The Corporate Couch: Work Stories I Only Tell My Friends

From Flatlander to WellSky: Lumberjacks, Startups, and Leading at Scale with Bill Miller

What does a former choker setter in the Washington woods have to do with leading one of the country’s largest healthcare technology companies? More than you might think. Bill Miller (see bio below), Chairman and CEO of WellSky, shares a career journey that started far from the executive suite: growing up in a big Midwest family, running a paper route at seven years old, chasing football dreams, getting injured, and unexpectedly spending a summer in Washington working one of the most dangerous jobs in the country. His logging crew called him “Flatlander,” hid his horse, and gave him the kind of life lessons that do not show up in most MBA programs. From there, Bill’s path took him from Capitol Hill to urban planning, early internet startups, Cerner, OptumInsight, and eventually WellSky, where he has helped transform the company into a healthcare technology leader serving more than 20,000 clients across acute, post-acute, and community care. We talk about: • Why work ethic started early, with a paper route before sunrise • The summer as a Washington “Flatlander” that changed his perspective • What startups taught him about risk, resilience, and eating what you kill • His front-row seat to the early internet boom in Kansas City • What he learned at Cerner and Optum about scale, healthcare, and leadership • How WellSky grew from a struggling 400-person company into a 3,200-person platform • Why culture, communication, and mentorship matter even more as companies grow • How AI is reshaping healthcare technology and changing what is possible Bill also shares candid thoughts on leading through COVID, bringing people back to the office, building culture intentionally, and why he still attends new-hire onboarding sessions to stay connected to the people joining WellSky. This is a conversation about grit, timing, technology, leadership, and building something meaningful without forgetting where you came from. And yes…we also cover paper routes, Porsche road trips, hidden horses, and why sometimes the best leadership development program is surviving a summer with lumberjacks.   This episode is brought to you by... Ever wish your company updates could be less "quarterly earnings report" and more "late-night talk show"? At Pelaccio & Partners, we're revolutionizing internal communications with podcasts that employees actually want to listen to. Imagine podcast episodes that make your employees laugh while staying informed. Our founder, Jeff Pelaccio, doesn't just create podcasts; he creates conversations that break through the noise. Whether you're a growing startup or a massive corporation, we turn your company's story into audio gold. Leadership becomes human. Remote teams feel connected. Your message cuts through the clutter. Jeff is happy to share his insights on improving your culture, increasing employee engagement, and retention. You can contact him via LinkedIn or schedule a Zoom call via this link - 15-minute call with Jeff [https://calendly.com/jeffpelaccio/zoom-15-minute-call-with-jeff].   About Bill: Bill Miller is the Chairman and CEO of WellSky, one of America’s largest and most innovative healthcare technology companies, serving more than 20,000 clients across acute, post-acute, and community care.  With more than 25 years of experience in healthcare technology, Bill has built a career around growth, innovation, and leading companies through meaningful transformation. Since joining WellSky in 2017, he has guided the company into new markets, overseen more than 14 strategic acquisitions, and helped establish the WellSky Foundation. Before WellSky, Bill served as CEO of OptumInsight, where he helped drive major revenue growth and expanded the company’s position in healthcare analytics. Earlier in his career, he held senior leadership roles at Cerner Corporation, with global responsibility for managed services, outsourcing, and technology services. Bill is a University of Kansas graduate and currently serves on the boards of Lyric and the WellSky Foundation.

From Classroom Chaos to Manufacturing Momentum with Katherine O’Toole

What do baby chicks, broken feet, youth sports, elementary school classrooms, and precision manufacturing have in common? Katherine O’Toole (bio below). Katherine’s career journey starts in the classroom, where she spent 11 years as an elementary educator, and eventually leads to her current role as Executive Director of the Kansas City Chapter of the National Tooling & Machining Association. Along the way, she discovered that teaching, workforce development, and manufacturing have more in common than you might think: people, problem-solving, communication, and the willingness to build something better. Katherine brings tremendous energy and honesty to this conversation. She talks about growing up in Kansas City, following her mother’s path into education, leaving teaching to explore a new chapter, and eventually stepping into the manufacturing world, an industry already connected to her family through her dad’s tool and die shop. We talk about: • Why teaching prepared her for leadership, advocacy, and workforce development • How she helped rebuild momentum for the Kansas City NTMA after COVID • Why manufacturing companies can compete and still collaborate • The importance of exposing students, parents, and educators to skilled trades • Why college is not the only path to a successful career • Her work supporting women in manufacturing through She Leads: Women Driving Manufacturing • Why mentorship, networking, and showing up matter so much early in a career. Katherine also shares some wonderfully Corporate Couch stories, including being a “passenger princess,” raising chickens in her basement office, breaking her foot while setting up a BattleBot event, and somehow still making it to a pickleball gathering before finally going to the ER. This is a conversation about career reinvention, community building, workforce development, and the power of bringing the right people into the right rooms. And yes…if you are looking for someone to back up the car on a road trip, Katherine would like to respectfully nominate literally anyone else.   This episode is brought to you by... Ever wish your company updates could be less "quarterly earnings report" and more "late-night talk show"? At Pelaccio & Partners, we're revolutionizing internal communications with podcasts that employees actually want to listen to. Imagine podcast episodes that make your employees laugh while staying informed. Our founder, Jeff Pelaccio, doesn't just create podcasts; he creates conversations that break through the noise. Whether you're a growing startup or a massive corporation, we turn your company's story into audio gold. Leadership becomes human. Remote teams feel connected. Your message cuts through the clutter. Jeff is happy to share his insights on improving your culture, increasing employee engagement, and retention. You can contact him via LinkedIn or schedule a Zoom call via this link - 15-minute call with Jeff [https://calendly.com/jeffpelaccio/zoom-15-minute-call-with-jeff].   About Katherine: Katherine O’Toole is an Executive Director, career and technical education advocate, and workforce development champion. She currently serves the Kansas City Chapter of the National Tooling & Machining Association, where she spearheads networking, advocacy, and workforce development initiatives. Katherine is also a founding member of She Leads. Women Driving Manufacturing, a network of leaders dedicated to educating and empowering women in and around the manufacturing industry. Prior to entering the industry, she spent eleven years as an elementary educator in the Gardner Edgerton School District.

