The System Has LIED to You... Here's How To Get Rich | Simon Squibb

Simon said he has invested in 81 companies and built multiple multimillion-dollar businesses. He also said he is now worth hundreds of millions of dollars, while stressing that wealth has not removed the need for him to keep working directly on his ventures.

His entrepreneurial life began after his father died suddenly from a heart attack when Simon was 15. He went from expecting to become a lawyer and living in a secure family environment to becoming homeless.

Simon was homeless for roughly eight weeks. He said the experience abruptly convinced him that his 13 years of schooling had failed to teach him practical skills such as money management, communication, selling, pitching and hiring.

He tried to get a conventional job but lacked the qualifications required. He then approached social services for help and said he was effectively told to leave and solve the problem himself.

After about a week of sleeping rough and feeling sorry for himself, he decided he had to create his own way out. He describes this as the moment his “entrepreneur muscle” activated and he understood that an idea could be turned into something real.

His first business began when he noticed a wealthy household in Cambridge with an untidy garden. He knocked on the door, offered to clean it up and improvised a price of £200 when the owner asked what he would charge.

Simon says necessity, rather than a childhood ambition to become an entrepreneur, drove him into business. His distinction was that he did not merely want entrepreneurship; at that point he needed it to survive.

He rejects the idea that people normally need £50,000 or £100,000 before they can start something. His example was that someone needing a £350 camera could wash ten cars at £35 each rather than treating lack of capital as an immovable barrier.

The School of Hard Knocks hosts made the same point from their own experience: their media business began with an iPhone and eventually grew to more than 21 million followers. Their early customer-acquisition equivalent was simply going out, approaching people and producing content rather than waiting for ideal equipment.

Simon says there is no meaningful form of completely passive income. Even with substantial wealth, he argues that somebody still has to perform the work and that founders cannot simply outsource every function that depends specifically on them.

His gardening operation eventually reached 126 monthly clients. Because he discovered that he was not particularly good at gardening, he hired other homeless people who were better at the actual work.

The gardening business taught him that his strongest early skill was sales rather than service delivery. He concentrated on knocking on doors and winning clients while using other people to perform work in areas where they were stronger.

The gardening company collapsed because Simon failed to anticipate seasonality. When winter arrived in England, demand for garden maintenance disappeared; he identifies failure to plan ahead as his first major business mistake.

The failed gardening business was nevertheless financially and educationally valuable. Simon said he had accumulated a substantial amount of cash before it failed and had learned how to recruit people, acquire customers, serve them and generate referrals.

Simon treats failed ventures as sources of both accumulated skills and, sometimes, accumulated capital. His point was that a business does not have to survive forever for the founder to carry valuable assets and knowledge into the next venture.

He considers follow-through one of the main differences between people who merely want something and those who build it. His repeated emphasis was continuing through difficulty rather than expecting an idea alone to produce results.

Simon argues that successful businesses are fundamentally team achievements. He described the effect as “1 + 1 = 11” and said his own operation now has 48 full-time employees.

The School of Hard Knocks itself is run by three partners—James, Jack and Josh. Simon used their partnership to illustrate his argument that business rewards collaboration more than the individual, closed-book model encouraged by traditional examinations.

By age 16 Simon had acquired a UK National Insurance number and an address, making conventional employment possible. He took a hotel job and enjoyed it for roughly eight months because it brought money, colleagues and stability.

He eventually became uncomfortable with spending his time increasing somebody else’s business value. That pushed him back toward entrepreneurship even though employment had become comfortable.

His next venture, Accommodation Express, originated from a problem he noticed while working at the hotel. When the hotel was full, receptionists simply rejected additional callers even though the hotel had already spent money generating those enquiries.

Simon began capturing rejected booking enquiries and finding rooms for them at nearby hotels with spare capacity. Accommodation Express received approximately 15% commission for successful placements.

Accommodation Express effectively operated as an offline hotel-booking intermediary before internet booking platforms became dominant. Simon described it as being somewhat like Hotels.com before Hotels.com.

