Milo

Preston Lee started Milo in 2009 as GraphicDesignBlender.com—a tiny side project born from curiosity, not ambition. He wanted to experiment with blogging and see where it could lead, with zero expectation of building a business. "I didn't start it as a business," he explains. "I started it to sort of experiment with blogging and see where it could take me." For the first four to five years, the site made almost nothing—"less than $500 a month probably." But Preston wasn't discouraged; he was learning.

The blog evolved organically, publishing three to four times a week with content from freelancers and founders sharing real strategies. By the time Nathan Latka interviewed him, Milo had become a top 100,000 website globally with 30,000 email subscribers growing by 1,500 every month. High engagement was the real signal—articles attracted 20-25 comments regularly, suggesting a vibrant, invested community. "It's not sort of me as a math piece," Preston noted. "It's dozens and dozens and hundreds of entrepreneurs and freelancers all discussing what's working and what's not."

The sponsorship model emerged naturally from having built an audience. Companies in the freelance and SaaS space started connecting with Milo, seeing the engaged audience as valuable. Rather than broadcast sponsorship requests, Preston took a relationship-first approach: "They connect with us a lot of times and we present them with some of our sponsorship packages." His longest-running sponsor, Design Cuts, had been partnering for three years, sending dedicated emails about their design bundles every two weeks. The model was personalized—each sponsor got a tailored package rather than a one-size-fits-all offering.

What worked was patience and audience-first thinking. Preston refused to maximize revenue, instead keeping Milo as a side project while maintaining a full-time content marketing role at a print magazine. "Right now our goal is not necessarily to amass, you know, we don't want to raise any capital or we don't want to build a huge, enormous team," he said. This constraint forced better unit economics: $8,000/month with only 3-8 sponsors and working just 5-8 hours per week made the business incredibly efficient. Sponsorship tiers ranged from $400/month (unpopular) to $1,850/month (most popular), with the top tier delivering on-site mentions, 16 email placements monthly, and customizable dedicated emails.

By the time of the interview, Milo was generating $8,000 monthly—$96,000 annualized—from a side project that required minimal time. Preston had three kids, including a newborn, yet still managed the growth. He reflected: "I wish I'd gotten to that point quicker because as I've gotten to that point and not only does it bring in revenue, which is, you know, that's important obviously, but it's allowed me so many more opportunities." The business had evolved beyond revenue—it opened doors to collaborate with other entrepreneurs, appear on major podcasts, and build meaningful relationships across the creator economy.