracing private entrances and reserved tables. Special dinners and yacht parties. Founders waiting patiently for a chance to introduce themselves while event organizers scramble to explain that the investors are taking a short break from the unbearable burden of being asked questions.

It is deceptively easy to get swept up in that sort of atmosphere, absorbed by the dizzying allure of it all.

People lean in closer when you speak and hang on tightly to every last, insignificant word. They listen carefully to your opinions about markets you may only understand at a surface level. They laugh at jokes that did not deserve anywhere near that level of enthusiasm.

Soon they are asking what you think about artificial intelligence, geopolitics, interest rates, robotics, the future of labor, the collapse of Western civilization, and whether the hors d’oeuvres contain gluten or not.

After enough of this, you may even begin to feel somewhat important. It’s intoxicating.

Well, until you encounter that next level.

You want a truly humbling experience? Try going to Davos in January.

Maybe a side event at a conference for family offices and ultra-high-net-worth individuals appears on your screen. The website is tastefully beige and unassuming. There are photographs of villas, mountains, cigars, and people staring thoughtfully across bodies of water they presumably own. All of the hallmarks of cliché wealth stirred together.

You look at the ticket price.

You rub your eyes and look again.

Surely it includes a small apartment. Possibly a sports car.

Spoiler: It doesn’t. It doesn’t guarantee any favorable outcome at all, actually.

Suddenly, you are no longer the important, big-shot investor entering through the private door. You are another forgettable fund manager hoping to gain access to the bigger fish that swim in grander seas. The people who possess enough capital to materially alter the trajectory of your business and life.

Same exact person. Different tag or badge. How very sobering.

In one room, I am treated like the money. In the next, I cannot reasonably justify the price of being allowed near it.

This caste system becomes impossible to ignore after that.

A founder may look at a venture fund and see an almost unimaginable concentration of wealth. Millions of dollars available to place into ideas, sometimes on little more than conviction, relationships, or an alarming tolerance for risk.

The fund manager may look at an institutional allocator controlling billions and feel roughly the way a child feels when begging a parent for spare change while the ice cream man drives by on a hot summer day.

The allocator then spends the following week attempting to impress a sovereign fund, a prehistoric banking family, or some private office representing a fortune accumulated through shipping, mining, manufacturing, real estate, or an ancestor who made one excellent decision in 1794 and permanently altered the reproductive incentives of the entire bloodline.

There is always another layer, another dinner, another committee, another person whose time is treated as more valuable because the money behind them contains a few additional, pesky, little zeros.

And you know what? That hierarchy does not dissolve into thin air as you move upward. It just becomes a hell of a lot more expensive. 

And this is not merely the social theater of Davos.

In the first quarter of 2026, six venture firms collected more than three quarters of all the capital raised by US funds. Experienced managers captured more than 90 percent of it.

There may always be a richer investor, but an increasingly small number of firms appear to own the building.

I have also met smug LPs who seemed to enjoy the imbalance more than was strictly necessary. They communicated through ambiguity, maintaining enough interest to keep the conversation alive without offering anything remotely resembling a decision or an indication of which direction they may be leaning in.

They may have been evaluating. They may have been preserving optionality. Some, I suspect, are likely intoxicated by the enjoyment of being pursued. The thrill of being chased has its appeal.

That possibility does not appear often in the official literature on institutional capital allocation, but I remain convinced it explains a nontrivial amount of human behavior.

The most frustrating part is not necessarily rejection…

A clear no can actually be quite liberating, providing closure that allows everyone involved to move on with their lives, update a spreadsheet, complain privately, and set off to find someone new to disappoint them.

The maybes are worse. Heartbreaking even.

A warm meeting followed by silence. The vague suggestion to kick the can down the proverbial road and reconnect after another milestone is hit. A request for additional information that you send immediately, only for it to be placed inside the infinite warehouse at the end of Raiders of the Lost Ark, never to be seen by another living soul.

Enthusiasm seems to evaporate without ever becoming negative enough to acknowledge.

