He Sold 2 Tech Companies At 16… Now His AI Company Is Worth $1.5 Billion | John Imah

John said he sold two technology companies before turning 16 and became a millionaire while still a teenager. The hosts described him as the youngest millionaire to appear on School of Hard Knocks; John said he is now in his 30s but does not publicly give his exact age.

He grew up in severe financial hardship in a Nigerian immigrant family in the United States. His parents slept in a car for several years before affording an apartment, the family used food stamps, the children shared a room, and he and his brother sometimes wore the same clothes because separate wardrobes were unaffordable.

His interest in technology began at seven, when he secretly dismantled the family's newly purchased computer and successfully rebuilt it. Afterward, his father contacted a friend at IBM, who suggested testing him further; John was taken to Fry's Electronics, given computer parts, and successfully assembled a computer from scratch.

From roughly ages seven to 13, he taught himself programming, hacking and broader computer skills. He described himself as intensely curious and ambitious and said technology quickly became the central interest of his childhood.

His first two businesses were a rendering company and a game company called Revenge of the Nerds. The game grew directly out of his experience of being bullied and revolved around nerds fighting bullies, somewhat like an Angry Birds-style concept; both companies were eventually acquired.

The internet allowed him to operate professionally without most collaborators knowing how young he was. He said almost all his friends were online—including people who were early Google employees—and they worked together on projects and companies through online forums before services such as GitHub existed.

The companies attracted acquisition interest because large-company employees discovered their work on online forums, not because John was actively shopping the businesses. On the first acquisition call, the caller initially asked to speak with the company's owner because John's young voice made it difficult to believe he was the person in charge; his parents were then brought onto the call.

John owned 100% of both teenage companies but said he voluntarily divided the acquisition proceeds equally among the people who had helped him build them. His collaborators had largely contributed as side projects rather than as formal co-owners, so the equal distributions were not contractually required.

He considers assembling people and identifying talent one of his earliest strengths. Even as a teenager, he said he could recognize who was strong at design, programming or other disciplines and organize those people around a project.

John was also a serious high-school athlete, participating in soccer, football and track and saying he became a state high-jump champion. He acknowledged that sports partly helped him fit in socially at a time when being highly technical was less socially accepted.

He was frequently mocked for being skinny and nerdy, including being called “ET,” and spent years balancing his technical identity against the desire to fit in. By late senior year he decided to stop hiding it, become a “full-blown nerd,” and pursue technology whether or not other students accepted him.

He went to college largely to satisfy his parents rather than because he believed he needed it for his technical career. His two teenage exits had already made local news, and he said his family came from a culture in which conventional success meant becoming a doctor, lawyer or similarly established professional.

He described himself as the first entrepreneur—and first millionaire—in his family line. Entrepreneurship was unfamiliar enough to his parents that even after his early exits they still encouraged him to get a conventional good job.

Academically, he said college taught him relatively little technical material because he already knew much of it. Some professors reportedly asked him to teach portions of classes because other students were already relying on him for help.

The main value he says he received from college was personal rather than technical. Living away from home forced him to become responsible for himself and gave him social, dating and heartbreak experiences he had largely missed while spending his childhood immersed in technology.

His mother died while he was in college, and he described her as his best friend and the first person who fully believed he would become someone significant. During periods of self-doubt, he says he still thinks about her sacrifices and uses that memory to push himself forward.

John connects much of his drive to hardship: poverty, bullying and the loss of his mother. He said many highly successful people he knows have some form of formative trauma, and he believes those experiences contributed to his refusal to give up.

Samsung was his first corporate job, and he joined before the Samsung Galaxy phone had been built. He says he saw the Galaxy evolve from an early internal product into a major consumer line.

Samsung taught him process, discipline and scalability. Coming from entrepreneurship, where he had been accustomed to simply moving fast and getting things done, he was struck by the fact that nearly every activity at Samsung had an established process.

