Risky Business With Brett

Brett Saint Sing

Risky Business with Brett is about looking behind the curtain at the decisions, incentives, and risks that shape business, benefits, healthcare, and the workplace. Hosted by Brett Saint Sing, an insurance and employee benefits consultant, the show breaks down complicated topics in a way that business leaders and everyday consumers can actually understand. From self-funded health plans, PBMs, prescription drugs, stop-loss, and rising healthcare costs to leadership, financial decisions, risk, and the challenges facing employers today, nothing is off limits. Some episodes are Brett sharing what he has learned from years in the insurance business. Others are conversations with industry experts, business leaders, healthcare professionals, and people with perspectives worth hearing. The goal isn't to sell you something. It's to ask better questions, challenge conventional thinking, and help you understand what's really happening behind the scenes. Business is risky. Healthcare is complicated. Insurance can be confusing. Let's talk about it.

Episodes

  1. 2d ago

    Benefits...Bueller...Bueller - Featuring Dale Alexander

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! Benefits... Bueller... Buehler... | Risky Business with Brett featuring Dale Alexander Anyone? Anyone? Bueller? Employee benefits might not be the most exciting subject in the classroom, but the decisions school districts and their employees make about benefits can have a tremendous impact on their financial futures. In this episode of Risky Business with Brett, I'm joined by my friend and fellow HUB colleague, Dale Alexander, CFP® and founder of Alexander & Company. Dale has spent decades working with educators and school systems, helping them better understand employee benefits, financial planning, and the decisions that shape their futures. We cover a lot of ground, including: Why public school employee benefits are different from those in the private sector.The biggest mistakes school districts make when evaluating benefits.How benefits affect teacher recruitment, retention, and financial security.Why financial education matters just as much as the benefits themselves.Dale's work teaching young people about money through The Talk (About Money).The relationship between financial success, generosity, and stewardship.How faith and family shape our definitions of success.And yes, we talk about God. Because sometimes the most important conversations have very little to do with insurance. My goal with Risky Business isn't to sell you something. It's to help people ask better questions, challenge conventional thinking, and make more informed decisions. Whether you're a superintendent, school board member, HR professional, educator, business owner, or just someone interested in making smarter financial decisions, I hope you'll find something valuable in this conversation. Subscribe to Risky Business with Brett for more conversations about insurance, healthcare, business, leadership, and life. #RiskyBusinessWithBrett #EmployeeBenefits #SchoolBenefits #FinancialPlanning #Education #Leadership #Faith #Insurance

    Benefits...Bueller...Bueller - Featuring Dale Alexander

  2. Sep 23

    The Man Behind The Curtain - Leadway Rx - PBM

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! For the first episode of Risky Business with Brett, I sit down with Jay Gulley of Leadway Rx to pull back the curtain on one of the most complicated and misunderstood pieces of an employer’s health plan: pharmacy benefits. Jay brings a perspective you don't always hear in the PBM conversation. He comes from the pharmacy side of the business and has seen firsthand how decisions made throughout the prescription drug supply chain affect pharmacists, employers, health plans, and ultimately the people paying for their medications. We get into rebates, specialty drugs, GLP-1s, biosimilars, J-code and infusion drugs, vertical integration, GPOs, PBM legislation, and some of the incentives buried inside a system that most employers rarely get to see. But this isn't just a conversation about what's wrong with pharmacy benefits. It's about understanding how the system actually works, where the money goes, and what employers should be asking about their own plans. No sales pitch. No pretending the answers are simple. Just a conversation about an incredibly complicated business that deserves a little more transparency. Come take a look behind the curtain.

    The Man Behind The Curtain - Leadway Rx - PBM
  • 2 Episodes

About

Risky Business with Brett is about looking behind the curtain at the decisions, incentives, and risks that shape business, benefits, healthcare, and the workplace. Hosted by Brett Saint Sing, an insurance and employee benefits consultant, the show breaks down complicated topics in a way that business leaders and everyday consumers can actually understand. From self-funded health plans, PBMs, prescription drugs, stop-loss, and rising healthcare costs to leadership, financial decisions, risk, and the challenges facing employers today, nothing is off limits. Some episodes are Brett sharing what he has learned from years in the insurance business. Others are conversations with industry experts, business leaders, healthcare professionals, and people with perspectives worth hearing. The goal isn't to sell you something. It's to ask better questions, challenge conventional thinking, and help you understand what's really happening behind the scenes. Business is risky. Healthcare is complicated. Insurance can be confusing. Let's talk about it.

Information

  • Creator
    Brett Saint Sing
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © Brett Saint Sing
  • Show Website
    Risky Business With Brett