What do red shoes and a sloth mascot have in common? They’re all part of the wild ride that is Mike Stafiej’s leadership style.

In this delightfully unfiltered episode of Inside the C-Suite, Christy Honeycutt sits down with Mike Stafiej, CEO of ERIN - a referral automation platform with serious enterprise muscle and an even stronger personality.

Known as “The Fun CEO” for a reason, Mike shares how he’s

They dive headfirst into:

Whether you’re bootstrapping your dream or riding the post-funding rollercoaster, Mike’s story is a masterclass in leading with grit, humility, and a touch of ridiculous.

And if you’re not building something fun… why build it

| Connect with Us |

Learn more about ERIN:

https://erinapp.com/

Follow Mike Stafiej:

LinkedIn - https://www.linkedin.com/in/michaelstafiej/

(The Fun CEO himself – known for sloth-themed branding, pixel-perfect marketing, and leading Aaron with equal parts grit and weirdness) 

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Giuliana Corbo, the CEO of Nearsure, scaled her company to 22 countries by the age of 32, proving that age is just a number when it comes to leading a global business. She shares her no-BS approach to leadership, project management, and building a company culture that thrives under pressure. Along the way, Giuliana reveals the untold challenges of being a young CEO in the tech industry.

In this episode, we look at entrepreneurship, project management, leadership, mentorship, company culture, software development, business growth, and the impact of women in tech. Giuliana's insights uncover the importance of decisive communication, handling emotional challenges, and staying agile while scaling a business rapidly.

➡️ Nearsure operates in 22 countries solving business problems through technology.

➡️ Most of Nearsure’s clients are in the healthcare space, highlighting a niche focus.

➡️ Effective project management is crucial for successful outsourcing and client satisfaction.

➡️ Giuliana's journey into entrepreneurship began at a young age, driven by a passion for tech.

➡️ Crafting a business plan was an emotionally challenging but necessary step.

➡️ Leadership, for Giuliana, means making tough decisions while prioritizing team well-being.

➡️ Mentorship played a significant role in Giuliana's career development and growth.

➡️ Company culture is a cornerstone of Nearsure's rapid growth and team dynamics.

➡️ Strategic communication within teams helps maintain alignment and efficiency.

➡️ Giuliana’s leadership style has evolved with the company’s expansion and challenges.

➡️ Investing opportunities are being explored as Nearsure scales further.

➡️ The nearshore business model offers a unique advantage in talent accessibility and cost-efficiency.

💬 Hot take or just hype? Are we headed toward a new normal, or is this just workplace chaos rebranded? Drop your thoughts in the comments!

00:00 — Introduction to Giuliana Corbo and Nearsure

02:55 — Exploring Nearsure's Business Model and Clientele

05:58 — Project Management and Team Dynamics

09:04 — Giuliana's Journey to Entrepreneurship

11:46 — The Challenges of Writing a Business Plan

14:59 — Leadership and Company Growth

18:08 — Mentorship and Personal Development

20:48 — The Reality of Being a CEO

23:52 — Cultural Integrity in Rapid Growth

26:54 — Reflections on Leadership and Future Aspirations

🔗 Connect with Giuliana Corbo: https://www.linkedin.com/in/giulianacorbo/

🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/

🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/

🔗 Site: http://www.wrkdefined.com

🎥 TikTok: https://www.tiktok.com/@wrkdefined

💼 LinkedIn: https://www.linkedin.com/company/wrkdefined

📘 Facebook: https://www.facebook.com/WRKdefined/

🐦 Twitter (X): https://twitter.com/WRKdefined

📩 Substack: https://wrkdefined.substack.com

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Nicole Sahin shares her journey from anthropology to entrepreneurship, leading G-P to simplify global employment. She discusses the challenges of compliance, the acceleration of remote work due to COVID-19, and the role of intuition in business decisions. Nicole’s insights on building a global infrastructure and the hurdles faced by female entrepreneurs highlight the intricacies of leading a global company.

In this episode, we look at globalization, remote work, compliance, entrepreneurship, AI, SaaS, hiring, business growth, leadership, and data ownership. Nicole’s experiences and strategies offer valuable lessons for navigating the complexities of global business and building high-performing teams.

➡️ G-P simplifies hiring across borders.

➡️ The complexity of global compliance is often underestimated.

