Gig Mindset

All Episodes


Welcome To Your New Office: Planet Earth

Season 1, Ep. 8

Companies all around the world are starting to embrace new technologies and new ways of working. Nowadays, the best person to do a job may not be the person sitting next to you in the office. They might be sitting in a coffee shop in another city or even at home in another country.

With new technologies and platforms in place to connect companies with a seemingly unlimited source of global freelance talent, there is no reason not to hire freelancers. As Eric Gilpin says, “It’s no longer an ‘if’ question. You need to just get started.”


In this episode, Eric Gilpin busts several myths around hiring freelancers. As the Senior Vice President of Enterprise Sales at Upwork, he is very familiar with the transition that large companies have to make to hire freelancers.

Eric shares some insights into how to get started working with freelancers, how to protect yourself and your intellectual property, and even how to manage time zones to optimize productivity. It’s time for companies to wake up and pay attention to the rise of the gig economy.


Get ready to listen to Eric’s insights on how to start working with high-quality talent from around the world today.


In This Episode, You Will Learn:

·      How companies’ need to have a competitive advantage contributes to the gig economy.

·      How companies get rid of the skill gap.

·      How time zones affect productivity when working with freelancers.

·      How to acclimate yourself and your business when working with freelancers for the first time.


Some Questions I Ask:

·      What characteristics did you have a child that help you today? (2:57)

·      Why is it important for companies to wake up and pay attention to the rise of the gig economy? (6:11)

·      Tell me a recent and impactful customer story. (7:44)

·      How do you deal with preconceived notions around what a freelancer is? (10:57)

·      How do you handle information security while working with freelancers? (16:29)


Connect with Eric Gilpin:




Love Is the Killer App by Tim Sanders

M365 Freelancer Toolkit

Paul’s Twitter

Paul’s LinkedIn


The Future Of Work Is Now

Season 1, Ep. 7

The future is here - and it’s here to stay.

The new wave of technology that is currently sweeping across the world is happening 10 times faster and at 300 times the scale of the first industrial revolution. This new wave, of course, is rapidly transforming the workplace as well.

In this episode, Anka Twum-Baah discusses various new ways of working that accelerate growth and change, and why companies need to start looking to the future today. Anka is the Senior Director within the Microsoft 365 Enterprise Marketing group. She currently leads modern workplace thought leadership discipline with a focus on the future of work

Anka shares her experiences, insights into the future, and practical strategies for embracing and inviting innovation into work. As a futurist, she believes that the future of work will provide new methods for extracting the best versions and the best talents out of all of us.

Get ready to learn how to keep up with the swift changes of the future that are impacting the culture of work today.

In This Episode, You Will Learn:

  • How the future of work will foster more innovative space for human creativity. 
  • Why business leaders are starting to embrace the notion of their employees collaborating with technology.
  • How leaders can begin making employees comfortable with cultural change with technology implementation.
  • Why it’s important to both communicate the vision and live it out when going through change.
  • Why it’s okay to fail.

Some Questions I Ask:

  • What does a day in the life of a futurist look like? (1:29)
  • What is the future of work? (2:28)
  • What keeps you excited every day? (5:04)
  • What are your thoughts on the gig economy? (10:34)
  • What film or book has made the biggest impact on you in the past year? (24:35)

Connect with Anka Twum-Baah:



Brené Brown

M365 Freelancer Toolkit

Paul’s LinkedIn


The Way of the Interplay: AI + Gig

Season 1, Ep. 6

The world around us is transforming at a rapid pace. With new technologies constantly emerging, other technologies get pushed out of sight and eventually become irrelevant. For business owners, freelancers, and entrepreneurs to stay relevant themselves, it’s crucial to stay up-to-date with the latest technological developments. 

In this episode, Peter Loforte talks about his experience with the evolution of the gig economy. With his 26 years of experience working at Microsoft, Peter is well-acquainted with the staggering speed at which new technology is demanded, developed, and produced. 

As someone who is responsible for various aspects of development of new technology, Peter is required to identify trends early on and stay ahead of the curve. He shares some strategies for staying on top, employing communication technology to cross-culturally collaborate, and defining what it means to be part of the gig economy. 

Get ready to listen to Peter’s take on the transformation of the world of work, life, and everything in between. 

In This Episode, You Will Learn: 

  • Why it’s imperative to stay ahead of the learning curve. 
  • Why virtual assistance will eventually become man’s best friend. 
  • How new collaborative and communicative experiences create new economic opportunities as well. 
  • How company leaders view their responsibilities to freelancers and gig workers. 
  • How interconnectivity can be used for the betterment of the world. 

