Bootstrapped, Global, and still growing
Alessandro Bogliari didn’t follow a playbook.
He didn’t raise capital. He didn’t work in big tech. He didn’t even get a “real” job.
He grew up in Milan, the son of small business owners who ran their own creative studio. Watching them navigate the ups and downs of entrepreneurship planted a seed early: if you want to build something, no one’s going to hand you permission—you just start.
So he did.
He taught himself HTML in middle school, built his first website at 12, and by 18, had already launched a 20-person creative team—earning $0, but learning everything.
“I didn’t know how to make money yet, but I knew how to build teams and create momentum,” he says.
That mix of self-taught grit and creative obsession eventually led him to launch Influencer Marketing Factory, a fully bootstrapped agency that now operates globally with a team of 60+ across the U.S., Europe, Latin America, and the Middle East.
It’s one of the few agencies in the space that’s scaled this fast without raising a dollar—and done it while staying profitable, remote-first, and people-centered.
“We hit 7 figures in year two. 8 figures in year three,” Alessandro says. “That kind of growth is exciting, but it can blind you too.”
He’s learned that lesson the hard way.
As revenue grew, so did the complexity: healthcare, HR, legal, infrastructure, finance. And without a background in ops or a CFO in his corner, Alessandro did what most underestimated founders do—he figured it out as he went.
“If I could go back, I would have slowed down to focus on margins and ops earlier. But when things are going fast, you’ve got your head down. You don’t always see the big picture.”
It wasn’t just systems that needed attention—it was people, too.
Even with a 5-star Glassdoor rating and a values-driven culture, Alessandro learned that being a great employer doesn’t mean everything always goes smoothly.
“You can do everything right and still deal with miscommunication or conflict. That’s part of working with humans.”
And that’s the point. Alessandro believes business isn’t just about revenue—it’s about how you treat people while you’re growing. He’s not building an empire. He’s building something sustainable. Something real.
“Try to be a good person. You won’t please everyone, but if you lead with care and integrity, the right people will stay.”
He never worked a corporate job. Never believed in the 9-to-5.
And he credits his success not to theory, but to his lifelong obsession with building, experimenting, and learning from the real world.
“You can learn more about marketing from YouTube than from most MBA programs,” he says. “But you can’t replace the value of human connection. That’s what matters.”
Today, Alessandro’s agency is thriving—but he’s still in the trenches. Still iterating. Still obsessed with what’s next.
This is what underestimated looks like.
Let’s Thrive,
—Eric
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