He eventually sold Accommodation Express even though he had not originally built it for sale. He regarded the relatively small payout partly as payment for the experience of selling a company.

After the sale, a friend invited him to Hong Kong in 1997, around the time of the handover to China. Simon travelled there with little more than that single existing connection.

Hong Kong dramatically expanded his sense of what was commercially possible. Sitting on the harbourfront, he saw the city itself as evidence that enormous things could begin as ideas and then be financed, engineered and built.

That experience convinced him that exposure changes ambition. He felt he had been living inside a relatively small British frame of reference and decided he wanted to build a significant company in Hong Kong.

One of the hosts related this to his own childhood exposure to roughly 20 countries through his father’s military career. His broader point was that people often cannot aspire seriously to possibilities they have never seen.

Shortly after arriving in Hong Kong, Simon was invited onto a billionaire family’s boat on a Sunday. Watching the family simultaneously socialize and discuss business changed his assumptions about separating work from personal life.

Simon concluded that for some highly successful entrepreneurs, work and life are integrated rather than divided into a rigid “work-life balance.” He does not advocate a fixed 5 a.m. routine; he says he may work all Sunday and stop on Monday if he is tired.

The most valuable benefit of entrepreneurship for Simon is control over his own time. Avoiding a situation in which somebody else dictates his hours remains one of his strongest motivations.

The billionaire family also exposed Simon to much larger-scale thinking. He recalled hearing plans for Hong Kong’s IFC discussed in straightforward terms—acquire land, design the project, raise capital and build an 88-storey building.

His lesson from that environment was that capital can be treated as something to assemble around a sufficiently strong idea rather than merely as a fixed constraint. He contrasted this with aspiring entrepreneurs whose first response to an ambition is that they lack money.

Simon said becoming a father changed his relationship with ambition. His son is now eight, and Simon acknowledged the tension between keeping professional commitments and wanting to spend that time with his child.

He advises younger people to take major risks before they have children when possible. His reasoning is not that ambition ends with parenthood, but that the personal cost of time and risk becomes substantially more complicated.

Simon eventually committed full-time to Hong Kong, partly because he fell in love with the city and partly because he met the woman who became his wife. His wife is Chinese.

Living in Asia challenged many assumptions he had absorbed in Britain about the region being backward or merely catching up with the West. He came to believe that parts of Asia were already ahead in areas of technology and business.

He argues that high-level business relationships in Hong Kong often develop through years of trust before a major transaction happens. He supported the billionaire family he knew for years before a substantial commercial deal emerged.

Simon later concluded that this is less an East-versus-West distinction than a feature of doing business with highly wealthy or sophisticated people. Because Hong Kong concentrates many high-net-worth individuals, he encountered that relationship-driven behaviour unusually early and often.

At around 40, after approximately 25 years of intense work, Simon received an offer from PwC to buy his Hong Kong company, Fluid. He initially saw the sale as the culmination of the entrepreneurial dream: enough money to stop working permanently.

Fluid was a strategy, branding and creative business launched around 2000. Simon said its work included helping CNN expand outside the United States and helping Estée Lauder introduce products into China.

Fluid performed far better than Simon had expected when he founded it. It generated sufficient cash that he was already using company profits to make investments in other businesses before the eventual sale.

Simon said the PwC sale produced enough money that, on his calculations, he would never need to work again unless he lived beyond approximately age 104. At the same time, he and his wife had decided to have a child, making retirement initially seem especially attractive.

The first six months after the sale felt enjoyable because he had substantial cash and freedom, but retirement became what he calls the worst two years of his life emotionally. He said he experienced a mental-health crisis despite loving his new role as a full-time father.

The sale removed an identity Simon had spent decades building. In Asia he had been known as the founder of Fluid; after selling it, he felt he had stopped learning, building and applying his accumulated knowledge.

His conclusion is that financial independence and purpose are separate problems. Family mattered enormously to him, but he still needed another mission that made him feel useful and intellectually engaged.