Founders have complained about this behavior for as long as venture capital, or any sort of investing, has existed, and they are normally right on the money.

None of this was new information, although my place in the machinery of capital formation and allocation had shifted.

When the silence belongs to someone else, I suddenly feel every hour of it. A delayed response looked less like an overflowing inbox and more like carelessness. Ambiguous enthusiasm sounded more evasive. The reluctance to say no and relinquish me from my hopeless optimism felt unnecessarily cruel.

I catch myself asking why people could not simply be direct, then I remember how often directness becomes complicated when you are the person trying to preserve a professional relationship, an option, or the likely possibility that circumstances could change later.

That did not and does not make every delay reasonable, nor does it absolve anyone who enjoyed keeping fundraisers suspended in uncertainty. It simply makes the resemblance harder to casually dismiss.

I’ve always understood that pressure founders carry. Raising capital did not magically install empathy where none existed before. It did, however, highlight how easily empathy can coexist with habits you would dislike immediately if they were mirrored back in your direction.

The investor and the fundraiser are NEVER fixed identities, simply temporary roles assigned by the location of the money in that particular situation.

Move it into another snapshot in time and the person who seemed powerful five minutes earlier is checking their inbox, rereading a polite sentence, and wondering what in the world “very interesting” was supposed to mean in this particular instance.

People Like You More When You Write Checks

Who would have guessed that handing out capital makes people like you more? Duh.

The strange thing is that the money begins working before anyone actually writes a check.

Simply being tangentially associated with capital changes the temperature around you. 

It has a mysterious way of making messages get answered faster. Invitations pop out of left field. People who might otherwise have offered a polite nod immediately become intensely curious about your thoughts on the future of technology, markets, human civilization, or whatever subject happens to be floating through the room at that particular point in time.

Sometimes they even ask about you. Like how you are doing or what’s been going on in your life. Sometimes it even feels sincere!

I have watched colleagues move on over from venture capital into operating roles or become founders themselves, only to discover that a portion of the warmth surrounding them had apparently belonged to their job title.

The invitations slowed down. People became much harder to reach. Conversations that once happened easily began requiring introductions, follow-ups, reminders, friendly bumps, pings, and perhaps the occasional small ritual sacrifice at the altar of the gods of calendar availability.

These were the same exact people, with the same exact experience and roughly the same exact personality. They had simply moved from one side of the table to the other.

Unsurprisingly, money generates a great deal of ambient affection.

It makes people laugh slightly harder or turn ordinary opinions into brilliant, strategic market insights. It causes otherwise busy individuals to discover unexpected openings in their crowded calendars. People unexpectedly want you for their conference panels and podcasts.

Then the perceived access disappears and some of the affection goes with it.

That raises an uncomfortable question.

Did they like the person, or did they like what could move through them?

The even less comfortable question is how often I have been guilty of the same thing.

I would love to say that I treat every person with identical enthusiasm regardless of whether they are useful to me, but this would be an outright lie and a worrying sign that I had learned absolutely nothing from writing the previous several thousand words.

Despite my best efforts and my genuine approach to networking and conversing with other people, we all allocate attention.

We respond faster to certain people. We prioritize conversations that might lead somewhere. We remain vaguely connected to individuals who could become important later and quietly lose touch with others once our lives stop overlapping. It’s a universal axiom in our industry, whether we want to admit it to ourselves or not.

This is not unique to venture capital either. It may simply be adult social life with a spreadsheet or CRM attached.

Nor is every transactional relationship dishonest.

Founders want investors. Investors want returns. Fund managers want LPs. LPs want access to attractive opportunities. Everyone wants introductions, information, credibility, distribution, employment, customers, influence, or at minimum a seat at the dinner where the good wine is being served.

Mutual usefulness is not some sort of blight on society or a moral shortcoming.

Many genuine friendships begin because two people were professionally useful to one another. Affection and utility can occupy the same relationship without immediately strangling each other.

