Startup Lessons from History: Plato

I’m a startup guy that likes to read about history, and spend a lot of time thinking about… well, stuff. This ongoing series is an exploration and tribute to what history can teach us about startups, and perhaps life itself.

Today we return to our ancient philosophers, and one of the more controversial figures at that: Plato. Was he the origin of western philosophy and all rational thinking, or a hack that rambled on endlessly making pointless arguments? Let’s examine.

These posts are long and rich. So enjoy it like a nice bottle of wine. Pour yourself a glass. Don’t just drink to consume. Take a few sips, consider the flavor. Take your time. Share with a friend. Maybe don’t finish the whole bottle at once. Bookmark this and come back to it later. It ages well.

Future sources, ranging from fact to historical fiction, may include famous generals, philosophers, statesmen, and a whole bunch of Romans.

Detail from Raphael painting, supposedly modeled by the aging Leonardo Da Vinci.


Taught by Socrates, and himself the teacher of Aristotle, there is a clear lineage of the birth of Western philosophy and Plato’s central role in it. He is also the founder of The Academy in Athens, Greece. His hallowed name is also the origin of the platonic relationship, still relevant today, much to the chagrin of all those fallen heroes who have been friend-zoned.

The Republic is one of his cornerstone works, and is presented in the form of a dialogue between his teacher Socrates and various fellow Athenians. It’s unlike anything I’ve read before. What strikes me is how readable and somehow relatable this text is. It was created 2,400 years ago, just think about that for a moment. Egypt still had pharaohs at the time…

…on advisors. Some say they’re a waste of time and equity, some say an advisory board is a prerequisite to investment. At the end of the day, it’s pretty simple: do you need them? If your founding team are experts in the industry, technology, and business model you’re targeting, then keep your equity. If there are big gaps, maybe fill them with an advisor?

…on startup culture. Your job isn’t to participate in startup culture. There is no value in engaging in the community. This is a fallacy that seems to perpetuate through failed founders. Stop networking. Stop participating. You’re either helping your own business, or you’re wasting your time.

…on founders and employees. Do not separate these in day-to-day matters. If you’re a founder, and you have a closed office, please stop reading this and go away. Do not separate yourself from your team. Do not allow yourself perks they do not enjoy. Do not take liberties they are not allowed. Be among the men. Be a member of the team. Lead by example, not by order.

…on pitching investors. Generally speaking, nothing you say will turn an investor who doubts your business into an investor. Especially VC’s will have a profile they’re looking for, and if you don’t fit, your fancy slides won’t change that. Therefore do your homework and only focus on investors who generally invest in your industry and size of business. Then it’s a matter of statistics. Most will still say no, so repeat until in the money.

…on hiring keepers. You should resist the temptation to hire the best people by industry standards. Those people know their value and will bring a mercenary attitude into your business. They will only stay if you pay them more and more, and will keep knocking on your door. You want people who enjoy working for you.

Original papyrus of The Republic by Plato.

…on talking vs. listening. It’s easy to get caught in a cycle of just pitching everyone, everywhere, every time. The outcome is that you stop listening. This is very dangerous for a startup. When meeting with clients, don’t just pitch. Use the opportunity to learn about your product/market fit.

…on hustle. Despite what your ego may tell you, time waits for no man. The world expects nothing of you except death and taxes. Anything above that is on you. But hustle wisely. Do not network. Do not just participate. Take actions that drive your business forward: get revenue, get team, get investment.

…on the right reasons. Starting a company requires incredible resilience, and the statistics of failed early startups are padded with those who had the wrong reasons. Do not buy the hype. Only work on problems that are natural to you, and only when you have the luxury of focusing 100% on the solution. There are no quick wins. No overnight successes. There is only hard work.

…on protecting your capacities. Everyone has a limit. You can only do so much. Your will be drained. Emotionally. Intellectually. So don’t waste your capacities on things which expend those capacities, unless they are very valuable for you or your business. Stop reading the news, and save room for new ideas rather than those of others. Stop networking, and start selling. Your capacities are your soil, so tend to it carefully.

…on doing the hard things. Social conventions have set limits to what we believe we can do, and when things are too hard. Friends said your idea is stupid? Too hard. Didn’t get investors without revenue? Too hard. Didn’t get clients with no product? Too hard. Can’t pay salaries next month? Too hard.

