

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

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

Feb 22, 2023 • 53min
Ep. 84: Cory Hymel, How ChatGPT Will Impact The Freelance Economy
Cory Hymel is our innovator of the month, teaching us how we need to think about and act on ChatGPT and Generative AI.
Cory and I go way back in building custom software using freelance networks. Everything from building the mobile app for North America's leading manufacturing company, to helping Enterprises identify how they can best use AI by plugging in expert AI freelancers.
3:47 - the shift from marketing budgets to IT budgets
5:47 - the shift from this is to cool to "we know this will happen, how do we do this securely"
7:25 - how ChatGPT unlocks the power of synthesis
12:51 - the evolution from IBM Watson to ChatGPT
18:49 - how to start embracing ChatGPT
24:01 - the move to an A-sync future
36:31 - best way to adopt ChatGPT, small working teams
Check out Cory's Leader Portal:
https://humancloud.substack.com/s/leaders

Feb 13, 2023 • 53min
Ep. 83: Talking Workstyle With Lizzie Penny and Alex Hirst of Hoxby
Hoxby is a creative freelancer collective that's fundamentally transformed how clients work with freelancers. Instead of one-off gigs, Hoxby has ushered in scaling project based work within their clients. On this episode we'll talk tactical about how they did this and preview their new book Workstyle!

Feb 6, 2023 • 52min
Ep. 82: Matteo Cellini, CMO and Founder of Work 3
Matteo is our innovator of the month. A Chief Marketing Officer and prior Director at Expedia, Matteo came into the Human Cloud from a frustration with merit and geographical limitations in traditional hiring. In this episode we'll talk:
4:30 - Geeking out over Rome, where he resides
17:28 - The culture problem of the freelance economy
26:04 - Evolution of careers
28:01 - Proof of work and credentialing
43:30 - Navigating data abundance

Jan 11, 2023 • 54min
Ep. 81: Brooks Lockett, SaaS & B2B freelancer
Matthew Mottola
Thu, Dec 29, 2022, 5:03 PM (13 days ago)
to brooks, me
Brooks, hope you've had an incredible holiday and are ready for a great year. We plan to release this mid Jan. Feel free to edit anything below!
Title: Brooks Lockett, SaaS & B2B freelancer
Description:
Leaders, we seldom bring on individual freelancers for an entire episode.
The reason is absolutely NOT that we don’t leave freelancers (they are the hero’s of our industry).
The real reason is that the best freelancers aren’t usually talking, they’re building, and a podcast for them is typically a distraction.
BUT. Their voices need to be heard. And you need to understand their problems and their motivation in order to attract and retain the best one’s.
Which is where Brooks comes in. Brooks' would be your VP of marketing. Instead he’ll still do what a VP of marketing can do, but as an independent contractor, he’ll be your go to for every piece of SaaS & B2B content.
We’re going to hit on everything.
Why he freelances.
Why freelancing is better than a full time job for him.
Why hiring him leads to better results than full time employees.
What sucks about freelancing.
Make sure to check out Brooks' leader portal: https://humancloud.substack.com/s/leaders

Jan 4, 2023 • 57min
Ep. 80 - Steve King, Industry Overview
Leaders, Jon Younger and Steve King are the brains behind many of our industries leading stats.
What’s unique about Steve is that he’s the perfect example of freelancing becoming the natural evolution of work. Steve wasn’t a pissed off employee that wanted to ‘ditch the 9-5 to sit on a beach’. He was a VP & GM at leading companies like Lotus Development and Macromedia. In terms of the corporate ladder, he made it, yet he chose to blaze the solopreneur path instead through his firm Emergent Research,
There are 7 massive themes that Steve and I discuss.
There’s now a middle class to the freelance economy
55% of individuals have been independent at some point in their life
60% of Americans don’t have the risk profile of a freelancer
There was 20%+ growth from 2021 to 2022, with full time freelancers as the leading segment
Freelancing is overwhelmingly chosen, and freelancers have the highest levels of fulfillment
Misclassification is protecting 25% of the population at the expense of the entire freelancer population
We’ll also break down MBO Partners recent State of Independence in America 2022 Report.
Make sure to check out Steve's leader portal: https://humancloud.substack.com/s/leaders

Dec 19, 2022 • 55min
Ep. 79: 2022 Year in Review
The Matts review an explosive and exciting year for freelancers around the world. With lots of acceleration and changes in the industry in the past year, it has become essential to adjust and strategize. With AI on the horizon, many workers fear for their jobs - but the smart ones are utilizing it.
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