Special Edition: It’s 5 O’Clock Somewhere – Big Goals, Parking Lot Pranks, and Vacationing in Your Own City Your Own City

In this May edition of *It’s 5 O’Clock Somewhere*, Marc Shaffer and I are back with another happy hour-style conversation about what’s working, what we’re learning, and why the best connections often happen when you least expect them.  We start with the aftermath of Searcy Financial’s 50th anniversary celebration, including a harmless little parking lot prank involving Marc’s car. From there, we talk about the incredible momentum behind Run for the Roses, which has raised more than $320,000 for Growing Futures, crushing its original $150,000 goal.  We also dig into: * Searcy’s strategic planning week and what it means to think 3 and 10 years ahead * The challenge and opportunity of leading a team spread across the country * Volunteering, scavenger hunts, streetcars, and “vacationing” in your own city * Kansas City restaurant shoutouts, including Ragazza, Joe’s Kansas City, OurHouse, Bamboo Penny’s, and Classic Cup * Our upcoming tag-team talk for Next KC * Teaching kids about money before they start charging property taxes on their toy Lexus * Adam Grant’s *Think Again* and the importance of questioning what we think we know Marc also previews a trip to Pittsburgh, a new advisor credential, and a visit to PNC Park, which leads, naturally, to a little downtown baseball stadium talk. As always, this episode is part business, part life, part community, and part “two friends talking over drinks.” Grab a drink. Pull up a chair. It’s five o’clock somewhere.   This episode is brought to you by Searcy Financial. Your financial future begins with a simple question: Where do you want to be? At Searcy Financial, we help successful individuals and families through our mission to simplify your financial journey, empowering you to enjoy life and wealth on your terms. The question sparks a conversation that goes beyond numbers, helping us understand what truly matters to you and the kind of financial plan that aligns with your life goals. It also allows us to identify potential challenges and opportunities so we can proactively address them. The outcome is a plan that empowers you to acquire, grow, and preserve your wealth. Searcy Financial is gearing up to celebrate 50 years of service. Don’t miss out on any of the excitement! To sign up for information on Marc’s book, “One for All,” including where to buy and exclusive website content, or to sign up for the Searcy Financial Wealth Matters email newsletter, use the links below: - Marc's Book "One for All": Keep Me Updated! [https://searcyfinancial.com/oneforall] - "Wealth Matters" newsletter: Sign Me Up! [https://searcyfinancial.myflodesk.com/news]   The opinions expressed herein are those of certain Searcy Financial Services, Inc. personnel and are subject to change without notice. The opinions referenced are as of the date of publication and are subject to revision due to changes in the market or economic conditions and may not necessarily come to pass. Any opinions, promotion, endorsement, projections, or forward-looking statements expressed herein are solely those of the author, may differ from the views or opinions expressed by other areas of the firm, and are only for general informational purposes as of the date indicated. Searcy Financial Services, Inc. was not compensated, nor are there material conflicts of interest that would affect the given statement.