➡️ COVID-19 has accelerated the acceptance of remote work.

➡️ Entrepreneurship requires strong intuition and adaptability.

➡️ Building a global infrastructure takes time and investment.

➡️ Female entrepreneurs face unique challenges in business.

➡️ High-performing teams are essential for company growth.

➡️ The role of board members is crucial for support and guidance.

➡️ Data ownership is vital for compliance and scalability.

➡️ The evolution of work culture is reshaping hiring practices.

➡️ Intuition can be a powerful tool for business decisions.

➡️ Managing team dynamics requires clear communication and trust.

Chapters

00:00 Introduction to G-P

03:10 The Global Employer of Record Model

05:55 Nicole's Journey to Founding G-P

08:48 The Evolution of Global Hiring

10:45 Navigating Compliance and Legal Risks

12:49 The Impact of COVID-19 on Remote Work

15:40 The Future of Global Employment

20:20 The Journey of a Female Entrepreneur

21:57 Building High-Performing Teams

24:57 Navigating Difficult Conversations

29:01 Managing Team Dynamics

32:31 The Role of Board Members

35:16 Finding Trusted Advisors

💬 What’s your take? Are we headed toward a new normal, or just workplace chaos? Drop your thoughts in the comments!

🔗 Connect with Nicole Sahin: https://www.linkedin.com/in/nicolesahin/

🔗 Connect with G-P: https://www.globalization-partners.com/

🔗 Site: http://www.wrkdefined.com

🎥 TikTok: https://www.tiktok.com/@wrkdefined

💼 LinkedIn: https://www.linkedin.com/company/wrkdefined

📘 Facebook: https://www.facebook.com/WRKdefined/

🐦 Twitter (X): https://twitter.com/WRKdefined

📩 Substack: https://wrkdefined.substack.com

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Startup life isn’t for the faint of heart—especially for women entrepreneurs. Caitlin MacGregor, CEO and co-founder of Plum, pulls back the curtain on what it really takes to build a company, secure funding, and challenge gender bias in venture capital. From navigating the complexities of co-founding a business with her husband to finding the right mentors, Caitlin shares the highs, lows, and lessons from her journey.

In this episode, we look at the fundraising hurdles women face, the unique mindset of Canadian entrepreneurs, the evolving role of venture capital in supporting social impact, and how mentorship and executive coaching shape leadership success.

➡️ Plum helps companies match candidates to roles for better productivity and fulfillment.

➡️ Co-founding a business with a spouse brings unique strengths and challenges.

➡️ Mentorship is a game-changer in leadership growth and career success.

➡️ Women face systemic barriers in raising venture capital compared to men.

➡️ Female investors are often more supportive of women-led businesses.

➡️ Caitlin’s executive coach transformed her approach to leadership at 27.

➡️ Work-life balance is a myth—what matters is setting the right boundaries.

➡️ Canadian entrepreneurs approach risk differently than their U.S. counterparts.

➡️ The startup world is shifting toward a greater focus on social impact.

➡️ Engaging men in women’s leadership conversations is crucial for real change.

➡️ Entrepreneurs shouldn’t rely on luck—everyone has the potential to lead.

➡️ The venture capital landscape is slowly evolving, but there’s still work to do.

Caitlin MacGregor: https://www.linkedin.com/in/caitlinmacgregor

Learn more about Plum here: https://www.plum.io/about

🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/

🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/

🔗 Site: http://www.wrkdefined.com

🎥 TikTok: https://www.tiktok.com/@wrkdefined

💼 LinkedIn: https://www.linkedin.com/company/wrkdefined

📘 Facebook: https://www.facebook.com/WRKdefined/

🐦 Twitter (X): https://twitter.com/WRKdefined

📩 Substack: https://wrkdefined.substack.com

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HR isn’t what it used to be, and neither are career paths. In this episode, we sit down with Jon Lowe, Chief People Officer at DailyPay to explore the evolution of HR, the importance of self-awareness in career choices, and why adaptability is the key to success. From home improvement projects that went hilariously wrong to lessons learned in the workplace, we discuss how grit, intentionality, and accountability shape personal and professional growth.

In this episode, we look at earned wage access, HR transformation, professional development, and career pivots—breaking down the unpredictable nature of the job market and how to find the right workplace fit. Whether you’re in HR, exploring new career opportunities, or just trying to navigate life’s unexpected turns, this conversation is packed with insights and laughs.

