

The Human Cloud Podcast
The Human Cloud Podcast
Welcome to the Human Cloud Podcast, where talent and technology intersect.
With guests from NASA, Microsoft, and McKinsey, along with leading economists, technologists, and founders, listeners of the Human Cloud Podcast are at the forefront of using innovative technology and talent models to transform businesses.
Led by Matthew Mottola, a global entrepreneur, author, and investor in the flexible workforce, the podcast covers topics ranging from generative AI and blockchain to innovative talent models like freelance, fractional, and digital talent platforms.
With guests from NASA, Microsoft, and McKinsey, along with leading economists, technologists, and founders, listeners of the Human Cloud Podcast are at the forefront of using innovative technology and talent models to transform businesses.
Led by Matthew Mottola, a global entrepreneur, author, and investor in the flexible workforce, the podcast covers topics ranging from generative AI and blockchain to innovative talent models like freelance, fractional, and digital talent platforms.
Episodes
Mentioned books

May 31, 2023 • 50min
Ep. 94: Barry Matthews, CEO of Open Assembly, Future Of The Freelance Economy
Leaders, we need to talk about how organizations can scale their freelance usage. The freelance economy V1 & V2 was built for entrepreneurs and small businesses, not large companies. The problem as Barry Matthews, CEO of Open Assembly and 20+ year vet describes it, is that Enterprises don't know which partner to turn to, and don't know how to scale a model that's new, risky, and has no existing best practices. The impact is that while 90% of leaders are prioritizing freelancers according to HBR, seldom few leaders are succeeding at scaling their organization beyond small pilots and small working teams.
Barry and Open Assembly is building one of the leading solutions to scale freelance talent across large Enterprises through a single Enterprise entry point, what they call the gateway.
If you remember the guest Mina Bastawros of Airbus, he said the future of the freelance economy is enabling enterprises the Amazon experience of engaging talent. One place for multiple marketplaces, multiple skills, yet a seamless and convenient end user experience.
In this episode we'll discuss how to do this, along with the key themes below:
How outsourcing has become skill sourcing, and the freelance economy is just the digitization of sourcing
The Enterprise business case, specifically speed, size, and elasticity of accessing talent
The Enterprise challenge...(1) which platform for what need, (2) we're new and risky with no existing processes
Why there won't be ONE marketplace
Enjoy!
http://humancloud.work/barry-matthews

May 25, 2023 • 56min
Ep. 93: Angie Moody, CEO of Ruby Money, Formerly of Instagram, Visa, Capital One, Microsoft
Angie represents one of the sexiest shifts in our industry, the shift in the most talented corporate leaders choosing the freelance economy over the traditional career path. In her case, this looks like choosing to build her own fintech, Ruby Money, over the full time corporate opportunities that came from having experience at Microsoft, Instagram, and Visa to name a top few of her numerous logos.
We'll get in the weeds over Angie's own freelancing path, her peers, and what's required to make the freelance economy a sustainable career path and industry.
*Also shout out to Ernie Park of Part Time Tech for referring Angie!
Enjoy!
http://humancloud.work/angie-moody

May 11, 2023 • 52min
Ep. 92: Marc Clemens, Founder & CEO of CodeControl & 9am
On this episode we talk with Marc Clemens, CEO and Founder of CodeControl and 9am. Companies are recognizing the value of independent professionals, and despite challenges in worker classification and regulations, systems are becoming more streamlined for businesses to engage with freelancers. The convergence of entrepreneurial and freelance mindsets, along with platforms like Code Control, are allowing freelancers to focus on their skills while offloading business aspects to dedicated services, ultimately creating a more flexible, collaborative work environment.
00:09:20: The intersection of freelancing and entrepreneurship
00:15:18: Structuring and building a community
00:26:08: Attracting technical talent in marketplace
00:36:07: Creating optimized profiles for freelancers
00:44:30: Go-to-market strategy in the next 6 to 12 months
Learn more: https://humancloud.work/marc-clemens/

4 snips
Apr 26, 2023 • 54min
Ep. 91: Ernie Park, Part Time Tech and The Future of Fractional Leadership
Leaders, Ernie is the epitome of the most exciting trend in the freelance economy...future VP's choosing to freelance over the corporate ladder. Ernie runs Part Time Tech, a newsletter highlighting the benefits of freelance models for tech talent like him. Prior, he majored in computer science at MIT, and was a software engineer at Hubspot for over 7 years.
It is crucial to understand how this new freelancer demographic thinks. A couple core differences:
The best people were great in corporate, better fit their lifestyle and ability to make an impact (they don't need to follow the corporate 'Kingdoming')
The best people aren't looking for a job, they're prioritizing opportunities
The best people find work through peer connections
3:51, Why Ernie made the switch
5:11, Why working this way makes sense for top talent
11:18, Impact of the pandemic
14:31, The corporate disconnect
20:43, The future of fractional leaders
40:51, The real tradeoffs between 1099 & W2
41:49, What do marketplaces have to do
Learn More: http://humancloud.work/ernie-park

Apr 19, 2023 • 50min
Ep. 90: Jeremy Johnson, CoFounder and CEO, Andela
Leaders, Andela is a leading marketplace for developers, engineers, product designers, and technology experts. Beyond the platform, Jeremy has spent over 15 years unlocking the power of global, digital networks to drive business change.
Jeremy hit on a couple themes that every single one of us needs to be aware of.
1: The blurring of freelance and full time
2: The science of managing remote freelancers at scale
3: The macroeconomic climate, specifically how our space has never been more attractive to Enterprises
He also gives us the inside scoop on how their recent acquisition of Qualified.io and Codewars enables them to assess and deliver human potential more effectively.
Learn More: http://humancloud.work/jeremy-johnson