From Hard Knocks to Big Wins: Building Teams That Actually Execute with Ron Cox

What does it take to turn a company losing millions into a high-performing organization with hundreds of millions in revenue? Ron Cox (see bio below) has lived that story. But his leadership journey started long before the turnaround. In this episode of *The Corporate Couch*, Ron shares a powerful story of resilience, reinvention, and purpose. He opens up about overcoming deep personal hardship, including childhood abuse, serious health challenges, and a moment in his life when he nearly gave up completely. Those experiences didn’t break his desire to lead. They shaped it. Ron went on to spend nearly 40 years helping organizations grow, adapt, and win. As the former CEO of The Kincaid Group, he helped lead an extraordinary turnaround, moving the company from a $2.5 million loss to roughly $320 million in revenue while building a culture rooted in performance, accountability, and execution. We talk about: • Turning pain into purpose • Leading a company through a dramatic turnaround • Why accountability only works when people know you care • How Stephen Covey’s principles shaped his coaching and leadership • What it takes to turn big vision into real-world execution • Why developing people is the real work of leadership Ron also shares lessons from entrepreneurship, city development, education, executive coaching, and his current work through RC Development Solutions, where he helps leaders and teams turn ideas into action. This is a conversation about survival, service, leadership, and leaving people and organizations better than you found them. If you care about resilience, growth, culture, or what it really takes to lead through adversity, this episode delivers.   This episode is brought to you by... Ever wish your company updates could be less "quarterly earnings report" and more "late-night talk show"? At Pelaccio & Partners, we're revolutionizing internal communications with podcasts that employees actually want to listen to. Imagine podcast episodes that make your employees laugh while staying informed. Our founder, Jeff Pelaccio, doesn't just create podcasts; he creates conversations that break through the noise. Whether you're a growing startup or a massive corporation, we turn your company's story into audio gold. Leadership becomes human. Remote teams feel connected. Your message cuts through the clutter. Jeff is happy to share his insights on improving your culture, increasing employee engagement, and retention. You can contact him via LinkedIn or schedule a Zoom call via this link - 15-minute call with Jeff [https://calendly.com/jeffpelaccio/zoom-15-minute-call-with-jeff].   About Ron:  Ron Cox is a seasoned executive, entrepreneur, and leadership coach who has spent nearly 40 years helping organizations grow, adapt, and win. As CEO of RC Development Solutions, he works with leaders and teams to turn big vision into real-world results.  Ron previously led The Kincaid Group through an incredible turnaround—taking the company from a $2.5M loss to roughly $320M in revenue—while building a culture focused on performance and accountability. His career spans both the public and private sectors, including nationally recognized work in city development and education. Along the way, Ron has coached leaders using principles from Dr. Stephen Covey, collaborated with influential business figures, and authored an Amazon best-selling book. At his core, he’s passionate about developing people, creating opportunities, and leaving organizations better than he found them.

Leadership Isn’t a Light Switch: Parenting, Pressure, and Showing Up Whole with Kori Bloom

What if the best leadership lesson of your life didn’t happen in a boardroom…but in a preschool? That’s exactly what happened for Kori Bloom  (bio below). In this episode, Kori shares how her journey from high school art teacher to corporate trainer, pharmaceutical sales professional, parent, author, speaker, and leadership coach helped her discover one powerful truth: We don’t lead in pieces. We lead as one whole person. Kori’s new book, The Business of Parenting, explores the connection between how we lead at home, how we lead at work, and how we lead ourselves. And as she shares in this conversation, the toughest leadership role she ever had wasn’t managing employees or speaking to a room full of adults. It was parenting two young children and realizing she needed to stop trying to “fix” them and start leading herself differently. We talk about: • Why parenting and leadership require many of the same skills • How a preschool philosophy changed the way she sees human development • Why curiosity beats control, at home and at work • The danger of overprotecting kids and over-managing employees • Why values only matter if you actually model them • How leaders can assume positive intent without avoiding accountability • Why “balance is bullshit” and the glass-ball/rubber-ball analogy matters Kori also shares her belief that traditional education often fails to build the critical thinking, resilience, creativity, and problem-solving skills people need in today’s world. Her perspective connects parenting, education, leadership, and culture in a way that is both practical and deeply human. This is a conversation about self-awareness, messy growth, leading through real life, and why the way we show up in one room follows us into every other room. And yes, we also discuss why “do it scared, do it messy, and do it before you’re ready” might be some of the best career advice out there.   This episode is brought to you by... Ever wish your company updates could be less "quarterly earnings report" and more "late-night talk show"? At Pelaccio & Partners, we're revolutionizing internal communications with podcasts that employees actually want to listen to. Imagine podcast episodes that make your employees laugh while staying informed. Our founder, Jeff Pelaccio, doesn't just create podcasts; he creates conversations that break through the noise. Whether you're a growing startup or a massive corporation, we turn your company's story into audio gold. Leadership becomes human. Remote teams feel connected. Your message cuts through the clutter. Jeff is happy to share his insights on improving your culture, increasing employee engagement, and retention. You can contact him via LinkedIn or schedule a Zoom call via this link - 15-minute call with Jeff [https://calendly.com/jeffpelaccio/zoom-15-minute-call-with-jeff].   About Kori:  Kori Bloom is a keynote speaker, author, and leadership coach who brings energy, clarity, and real-life perspective to the conversation around leadership. With more than two decades of experience across business, education, and leadership development, Kori helps leaders communicate with intention, build trust, and show up with greater alignment in every room they enter. Her work is grounded in a powerful belief: leadership is not something we turn on and off. We lead as one whole person. Through relatable stories and practical lessons, Kori helps people strengthen self-leadership, navigate pressure, and create cultures rooted in trust and accountability.  Kori lives in the Kansas City area with her two children and believes the most powerful leadership lessons are not just taught, they are lived.