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PODCAST

Leaders & Legacies

The Leaders & Legacies Podcast celebrates leaders who are making a difference beyond themselves. It was inspired from events in 2021 when the host, Craig Andrews went into a 6-week coma. Even after waking up, his brain was scrambled for another two weeks. When his mind cleared, his wife started telling him how his team stepped up and ran the company without him. Freelancers reached out to his team and offered to do whatever was necessary while he was in the hospital. Craig believes we all make an

business entrepreneurship

All Episodes

37:01

244 - Reclaiming the American Dream Through Smarter...

Leaders & Legacies ·

2025/12/11

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-Genie offers unlimited $0 generics, discounted brand-name drugs, and

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38:09

243 - From Purple Branding to Powerful Follow-Up: Ely...

Leaders & Legacies ·

2025/12/04

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 full self, even when it’s unconventional. Ely discusses how revealing

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29:17

242 - Leadership Born in the ICU - Kimberly...

Leaders & Legacies ·

2025/12/02

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 a deeper calling.That experience became the foundation for U.S

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28:50

241 - From HR Hater to Growth Strategist - DeeAnn...

Leaders & Legacies ·

2025/11/25

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 compliance function — and how, when done right, it becomes a

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35:10

240 - From Marine to Media Mogul - Jesse Sieff on...

Leaders & Legacies ·

2025/11/20

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 execution. His studio isn’t just about producing polished videos—it’s

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33:20

239 - The Power of Presence - Why Fathers Matter More...

Leaders & Legacies ·

2025/11/18

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 unfiltered honesty, he discusses how fatherlessness isn't confined to any

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33:46

238 -Why Your CPA Isn’t Your Tax Strategist - And...

Leaders & Legacies ·

2025/11/13

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 owners should think of tax strategy the same way they think about

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30:59

237 - Ashley Connell on Unlocking Hidden Ops Talent...

Leaders & Legacies ·

2025/11/06

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 rigor to operations roles. These women aren’t looking for handouts;

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30:48

236 - Why Justin Dixon Quit a Six-Figure Job to Build...

Leaders & Legacies ·

2025/10/30

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 COVID as a new business owner, giving away free career advice when no

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28:57

235 - Why “Scared Money Doesn’t Make Money” - Sonny...

Leaders & Legacies ·

2025/10/28

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 accounting, and never looked back. After years in the corporate grind,

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35:12

234 - Why Transparency in Pharmacy Benefits is a...

Leaders & Legacies ·

2025/10/23

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 serve or exploit employers.He highlights the fiduciary

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39:24

233 - The ABCs of Charisma - Leadership Lessons from...

Leaders & Legacies ·

2025/10/21

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: Authenticity, Boldness, and Curiosity. He reveals how top leaders like Jack

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31:12

232 - Reinventing Voice of the Customer with AI - Eli...

Leaders & Legacies ·

2025/10/16

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 surveys and adopting tools that capture real, unfiltered customer

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30:39

231 - 25% of Waste Hiding in Your P&L with Donovan Pyle

Leaders & Legacies ·

2025/10/14

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 are often rewarded for selling the most expensive plans—not the best

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29:48

230 - From Solo Act to Sustainable Business - William...

Leaders & Legacies ·

2025/10/09

William Bissett, founder of Portus Wealth Advisors, joins Craig Andrews to unpack what it really takes to lead a company that survives and thrives beyond its founder. William shares how watching his father struggle in solo practice shaped his commitment to team building. His insight is simple but powerful: don’t just hire talent—hire people who fill your gaps, not mirror them.The episode cuts through leadership myths and focuses on what makes businesses last—trust, delegation, and the willingness to

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36:33

229 - The Ezra Principle - Leadership Lessons That...

Leaders & Legacies ·

2025/10/02

Brian McRae walked away from a comfortable W-2 job to chase something more fulfilling—control, freedom, and impact. What followed was a leadership journey rooted in service. In this episode, Brian shares how he transitioned from the mortgage world to building a coaching and mastermind business that thrives on authentic relationships.He didn’t advertise. He didn’t pitch. Instead, he launched a free monthly event focused on giving away practical strategies—like handwritten notes—that made attendees

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33:58

228 - Why Leadership Isn’t Taught - It’s Lived -...

Leaders & Legacies ·

2025/09/30

Kyle Schwarz brings clarity to what leadership really looks like. A U.S. Naval Academy graduate and surface warfare officer, Kyle shares how a blunt rejection from his blue and gold officer nearly derailed his academy ambitions—but ultimately became a catalyst for transformation. He didn't quit. He trained, returned, and earned one of the strongest recommendations in years.Now with 17 years of leadership experience, including more than a decade in recruiting, Kyle shows how those same principles

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40:27

227 - The Wisdom of Ignorance - Why Not Knowing Can...

Leaders & Legacies ·

2025/09/25

Alan Gregerman nearly lost everything after a stroke robbed him of his ability to speak and see. But instead of giving in, he turned that moment into one of his greatest leadership lessons. In this episode, Alan shares how navigating life without communication forced him to rethink how leaders engage, innovate, and lead. Through his recovery, he uncovered deeper truths about humility, clarity, and the need to constantly evolve.Alan breaks down why most organizations fail at innovation—and how the

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27:37

226 - From Hospice to High Impact - How Emily Erstad...

Leaders & Legacies ·

2025/09/23

Emily Erstad joins Craig Andrews for a candid conversation about the real heart of leadership—emotional intelligence. A former speech-language pathologist turned hospice leader, Emily shares how leading in high-stakes environments taught her the power of trust, vulnerability, and consistency.She explains why leadership isn’t about commanding—it’s about partnering. Whether guiding patients through recovery or teams through chaos, Emily leans into emotional truth over cold logic. She emphasizes that

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32:12

225 - Why Great Leaders Set the Strategy - Then Get...

Leaders & Legacies ·

2025/09/18

Lee Pepper brings battlefield-tested leadership into the boardroom. In this episode, Lee breaks down how military strategies—some dating back to the Romans—can drive success in today’s marketing and business landscape. Drawing from his Army background, time at Fort Knox, and career in behavioral healthcare marketing, Lee explains how setting clear intent and empowering teams to execute leads to superior outcomes.He makes the case for clarity over control and strategy over tactics. Citing leaders

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244 results

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