Wes Bos (Personal Brand / Course Business)

Wes Bos's entrepreneurial journey began long before courses became trendy. At 17, during the MySpace era about 17 years before this interview, he started building websites and MySpace designs for bands. "I just started doing sort of freelance consulting all the way through high school and through university," he recalls. By the time he graduated, he was running his own consulting business. But the real turning point came when he got involved with Ladies Learning Code in Toronto, teaching weekend workshops on WordPress. That experience ignited something: "I love to teach."

Wes didn't start by building a course platform or launching a sophisticated product. Instead, he did what many great teachers do—he shared what he knew freely. "I just did a whole bunch of blog posts, YouTube videos, lots of other teaching," he explains. The blog posts about Sublime Text became particularly popular, attracting significant organic traffic. One blog post got so much traction that publishers started knocking on his door offering book deals. But traditional tech publishing didn't appeal to him: "Writing a book with a tech publisher is a bum deal and you don't make much money on it."

So Wes did something radical—he self-published. He recorded screencasts, wrote the entire book himself, and put it out there. The result? "I had written all these blog posts about sublime text and they were getting lots of traffic... I had about 2,000 people on my email list from those blog posts, and of that about 300 people bought it within the first day or two." That was his "whoa, this actually works" moment. But it didn't happen overnight. "I was very vocal about writing this thing for a year and a half... I had lots of doubt doubter moments... but by being vocal about it people kept asking like when's it coming out?"

The first 300 sales came directly from his email list built organically through valuable blog content. But Wes had already been building an audience on Twitter since its early days—"I've been on Twitter for about 11 years now and I've got a hundred thousand people following me." His Twitter strategy was deliberate: share bite-sized "hot tips" with screenshots, help people in real-time conversations, and genuinely participate in the web developer community rather than just promoting himself. "I think that there are some industries where Twitter doesn't make sense... But I think for web developers, for marketers... that's where people hang out."

He also participated heavily in IRC (the precursor to Slack), spending significant time helping people debug their JavaScript code. This wasn't a marketing tactic—it was genuine community participation that built credibility and trust.

The biggest misconception Wes had to overcome was that if someone else had already done something, there was no point in doing it. "When I had written my sublime book... I would always be like, 'oh, there's already a blog post about this out there. Maybe it's not worth it.' But I sort of pushed past that and put it out anyway." This insight proved invaluable: "All of my courses out there, there's equivalent courses. There's tons of equivalent courses. There's way cheaper courses that are out there, but that doesn't stop me anymore because I know that there's a lot of people out there that like the way that you explain something."

What worked spectacularly was focusing on quality content first, then marketing. Wes emphasizes: "At the core of what I do is very good content and then the marketing and all the techniques are just on top of that to expose the very good content." He rejected the approach of cranking out mediocre PDFs with aggressive marketing tactics. Instead, he built real value.

He also built a custom Node.js platform (Boss Monster) to power all his courses, giving him full control over pricing strategies—like implementing purchasing power parity discounts for different countries, something most platform users couldn't do. This technical foundation became a competitive advantage that allowed him to iterate quickly on monetization and user experience.

Today, Wes's business metrics are substantial. He has approximately 30,000 paid users across four major courses, with React for Beginners leading at 14,000 students. His email list has grown to 165,000 subscribers with exceptional engagement (30-70% open rates, compared to industry averages of 15-25%). He gets hundreds of replies when he sends vulnerable, personal emails asking people what they're struggling with, which he personally reads and uses for course development.

Wes transitioned from doing client work to full-time course creation about 8 months before this interview. His philosophy on time management is distinctive: he chunks off dedicated time for business building while maintaining family-first values, avoiding the "16-hour work days" culture promoted by some entrepreneurs. He's hired help for graphic design and ads, though he admits he struggles with delegation.

The courses span JavaScript fundamentals (ES6 for Everyone), React, Node, and Sublime Text training. Each course gets its own domain name and custom setup within his Boss Monster platform. Revenue is driven primarily through his email list and organic discovery, with Twitter serving as a pulse-checking tool for market demand rather than a direct sales channel. He measures success not just in dollars, but in transformation—stories from students who landed jobs or got raises using skills they learned from him.