➡️ Home improvement projects can spark unexpected (and hilarious) neighbor disputes.

➡️ The role of HR is evolving—fast.

➡️ Self-awareness is critical in shaping career paths.

➡️ No two days in HR look the same.

➡️ Personal growth often comes from career pivots.

➡️ Humor makes even the toughest career lessons more bearable.

➡️ Workplace dynamics are changing, and adaptability is key.

➡️ Career paths are rarely linear—embrace the pivots.

➡️ HR titles and responsibilities are often misunderstood.

➡️ Family expectations can heavily influence career choices.

➡️ There’s a lack of real resources for career guidance.

➡️ Most people don’t end up working in their college major.

➡️ Finding work you enjoy is more important than chasing a title.

➡️ Grit and adaptability determine long-term success.

➡️ Building something meaningful beats maintaining the status quo.

➡️ Intentional career choices lead to better opportunities.

➡️ Self-reflection is essential for personal and professional growth.

➡️ Accountability is the backbone of career development.

➡️ The job market is always changing—flexibility is a must.

Chapters

00:00 Building Projects and Neighborly Relations

05:01 Introduction to DailyPay and HR Evolution

10:00 The Changing Landscape of HR

12:50 Jon Lowe's Journey: From High School to Career

20:00 Self-Awareness and Career Choices

20:32 Navigating Career Choices and Education

23:00 The Journey from College to Career

29:01 Finding the Right Fit in the Workplace

35:12 Building a Career in Tech and Beyond

41:11 The Importance of Grit and Adaptability

46:52 Intentionality in Career Growth

🔗 Connect with Jon Lowe: https://www.linkedin.com/in/lowejon/

🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/

🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/

🔗 Site: http://www.wrkdefined.com

🎥 TikTok: https://www.tiktok.com/@wrkdefined

💼 LinkedIn: https://www.linkedin.com/company/wrkdefined

📘 Facebook: https://www.facebook.com/WRKdefined/

🐦 Twitter (X): https://twitter.com/WRKdefined

📩 Substack: https://wrkdefined.substack.com

🔥 What’s your take? Is career success more about luck or grit? Drop your thoughts in the comments!

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Lara Abrash didn’t just climb the corporate ladder—she redefined the ascent. As Chair of Deloitte’s US firm, she leads one of the most influential professional services organizations in the world. But leadership isn’t just about strategy and governance; it’s about listening, making tough decisions, and preparing the next generation for success.

In this episode, we dive into Lara’s career journey, the lessons that shaped her leadership style, and the pivotal role mentorship played along the way. She shares why listening is an active skill, why calculated risks drive innovation, and how personal fulfillment should be at the core of career decisions. From navigating the complexities of corporate governance to the evolution of mentorship in a fast-changing business world, Lara offers an unfiltered look at what it takes to lead at the highest level.

Chapters

00:00 Who is Lara Abrash and Deloitte

02:52 The Role of the Chair at Deloitte

05:59 Navigating Decision-Making in a Complex Environment

09:00 The Importance of Listening as a Leader

11:58 Personal Influences and Early Aspirations

15:00 Career Journey and Growth at Deloitte

18:58 Navigating Corporate Culture and Personal Growth

21:10 The Importance of Fulfillment in Career Choices

22:48 Understanding the Art of Accounting

25:37 The Role of Leadership vs. Management

28:06 Transitioning from Manager to Leader

35:07 The Evolution of Mentorship

38:47 Key Ideas for Aspiring Leaders

42:04 Stewardship and Future Leadership

🔗 Site: http://www.wrkdefined.com

🎥 TikTok: https://www.tiktok.com/@wrkdefined

💼 LinkedIn: https://www.linkedin.com/company/wrkdefined

📘 Facebook: https://www.facebook.com/WRKdefined/

🐦 Twitter (X): https://twitter.com/WRKdefined

📩 Substack: https://wrkdefined.substack.com/

🔥 Share your brand across the WRKdefined Podcast Network: https://wrkdefined.com/work

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James Cross’s career has been anything but linear. A musician turned teacher turned tech entrepreneur, he’s spent years figuring out how to make learning more engaging, scalable, and effective. Along the way, he’s explored how AI can transform leadership development, making personalized coaching accessible to the next generation of managers.

