Leaders & Legacies

Nils Vinje helps CEOs scale by aligning their leadership teams. In this episode, he breaks down how misalignment at the top quietly drains momentum—and what to do about it. Drawing from his time in Silicon Valley, where leadership teams were swapped out like batteries, Nils explains why true alignment starts with shared understanding and ruthless simplicity.

Nils outlines the five principles that power every successful business: Peo...

James Elliman planned to be a Marine officer, following a family legacy of military service. But a last-minute medical disqualification forced a hard pivot. Instead of serving in uniform, he leaned into his lifelong love of tech and launched Elliman Technologies to simplify IT for small businesses.

In this episode, James shares how leadership isn't just about titles—it’s about clarity, adaptability, and serving others, even when pla...

Craig Andrews opens up about the most defining moment of his life—a six-week coma after a severe case of COVID-19. Doctors told his wife he wouldn’t survive. But he beat the odds. When he woke, he discovered that his team and community kept his business running. That, he says, is his proudest leadership moment.

In this solo episode, Craig reflects on the radical recovery process and the outrageous goals that powered his comeback. Fr...

Craig Andrews opens up about the most defining leadership moment of his life—one he wasn’t even conscious for. After slipping into a six-week coma from COVID-19, doctors told his wife he wouldn’t survive. But his team kept the business running. Freelancers stepped in unasked. That’s when Craig knew he had built something more than a company—he built loyalty.

In this special Christmas episode, Craig reflects on that recovery period a...

Camille Diaz’s leadership story is rooted in reinvention. A science teacher turned ballroom dance studio co-founder, she built a thriving business—until a partner change derailed everything. Faced with debt, a lawsuit, and burnout, Camille hit rock bottom. But when friends began asking her for business advice, she discovered a new path: optimization coaching.

Camille now leads Serenity Financial, helping businesses and individuals c...

Chris Mathew, Chief Growth Officer at Well-Genie, joins Craig Andrews to reveal how his father’s tragic and avoidable death shaped his mission to transform American healthcare. With deep family roots in Kerala and a legacy of firstborn leadership, Chris channels that sense of duty into helping employers radically cut costs while increasing wellness benefits for their teams.

Chris doesn’t just talk cost savings—he proves it. Well-Gen...

Ely Delaney doesn’t just teach follow-up marketing—he lives it. On this episode of Leaders & Legacies, Ely shares how authenticity and consistency transformed his business and leadership style. From his signature purple branding to a three-year evergreen email campaign, Ely leans into what makes him different—and encourages others to do the same.

He and host Craig Andrews explore the leadership lesson behind showing up as your f...

Kimberly Carleson didn’t set out to become a leader in health care reform. Life forced her into it.

When her husband was diagnosed with stage four metastatic bladder cancer, Kimberly found herself navigating a health care system built for confusion, not care. Pregnant and raising a young daughter, she refused to accept the death sentence doctors gave her husband. Her advocacy, persistence, and leadership saved his life—and revealed ...

DeeAnn Palin doesn’t just fix companies — she rebuilds them from the inside out. In this episode, Craig Andrews talks with the founder and CEO of OnPoint Business Solutions about her radical journey from corporate HR skeptic to trusted strategic partner for CEOs.

Palin pulls back the curtain on toxic culture, ethical blind spots, and the cost of keeping the wrong people in leadership. She explains why HR should never be treated as a...

Jesse Sieff is no stranger to reinvention. From military barracks to media production, he’s built a career on sharp pivots and sharper leadership. In this episode, Jesse breaks down how his time in the Marine Corps Drum & Bugle Corps instilled in him a deep respect for discipline, detail, and public representation—skills that now fuel his work at Sieff Studios.

Jesse’s leadership style blends strategic vision with creative execu...

Marquess Dennis doesn’t just talk about fatherhood—he’s on a mission to redefine it. As the founder of Birthright Living Legacy, he joins Craig Andrews to challenge cultural narratives, unpack generational trauma, and spotlight the deep systemic impact of absent fathers. Dennis shares his own journey from poverty in North Tulsa to building a nonprofit dedicated to helping fathers of all backgrounds reclaim their influence.

With unfi...

Paden Squires grew up in rural Missouri with firsthand experience of financial insecurity. That early exposure shaped his mission: help entrepreneurs grow wealth with clarity and confidence. In this episode, Paden breaks down why relying on your CPA for tax strategy is a mistake. Most CPAs are set up to file returns—not proactively plan.

He walks through high-impact tax strategies like the Augusta Rule and explains why business owne...

Ashley Connell, CEO of Prowess Project, joins Leaders and Legacies to unpack a bold truth: leaders don’t need another version of themselves. They need a “not you”—a skilled operator who thrives on structure, details, and execution.

In this episode, Ashley shares how she built a talent pipeline of highly qualified caregivers—primarily mothers and sandwich-generation women—who bring unmatched emotional intelligence and professional ri...

Justin Dixon walked away from a comfortable six-figure job and launched a recruiting firm—just weeks before the world shut down. In this episode, he joins Craig Andrews to unpack what it really takes to lead when the timing couldn’t be worse.

Justin shares the personal finance moves he and his wife made to de-risk the leap, and why reading Rich Dad Poor Dad flipped his entire outlook on life and career. He talks about navigating COV...

Sonny Grappone didn’t follow a straight path to success. Raised by a single mother from Guyana and a hardworking Italian-American stepfather, Sonny grew up in Queens, New York, sharing a bed with his mom and sister. That early scarcity drove his work ethic—bagging groceries at 12, building computers in high school, and running an auto detailing business in college.

At 25, he pivoted. He went back to school, discovered a knack for ac...

Justin Jasniewski, CEO of Serve You Rx, breaks down one of healthcare’s murkiest corners—pharmacy benefit managers (PBMs). In this episode, he exposes how PBMs sit at the crossroads of drug manufacturers, employers, and pharmacies—often inflating costs instead of controlling them. With plain talk and sharp insights, Justin walks through how the system evolved from a simple IT add-on to a high-stakes financial engine that can either...

Milam Miller, founder of Be Confident and Kind and author of The Charisma Craft, joins Craig Andrews to challenge everything we think we know about charisma. A former executive for a billionaire sports team owner and affectionately nicknamed the “real-life Ted Lasso,” Milam shares how charisma isn’t innate—it’s a skill any leader can develop.

Through bold stories and sharp insight, Milam breaks down his ABCs of Charisma: Authenticit...

Eli Portnoy, CEO and co-founder of BackEngine, joins Craig Andrews to expose the flaws in traditional customer feedback systems—and why leadership demands better data. A seasoned entrepreneur and Harvard Business School Executive Fellow, Eli dives into how B2B companies often make strategic decisions using flawed insights from biased surveys.

Eli unpacks how leadership in the AI era means throwing out broken instruments like opinion...

Donovan Pyle pulls back the curtain on an industry most business leaders misunderstand: employer-sponsored health care. In this episode, Donovan explains how companies are overpaying by as much as 25%—often without realizing it—and why the current broker model keeps them trapped. Drawing on his own experience inside a major insurance company and later as a broker, Donovan saw firsthand how incentives are misaligned and how brokers ...