A New Chapter in How We Work
Let’s be honest, no one really knows what to call it anymore – freelance, fractional, gig, flexible. I just call it independent.
Matthew Mottola, the CEO of Human Cloud, has spent the past decade at the frontlines of the freelance revolution. From helping enterprises design flexible workforce programs to co-authoring The Human Cloud with HarperCollins, he’s seen the evolution of work unfold – from the early job boards of the late ’90s to the AI-enabled global platforms of today.
We’re in the trenches with leaders scaling flexible talent solutions,” Matthew explained. “From NASA to Microsoft, from startups to global enterprises – everyone is trying to figure out how to make independent work a core part of their business model.”
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The Freelance Economy Is Not a Trend
If you think freelancing is a side hustle economy, think again. According to Matthew, the growth has been steady and resilient.
The independent workforce has grown between 10% and 33% every year since 2016 – even during economic downturns, layoffs, and inflation. That’s not a blip. That’s a movement.
In fact, one of his favorite indicators of health in the industry is the rise of six-figure freelancers:
The number of freelancers earning over $100,000 grew by nearly 20% in the last year. That’s the signal that the market is maturing – companies aren’t just experimenting anymore. They’re investing.
The Real Barrier: “We’ve Always Done It This Way”
So why aren’t more big companies fully embracing the model? Matthew didn’t hesitate.
The number one blocker is always status quo. The simple phrase, ‘but we’ve always done it this way,’ is the biggest barrier to innovation
Many enterprises still cling to the idea of ownership and control – the belief that talent needs to be “theirs” to be loyal or effective. But as Matthew puts it: The best talent doesn’t live 15 minutes from your office. The best talent doesn’t need to be managed every second. They deliver results because they care, not because they’re on payroll.
It’s not risk that’s holding companies back – it’s comfort. And comfort rarely leads to innovation.
Risk, Responsibility, and Reality
When companies do take the leap, one of their first concerns is compliance and risk. What happens if a freelancer makes a mistake? Matthew laughed softly.
Here’s the thing – employees make mistakes too. Agencies make mistakes. The difference is, with big suppliers, you can sue them. With individuals, you can’t. So the system has to evolve.
He emphasized that today’s solutions – like EORs (Employer of Record) and freelance compliance platforms – already solve 90% of these problems. The rest is mindset.
Everything is solvable. The real question is – are you ready to let go of control and focus on outcomes instead?
From Control to Collaboration
When I asked Matthew what the perfect system for integrating freelancers would look like, his answer was refreshingly simple: “Be ruthless about outcomes. Don’t tell them what to do – tell them what success looks like.”
He encouraged companies to treat freelancers like partners, not outsiders. Invite them to your Slack, bring them to your offsites, include them in the culture. Treat them like your best employees – because often, they are.
The key, he says, is to balance trust with accountability:
Give up control, but double down on clarity. The moment you replace control with accountability, your organization becomes unstoppable.
Breaking the Stigma
As we discussed how to normalize the use of independent talent, Matthew’s conviction was clear: “We have to show the wins. Growth beats everything. Tell the stories, share the results – make it visible.”
He believes that success stories – not policy debates – will drive the future adoption of freelancers.
When a startup founder says, ‘We scaled from 5 to 50 using fractional talent,’ no one argues with that. Results speak louder than buzzwords.
And the wins are everywhere: from TurboTax using freelance CPAs to power its expert network, to major tech firms running multi-million-dollar programs built entirely on flexible contributors.
Advice for Companies (and Freelancers)
When asked what advice he’d give companies just starting to work with freelancers, Matthew offered a practical, almost playful idea:
Find one ambitious employee in your company, give them $10,000, and tell them to spend it on freelancers or platforms. No rules. Just results. You’ll be shocked at what they achieve.
And to freelancers, his advice mirrored his respect for professionalism and partnership:
Every time you deliver great work, you’re not just helping your client – you’re shaping how the world sees freelancers. We’re all part of building this trust, one project at a time.
Final Takeaway
The future of work isn’t coming – it’s already here. It’s diverse, decentralized, and deeply human.
“Independent work is not a threat to employment,” Matthew said in closing. “It’s the evolution of it. It’s about giving people freedom and giving companies flexibility. That’s how we grow together.
And as the Independent Workforce continues to expand, one thing becomes clear: the companies that embrace flexibility today will define success tomorrow.