Apr 12, 2023 • 49min
Ep. 89: Matt Dowling, Founder of Freelancer Club
Leaders, the freelance economy is shifting from being dominated by large, horizontal marketplaces to small, niche, hyper relevant communities of freelancers. We call this freelance first, and Matt's 8+ year old community of 60,000 freelancers is the epitome of this. Built with education, mentoring, and opportunities as the three pillars, it is the epitome of how winning freelance networks will look in the next few years.
There are a couple themes we want you to listen out for:
Myths of the freelance economy, what's changed in the last 10 years, and what will change in the next 5 years
How finding freelancers and freelancers finding work is going from push to pull thanks to the increasingly advanced search capabilities that can find the exact match of skillset/industry/levels of experience needed.
What branding means for freelancers, why it's integral, and why blitzing social media is a damning strategy
Only 1 in 5 individuals is succeeding in their first year of freelancing (this number is definitely higher)
If you can master above, you can lead hyper-engaged, high quality, successful freelancer networks.
Learn More: https://humancloud.work/matt-dowling

Mar 29, 2023 • 38min
Ep. 88: Gale Wilkinson, Managing Partner at VITALIZE, Investing In The Freelance Economy
Leaders, are we really grown up enough to be a venture backable space? According to Gale, absolutely, as her fund is focused on the future of work, and invests in a number of freelance economy startups each year.
We'll talk about what the venture space looks like for the freelance economy, how she sees the freelance economy in the future (hint...2 to 3x growth), and how freelance models can be well positioned for venture capital (hint...not ALL companies should be venture backed, and that's a good thing).
A couple themes that we think you need to know asap...
The freelance economy will never be one large marketplace because it's an industry of people, nuance, and intricate user experiences
The freelance economy is a natural societal evolution of what people want out of work and what technology now allows for
Consulting can be a lucrative business on it's own without venture capital
Learn more: http://humancloud.work/gale-wilkinson

Mar 22, 2023 • 60min
Ep. 87: Ben Ross, Innovator, Product SME
Leaders, your head will be sore from the technical product learnings Ben will teach us. Ben is an entrepreneur that has built freelance related products for over 10 years.
From a technology and product lens, we answered two key questions, what has changed in the last 10 years that makes now the right time for the freelance economy, and what will change in the next 5 years.
Hint 1...what changed was (1) consumer behavior with matching related technologies (think the taboo of E-Harmony vs the acceptance of Hinge, this is what's happened with the gig economy being taboo and now freelancing being preferred), (2) Cloud computing enabling digital sourcing and collaboration, (3) effective data science search algorithms.
Hint 2...what will change in the next 5 years is (1) bundling of a singular plumbing infrastructure with partnerships between marketplaces built on top, (2) single pains of glass and identity tokens.
We know...very geeky, but very important for being able to plan and build for where the puck is going in the freelance economy.
6:18 - Defining where work is going...project based, open
8:38 - The problem with talent acquisition today and where it's going
13:41 - Why the freelance economy isn't already the default
21:26 - How to balance outcomes and process
23:13 - HR needs to change their metrics
30:38 - Why hasn't LinkedIn built a freelance marketplace
35:33 - What's different today
46:32 - What will change in 5 years
Find Ben's Leader Portal: humancloud.work/ben-ross

Mar 14, 2023 • 51min
Ep. 86: Kelvin Wetherill, CEO & Founder - Supportwave
Leaders, our industry is in the midst of a massive transformation away from broad horizontal marketplaces and towards skill specific platforms. Take Paro for finance/accounting, or Catalant & Graphite for management consulting, the future of our industry belongs to marketplaces that can use technology and freelancer first practices to ensure a consistent, low friction, high quality experience.
NerdApp is the IT ecosystem that best personifies where the freelance economy is headed. NerdApp stemmed from Kelvin's personal experience in the IT services industry for 15+ years, where he saw the inefficiencies and poor experiences that the legacy IT industry routinely delivers.
Warning: We're going to get real geeky on the software and user experience driving NerdApp. If you're a nerd or an entrepreneur, you'll love it.
11:12 - Why the freelance economy, the combo of Kevon's corporate experience and the problems in IT Services
17:31 - Secret sauce behind the meteoric 15 month growth of NerdApp
20:59 - What's wrong with the IT Services Industry
22:24 - Why doesn't Nerdapp already exist
27:38 - The importance of user experience
29:42 - Biggest barrier of the freelance economy is company education
30:52 - Biggest barrier of growing marketplaces is the first experience
44:27 - What will change in the next 5 years
Find Kelvin's Leader Portal: https://humancloud.work/kelvin-wetherill

Mar 6, 2023 • 49min
Ep. 85: Adrian Tan, Singaporean Fractional CMO
Leaders, what if freelancers are both your future Directors and your future employee role models? That's the future for leading brands as leaders like Adrian Tan drive the best ROI. Enjoy!
3:43 - Defining a freelancer, "was a freelancer prior, now fractional"
7:20 - Why Adrian freelances
10:45 - Entrepreneur vs solopreneur
11:29 - How he got his first 3 clients
14:34 - Perception of freelancing in Singapore
21:00 - His view on marketplaces
25:15 - How Covid made people comfortable with remote, re-set their relationship with work, and accelerated freelancing
31:38 - His portfolio (3 retainers) and how he manages his time
38:47 - How fractional is the most efficient way to work