Working at Take-Two Interactive strengthened his creative and commercial skills. Being inside the company behind franchises such as Grand Theft Auto and NBA 2K exposed him to marketing, digital business and areas in which he felt weaker than in technology.

He met Take-Two CEO Strauss Zelnick and particularly noticed Zelnick's commitment to physical fitness. John described him as one of the first senior executives he had seen make personal health such a visible priority.

Twitch taught John sales because, in its early days, publishers still had to be convinced that live streaming mattered. YouTube dominated online video, and he had to approach companies such as EA and Activision, explain why Twitch was different, and build KPIs, metrics and presentations capable of winning them over.

His corporate-process background was relatively unusual inside early Twitch. He said much of the company came directly from gaming communities, whereas he arrived with experience from larger companies and could combine that structure with an entrepreneurial environment.

Twitch was also the first workplace where he felt deeply accepted for being a gamer. Almost everyone around him played games, eliminating much of the identity tension he had experienced earlier in life.

At Meta, John struggled with self-doubt despite his previous success because many colleagues had elite academic credentials and advanced degrees. He compared himself with coworkers from Stanford, Harvard and MIT and initially questioned whether he belonged at their level.

During his first week at Meta, he announced that he intended to win his division's employee-of-the-year recognition; he said he achieved it two years later. Winning became important personal proof that he could compete successfully with colleagues whose academic backgrounds had intimidated him.

Meta also taught him that organizational success depends on relationships and internal support, not intellectual ability alone. He described highly talented workplaces as politically competitive environments in which people must perform well but also build enough trust and support for others to rally behind their ideas.

He later joined Snapchat when the company was struggling and its share price was below roughly $5. Instagram had replicated a feature central to Snapchat, and John said he deliberately liked joining the underdog because Snapchat's situation reminded him of his own history of being underestimated.

At Snapchat he worked across areas including fashion and gaming, helping create the bridge between his technology career and his later fashion business. He said Snap's stock rose from below roughly $4 during his tenure to about $85 at one stage, and as an employee he benefited from stock compensation.

He said almost every major company he joined recruited him rather than receiving an application from him. Friends already working at companies such as Google and Meta had repeatedly encouraged him to enter major technology firms.

He always intended eventually to return to entrepreneurship. Corporate America partly satisfied his parents and partly gave him experience in product launches, process, scaling and organizational politics; when founding his own company, he consciously tried to retain the useful lessons while excluding aspects of corporate life he disliked.

John said he met Bill Gates when he was young and told Gates that few people in technology looked like him. According to John, Gates replied that he should help change that and repeated the line about being nice to nerds because people may one day work for one.

He says he had some degree of contact with the founders or top leadership at nearly every technology company where he worked. Rather than copying one founder, he says he studied their very different approaches and incorporated selected lessons into his own management style.

Being one of relatively few Black people in his parts of the technology industry became, in John's view, a networking advantage as well as a diversity challenge. He felt that being distinctive made him memorable to executives, venture capitalists, celebrities and other contacts he met throughout his career.

Those accumulated relationships became a major asset when he returned to entrepreneurship. He had developed a substantial network across fashion and technology before starting SpreeAI and could approach senior fashion executives directly rather than beginning entirely cold.

SpreeAI was founded in 2023, and John said the company was worth approximately $1.5 billion at the time of the interview. The valuation figure was presented by John in the conversation rather than independently substantiated within it.

The company began from John's desire to combine his two major interests: technology and fashion. He traced his love of fashion partly to his mother and said his technology jobs had already helped him form relationships throughout the fashion world.

Before building SpreeAI, he flew to Europe and interviewed senior fashion executives about their problems. He already had an intuition about what could be built, but he deliberately tested his thesis against prospective customers rather than assuming his original idea was correct.

The executives consistently described online sizing, returns and personalization as major problems. Consumers often do not know their correct size, sizes differ between brands, customers cannot experience garments naturally online, and online stores lack the human guidance provided by an in-store sales associate.

SpreeAI was therefore built as a B2B technology company whose products are integrated by fashion brands for consumers. Brands can deploy its tools on websites and in stores rather than consumers purchasing SpreeAI directly.