What is actually hard? Only you can know the right answer. If you have to resort to illegal means, then it’s probably too hard. But remember this: only do great things. Do not waste your capacities and time on futile pursuits. It’s a waste of your talent, and the resources available to you.

Renaissance master Raphael depicts all the ancient wise men of Athens, with Plato and Aristotle top center.

…on the value of sales guys. No sales, no revenue. No revenue, no growth. It’s easy to confuse raising lots of money with growth. In fact, the availability of private equity has distorted many a business model. Growth in users is equivalent to growth in revenue. In reality, this is not true. You can fool yourself and your investors, but growth requires revenue.

If you’re doing B2B, the life-blood of your business is your sales team. In most early stage startups, that’s your founding team. The people with the dream, with the passion, are the best to sell. Even without any qualifications in sales. Buyers are callused, and authenticity beats fancy dress and smooth small talk every time.

…on solving problems with more technology. A new CRM won’t get you sales. Cloud-based HR software won’t hire the right people. Don’t even say blockchain. Most critical tasks in early stage startups are manual. You probably need a phone and email. Every other “need” or “want” you self-impose are just a form of mental weakness.

…on focusing on UX. While Plato didn’t perhaps see the iPhone coming 2,500 years after his time, technology has turned this dream into reality. In fact, if the “tool” which you’re selling isn’t self-explanatory, you just have bad UX. If your team has no experience in UX, you need to check your priorities. The easiest way to destroy a business is poor UX. It will decrease conversion, erode sales, and increase churn.

…on the first few months. This is the best time, but also the hardest. Anything is possible, so how do you narrow it down? Are you going B2C or B2B? Are you a service or technology company? What’s the name going to be? The best approach is to talk to customers all the time. Let the market decide, so you don’t have to. If you can sell it, you’re on to something. If not, revisit your assumptions and try again.

…on managing risk, or ignoring it. Every startup journey will include time on the knife-edge. One day, or one week, or one month away from total and utter disaster. The definition depends on your risk appetite. Run out of funds? Run out of credit cards? Run out of personal loans? Run out of family? You have to know when enough is enough.

However, once you establish this, and hopefully agree amongst your founding team, don’t talk about it again. Worrying puts focus on the negative outcome, when all your energy needs to go into turning it around.

So again, when on the knife-edge, the founder resumes his ordinary habits, and either the company survives, or, if it all burns in ashes, the company dies and the founder has no more trouble.

Plato depicted with his students in the academy.

…on what it takes. You don’t get style points. Startups are 0 to 1, and you can always go back to 0 at any time.

What words will you utter to the team, when your cause is failing, and your company is going to wounds or death? Will you be able to meet the blows of fortune with firm step? Do you have a dogged determination to endure?

This is what it takes.

…on the founder lifestyle. There are no sweet sauces. You should embrace it. Make that your calling. Be like the warriors of the Iliad. Be a Spartan. Walk away from the comforts, and take pride in your suffering. Go further from the warmth of the fire, and sit in the cold. There are no corporate expense accounts. Every dollar you spend, you better sell in revenue, or you’ll give up in equity. Reject the sweet sauces.

…on purpose. If you don’t relate to this deeply, you’ll probably give up when it gets hard. Startups are always hard. Maybe not today, but soon you will be tested. New, young things are fragile things. If your only motivation to keep struggling is that of money or glory, you should find easier ways to achieve both. Ask yourself, would you work on this problem if you were monetarily set for life already? If not, check yourself.

…on the grind. There are two schools of thought when it comes to doing what it takes: one where you want to be the good guy, one where you don’t care.

Always care. Always be the good guy. What goes around comes around. Your reputation both as a founder and company matters. It sticks, too. The world is a lot smaller than you think. Never burn bridges. Not with customers. Not with staff. Not with investors. Always take the high road. Always say thank you. Always turn the other cheek. Always walk away from a fight.

…on incentives. Never allow your team to optimize for anything less than the company. Having the best HR process counts for nothing. Kicking ass in sales is useless. There are no beauty contests for your backend architecture. Nothing matters individually. Either your business is growing, or it isn’t. No growth, and you’ve all failed. Never pay bonuses for individual or team, always company if at all. Don’t let individual or team success seep into the culture, it’s like cancer. Company success or die.

Painting of a scene in Plato’s Symposium by Anselm Feuerbach.

…on losing the edge. Will you allow the silk slippers of success soften your constitution? Will you start letting yourself off the hook, just once in a while? So you got Series A, and you’re set for a few years. Can you slow things down, and do things “right” finally?

