Gig Mindset

All Episodes


Gold Watches Can't Do Yoga

Season 1, Ep. 12

Just try it.

Times have changed since the days of pensions and retirement gifts of golden watches. Just like with any big changes, the change itself is met with uncertainty and fear. The reaction to the gig economy and how it’s transforming work is no different.

The truth is, studies by ClearlyRated show that freelancers’ productivity, communicativeness, and engagement is no different from that of a traditionally hired full-time employee. In fact, if the company embraces the gig economy, then freelancers will be just as—if not more—engaged, skilled, and productive as traditional employees.

In this episode, Eric Gregg discusses how corporations will benefit from investing in the gig economy. Eric Gregg is the CEO and founder of Inavero Research (now called ClearlyRated), which focuses on finding ways to create satisfaction for employees and clients alike.

Eric shares insights into the changing nature in work, how companies look at different ways to innovate and compete, how traditional employees and freelancers need to continuously reskill to stay relevant in their work. With the evolution of work, Eric urges employers to just try it.

Get ready to learn about the barriers to investing in the gig economy today and why they should be overcome.

In This Episode, You Will Learn:

·      How meritocracy is relevant to the gig economy.

·      What systems thinking is and the role it plays in the workplace.

·      How the role of job security has changed throughout generations.

·      How taking control of your career path leads to long-term achievement and staying relevant.

·      What the biggest fears employers have about hiring freelancers.

Some Questions I Ask:

·      Why employee and client satisfaction important to you? (1:27)

·      Whose responsibility is it to reskill? What is reskilling in the gig economy? (4:31)

·      What are the barriers to employers investing in the gig economy? (15:22)

·      What myths do you hear in your work? (22:39)

·      If you could tell Fortune 500 CEOs one thing based on your research and experience, what is it? (25:39)

Connect with Eric Gregg:


ClearlyRated (Inavero)


Made to Stick by Chip Heath & Dan Heath

The Forgotten 500 by Gregory A. Freeman

M365 Freelancer Toolkit


The Six-Figure Freelancer

Season 1, Ep. 11

How do you handle change?  

Change is one of the toughest barriers that prevents companies from hiring freelancers, and “traditional” workers from becoming freelancers. Diving into the unknown is daunting, especially when it means transforming an individual’s entire livelihood, or a company’s way of retaining talent. But once a flow is established and the unknown becomes familiar, it’s completely worth it.

In this episode, Jody Miller talks about her experience with hiring high-level executives with expertise and knowledge—who also happen to be freelancers themselves. She is the co-founder for Business Talent Group: a global platform for high-end business talent that seeks project-based work. She will help us see what companies have to do to engage these high-level freelancers, and how it will ultimately change companies for the better.  

Get ready to listen to Jody’s advice on how to gain a competitive edge in your industry through working within the gig economy.  

In This Episode, You Will Learn:  

  • Why it’s important to have flexibility and professional control over talent and ways to work.  
  • How freelancing removes stress from office politics.  
  • How companies can restructure work to incorporate the gig economy.  
  • How independent work can help individuals pursue work they love.  
  • What mindset change companies must have to effectively hire executive gig workers.  

Some Questions I Ask:  

  • Why is the gig economy the perfect economy for so many workers? (5:05) 
  • What obstacles affect companies looking to start hiring freelancers? (9:13) 
  • How can people find security within the gig economy? (11:35) 
  • What stigmas exist around hiring executive freelancers? (16:07) 
  • What myths have you encountered around the gig economy? (22:30) 

Connect with Jody Miller:  

Business Talent Group 



Angle of Repose by Wallace Stegner 

M365 Freelancer Toolkit 


MacGyver, College Parties, and the Gig Economy

Season 1, Ep. 10

The first step is always the hardest step.

When it comes to hiring freelancers or gig workers for large or small projects, picking the very first contractor is a daunting task on its own. It’s difficult to give up that control over the execution, no matter what size the task is.

The truth is, there are a lot of experts out there in the gig economy, just waiting for the right job to get posted for them. Once you find that freelancer who delivers above and beyond the expectations, tons of new opportunities open up.

In this episode, Liane Scult discusses her methods for identifying appropriate work to contract out and how to find that first freelancer for the job. Liane Scult is the Senior Freelance Program Manager at Microsoft. Her superpower is bringing people together, finding the right experts, and building something out of those resources she gathers.

Liane shares her insights into the importance of always asking why whenever the answer is no, and how to learn to delegate to a freelancer for the first time. She also discusses the long-term benefits of developing relationships within the gig economy, including how it impacts her career and the time she gets to spend with her family.

Get ready to learn how throwing in some grit, hustling, and creatively breaking down barriers can create your pathway to success in your work. 

In This Episode, You Will Learn:

·      What a day in the life looks like for Liane.

·      The importance of asking why? when creating solutions.

·      How Liane handles balancing work and life with the use of freelancers. 

·      How to handle the fears that come along with hiring freelancers for the first time.

·      The long-term value of developing relationships within the gig economy. 

Some Questions I Ask:

·      When did you realize your superpower of bringing people together and finding experts could make a change in the world? (3:38)

·      What’s something in your life that’s really inspired your work? (10:15)

·      How do you identify work that would be good for a freelancer? (13:02)

·      What have you learned about delegation? (18:12)

·      What advice would you give to someone thinking about doing a project with a freelancer? (21:15)

Connect with Liane Scult:




Give Work by Leila Janah

Wired to Care: How Companies Prosper When They Create Widespread Empathy  by Dev Patnaik

M365 Freelancer Toolkit


When Work Goes From Fixed to Fluid

Season 1, Ep. 9

Are you an expert? What does that mean?


Everything seems to be moving at the speed of light in today’s world, especially when it comes to the technology that makes it essential to work. Oftentimes, many professionals think that they’re experts in certain areas. In other words, people are generally poor judges of their own areas of expertise.


According to Antony Brydon, efficiency in a given problem area is what makes someone an expert. Antony Brydon is the co-founder of Directly, which is a leader in CX automation, helping companies deliver better customer service at scale. This sits at the center of AI and the gig economy, essentially helping replace outsource call centers with global networks of experts that deliver better answers.


In this episode, Antony discusses how utilizing real experts within a dynamic and fluid model will transform customer experiences. Specifically, Antony discusses what makes an expert, how to curate a pool of experts, and what role the marketplace plays in compensating experts for what they’re worth.


Get ready to learn how AI is transforming the meaning of expertise and how that’s impacting the gig economy.


In This Episode, You Will Learn:

·      Why focused marketplaces succeed more than broad marketplaces.

·      How Antony evaluates one’s level of expertise.

·      How Antony seeks to transform customer experiences.

·      Will Work persist over time?

·      Why listening skills are essential to success for entrepreneurs.


Some Questions I Ask:

·      How do you curate a pool of experts? (4:02)

·      What are some examples where AI and machine learning are being democratized? (7:45)

·      What’s the endgame? (10:30)

·      How does the marketplace handle different levels of expertise in relation to compensation? (17:06)

·      What film or book has made the biggest impact on you over the past year? (20:29)


Connect with Antony Brydon:





The Audacity to Win by David Plouffe

M365 Freelancer Toolkit


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


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


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: