• Launch your own robo-advisor now! For US$99/month. Click here to find out more about Bambu GO.

© 2022 Mangosteen BCC Pte Ltd. All Rights Reserved.

Startup Lessons from Ayn Rand

I’ve written quite a few “episodes” of Startup Lessons by now, mostly focusing on history, i.e. ancient philosophers and generals. Not today. This is fiction. But not just any old fiction. Ayn Rand, for those unfamiliar, was something of an amateur philosopher, culminating in what we know call Objectivism. It’s a real thing. Most of this philosophical framework was in fact framed through her two famous novels, The Fountainhead and Atlas Shrugged. Mind you, these are pretty ancient being written before and during World War II. So what’s the relevance to today, and startups?

“Certain writers, of whom I am one, do not live, think or write on the range of the moment.” — Ayn Rand

Ayn Rand didn’t write for her period, or any period for that matter. She wrote on principle. She’s clearly influenced by her one and only preferred philosopher, Aristotle, in her pursuit of the ideal man. Much of the content of her expansive novels is dedicated to this specific theme, exploring it through characters both on good and bad ends of that spectrum.

Ayn Rand, courtesy of

More than that, Ayn Rand didn’t write for you. Or me. Or anyone, but herself. She lived and breathed her philosophy in her life and works, and it does shine through as you’ll see. Besides selling millions of books, her work has been very influential in Silicon Valley, economics, the formation of the libertarian political movement (she wasn’t a fan). One of her early close associates was, in fact, Alan Greenspan, later chairman of the Federal Reserve. Solid groupie. Other vocal followers include Nobel prize winners like Milton Friedman, journalist Hunter S. Thompson, business guru Mark Cuban, economist author Tyler Cowen, entrepreneurs like Jimmy Wales (Wikipedia), Peter Thiel (Paypal), and John Mackey (Whole Foods), and many politicians including Ron Paul.

“It does not matter that only a few in each generation will grasp and achieve the full reality of man’s proper stature — and that the rest will betray it.

It is those few that move the world and give life its meaning — and it is those few that I have always sought to address.

The rest are no concern of mine; it is not me or The Fountainhead that they will betray: it is their own souls.“— Ayn Rand

This first part of two will focus on her breakthrough novel The Fountainhead. It’s around 800 pages, so I’m unlikely to motivate you to read it if you haven’t already, but good news, there’s a movie that Ayn Rand was even part in producing.

No spoilers are needed here as the quotes are from the various characters but ultimately represent Ayn’s own thinking. All you need to know about the story is that the central character is an idealistic architect struggling to implement his vision for modern design in a classical world. This could be any founder in any industry, doing anything new. It’s fit for our purposes here.

Without further ado, let’s dive in.

MUSIC: If you want to really get the vibe, play Rachmaninoff’s second piano concerto, which is mentioned in the book. Here is my favorite interpretation by pianist Arthur Rubinstein on Spotify.

NOTE: These quotes are not chronological but split into themes.


This book is more than anything a celebration of the ability and creativity of man, and all that we can accomplish. Much of this is also mirrored through the aimless masses that try to stomp the ideal man from achieving his pursuits. There is always a bittersweet tone to Ayn’s writing, in that nothing is ever easy for the good guy. Such is the life of the entrepreneur! I find her writing very much relevant to my thoughts and emotions on this startup rollercoaster journey.

The first New York skyscraper by modern architectural legend Frank Gehry, completed in 2010. Photo by Ricardo Gomez Angel on Unsplash.

“Can’t you ever be comfortable — and unimportant? ”

“ No. ”

The thing about these books is that they’re clearly written for a certain type of personality. Idealistic. Principled. Uncompromising. I’m not sure how to define it, but I know it just speaks to me across the centuries like I had written it myself in 2019. It’s not that I am that way, more so that I wish I were.

Some people are just born to not be content with where they are, and what they are. You hear it from a lot of top athletes, who separate themselves in the minutiae of seeking the extra 1% that will put them on top. These are people who don’t expect an easy road but embrace the grind of walking their own path. I am going to extrapolate and assume most entrepreneurs will find a lot of sympathy here, hence the post.

“Before you can do things for people, you must be the kind of man who can get things done. But to get things done, you must love the doing, not the secondary consequences. The work, not the people. Your own action, not any possible object of your charity.”

This has been an ongoing theme of my own career. The balance between doing things for passion about the action, and the desire for the consequences. Those might be things like salary, lifestyle, shiny objects like cars, or just peer recognition or a general sense of career progress. The same goes for my startups. Do you go for revenue and growth and valuation and glory? At what cost? Can you compromise on your vision? Your personal values? It’s fine to say you want to get rich, but it’s hard to keep pushing at 100% every day if the action itself becomes unappealing. In fact, I propose that many startups that pad the 99% failure rates chased the paper, and fell out of love. It’s easier to quit on money than your life, no matter your ambitions.

“A truly selfish man cannot be affected by the approval of others. He doesn’t need it. ”

As an entrepreneur, if you need the approval of others, you should probably start with deep pockets or an instantly profitable business model. The rejections from customers and investors are brutal. Brutal. Every day someone says your idea isn’t good enough, you’re too “early”, or you need to pivot. It really makes you question everything. You just have to be a special kind of stupid to ignore it and keep on trucking.

“Now I don’t see anything evil in a desire to make money. But money is only a means to some end. If a man wants it for a personal purpose — to invest in his industry, to create, to study, to travel, to enjoy luxury — he’s completely moral. But the men who place money first go much beyond that. Personal luxury is a limited endeavor. What they want is ostentation: to show, to stun, to entertain, to impress others.”

This applies to you as an individual, but also as a company. Why raise so much money? Why pay top dollar for everything? Best people. Best office. Best tools. It seems “lean” startup came and went, and now it’s just all about unicorns. Well, has been. The recent implosion of WeWork along with lackluster IPO’s of the other VC darlings lead by Uber are leading to a lot of head-scratching. Maybe funding the millennial lifestyle of everything delivered through an app isn’t a sustainable business model after all? While unicorns are growing and dying in spectacular and dramatic fashion, the cockroaches crawl in the undergrowth, unnoticed, ready for anything including nuclear winter.

“He does not suffer, because he does not believe in suffering. Defeat or disappointment are merely a part of the battle. Nothing can really touch him. He is concerned only with what he does. Not how he feels. How he feels is entirely a matter of his own, which cannot be influenced by anything and anyone on the outside .”

There is a good measure of stoic philosophy embedded into the ideal man template here. The book is an exercise in visionary innovation, market timing, and the interim years of rejection before overnight success arrives, or doesn’t. The startup story is truly one of repeated and ongoing failure, interjected with moments of rapturous success. It’s gonna be tough sledding if you’re mainly motivated by emotions, because most of us aren’t robots and are unconsciously yet deeply influenced by external factors. The outcomes of winning and losing are both external, by the way. We should strive therefore to be motivated by our own actions, rather than our emotions. The former being fully in our control, the latter only partially, often not at all.


Ah yes. At the core of the narrative is the creator. If the main character is the ideal man, then the sole purpose of that man is to create. This is the essence of the entrepreneur. This is going to be juicy…

Quote in stone at Walt Disney’s famous Epcot Center. Courtesy of

“We live in our minds, and existence is the attempt to bring that life into physical reality, to state it in gesture and form.”

This is me. This is my life. I often wonder if I’m the only one truly living in my mind, and everyone else is normal. Meditation practice has given me limited respite, but I’m not seeking to externalize my experience, just to gain some control over it. I believe this inner life to be the source of all my creative capacities, so all I need is some housekeeping to keep the bugs (and monsters) in check. This also means my work is simply my attempt at making physical what is virtual and perfect in my mind, usually having to compromise because of external factors such as the existence of other people. Most of the truly great things in the world have been created by the vision of a singular mind, and this I believe is at the heart of the problem. We can only attempt to verbalize and visualize our mind’s contents, but only you have the original copy. Any second-hand interpretations will lead to compromise of that vision, and something short of true greatness. Well, assuming the vision was great, to begin with…

“When I look at the ocean, I feel the greatness of man. I think of man’s magnificent capacity that created this ship to conquer all that senseless space. When I look at mountain peaks, I think of tunnels and dynamite. When I look at the planets, I think of airplanes. ”

This is one of those universal dividers. Some people see problems, dangers, risks, and questions. Others see solutions, experiences, opportunities, and answers. I believe this isn’t an innate feature dictated by genes. Or rather, it certainly comes more naturally to some, but can also be trained and taught. Parents, teachers, and friends in childhood certainly play a big part in shaping your worldview and what part you play in it. But so does the inner experience of your mind. Creative outlets like reading, arts, sports, even gaming can help develop this eye for action overreaction. You want to be the one that does things, not the one that things happen to. It’s a choice that can be made.

“The great creators — the thinkers, the artists, the scientists, the inventors — stood alone against the men of their time. Every great new thought was opposed. Every great new invention was denounced. The first motor was considered foolish. The airplane was considered impossible. The power loom was considered vicious. Anesthesia was considered sinful. But the men of unborrowed vision went ahead. They fought, they suffered and they paid. But they won.”

This is probably my favorite passage of the book. I’ve been involved in enough new ideas and new products to see that generally speaking most people are not open to new ideas. To be more specific, people like their own new ideas but not those from external sources. Life is more manageable if predictable, and anything that perturbs that prediction is an evolutionary danger sign. The wind is unusually strong. We shouldn’t wander from the cave. We don’t know what’s beyond that hill, but it’s probably dangerous and bad. You can assume rejection as the baseline. Your job as the entrepreneur is to seek out those who can see the opportunity beyond the hill, and take that leap of faith with you. Your cofounders. Your early adopters. Your first paying customers. Your first investors. That is the tribe that will conquer that first hill. Nobody else matters. They will never get it, and that’s okay.

“ Man cannot survive except through his mind. He comes on earth unarmed. His brain is his only weapon. Animals obtain food by force. Man has no claws, no fangs, no horns, no great strength of muscle.”

Modern society has actually conquered nature completely and made it safe to be born into this world. But even if physical danger is rarely from predators, the battle of minds is fierce and never-ending. We’re all fighting for the same finite resources. Life is a zero-sum game. Who gets their food first. Who gets the job. Who lands the deal. So sharpen your damned weapon at every opportunity. Stop watching TV. Sleep. Stop social media. Meditate. Stop reading the news. Read books. Think of all the others out there, sharpening their weapons while you lounge and chill. They will eat your damned breakfast, and leave no scraps behind.

“ The creator lives for his work. He needs no other men. His primary goal is within himself. The parasite lives second-hand. He needs others. Others become his prime motive.”

Okay, that’s pretty hardcore. But let’s just focus on the core message. Your primary goal should always be within yourself, never others. Even if your goal is to serve others, you do that best by serving yourself first. It’s a matter of scale and impact. The more you do for yourself, the more you can do for yourself and others. If you live for others, they may not return the favor.

“ The basic need of the creator is independence. The reasoning mind cannot work under any form of compulsion.”

This is a critical truth I’ve only discovered mid-career. They don’t teach focus and creativity in technical university programs. Maybe not even art programs. Once you have any skillset, the difference between average and great is mostly going to be a function of focus and creativity. Focus can be just taking the time to do it right. Creativity is harder to pinpoint, but I like to think of it as being aware of the moment and environment in which you feel creative. If you feel creative, you may just do your best work. So resist the productivity gang and take the time and space to get creative. The ends will justify the means.

“The creator is not concerned with disease, but with life. Yet the work of the creators has eliminated one form of disease after another, in man’s body and spirit, and brought more relief from suffering than any altruist could ever conceive.”

This is why I do startups. I don’t believe in philanthropy or altruism, at face value at least. If the world is sick, which it kind of is, then you solve the root causes. Treating the symptoms is a bottomless pit. For every life lifted from the grips of disease and poverty, another ten are born hoping to be rescued. The world is changed by changing the rules, not by doing more within the rules. Systems thinking, not process thinking. Don’t fish for the villager. Don’t teach them to fish. Invent a better, cheaper fishnet and make a profit. Grow the business and every village will be fishing soon. There is so much incremental innovation done every day by researchers, inventors, and entrepreneurs, that in aggregate defines exponential human progress. At scale, anything incremental becomes exponential. That’s why we’re going to Mars.

“ Men have been taught that it is a virtue to agree with others. But the creator is the man who disagrees. Men have been taught that it is a virtue to swim with the current. But the creator is the man who goes against the current. Men have been taught that it is a virtue to stand together. But the creator is the man who stands alone.”

There’s the abstract sense in which you should stand alone. The most value is created going against the trend, not following it. That’s how you get into the rarified air of real innovation, real differentiation, and real intellectual property. This doesn’t apply to most startups, but that’s okay. We can’t all be Elon.

There’s also the practical sense in which you stand alone. There’s a special kind of loneliness that comes with starting your own business. All problems are your problems. At the end of the day, the buck stops with you. You’re an aggregator of problems. You can find people to share the pain with, but nobody else has all the problems except you. You feel the weight of each risk personally. Gotta get revenue. Gotta get clients. Gotta get investors. Gotta pay the staff. Gotta pay the bills. Gotta not get sued. People around you all have sight into some slice of that, but you need to carry them all through each and every solution. It’s too much for most, and something you can’t appreciate or prepare for it until you see it and live it firsthand. Probably why quitting is the easy option. Is what you’re trying to achieve worth the never-ending personal sacrifice? Usually not.