This experience also shapes Simon’s main concern about AI. He is less worried about the disappearance of particular jobs than about a future in which technology removes people’s sense of purpose without society replacing it with meaningful activity.

Simon believes entrepreneurship can continue compounding long after careers that depend on physical performance would normally end. At 50, he sees little reason to discard approximately 35 years of accumulated entrepreneurial knowledge.

He rebuilt his own sense of purpose by focusing on the information he wished someone had given him when he was homeless at 15. At that age, he had asked a business figure for help and was told he would receive it only if he could pay.

Simon said the absence of that help forced him to spend four or five years learning things independently that he believes somebody experienced could have taught him far faster. That memory became the foundation of his commitment to making substantial business education freely available.

His original content strategy was deliberately small in ambition: help one person each week. Early videos sometimes received zero, one, ten or fifty views, but he considered them worthwhile if one viewer genuinely benefited.

That content eventually grew to roughly 21 million followers. Simon described himself as the most-followed UK business influencer across Instagram and TikTok, while emphasizing that enormous audience growth was not his original objective.

Simon wants education to begin with the question “What problem will you solve?” rather than “What will you be when you grow up?” He believes asking young children to select a profession prematurely narrows their thinking around a fixed career path.

He recalled his son being asked about his future profession at nursery when he was four. Simon felt the child was effectively trying to guess which conventional answer—such as doctor or lawyer—would please the adults.

Simon expects AI to transform professions such as medicine and said he would prefer an AI diagnosis if it were demonstrably more accurate than a tired or distracted human doctor. He uses this possibility to argue that educating children around fixed future job titles is increasingly fragile.

He has written a children’s workbook built around this problem-solving philosophy, titled What’s Your Dream: The Workbook. He has also written What’s Your Dream? for a broader audience.

Simon argued that conventional education leaves many graduates with debt but weak employment prospects. He cited a figure of more than 700,000 university-educated young people in England unable to find work, presenting this as evidence that a degree no longer guarantees the outcome students were promised.

He objects to systems that make very large amounts of financing available for university while leaving young people struggling to obtain comparable capital for a business. His broader complaint is that teenagers are encouraged to assume debt before they have been taught enough about money to evaluate it properly.

Simon makes a sharp distinction between legitimate paid education and “get rich quick” information businesses. He has no objection to courses whose customers genuinely receive useful training, citing Ali Abdaal’s YouTube education as an example.

He strongly criticizes people whose real business is selling a formula for supposedly becoming rich through property, trading, crypto or e-commerce when their own wealth primarily comes from selling the course. His objection is deception about where the seller’s success actually came from.

Simon rejects the claim that people necessarily value information only when they pay for it. His view is that urgency and genuine need create attention; free material fails when creators deliberately withhold the useful part and then blame the audience for not valuing it.

One of Simon’s long-form business videos runs approximately 2 hours 26 minutes and, he said, accumulated around 60 million organic views. YouTube had told him it was its most popular business video.

He said he was advised that the same information could have generated roughly £20 million as an expensive course. Instead he released it freely and said the video itself had nevertheless generated roughly $850,000 while reaching vastly more people.

He believes giving substantial information away can itself be a strong business strategy because reach creates other forms of value. He compared this to books, Facebook and Instagram: limiting access with an upfront charge can reduce the network and reputation that later create commercial opportunities.

Across the 81 companies he has backed, Simon says one of his strongest investment signals is a founder who is not building primarily for an exit. He prefers people who would willingly keep operating the company indefinitely and would sell only if an exceptional offer appeared.

His second major investment pattern is founders solving a problem they personally experienced. He sees personal frustration as a stronger foundation than selecting a market merely because it appears financially attractive.

Simon cited Lovable as an example of that pattern and said he invested early. He described it as now valued at about $6.6 billion and claimed it had become the fastest-growing revenue business in history.

According to Simon, Lovable originated because its founder, Anton, had a friend repeatedly asking for a CTO to turn an idea into software. The resulting product effectively became a “CTO in your pocket”: users describe an application and the system helps build it.