One core product is photorealistic virtual try-on. A shopper can choose a garment and see a representation of themselves wearing it before buying.

Another product predicts clothing size, with John claiming approximately 99% accuracy. This is intended to reduce uncertainty caused by different sizing standards across brands and, ultimately, reduce returns and related costs.

SpreeAI is also developing AI styling and recommendation systems that attempt to reproduce a store sales associate online. The envisioned system uses information about the shopper to suggest products they are likely to wear and combines recommendations with visualization and sizing.

John personally studies physical stores to map the customer journey into AI products. He watches what happens when a sales associate greets someone, how customers learn about products, enter fitting rooms, judge appearance and establish size, then asks how each step can be reproduced digitally.

His larger product goal is not simply virtual try-on but recreating much of the physical fashion-shopping experience online. Virtual styling, visualization and sizing are pieces of a broader attempt to make digital shopping feel more like being assisted inside a store.

SpreeAI's original market entry relied heavily on free trials and free usage. John offered early fashion contacts an MVP at no cost so they could determine whether it created real value; he explicitly views free initial access as a way to create product “stickiness.”

After customers adopt the technology, SpreeAI operates broadly like a SaaS business. Brands pay recurring fees that can vary with traffic, demand and the collection of features they use.

Fashion's dependence on brand reputation made adoption more difficult than a conventional software sale. John said luxury houses are particularly cautious because a failed customer-facing technology experiment can damage a carefully built brand.

SpreeAI therefore changed its deployment model after learning that asking brands to immediately put experimental technology on live products created too much risk. It built sandbox environments in which a brand can test privately with employees, staff and focus groups before allowing customers to use the technology.

The company's large-enterprise sales cycles can be long. John declined to identify many customers because they were still operating in sandbox mode but said SpreeAI was working with some of the world's largest fashion companies.

John believes technology companies often fail in fashion because they build technology first and then try to force it into the industry. His strategy was to reverse that process: demonstrate respect for fashion as art and craftsmanship, understand the industry's business practices, and introduce technology only where it improves them.

He explicitly positioned SpreeAI's technology as a tool for workers rather than as a program designed primarily to eliminate their jobs. He expects disruption, but described it as helping existing people perform their jobs and grow the business.

The team initially made a major sales mistake by showing up to fashion companies like a conventional technology startup. They wore SpreeAI hoodies, delivered normal slide presentations and emphasized technology credentials, but John realized this language did not resonate culturally with fashion executives.

After attending a fashion show, he concluded that SpreeAI needed to “download the industry”—understand how its people dress, communicate, behave and experience products. When meeting a luxury brand, he began wearing that brand's products and treating personal presentation as part of the business pitch.

SpreeAI also transformed product demonstrations into fashion-style experiences. John said it flew models into conference rooms, used music and presented its technology more like a fashion show than a software demonstration; he believes this dramatically increased engagement and helped establish his reputation inside fashion.

He applied the same strategy to industry access, deliberately pursuing events advisers told him would be difficult or impossible to enter. He said that in SpreeAI's second year, Vogue and Anna Wintour invited him to the Met Gala and that he became the first fashion-tech AI CEO to attend; he said he subsequently attended again.

John says he has a personal relationship with Anna Wintour and that her support gives SpreeAI credibility within fashion. He also cited relationships or partnerships with Vogue and the CFDA as strategically important.

SpreeAI has strategic relationships with MIT and Carnegie Mellon, which John says assist with product development and talent recruitment. He described SpreeAI as the only fashion-technology company with strategic partnerships with both institutions, a claim made in the interview.

The company's team includes people with backgrounds at companies such as Netflix, Google and Microsoft. John repeatedly described team quality as one of the foundations supporting the business and investor interest.

He said some of the world's largest venture-capital firms were interested in investing in SpreeAI. He attributed that interest not only to the company's products but to his personal track record, senior team, university partnerships and established industry relationships.