The trouble begins when we lose track of which one is doing the heavy lifting.

Strategic interest starts dressing itself as friendship and disingenuous pleasantries. Wealth gets mistaken for wisdom. A person becomes endlessly fascinating because everyone knows they can say yes, while the person asking for something is treated as a minor administrative inconvenience.

The investor who arrives forty minutes late or blows off calls is busy and important.

The founder who arrives flustered is disorganized and unserious.

The wealthy person’s laconic nature becomes intimidating confidence. Their silence suggests deep insight and brooding thought. Their basic inability to respond to an email is recast as evidence that their time is simply more valuable than yours.

People searching for capital rarely receive such flattering interpretations.

We scrutinize their tone, follow-ups, body language, confidence, and timing, hoping to detect weakness from the normal human debris left behind by someone doing something stressful.

I have routinely caught myself doing this.

A founder follows up too soon, and it feels desperate, like a clingy date texting after a tepid first meeting.  Another waits too long and apparently lacks urgency. Someone is nervous, so perhaps they cannot lead. Someone else appears completely tranquil, so they must not understand the danger.

The rules mutate depending on who is being judged, and how much power, capital, or influence is involved in the equation.

It is an extraordinarily convenient system for the person doing the judging.

I do not, for the record, think every connection in finance is fake. That would be much too easy or lazy, and it would also be very, very wrong. 

I have met generous people, sincere people, and people who offered help without calculating what might return to them later. Hell, I’ve even made a few friends in my time as a VC. And somehow it’s not very easy for me to make friends (I know I know I must be a lot of fun at parties).

I have also watched a room become more interested in someone the moment it learned how much money they controlled, or which fund or Fortune 500 company logo sits neatly beside their name.

Money does not create every hierarchy, but it makes this one easier to see.

It reveals who receives patience and who is expected to earn it.

Some Money Is Too Expensive

I hope that this doesn’t come across as a suggestion that you should simply give up hope, submit to the caste system, and play its hideous game. None of this means that a person raising money should ever become endlessly agreeable.

Fundraising does indeed require humility. You are asking another person to trust you with capital, often based on limited evidence and a future that exists primarily inside a collection of slides. They are, in turn, are allowed to ask difficult questions. They are allowed to hesitate. They are allowed to decide that you are woefully wrong.

You are even allowed to dislike the decision without concluding that the person who made it is stupid, cowardly, or personally committed to sabotaging your destiny to be a unicorn founder or the world’s next Warren Buffett.

But humility has its limits.

The fact that someone possesses money does not require you to admire them.

I have encountered people in family-office and UHNWI investor circles whose public personas appeared almost scientifically engineered in a laboratory to repel and disgust me. Wealth displayed as personality (or lack of). Arrogance presented as aspiration. Social media profiles filled with expensive objects, shallow proclamations, and the unmistakable energy of someone who had never encountered a room where another person was permitted to disagree.

One in particular made me pause recently while doing some investor networking.

This person is capable of writing a meaningful check. The sort of check that could help build something, extend the runway, create momentum, or at least make several difficult conversations temporarily less difficult.

But I do not want to flatter them.

I do not want to pretend that their vulgarity is fascinating or that their money has transformed a collection of terrible instincts into an investment philosophy.

That sounds easy to say when the money is hypothetical. The decision becomes more complicated when you need it.

This is where all the cheerful talk about alignment usually becomes very technical. People discuss time horizons, return expectations, liquidity, governance rights, reporting requirements, and the many other ways two parties can discover several years later that they agreed to completely different things.

All of that matters. Character matters even more.

An LP can be passive on paper while still changing the culture surrounding a fund. Their expectations influence behavior. Their reputation becomes attached to yours. The kinds of conduct you tolerate in exchange for the capital rarely remain isolated to the fundraising process.

Not every check improves the institution it enters. In fact, some checks can actively harm the institution and invite chaos and discord.

Some money arrives carrying expectations you do not want. Some money requires a degree of personal obedience that no management fee can make respectable. Occasionally the cost has very little to do with the terms written in the actual contractual agreement.