If nothing else, Ayn is one of those people you would imagine not disappointing you even under close scrutiny. From all that we can gather posthumously, these were not thoughts and ideas put into writing. This was her worldview and ultimately resulted in a philosophical movement that is still alive, and continues to influence movers and shakers across generations. Let’s examine some of those principles that we can still apply today.

“Is it beauty and genius they want to see? Do they seek a sense of the sublime? Let them come to New York, stand on the shore of the Hudson, look and kneel.” — Ayn Rand. Photo by me.

“There’s a particular kind of people that I despise. Those who seek some sort of a higher purpose or ‘ universal goal,’ who don’t know what to live for, who moan that they must ‘ find themselves. ’ You hear it all around us. That seems to be the official bromide of our century. Every book you open. Every drooling self — confession. It seems to be the noble thing to confess. I’d think it would be the most shameful one.”

Just like every other person that’s ever lived and is approaching 40, I’m starting to feel a larger and larger disconnect with the trends of today. The clothes kids wear look ridiculous, the music sucks, etc… well, the self-help shelf has never been busier in 2019. It seems everyone needs therapy just to participate in society, and struggling is generally a meme representation of life itself. Is it really that hard? Well, it is, if you’re not privileged. But ironically, it’s not the people hustling three job shifts that are online crying about it. It’s the lazy but privileged with too much time and comfort on their hands.

“I can accept anything, except what seems to be the easiest for most people: the half-way, the almost, the just-about, the in-between.”

Compromise is important in human interaction, but it’s deadly when it comes to ideas. The reason average rules the world is that statistically, an aggregate of views is… just average. Anything special must inherently be outside the average, for better or worse. Vision is a terribly overused and mistreated word. Vision is having clear ideas about what to do, and refusing compromise. Do you get the sense that guys like Steve Jobs and Elon Musk compromise a lot? I don’t. There the word visionary is appropriate. It’s not about coming up with ideas. Ideas are everywhere. It’s taking persistent action to execute on non-average ideas, and refusing to take no for an answer. This is innovation at its core. So the next time you have an idea, try something: what would happen if you doggedly made it happen, without allowing it to be watered down by anything or anyone?

“You’ll win, because you’ve chosen the hardest way of fighting for your freedom from the world.”

You know all those self-help guys on Instagram telling you how hard you have to work to be rich? The truth of the matter is that most people don’t want to work hard. It’s just not fun. Fun is watching Netflix. Going out with friends. Travel. Those are super fun things. Hard work, meh. You have to have some deep intrinsic motivation within you. Almost all billionaires grew up poor. They had that fire to be rich. Not stopping at millionaire, even. Nothing idealistic. Just a fire that wouldn’t go out, despite the failures, despite the refusals. They would push on because that’s all they knew. Becoming successful was incidental to the process. Caveat, most billionaires aren’t satisfied even now, and most are generally unhappy. No free lunch. No perfect life. Frankly, most people aren’t that motivated by money alone. The substance of the grind must serve some other purpose. Camaraderie. Making a difference. Recognition. As soon as you find something that you don’t mind working hard on, you will win. It’s that simple. Results don’t come from actions, they come from the refusal to give up, because most others will.

“The man who wants to tell you what a house should look like must either be able to design it better — or shut up.”

Something I’ve learned to appreciate later in my career is that real talent is rare. If you find it, treat it with some damned reverence. Some of the greatest talents the Earth has ever seen, like Leonardo Da Vinci, had to grovel for sustenance from princes born into wealth. They would have to tolerate the opinion of rich oafs on the masterpieces only their hands could create. Famously, when Michelangelo created the statue of David, arguably the most perfect physical object currently in existence, his patron commented that the statue’s nose was out of proportion. So the artist picked up some rubble and dust and pretended to chisel a few strokes of marble away to please his master. It’s a great injustice. So don’t do it, unless you can do it better yourself. Find the best talent you can in everything you do, whether hiring or partnering and give them full creative freedom. You owe it to them. Maybe someday, some noble-minded benefactor will give you that chance, too.

“The only thing that matters, my goal, my reward, my beginning, my end is the work itself. My work done my way.”