Wrong. WRONG. Your only real competitive advantage is doing things that don’t scale. Things your bigger competitors can no longer justify, because the spreadsheet model said so. Breaking your product to get new features in the market faster. Selling cheap to eke out competitors from deals. The moment you stop being a startup, is when others start catching up.

Fight against it, tooth and nail. Once you lose it, you’ve gone corporate. Guess what? There are hundreds of founders in the coffee shop phase, thinking about how they’re going to crush you. They’re fired up and full of piss and vinegar. Don’t go soft. Never go soft.

…on sustainable suffering. There is a fine line between hustle and grit, and just plain ruin. You have to keep yourself in the game, that’s the number one rule. Whatever #grindmode you’re in, it has to be sustainable long-term. The next hurdle is imaginary. You can’t just barely make it over. There’s a bigger one right after it. It’s a hurdle-marathon. With pits. Full of snakes. That spit acid. So you need to be ready for anything and everything, always.

You need a place to live. You have to spend time with your spouse. If you have kids, they need schooling and clothes. You need to eat. You need to exercise. You need to sleep. You can’t afford not to!

…on the golden middle. Don’t get the Lambo. Don’t be a Scrooge, either. Don’t give out crazy bonuses you’ll miss later. Don’t underpay your team, either. Managing a startup is a delicate affair. Generally lean towards being lean, because granted rewards can’t be later removed.

…on process. Don’t hire people to boss them around. Be like Steve Jobs. Hire good people so they can tell you what to do. In fact, never introduce process where disaster isn’t happening. Resist process unless fate forces your hand. That ensures you remain a true startup, flexible and agile, as long as possible.

…on drinking your own Kool-Aid. There is a real self-reinforcing gravity within the startup community. Success makes the headlines, winners take the accolades. The more successful you are, the more good things happen. Yes-men gather around you. Suddenly, you feel like it’s all you. It’s not all you. In fact, it’s mostly not you.

It’s about your team. It’s the product. It’s your customers. It’s the market. If you see a founder surround himself with yes-men, these are not much to be admired.

Map of ancient Athens circa 500BC, with the temple of Parthenon visible on top of Acropolis hill, above the city.

…on future regrets. Do only the things that you know are right. You answer only to yourself at the end, not your team, not your investors, not even your family. If it fails, you only have yourself to blame. Did you do enough, or did you let it happen? Don’t make a habit of creating excuses for your future self.

…on diversity. Forgive Plato for the blatant sexism, this was 2,500 years ago. If you can, avoid a single-gender, single-race founding team. You’ll do well to repeat that when hiring, because the risk is establishing subcultures and cliques if your initial team isn’t diverse. Those subcultures aren’t necessarily in your control, and will make growth harder down the line.

…on benchmarks. One of the great advantages of startups is the ability to cast away stale traditions, and exploit those as inefficiencies. Then again, we get pigeonholed as the “Uber of this” or “AirBNB for that”. Create something beautiful, and don’t worry about the comparisons and benchmarks. They’re only crutches less imaginative people need to understand what you’re doing. If they had your creativity, they would be on your side of the table already.

…on the risk of early success. There is inherent risk in early success, because success breeds stability. If it ain’t broke, why fix it? It is dangerous to accept your current level of achievement and settle. Once you give up the desperate, maniacal pursuit of knowledge and progress, you are effectively hanging up your gloves.

You may not know it when it happens, but you’ll look back at the moment when you stopped pushing, and started settling for how far you got. It was enough. We achieved a lot. F*ck that. Keep pushing. Keep grinding. Never rest on the laurels of success.

…on recognizing truth. There is a lot of conflicting feedback you receive in the early days. Mostly a lot of “NO” from customers and investors. A lot of opinions on what you should do differently. Just do this one thing, and I’ll buy your product. Just get to this milestone, and I’ll invest. Neither will ever give you money.

You have to build your business on positive feedback, instead of fixing for negative opinions. Money talks. Money is truth. Build for customers that pay. Listen to investors who invest. Everything else is opinion.

…on thinking like Elon and Plato. Elon actually applies ancient philosophy as his core tenant: only work up from first principles. Do not build on assumptions or hypotheses. This is very difficult to identify, as all of our society, education, and culture is built on a house of cards of layered assumptions.