His basic business framework is “skill, luck and timing.” Skill comes from continuously learning, luck often means unexpectedly meeting the right person through an event, coffee shop or other setting, and timing determines whether the relationship and opportunity can actually work.

He believes face-to-face relationships are especially important in traditional industries such as fashion. John said he will fly to Europe to meet brands rather than relying entirely on video calls because relationships need to become personal before remote interaction becomes sufficient.

The hosts compared this with a previous interview in which UK entrepreneur Richard Harpin said his company's U.S. expansion improved only after learning that Americans wanted to buy from people who understood and presented themselves appropriately for the American market. The broader point was that a seller must speak the cultural language of the market rather than expecting the market to adapt to the seller.

The hosts also cited Spin Master co-founder Ronnen Harary, who had described traveling to Japan to build important business relationships in person. John agreed with the broader principle that entrepreneurs sometimes have to spend money, take the flight and physically show up even when doing so feels risky.

John views entrepreneurship as fundamentally much riskier than corporate employment. Established corporations provide a safety structure in which an employee can often succeed by performing a defined job, whereas a startup faces existential battles continuously.

He consequently believes entrepreneurs have to accept calculated risk rather than wait for certainty. He compared it with aspiring actors moving to Los Angeles with limited resources because being physically present in the right environment may be necessary for the opportunity to exist.

John says he is naturally highly introverted but deliberately becomes extroverted when acting as CEO. He sees the modern founder as a major part of the company's marketing, so his public behavior, clothing and social-media presence are consciously aligned with the fashion industry.

For a new company, he believes basic public legitimacy has to be established immediately. A credible website, social-media presence and visible founder matter because potential employees, customers and partners will search online before deciding whether a new company is real.

When hiring, he gives passion unusually high weight and says he would sometimes choose a more passionate person over a more technically skilled one. His reasoning is that a passionate employee can learn missing skills, whereas technical competence does not automatically create belief in the mission.

His recruiting pitch emphasizes personal belief in the candidate and autonomy rather than merely selling the company. John tells experts that he will establish the vision, but they will control how their own discipline reaches that destination.

His management style is intentionally hands-off in areas where he has hired an expert. He believes startup employees often value owning a broad problem because highly ambitious people inside large corporations can become frustrated by narrow roles and internal boundaries.

SpreeAI's hiring values are “kind, smart, creative and moving fast,” a framework John said he partly carried over from Snapchat. He described those qualities as the company's desired cultural DNA.

He warns teams not to spend too much time mentally living inside five- and ten-year plans. Investors need long-range ambitions, but he believes those visions can distract talented employees from the execution required today.

SpreeAI's long-term ambition extends beyond fashion. John expects technology developed for fashion eventually to be adapted to other industries where greater personalization could improve customer experiences or business performance.

He believes SpreeAI could eventually become a public company. At the same time, he would consider an acquisition if the price, platform and outcome were right, particularly if it created a life-changing result for employees.

His preferred outcome is not simply a quick exit: he believes the company could exist for decades and continually evolve. He wants employees to experiment with side ideas that may become major products, citing the broader technology-industry pattern of internal experiments developing into large businesses.

John accepts that the people appropriate for an early startup stage may not necessarily be the people required at $100 million or $1 billion scale. He called personnel changes one of the hardest responsibilities because a founder must sometimes hurt an individual relationship in order to protect the company.

When someone clearly is not a fit, his advice is to act quickly rather than repeatedly postponing the decision. He said his experience of giving people extended benefit of the doubt has failed roughly nine times out of ten.

He believes a humane termination should still materially support the departing employee. He mentioned packages involving several months—and potentially as much as six months—of severance plus possible bonus compensation as ways to demonstrate appreciation even when separation is necessary.

Competition does not frighten him; he says he actively studies it. Employees continuously research companies building similar products, looking for things SpreeAI can learn from or improve rather than pretending competitors do not exist.

He distinguishes SpreeAI's overall strategy from individual technologies that competitors may also offer. John acknowledged other companies build similar products while maintaining that his company's broader strategic approach is differentiated.