I am not claiming there is morally pure capital somewhere waiting to be discovered by the sufficiently principled. There is not.

Money has a history. Institutions have contradictions. I have made compromises and will almost certainly make more of them. Anyone who operates inside finance while claiming total purity is either lying, delusional, or has inherited enough money to convert personal preference into their own moral philosophy.

The question is not whether the person or the capital is flawless.

The question is how much of yourself must be surrendered to obtain that capital.

In the first thing I published here, I wrote that leaving finance felt like handing the room over entirely to people I did not trust with it. I told myself I would rather remain inside and help direct capital with a conscience.

This is the less heroic part of that bargain.

Directing capital with a conscience means very little if you are willing to trade away the conscience to obtain the capital.

Fundraising should make you less arrogant. It should humble you and teach you that conviction alone does not entitle you to anyone else’s money and that the people across the table may see risks you have ignored.

It should not turn every wealthy person into someone worthy of reverence or worship.

There must remain some distance between adapting your pitch and reorganizing your personality around another person’s approval.

The hardest test of alignment is deciding whether you are willing to walk away from money that would genuinely help. 

But moral compasses cost a fortune these days.

Everyone Is Asking Someone Else for Money

All this brings me back to the founders circling conference rooms with decks prepared on lightly damaged smartphone screens.

Some will still approach at the worst possible moment. They’ll be socially awkward, unable to read the room, utterly missing the fact that the person they are pitching is already being pitched by another person just like them. 

Some will speak for far too long. Some will ignore every signal that the conversation has ended and then follow up the next morning to ask when we can continue it.

I will always find this irritating. I’m only human.

Empathy does not require investment, and it certainly does not require pretending every pitch is good. There are no participation trophies in fundraising for startups.

A founder can be a wonderful human being, and still be wrong, or early, or not cut out for entrepreneurship at all.

An investor can be empathetic and still politely reject an investment application.

The problem begins when the ability to say no starts feeling like proof that the person saying it belongs to a higher order of the species.

Capital creates real power… Everybody knows that.

Companies survive or thrive or crumble and disappear based on who receives it. Employees keep jobs or lose them. Teams shrink or grow. Ideas either gain enough oxygen to become real or remain trapped inside the heads of the visionaries that dreamed them up. 

Pretending the hierarchy does not exist would be dishonest and frankly, not very useful. Treating it as a measure of human worth is something far, far worse.

Someone needing your approval does not make them smaller than you. Needing another person’s approval does not place you beneath them. No amount of success or money should ever let you lose sight of that fact.

And treating people decently only because the roles might reverse later would miss the point entirely. That is still transactional behavior, only with a longer time horizon.

The founder deserves to be treated respectfully in a dignified manner, even if they never become successful, never raise another round, and never occupy a position where ignoring their message could cost you something. Regardless of whether they are a young, first-time founder from Nigeria fresh out of university, or an ex-OpenAI employee from Singapore with two unicorn exits.

The LP deserves honesty and respect even if they ultimately decline.

The investor should be able to reject a company without turning the founder’s vulnerability into entertainment.

The fundraiser should be able to hear no without surrendering their judgment, dignity, or ability to distinguish a useful relationship from a wealthy asshole.

None of us performs this ritual perfectly.

I sure as hell haven’t. This “journal entry” is a testament to the fact that I don’t stop thinking about this and won’t ever forget it.

There will be more bad pitches. More vague replies. More investor dinners, expensive conferences, private rooms, broken processes, unanswered emails, and people trying to appear calm while quietly wondering whether they have enough money to survive the next stage.

A whole lot of awkward, imperfect fumbling around.

The ecosystem will continue functioning.

More or less.

At the next conference, another founder will notice the investor badge or bracelet, and begin preparing their approach. The investor will see them coming, glance instinctively toward the nearest exit, and then check their phone as it gently vibrates inside their pocket.

An LP may have finally replied...