Electric cars aren’t a business models because batteries are expensive. Are batteries expensive because of physics? Is it a first principle? What is the cost of the raw materials for batteries? Not that expensive. So manufacturing them must be expensive. Why is manufacturing batteries expensive? Is the process already optimized? Are there new economies of scale?

Most things that people say, whether founders or investors, are based on assumptions. Most will never have fact checked their assumptions, because this is what other people have said. It’s in the news. This is how it’s always been. Assumptions are in fact the biggest opportunities, because nobody else is questioning them. Do the math. Do the homework. Check your assumptions.

If you can challenge a fundamental assumption of how the world works, you can change the world.

Roman era mosaic of Plato and students.

…on motivating your team. Do not ask them to do the hard things. Do the hard things together. Set few goals, not more than a few each year. Make them count. Make them laughably hard. Make a project of it. Make fun of it. Talk about it every day. Participate. If you don’t code, work on the requirements. Lead the test team. Get your hands dirty. It’s not about paying the bucks to do the job. It’s about working together on something meaningful.

…on appropriate ambitions. So how hard is good? You can’t be pulling all-nighters and work weekends forever. The team will gas out, even if you’re changing the world. Humans be mushy. You have to play the long game. Here and there you can ask too much, but then you need to recharge for the next battle. Focus on winning the war, not the battle.

…on founder vision. It’s rare to see transformative companies without a visionary founder at the helm. Bill Gates. Steve Jobs. Zuck. Elon Musk. Jeff who?

To corner a market, to build a winning culture, to disrupt entire industries, to change the world — these are hard things. Very hard things. It has to start with the founder, and the singular vision. If you don’t have a clear vision, how on Earth do you imagine it will happen? It won’t, if you don’t live and breathe that vision from day to day, from year to year.

…on rejection. There is a stigmatism and emotional baggage that comes with any rejection. It is like a mini failure. It takes a lot of practice to become ignorant of rejection. It always stings, even then. There are two ways in which to harness rejection.

One is statistical. No matter how many rejections you’ve gotten, the probability of a “YES” is never zero. It could be close, but never zero. If there’s a 1% chance of a “YES”, then try 100 times. Maybe 101 to be safe.

The other is experience. Each rejection is a learning opportunity. Why didn’t the client choose us? Why didn’t they invest? Don’t try to turn a NO into a YES, that never works. But consider the lesson, make your own adjustments, and try again.

…on product/market fit. Besides early traction like revenue and customers, you know you’re on to something lasting when you’re known for something. Not just a participant in a field of competitors, but you have something unique. Ideas that can be known without being seen. A reputation.

The greek goddesses have lost their heads, originally part of the Parthenon temple in Athens.

…on values. If you value pleasure as something good, steer away from startups. A cozy corporate gig with predictable bonuses, expense accounts, and general jones-keeping-upping is your thing.

If however, you happen to value knowledge, pursue science. If you can’t make it as a meaningfully contributing scientist, then try a startup.

…on making your own mind. Whether failing or succeeding, you will have people giving you unsolicited advice. Your parents. Your spouse. Your friends. Your investors, particularly. Having a clear vision from the very beginning helps tremendously, as it makes it easy to filter out noisy opinions. If there’s something you set out to achieve, and you believe it is still possible, keep at it.

Don’t pivot just to make your investors happy. They aren’t in the trenches with you. Don’t even pivot just to make your team happy. If you have your vision, sometimes it means making unpopular decisions to stay the course. You’re the one carrying the biggest risk, so don’t let others persuade you.

…on maintaining product vision. What does your product actually do? What is actually for? As a collection of individual features or requirements, what is the single idea that connects them? This is the essence of what you have, whether you set out to build it or something completely different.

There tends to be significant drift from the original product vision as life happens and customers complain, so periodically check in that the core idea is still there. Hopefully, this single idea is directly driving your vision and purpose. If not, then your vision is a figment of your egotistical imagination, and you’ve lost control of your product roadmap. Get back on the horse.

…on philosopher kings. Given the turbulence of the startup journey, the founder should ideally already possess one of these outlooks: blissful ignorance, or stoic indifference. Take your pick.

The foundations of Plato’s academy are still in existence in modern Athens, having survived through 2,400 years.

“I grow impatient at the length of your exordium.”

427BC — 348BC (Athens, Greece)

Is there a favorite quote here? Any other stoic philosophies you live by? Please share so we can benefit, too.

Thinks about the future a lot. Founder of two startups. Lives in Singapore.