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The PEO Speedwagon Podcast is a dynamic and engaging podcast that delves into the intricate world of outsourcing and PEOs. Focusing on how small businesses can leverage Professional Employer Organizations (PEOs) to their advantage. Each episode unpacks the complexities of PEOs in a conversational and accessible manner, aiming to demystify the process and highlight its benefits. With a blend of expert insights, real-world examples, and a touch of humor. The PEO Speedwagon Podcast is the go-to resource for anyone looking to optimize their opterations and foster growth.
Watch or listen on Spotify | Apple Podcasts | YouTube
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42:18
Adam Robin, Founder, Inbox Zero VA
Buying Back Your Time with Adam Robin | Hosted by Heather Applegate & Ryan Shapiro
In a first for the PEO Speedwagon Podcast, Heather Applegate officially takes her seat behind the mic alongside Ryan Shapiro as co-host. And she wastes no time diving into one of the biggest challenges facing founders and business leaders today:
How do you get your time back?
Joined by Adam Robin, founder of Inbox Zero, the conversation explores the reality of entrepreneurship, burnout, delegation, virtual assistants, AI, and the difficult transition from doing everything yourself to building systems that create freedom.
Adam shares his journey from physical therapist and practice owner to helping organizations reclaim bandwidth through intentional outsourcing and operational efficiency. Along the way, the group discusses:
✅ Why entrepreneurs hit the wall
✅ The hidden cost of doing everything yourself
✅ How to identify high-energy vs. low-energy work
✅ Virtual assistants, AI, and the future of productivity
✅ Leadership lessons for founders who struggle to let go
✅ Practical ways to buy back your time and focus on what matters most
If you've ever felt buried in admin work, stretched too thin, or trapped inside your own business, this episode is for you.
Because sometimes growth isn't about doing more.
It's about creating space to do the right things.
35:54
Heather Applegate, Founder, Pivot X
In this episode of the PEO Speedwagon Podcast, Ryan Shapiro sits down with Heather Applegate, founder of Pivot X, to explore leadership development, strategic planning, organizational growth, and the human behaviors that shape business success.
The conversation dives into:
• Why pivots are an inevitable part of business growth
• The difference between influence and authority in leadership
• How personality assessments can help leaders unlock greater impact
• Why some leaders thrive naturally while others must work harder to achieve the same results
• The role of self-awareness, feedback, and personal development in leadership success
• Strategic planning, organizational alignment, and executive decision-making
Along the way, Ryan and Heather share stories about entrepreneurship, leadership journeys, personality assessments, and the realities of building organizations through people.
45:01
PEO Speedwagon: Kasey Devine, CEO + Founder, Entravia
In this engaging interview, Kasey Devine, CEO + Founder of Entravia, shares with host Ryan Shapiro, his journey into the PEO industry, discusses industry challenges, and explores the future of PEO technology and market dynamics. Discover insights on industry evolution, technology adoption, and how small businesses can leverage PEOs for growth.
PEO industry, small business, HR technology, industry evolution, market consolidation, SaaS, innovation, broker relationships, industry future
Key topics
Industry evolution and consolidation
Technology and SaaS impact on PEO
Small business benefits and challenges in PEO
44:59
Marc Nudelberg, CEO, On the Ball
In this episode of the PEO Speedwagon, Ryan chats with Marc Nudelberg, CEO of On the Ball.
Marc shares insights from his diverse career, emphasizing the importance of mindset, behaviors, and preparation in achieving success. Discover how sports principles translate to business growth and the power of social media in modern sales.
KEY TOPICS:
• The role of mindset and behavior in success
• Translating sports principles to business
• The impact of social media on sales and networking
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52:58
Monica Thompson and Chris Hill, Vensure HR
In this episode, Rick Johnson and Ryan Shapiro host a dynamic duo from VentureHR, Chris Hill and Monica Thompson, to explore the intricacies of sales, trust-building, and technology demos in the PEO industry. Discover expert insights on how to accelerate sales processes, customize demos, and leverage AI and partnerships for growth.
45:47
Marcus Wilbers Part 2, Founder of MW Legal
In this episode of the PEO Speedwagon podcast, host Rick Johnson and co-host Ryan Shapiro welcome back Marcus Wilbers, the first returning guest. They discuss Marcus's new venture, MW Legal, and its role in the PEO space. The conversation explores the complexities of legal advice, the impact of AI, and the rise of fractional services. They also delve into the growing importance of PEO brokers and the evolving landscape of the PEO industry, emphasizing the need for specialization and the value of collective experience.
29:47
Rob Timmermann, Founder of Timmermann Group
In this episode of the PTO Speedwagon podcast, host Rick Johnson and co-host Ryan Shapiro welcome Rob Timmerman, founder and CEO of the Timmerman Group. They discuss Rob's entrepreneurial journey, the evolution of digital marketing, the importance of SEO and pay-per-click strategies, and the innovative flywheel concept in marketing. The conversation also delves into the role of AI in marketing, the balance between AI and human creativity, and the signs that indicate when a business should seek help in their marketing efforts.