Simon says he did not originally build either Accommodation Express or Fluid in order to sell them. That experience reinforced his belief that companies often obtain their highest valuation precisely when the owner neither needs nor particularly wants an exit.

He sees desperation as a major negotiating weakness in fundraising and acquisitions. A profitable, growing company that can continue without a deal can reject unattractive terms and therefore negotiate from a stronger position.

Simon expects to appear on Shark Tank and said he warned producers that his investment philosophy may differ from that of some other investors. He believes founders frequently give away equity when increased sales could have supplied the required cash internally.

His rule is that equity should generally be given to an investor only when that person can materially multiply the company’s value, not simply because the investor has money. In his language, the investor should be capable of helping “10x” the business.

Taking capital from somebody who contributes nothing beyond money can effectively create a new boss. Simon instead wants investors who bring scarce distribution, expertise, access, capabilities or another asset the company cannot easily obtain itself.

He said there are only about ten people in the world he would currently consider allowing to invest in his own company. At his present scale, money and media reach are not scarce enough; specialized expertise is more valuable.

He gave global beverage distribution as an example of expertise he would still value. Because he is building a coffee/drinks business, a person with deep Starbucks-level supply-chain or distribution experience could contribute something he does not already possess.

Simon also prefers investing directly in businesses where he can influence the outcome rather than buying public stocks where he has virtually no operating influence. His investment philosophy is therefore tied heavily to his own ability to add value.

The “What’s your dream?” street-video format emerged accidentally from a TikTok livestream. After TikTok introduced gifting, Simon earned about $150 during a live session and initially felt uncomfortable because he had promised himself he would help people without charging them.

He decided to give that money away and spontaneously asked a supermarket employee about her dream. She told him she wanted to open a care home after her mother had died alone and remained undiscovered for roughly a week.

Simon gave the woman money toward the dream but regretted not recording the conversation because the story was so compelling. He then began recording similar encounters with his phone.

The resulting videos performed far better than simply telling viewers what to do. Simon concluded that audiences were more motivated by watching ordinary people attempt their own dreams than by receiving abstract instructions from him.

School of Hard Knocks underwent a similar content shift. James, Jack and Josh initially made talking-head business-advice videos as young men in their twenties, then discovered that interviewing other people attracted much more attention.

The hosts said they had to suppress their own egos and accept that viewers did not necessarily want business lectures from unknown twenty-somethings. Their role became extracting knowledge from people with stronger experience and credibility.

Their early connection to the University of Texas helped them establish enough credibility to approach strangers for interviews. They also mentioned recognizable previous guests such as Mark Cuban when explaining who they were.

Simon spent several years trying to reach MrBeast because he saw alignment between MrBeast’s philanthropy and his own mission. At one encounter in Dubai, Simon approached him with “What’s your dream?” and said security pushed him away.

He continued trying to reach MrBeast until he eventually got through directly, and the two later agreed to collaborate. Simon uses this as an example of persistence through gatekeepers rather than treating an initial rejection as the decision-maker’s final answer.

The School of Hard Knocks hosts said similar gatekeeping delayed their interview with Tom Brady. Their lesson was that access to prominent people often requires navigating people whose specific job is to filter approaches.

Simon nevertheless warns that persistence without value is not enough. He said he receives roughly 5,000 direct messages a week, making it impossible to respond simply because somebody repeatedly asks for help.

His recommendation is to approach valuable people with something useful to them or to a mission they already care about. Early-stage creators might, for example, help a successful person with social media before expecting that person to provide access or assistance.

Simon sees collaboration rather than follower ownership as a major advantage of online media. If his followers also follow another creator, he does not consider that a loss; cross-pollination expands both parties’ networks.

He credits collaborations with other creators as a major reason his own audience grew. He told creators struggling for traction that refusing or neglecting to collaborate can significantly slow growth.

Simon believes many wealthy people are more willing to help than popular stereotypes suggest. His experience has been that self-made wealthy people frequently want to “put the ladder down,” particularly when another person’s project advances a mission they already care about.