Here's a quick breakdown: https://www.tiktok.com/@wrkdefined/video/7465459318578482462

In this episode, we look at football, e-learning, AI, leadership development, skills training, music education, technology, corporate training, personal journey, innovation, education, video technology, startups, corporate culture, business strategy, and employee engagement. James breaks down how startups can stay focused, why video is reshaping education, and the real-world challenges of scaling AI-powered learning solutions.

Connect with James here: https://www.linkedin.com/in/jamesrcross/

Connect with William Tincup LinkedIn: https://www.linkedin.com/in/tincup/

Connect with Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/

The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok

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Career agility isn’t just a buzzword—it’s the backbone of success. In this episode, Joelle Smith, President of First Advantage, dives into her journey from marine science to tech leadership. She reveals how learning agility, integrity, and hustle have fueled her path, offering insights on sales, mentorship, and thriving in male-dominated industries.

In this episode, we look at podcast, career development, learning agility, college experience, sales, integrity, hustle, Joelle Smith, First Advantage, technology, diversity, mentorship, decision-making, leadership, business strategy, team culture, women in business, networking.

William Tincup LinkedIn: https://www.linkedin.com/in/tincup/

Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/

Connect with WRKdefined on your favorite social network:

The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok

Share your brand across the WRKdefined Podcast Network

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Offboarding isn’t just a goodbye—it’s a strategy. Andy Hamilton dives into why this often-overlooked process can make or break employer branding. We explore how When is redefining offboarding to foster strong alumni networks, improve team dynamics, and boost long-term organizational growth.

In this episode, we look at offboarding, employee experience, employer branding, alumni network, career transitions, team dynamics, leadership, and startup challenges in the tech industry. From building transparent teams to balancing salesmanship with technical skills, Andy shares actionable insights that bridge the gap between career growth and business success.

Chapters

00:00 Philadelphia Roots and Real Estate Ventures

05:57 The Importance of Offboarding in Employee Lifecycle

11:56 The Financial Implications of Offboarding

17:54 Navigating Career Moves with Intent

23:18 Navigating Career Growth in Tech

30:03 Salesmanship vs. Technical Reality

37:41 Transitioning to Short-Term Rentals with Apartments Jet

44:19 Building and Leading Effective Teams

Connect with Andrew Hamilton is the Co-Founder and CEO of When, an AI-powered offboarding platform and severance solution. https://www.linkedin.com/in/hamiltonac8/

William Tincup LinkedIn: https://www.linkedin.com/in/tincup/

Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/

Connect with WRKdefined on your favorite social network:

The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok

Share your brand across the WRKdefined Podcast Network

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Jon Shanahan, CEO of Businessolver, shares the intricate journey of transforming employee benefits enrollment through technology. We dive into the challenges of annual enrollment, team building, and the psychology behind decision-making. Jon’s insights cover everything from mentorship to personal sacrifices, offering a roadmap for leadership and innovation.

In this episode, we look at Businessolver, employee benefits, annual enrollment, entrepreneurship, insurance industry, technology, team building, community, challenges, personal growth, organizational psychology, decision-making, leadership, company growth, mentorship, sacrifices, employee benefits, and culture.

Key Takeaways

Chapters

00:00 Who is Jon Shanahan and businessolver

03:04 The Evolution of Employee Benefits Enrollment

05:54 The Journey of Entrepreneurship

09:10 Navigating Challenges in the Insurance Industry

12:00 Building a Team and Finding Success

14:53 The Importance of Community and Timing

18:00 Personal Reflections and Future Aspirations

19:10 Understanding People and Organizational Psychology

21:31 The Evolution of Decision Making in Growing Companies

25:00 The Balance of Control and Trust in Leadership

28:32 Navigating Growth and Technological Advancements

32:11 The Importance of Mentorship and Career Growth

37:26 Sacrifices and Trade-offs in Entrepreneurship

Connect with Jon Shanahan, CEO and Co-Founder at businessolver: https://www.linkedin.com/in/jon-shanahan/

William Tincup LinkedIn: https://www.linkedin.com/in/tincup/

Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/

Connect with WRKdefined on your favorite social network

The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok

Share your brand across the WRKdefined Podcast Network

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