He sees focus as the startup's principal advantage against a giant corporation. Large companies can enter adjacent markets, but those projects may be experiments with limited staffing, while a startup can concentrate the entire company on making one thing work.

His prescription for competing with much larger companies combines the right team, motivation, relentless focus and unusually strong self-belief. He went so far as to describe a useful form of “delusional” confidence that the company can become the best.

A recurring theme of the discussion was that entrepreneurs should solve an actual market problem rather than build something merely because they personally enjoy it. John argues that passion without a real customer problem frequently produces businesses that cannot scale.

The hosts provided their own example: when School of Hard Knocks had only a few hundred thousand followers, they launched motivational canvas art and the business failed. After the audience eventually reached millions, they interviewed roughly 500–1,000 followers about what they actually wanted and developed a product that they said now generates several million dollars annually.

John used that example to argue that failure itself is normal; what matters is converting information from losses into better subsequent decisions. He also stressed that even a sophisticated team cannot replace direct listening to customers.

He believes fashion and technology historically clash because the industries value different things. Luxury fashion often celebrates slow craftsmanship and the time required to make an object, while technology tends to promise acceleration and efficiency, so a technology company must avoid appearing to disrespect the very process customers value.

His parents' experience immigrating to America remains his main model for persistence. He said they arrived with little money and limited English, lived in Texas when their surroundings were not especially diverse, and went door to door seeking work rather than giving up.

He warns that social media creates a false picture of entrepreneurial life because people publish accomplishments while hiding rejection, conflict and failure. He tries to interpret repeated “no” answers as part of a process that can eventually produce a “yes.”

He considers a strong support system essential because founders suddenly have to deal with far more than their original profession. A programmer can find himself responsible for HR, legal disputes, lawsuits and people problems, requiring both emotional resilience and trusted people around him.

He says the startup team itself becomes part of that support system. Although “work-life balance” is often discussed as if work and personal life were cleanly separate, he believes colleagues in an intense startup frequently become more like a family or sports team.

John deliberately limits exposure to people who send comparisons with competitors in ways he experiences as discouraging rather than constructive. His approach is to distinguish useful competitive research from personal noise and focus on people who genuinely help him stay motivated.

His business mind, by his own account, essentially never switches off. Friends can email or text him at almost any hour, and he noted that many highly successful executives he knows behave similarly, sometimes answering messages within about 20 minutes.

He nevertheless places importance on spending time with family and people he loves because losing his mother taught him that those relationships are finite. He candidly admitted that even when physically present, his mind may still be working: “I'm there but I might not always be there.”

Christian faith is foundational to John's personal life. He said he grew up believing in God through his parents, particularly his mother, and difficult experiences reinforced his feeling that God was present when he had nobody else.

He does not believe religion should be imposed on employees or other people. He treats faith as personal, turns to God during difficult periods, and simultaneously emphasizes that prayer does not replace doing the work himself.

When directly asked whether he believes in Jesus, John answered “Absolutely.” He connected faith with humility rather than presenting it as a corporate requirement.

Kindness is one of the leadership principles he says he emphasizes in company-wide meetings. His reasoning is that coworkers may be dealing with serious private problems that are invisible during a disagreement, so leaders should remember that professional conflict occurs inside people's larger lives.

He believes company culture begins with the CEO's behavior. John wants employees to see him not merely as technically capable and execution-focused but as somebody who treats other people well.

His advice to younger people is “aspire to inspire before you expire.” He believes people who possess useful ability have a responsibility to share and teach it rather than treating talent purely as a private advantage.

He applied that principle first inside his family by teaching his brother how to build computers and do basic coding. He now also speaks at schools and to entrepreneurs, using his career to educate and motivate people.

John ultimately says he cares more about the lasting usefulness of the technology than about personal fame. He compared the ideal to products whose creators are barely remembered even though the products endure, while still hoping to be associated with changing how people shop through scalable technology built with more personality and care than he believes is typical.