Welcome to our newsletter!
What can you expect?
Product-driven insights on the front lines of the Future of Work, Freelance Economy, and Artificial Intelligence. As CTO and CEO of technology companies, we’ll skip the buzzwords and give you the insights we use to grow our employees, empower our customers, and yes…keep our investors happy.
When will we bug you?
Honestly, we don’t know. We’ll try to stick to every few weeks. But we live and die by the products we make, so expect our insights to ebb and flow with the market conditions.
Allow Us to Introduce Ourselves
Matthew M: I have two firmly held beliefs.
1: Every human deserves the opportunity to embrace the freelance economy.
2: My hometown of Newburyport, Massachusetts is the greatest place on earth.
(Just look at it)
On a serious note, the freelance economy has changed my life. As a freelancer, it was my engine to opportunity. It opened my eyes to what I was truly passionate about. It accelerated my ability to learn and prove my worth. And it exposed me to pathways I could have never predicted.
It wasn’t just being a freelancer that changed my life. Hiring freelancers and leading freelance teams has been my secret weapon to drive change as an entrepreneur and within large companies. At Microsoft I built the Microsoft 365 freelance toolkit - Microsoft’s solution to hire/work with freelancers. No joke, in development I had a freelancer teach me how to use Microsoft products (you’re the best Russ Crowley), alongside researchers, designers, writers, developers. I might’ve been a PM, but tapping into freelancers enabled me the capacity to build, bring to market, and scale an enterprise product in under two years.
But most important, the freelance economy has blessed me with the deepest relationships. Try randomly meeting one of your freelancers in an airport (it’s the best!!!…also why’s the picture so big).
I’ve cooked with my freelancers. Slept at their house. Know where there kids go to college. I honestly have had deeper relationships with freelancers than most people have with their family.
And to top it all off, it introduced me to one of my best friends - Matt C (more on that later).
Matthew C: I know, from the outside I look like every other corporate executive. Tucked button down. Regular fit jeans. But deep down I am a Renaissance person with a punk-rock/hippie flair. I love to write. And play music. And create art. And program software. And … you get the point. But in the “old school” of career employment as the only viable path to prosperity, I had to specialize or risk being unemployed. So I went down the technology route and climbed the (mostly) traditional corporate ladder.
Most business books end there right? Another white corporate executive talking leadership or strategy.
Not today, though, because I can use human cloud platforms to meet amazing people searching for freelance talent and scratch my various creative itches. I ghostwrite, mentor, advise startups, and tinker with software, all from the comfort of my home office before my regular workday begins. I communicate through G Suite and Trello, use open source tools to build software, and get paid through various online platforms, without me needing to worry (too much) about bookkeeping and finance. The gigs are less about the money for me and more about how they create the opportunity to do exciting work I wouldn’t otherwise be doing.
Which is what brought me to the other Matt - he needed help with a report, and I was the technical editor. That is, until 200 pages later, when we realized this was more than a report: it needed to be a book, which was the genesis of what is now the Human Cloud.
Little did I know he’d also drag me into a mock wedding shoot (fortunately my wife wasn’t too jealous).
More Than A Book
The book was our nights & weekends project. As a CTO for a high-growth company and a product manager at the time (leading the Microsoft 365 freelance toolkit), we had our hands full from our day job. But we knew this couldn’t wither away on our Google Drive. We wanted to share it with the world. So we treated it like a software project, breaking down the project into its various parts, running two-week sprints, and leveraging our secret weapon … bringing in freelancers to help with many different aspects of the process: researchers, journalists, editors, designers, even a comedian.
Master OKR Spreadsheet
Master Sprint Board - we held two—week sprints
And the secret beyond any tool, was our kick-ass PM Samantha Mason who ran operations.
(yes, we dragged her into the mock wedding shoot too).
Sam: Meeting the two Matt’s epitomizes what’s best about freelancing – working with a team specifically formed for the task at hand, creating a superior product because of the synergy of the group, and building friendships. Is it scary sometimes? Absolutely! But I can’t imagine myself doing anything else.
I’m living proof that you don’t have to take no for an answer, and employers don’t hold all the power. I left my cushy job as an engineering VP at a publicly traded company to raise my boys. When they left for college, I was ready to jump back into the business world and apply my product management and organizational skills. Well, things didn’t go as planned. A recruiter told me that I would never find employment because I’d been out of the market too long. Undeterred, I kept going, only to be told the same by a second recruiter. So, I decided to create my own job, and I haven’t looked back.
I absolutely love being a freelancer, setting my own schedule, deciding who I work with and don’t!, and interacting with people in fields ranging from home construction companies to bio tech and everything in between. For all the stay-at-home moms and dads and retired people who want to re-enter the job market, freelancing is the way to do it! Don’t let anyone tell you that your skills are outdated.