Workaholics Anonymous, anyone? Ayn wasn’t very big on work-life balance, clearly. Lest we forget this was written before WWII. Holding convictions isn’t a luxury most people have. Not at work. Not in life. To pay the bills, you don’t get to say “no” very much. The customer is always right — good, practical advice. You will be richer for it, in the short term. The problem is just that the customer is rarely right. After all, they’re clearly paying you for the service or product, so you’re probably more of an expert on the matter. To build anything of any meaningful scale, you have to start saying “no”. That’s why few make it to scale and get to ring the NASDAQ bell.


Another recurring theme in these novels is the vilification of large corporations and all forms of social control. More so in The Fountainhead, which seems like much more of a personal declaration than the macroeconomic exposition of The Atlas Shrugged. Ayn and her husband Frank were independent artists throughout their lives, so they probably found little romance in desk jobs, and much glory in the creative freedom of the visionary individual. Personally, I find that startups allow far more of that creative juice to flow, which combines well with my own passion for writing. Work can inspire writing, and often writing inspires work.

The Vessel in Hudson Yards, Manhattan. Controversial modern design living sculpture designed by Thomas Heatherwick. Courtesy of

“He did not smile at his employees, he did not take them out for drinks, he never inquired about their families, their love lives or their church attendance. He responded only to the essence of a man: to his creative capacity.”

While this may seem fairly draconian to some millennials that like their office dogs and Chief Inclusion Officers, I do believe there is a subset of people that find this very attractive. The Platonic workplace, void of drama. Men and women of ability exercising their creative capacities towards a common good. Respect is only earned, never given. I know some software engineers who would go for this kind of thing. Yet, without taking these as literal rules to implement, we can take something from the essence. More meritocracy, less democracy. Yet not leading through spreadsheets. Leading through trust and allowing room for creativity. Making creativity a priority over productivity. Stop timesheets. Start meditation.

“Men are brothers, you know, and they have a great instinct for brotherhood — except in boards, unions, corporations and other chain gangs.”

Harsh but true. We’ve all been in such a fraternity or sorority situation. It could be school. A sports team. Military service. Maybe even work. But you almost never, actually precisely never see entire companies of any meaningful size where you can claim to have this kind of universal bond between people. I’m not talking about craft beer, Pizza Fridays, or religion as that common bond. A sense of mutual respect, shared hopes and dreams and problems, familial comfort or even a fraternal intimacy — these define a real bond within a group of people. Again, we should set our standard super high, then reach maybe 50% and end up in a good place. There’s really no reason to settle for average. I’ve seen this first hand in different situations, particularly during military service. You want to instill that “us vs. the world” mentality, a sense of a shared journey and great adventure. It’s doable to seed that in small cliques. If you can instill that in anything above 10 people, it’s great. Above 30 people, you’ve got something special. Above 100 people, you should write a book about it.

“There is no glory in war and no beauty in crusades of men. But this was a battle, this was an army and a war — and the highest experience in the life of every man who took part in it.”

This is that sense of adventure you want and need. There will be battle. There will be blood. No man left behind. We’re in this together. The rapture of victory. The gutwrenching losses. The gradual build of nostalgia for the romance of the early struggle. Do what you can to keep the early team engaged because they were there. They can tell stories. The stories are the torch that keeps the culture alive.

“An agreement reached by a group of men is only a compromise or an average drawn upon many individual thoughts. It is a secondary consequence. The primary act — the process of reason — must be performed by each man alone.”

It should come as no surprise that I have a deep-rooted yearning for the old world. Ayn goes back to Aristotle here. The rational man is the ideal man. One should only speak mindfully, to speak with as few clearly chosen words as possible, to present ideas with structure and eloquence. To speak irrationally should be scorned in society. Ideas should be debated, not people. Yet the world is run by emotional and irrational people. Companies aren’t much better. It’s all politics. All for the likes.

A fitting way to end this post is to quote part of one of Ayn Rand’s favorite poems, If by Rudyard Kipling, that she herself quoted, from memory, on her first date with future husband-for-life, Frank O’Connor.

If you can talk with crowds and keep your virtue,

Or walk with Kings — nor lose the common touch,

If neither foes nor loving friends can hurt you,

If all men count with you, but none too much;

If you can fill the unforgiving minute

With sixty seconds’ worth of distance run,

Yours is the Earth and everything that’s in it,

And — which is more — you’ll be a Man, my son!












Keep up with us!

Subscribe to our Newsletter

If you want to keep up with us and get the latest on #fintech and Robo-Advisory, leave your email. No spam, just gold.

Download our
free Case Study

To download our case study, please submit the form below and we will e-mail you the link to the file.