Mission alignment can therefore matter as much as immediate commercial value when approaching a wealthy person. Simon said an education venture aligned with his goal of changing education is far more likely to attract his interest than an unrelated pitch.

Simon home-educates his eight-year-old son because he believes sending him through a system Simon publicly calls broken would be hypocritical. His experience of home education strengthened his preference for personalized, interest-led learning.

He uses his son’s current fascination with sword fighting as an example of interest-led education. Questions about swords naturally lead into Henry VIII, history, warfare, engineering, manufacturing and economics without requiring those subjects to be imposed as disconnected lessons.

His central educational argument is that curiosity should be the entry point into subjects. He believes forcing children to learn the same material at the same age regardless of interest or development is structurally inferior to following what genuinely engages them.

Simon does not believe wealthy people are morally obligated to give money or help away, but he says giving has become one of his strongest sources of satisfaction. His point is that providing something without expecting an immediate return can itself be rewarding.

A personal failure shaped that belief: Simon once lent money to his brother, was not repaid and then fell out with him for roughly 15 years. Looking back, he believes he should either have given the money freely or not provided it at all rather than attaching an expectation that poisoned the relationship.

He describes his preferred principle as “give without take.” He contrasts it with helping somebody only because an equivalent repayment is expected.

Simon argues that happiness is too temporary to serve as a useful lifelong objective. A late train can make somebody unhappy minutes after a joyful family moment; purpose, in his view, remains meaningful through both good and bad days.

He illustrated this with Fluid: on one occasion the cleaner failed to appear before an important client visit, so Simon cleaned the toilets himself. The task made for an unpleasant moment, but the company subsequently won work that he said generated roughly £1 million in profit.

For Simon, how money is earned matters more than the amount alone. He says he knows wealthy people who remain deeply unhappy and argues that income generated through work a person despises can leave them materially rich but personally trapped.

Early in his career he envied university-educated friends buying cars and homes while he had fewer visible possessions. Later, he concluded that many had financed lifestyles requiring them to remain in jobs they did not enjoy, whereas his less visible asset was control over his time.

After selling Fluid, Simon bought a home outright in Hampstead, North London, near Ricky Gervais. Having no mortgage made the contrast with a neighbouring banker especially striking to him.

Simon described that banker as leaving around 6 a.m. and returning close to midnight despite being in his forties with a family. Simon interpreted the neighbour’s expensive, debt-supported lifestyle as evidence that a high salary does not necessarily produce freedom.

Simon takes an unusually hard line against debt and says he does not believe even supposedly “good debt” is harmless. He connected this view personally to his father, saying debt that was considered good ultimately contributed to trapping or destroying his father’s life.

His broader prescription is to accept the harder path early if it produces control later. He contrasts entrepreneurship’s early uncertainty with the risk of choosing easy salaried consumption early and finding oneself financially locked into that lifestyle decades later.

Asked for one final message to younger people, Simon answered: “The purpose of life is a life with purpose.” That idea ties together his experience of homelessness, entrepreneurship, retirement, fatherhood, content creation and investing.

Asked how he wants to be remembered, Simon focused first on his son rather than his wealth or companies. He wants his son to know that nobody matters more to him and to understand that children imitate what parents do more than what parents tell them.

Simon said he left his son that morning to honour the podcast commitment after a livestream on which his team helped 24 people pursue their dreams. He views that work as both improving the world his son will inherit and modelling the “give without take” behaviour he hopes his son adopts.

Simon and the School of Hard Knocks hosts jokingly raised the possibility of eventually combining their businesses because their missions overlap. No actual merger agreement was announced.

Simon is launching a drinks brand called Dream Brew. He said 10% of profits will be used to fund people’s dreams, with individual dreams also featured on the cans.

He said Dream Brew is intended for broad online distribution and positioned it as part commercial product, part funding mechanism for the dream-support mission. He also indicated he would soon be spending more time in the United States.