How Malcolm Ong Built and Tested Skillshare

TL;DR

Skillshare began by testing whether working professionals would teach practical skills and whether students would pay to learn from them. Malcolm Ong and his cofounder started with local, in-person classes, curated 30 classes across three months, and saw them largely sell out. That evidence gave them enough confidence to leave their full-time jobs and pursue the company.

Transcript

just because you're a coder doesn't mean you shouldn't care about the business doesn't mean you shouldn't care about revenues and so when you're working with those folks in the other departments you know spend a little bit more time and effort to to learn about what they're doing yeah we're recording now so uh yeah thanks so much for taking the tim... Read More

Key Insights

• Malcolm Ong's entrepreneurial experience began with an e-commerce company he started in high school. Running it through college allowed him to learn coding and business simultaneously, establishing the cross-functional perspective that later shaped his work in product development, entrepreneurship, education, and digital transformation.
• Ong's career combined experience at large companies and smaller startups. He worked at organizations including IBM, Microsoft, OMGPOP, Skillshare, and the South China Morning Post, giving him exposure to technology consulting, gaming, education, news media, product development, engineering, design, and organizational transformation.
• Skillshare emerged from a desire to build a mission-driven company. Ong and his cofounder considered education, healthcare, and other ideas, but education created a stronger emotional connection because the conventional American path from high school to college did not fit every learner or profession.
• The original Skillshare concept challenged the assumption that valuable teachers require formal teaching credentials. Its founders recruited active designers, coders, engineers, chefs, and other practitioners because their current professional experience was precisely what prospective students wanted to access and understand.
• Skillshare's first product was entirely offline and community-based. Classes occurred in offices, parks, classrooms, and other local settings, allowing participants to learn together instead of consuming educational material alone through the relatively immature online-video technology available around 2010.
• The initial marketplace test examined supply and demand separately. The founders needed to establish that professionals who had never taught would agree to lead classes, while also proving that students would purchase access to practical instruction delivered by people already working in relevant fields.
• Skillshare's early validation target was 10 curated classes per month for three months. The team reached 30 classes, recruited teachers who had almost entirely never taught before, and saw classes largely sell out, providing concrete evidence that both sides of the marketplace could participate.
• Early customer and teacher acquisition depended on personal networks, direct outreach, experimentation, and work that did not scale efficiently. The founders recruited technology professionals, entrepreneurs, restaurant owners, and chefs while testing subjects ranging from coding and design to StarCraft, poker, and chocolate truffle making.

Questions & Answers

Q: How did Malcolm Ong begin his career in technology?

Malcolm Ong became interested in technology when he was young and started an e-commerce company while attending high school. He continued operating that business while studying business and computer science at Carnegie Mellon. After graduation, he moved to Austin and joined IBM in technology consulting, beginning a career that later included large companies, startups, gaming, education, and news media.

Q: Why did Malcolm Ong and his cofounder create Skillshare?

Ong and his cofounder wanted to build a mission-driven company and explored education, healthcare, and other possibilities. Education stood out because the conventional American route from high school to college or graduate school did not suit everyone, particularly some people in creative fields. They believed learners should be able to study directly with practitioners already doing the work that interested them.

Q: What problem with traditional education inspired Skillshare?

The founders viewed American education as an overly linear system in which attending college was expected, even when it was not the right fit. Ong also cited approximately $1.5 trillion in student loan debt compared with about $1 trillion in credit card debt. These concerns encouraged them to explore more accessible learning from working designers, artists, musicians, engineers, and other practitioners.

Q: What did the first version of Skillshare look like?

The first Skillshare product was completely offline, with every class taking place in a local community. It began in New York before expanding toward other cities. Classes could happen in classrooms, offices, parks, or other spaces. This structure emphasized community and project-based learning while enabling the founders to test a marketplace connecting local practitioners with paying students.

Q: How did Skillshare validate its marketplace idea?

Skillshare tested two essential assumptions: whether working professionals without teaching backgrounds would lead classes and whether students would pay to attend them. The founders aimed to curate 10 classes each month during their first three months. They delivered 30 classes, recruited teachers who had almost entirely never taught, and found that the available class tickets largely sold out.

Q: How did Skillshare recruit its first teachers?

The founders initially relied heavily on their professional networks and direct outreach. They contacted people they knew in technology and approached local entrepreneurs, restaurant owners, chefs, designers, coders, and engineers. When prospective instructors said they were practitioners rather than teachers, the founders explained that current professional experience was the reason students would value learning directly from them.

Q: What subjects did early Skillshare classes cover?

Early Skillshare classes covered both professional and recreational subjects as the founders experimented with demand. Examples in the interview include coding, design, playing StarCraft, and playing poker. They also approached local business owners and specialists, including a Michelin-rated chef who could teach students how to make chocolate truffles. This variety helped the team discover which offerings attracted interest.

Q: Why did Skillshare start with in-person classes instead of online videos?

The founders wanted learning to be communal and project-based instead of solitary. Around 2010, Ong considered online education very new and said available video quality and technology were not yet sufficiently advanced. Watching educational content alone could resemble reading a book, while in-person classes allowed people from the same community to gather, work together, and experience direct interaction with practitioners.

Summary & Key Takeaways

• Malcolm Ong developed an interest in technology and entrepreneurship while young, starting an e-commerce company during high school and continuing to operate it at Carnegie Mellon. After studying business and computer science, he worked across large and small technology companies, including IBM, Microsoft, OMGPOP, Skillshare, and the South China Morning Post.

• Ong and his cofounder connected through a mutual contact and Twitter around mid-2010. They wanted to create a mission-driven company and considered education, healthcare, and other fields. Education resonated because conventional schooling followed a rigid path, student debt was enormous, and creative professionals did not always benefit from a four-year institution.

• Skillshare initially operated as an offline, two-sided marketplace for teachers and students in local communities. The founders recruited practitioners without formal teaching backgrounds, curated 10 classes per month, and tested whether people would pay. After delivering 30 classes in three months and largely selling out tickets, they committed to the business full time.