Some Questions I Ask: 

  • How do you identify and react to trends early on? (4:43)
  • What advice do you have for someone struggling to find time to stay on top of technology trends? (7:50)
  • How think about human interaction with technology in relation to data usage? (11:36)
  • What makes you excited about work? (17:29 )
  • What did you learn from asking top CEOs tough questions at the Gig Summit? (22:41)

Connect with Peter Loforte: 



No, I'm Not Working In My Bathrobe

Season 1, Ep. 5

Do you find meaning in your work? 

In America, generally at least a third of our lives is spent working. For many, this work is nothing but an obligation - a means to an end. 

Work culture is changing. Now, there are more options than ever to pursue work that's meaningful and flexible. Of course, that doesn't mean it's easy. 

Freelancing doesn't always mean working at home in your pajamas and bunny slippers. Actually, this type of work comes with unique challenges and some uncertainty. But, if you are truly dedicated and passionate about your work, the benefits are endless. 

This is one of the many reasons why so many people pursue freelance careers. For example, freelance work has given stay-at-home moms the opportunity to continue working and utilizing their skills while maintaining a healthy work-life balance. 

On today's episode of Gig Mindset, I talked with Shari Cruz. She's a former marine, stay-at-home mom, and successful freelancer. She works as an instructional designer and a learning development consultant. Through freelancing, she's successfully and continuously developed her skills, stayed relevant in the workforce - all while finding stimulating, meaningful work. 

Get ready to learn from Shari as she shares her freelance journey and busts some freelance myths along the way.

In This Episode, You Will Learn: 

  • How Shari got started freelancing.
  • Why Shari continues to turn down "traditional" work to continue freelancing.
  • Why meeting deadlines are paramount to a freelancer’s success.
  • Why freelancing requires an "all or nothing" mindset.
  • The benefits of beginning your freelance career young.
  • What freelancing looks like and why someone would pursue it.
  • How to figure out what to charge clients based on your skills and the project.

Some Questions I ask: 

  • How did you get into the instructional design space? (2:07)
  • Do you remember the first time you worked with a client? (4:34)
  • Would you encourage your kids to freelance? (10:05)
  • What's the most challenging part of freelancing? (12:37)
  • What's a freelancing myth that bugs you? (14:16)

Connect with Shari Cruz: 



A Small Fish Makes His Own Big Pond

Season 1, Ep. 4

Let’s talk about the money issue. 

Money can be a major motivational tool that pushes you to continuously work hard, but it can also deter you from pursuing your dreams. 

One of the biggest myths and misconceptions about freelancing and pursuing a career in the gig economy is that freelancers aren’t actually doing a real job; they only perform low-end work. Therefore, freelancers will never make a real, satisfying living. 

On this episode of Gig Mindset, Brad Martin busts these money-related myths. Brad is an architect-turned-XR-developer. He transformed his passions and areas of expertise into both a freelancing opportunity and a company that hires freelancers. His experiences give him a unique perspective as both the worker and the client. 

Highlighting his experiences, Brad discusses the reality and risks involved in diving headfirst into the gig economy, and why it’s totally worth it. He explains how to mitigate those risks, market yourself, and find a way to make freelancing work for you—no matter where you are in the world. 

Get ready to listen to Brad’s story of pursuing his passion and finding success. 

In This Episode, You Will Learn: 

  • How being an architect gave Brad an advantage in the extended reality industry.
  • Definitions of virtual, augmented, and mixed realities.
  • How Brad founded Another Reality Studio.
  • Why Brad decided to hire freelancers rather than full-time employees.
  • Why the focus on freelancing needs to shift away from money.
  • Why freelancing is not a transition position.

Questions I Ask: 

  • How did you get started in the extended reality business? (2:10)
  • Tell us about your journey into freelancing. How is it different from a traditional job? (3:59)
  • What’s it like being a freelancer who hires other freelancers? (9:01)
  • What are your thoughts on freelancers from the U.S. and international freelancers? (13:17)
  • What’s your advice to someone looking into the gig economy for the first time? (17:24)

Connect with Brad Martin: 



Why The Gig Economy Is At The Tipping Point

Season 1, Ep. 3

Why do you work? 

No matter where you work or what you do, there are generally two options to answer that question: either necessity or desire. It's even true for freelancers. 

There's a narrative around freelancing that says people freelance because it's exactly what they desire. Sometimes that's true, but there is an increasing number of freelancers that are also doing it out of necessity to survive.

The workforce is rapidly changing, and many companies are looking for new, innovative ways to get work done on-demand with the added bonus of cost savings. At the same time, many individuals are looking for ways to work flexible hours, when they want, and where they want. 

Both of these reasons are why the gig economy is flourishing and transforming work. 

On today's episode of Gig Mindset, I interview the CEO of Upwork, the world's largest platform for freelancers and clients: Stephane Kasriel. 

In this episode, Stephane walks us through how the global marketplace and the definition of "work" are both rapidly changing. He says that companies, governments, employees, and freelancers need a mindset shift in order to keep up and be successful today. 