22:53
Allison McCutcheon Barcz, Executive Partner of Glowe Connective
Rick Johnson and Ryan Shapiro sit down with Allison McCutcheon Barcz, Executive Partner at Glowe Connective, to unpack what truly drives successful organizational transformation. With more than two decades of experience in HR, leadership development, and change management, Allison brings a grounded, practical perspective on how leaders can shift culture, elevate performance, and handle the human side of growth.
Glowe Connective, a St. Louis-based consulting firm specializing in transformation, change management, strategy, executive coaching, culture, and communication, helps leaders execute their most important organizational changes through consulting, coaching, and training. Allison gives a behind-the-scenes look at how that work actually happens inside real companies.
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08:59
Season 2 Finale
In this reflective episode, Rick reviews the journey of the PEO Speedwagon podcast over its two seasons, sharing insights gained from conversations with industry leaders and the importance of understanding the human aspect of PEO relationships. He emphasizes the need for curiosity, deeper questioning, and the significance of cultural fit in PEO partnerships. The episode also highlights key lessons learned and expresses gratitude to listeners while looking forward to future seasons.
31:57
Busting the Biggest PEO Myths
Think PEOs are only for "the other guys"? Worried you’ll lose control of your employees? In this episode of PEO Speedwagon, Rick Johnson and Ryan Shapiro bust the most common myths about Professional Employer Organizations.
They break down what co-employment really means, why PEOs don’t replace your HR team, and how even small businesses can unlock big value—especially when it comes to benefits, compliance, and cost control. You’ll also get clear insights into SUTA rates, workers’ comp, and the key metrics to track when evaluating a PEO partnership.
If you’ve ever wondered, “Is a PEO right for me?”—this is your episode.
23:34
Rachel McDougall: CEO of PEOMG
In this episode of the PEO Speedwagon podcast, host Rick Johnson welcomes Rachel McDougall, the new CEO of PEOMG, and Ryan Shapiro, the president. They discuss the origins of PEOMG, its disruptive approach to the PEO industry, and Rachel's transition into the CEO role. The conversation highlights the company's commitment to small businesses, innovative client engagement strategies, and the importance of implementation and ongoing support. Rachel shares her vision for the future growth of PEOMG, including plans for events in various markets and the meaning behind the company's name.
32:06
Rick Shapiro: 70 years of Lessons, Leadership & Love
Ryan Shapiro interviews his father, Rick Shapiro, on the occasion of his 70th birthday. They discuss Rick's journey through entrepreneurship, the challenges of balancing work and family life, and the importance of genuine connections in both business and personal relationships. Rick shares valuable lessons learned over the years, emphasizing the significance of caring for employees and maintaining a human touch in an increasingly digital world. The conversation culminates in reflections on life, leadership, and the legacy one leaves behind.
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36:14
Episode 10: Season 1 Finale, Rapid Fire Evaluations!
In this season 1 Finale of the PEO Speedwagon Podcast Rick and Ryan look back on the first few episodes, the leaps and bounds made improving the show and then go into a rapid fire evaluation of 3 company profiles from all over the spectrum: On site bioscience laboratories, small non-profits, to nationwide tech companies. Hop in the speedwagon, join us, and learn how we evaluate which PEO or outsourced HR solution is the best fit!
See you in Season 2!
32:52
Episode 9: Kansas City, FTC, and Along Came a Spider
In this episode of PEO Speedwagon, hosts Rick and Ryan discuss the challenges of multi-state compliance and recent FTC rulings on non-compete agreements. Insights from Ryan's trip to KC highlight the importance of personal connections in understanding diverse market needs. The episode also touches on the role of PEOs in enhancing company culture and preparing businesses for regulatory changes affecting employee mobility.
Official FTC details: The FTC's recent ruling regarding Federal Trade Commission Act (FTC Act) (15 USC 45) potentially restricts non-compete clauses, suggesting they might unfairly limit employment opportunities, though this interpretation is subject to change pending further legal review.
16:11
Episode 8: Things are Lining Up!
Embark on a journey of reflection and change in Episode 8 of the PEO Speedwagon podcast, where we candidly share out experiences, from laughing off technical glitches of podcasts hosting and sponsored ballpark nights with clients. Delving into recent client onboarding, we explore the transformative impact of PEO platforms on organizational efficiency and employee employment. Uncover the seasonality of marketing efforts in the PEO industry as we navigate the dynamic landscape of decision making processes and the catalysts for change. Join us as we offer insights and stories that resonate with our "Wagoneers" old and new. Stay tuned for more episodes as we continue to explore the the intersections of technology, business and human connection.
20:23
Episode 7: Empower your Existing HR
In this Spring episode of PEO Speedwagon, Rick and Ryan discusses the nuanced process of matching Professional Employer Organizations (PEOs) with existing HR frameworks. They emphasizes the importance of understanding a company's current HR setup, the diverse range of PEO services, and the critical role of strategic alignment between a company's HR goals and a PEO's offerings. The conversation highlights the potential for PEOs to complement and enhance HR functions, fostering organizational growth and employee satisfaction.
Ready to do this?
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