Get ready to learn about the past, present, and future of work-and how you can keep up with the changes. 

In This Episode, You Will Learn: 

  • Why a mindset shift is important for the success of companies and the gig economy.
  • Lessons from Upwork's largest customers on why encouragement to use the platform is essential to success.
  • How enterprise executives can gain leverage through platforms like Upwork.
  • Why people resist relocation for work and how it's impacting the surrounding society.
  • How to build community even through remote work.
  • How the gig economy promotes lifelong learning.
  • How the ecosystem around "work" needs to be reinvented.
  • Why people should give freelancing a chance.

Some Questions I Ask: 

  • How did you get to be CEO of the world's largest freelance company? (1:47)
  • What are the main technological product challenges for Upwork? (2:58)
  • What are some lessons you've learned from your larger customers? (4:50)
  • How do you see the importance of locational work changing over time? Why? (7:50)
  • How should we view the disruptive changes by platforms like Upwork in relation to a government that's slow to adapt? (12:39)
  • Tell me a story about a freelancer that inspires you. (14:30)
  • What advice would you give to the audience of this podcast? (18:01)
  • What book or movie has made the biggest personal impression on you in the past year? (20:37)


Connect with Stephane Kasriel: 



Forget Coloring Inside The Lines

Season 1, Ep. 2

When you were a kid and handed a coloring book and coloring utensils, did you stay inside the lines or color on the outside? 

Parents oftentimes teach their children to carefully color inside the lines. It's what you're supposed to do - you're "supposed" to function within the boundaries that were already established for you. 

Entrepreneurs and innovators alike, however, reject that mindset. Instead, they metaphorically color outside of the lines. 

On today's episode of Gig Mindset, I talk with someone who colors outside of the lines, breaks norms, and embraces workplace culture change: Dyan Finkhousen. 

As a "serial disrupter," Dyan works as the Director of Open Innovation and Advanced Manufacturing at GE. She recognizes that the gig economy will play a big role in the future of work and defining the digital era of operations. She uses tools like crowdsourcing, freelance resourcing, and open innovation. 

Get ready to learn about how Dyan is changing hearts and minds - project by project. 

In This Episode, You Will Learn: 

  • About Dyan's career journey.
  • How Dyan's Art History degree influences her view of the world and workplace culture.
  • Why it's important to genuinely understand some of the brightest minds who are breaking into the gig economy.
  • How GENIUSLINK operates as an innovative workplace culture change.
  • How open innovation allows for opportunities to work with experts and benefits industries.
  • Why putting boundaries on the capabilities of the gig economy model is a disservice.
  • Why the expert economy and gig economy can productively work together.

Questions I Ask: 

  • How did you come to pioneer GE's access to the gig economy? (2:23)
  • How does your inspirational quote relate to you? (6:48)
  • Tell me the first time you felt like a disrupter? (7:54)
  • What's an example of success from leveraging flexible talent models? (13:36)
  • What's your advice to those who believe the gig mindset doesn't apply to them? (15:38)
  • How do you deliver on cost, quality, and speed within the gig economy? (18:36)
  • What advice would you give to someone who wants to pursue a career like yours? (20:12)
  • As a nation, what skills do we need to cultivate over the next few decades? (21:53)

Connect with Dyan Finkhousen: 



I Just Wanted to Be a Cartoonist

Season 1, Ep. 1

Everyone fantasizes about what it would feel like to have more time in a day or even to clone yourself. Of course, that is not literally possible - but it is possible to scale your own capacity and get more done. 

The gig economy allows for professionals to do more with less time, along with even improving quality output with a faster turnaround - all at lower costs. 

On today's episode of Gig Mindset, I interview Ken Circeo. He is a Creative Director at Microsoft. He's figured out how to essentially clone himself in the workplace, going from making 1 video per week up to 15 videos per week. 

Through platforms like Upwork, Ken built a workflow that optimized creative output and helped him continue to progress in his career. Each day is more fun and more satisfying. 

So get ready to learn to optimize yourself, embrace change, and redefine your work life.  

In This Episode, You Will Learn: 

  • What steps people have to take to embrace new technology.
  • How the military helped Ken embrace drastic changes in technology.
  • How Ken figured out a way to reproduce himself in order to maximize output.
  • Walt Disney's delegation methods can be applied to today's work.
  • How Ken jumped into the gig culture through utilizing Upwork.
  • Advice on how to embrace workplace change.

Some Questions I Ask: 

  • How did the PC revolution change the way people interact with technology? (3:42)
  • Have you always leaned into new things without ever feeling scared? (4:45)
  • How has technology changes collaborative cultures? (5:31)
  • Tell me about the process that you use to scale? (8:23)
  • How did Walt Disney inspire you to embrace the gig mindset? (11:58)
  • How did you learn to delegate? (15:28)

Connect with Ken Circeo: