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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

35:06

266 - Financial Leadership for Law Firms: Turning...

Leaders & Legacies ·

2026/04/09

Leadership often hinges on decisions made with incomplete information. In this episode of Leaders and Legacies, John C. Scott explains why strong leaders build financial clarity into their organizations rather than relying on intuition or a bank balance.John, a CPA and partner at Anders, specializes in helping law firms understand the business side of their practice. Many attorneys excel in legal reasoning but never receive training in finance or firm management. That gap often leads to poor cash

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30:56

265 - AI-Driven Leadership: How Smart Operators 10x...

Leaders & Legacies ·

2026/04/07

Nick Jain, co-founder of Eagle Rock CFO, believes leadership in the AI era comes down to leverage. The best leaders won’t be replaced by AI—they’ll use it to multiply their impact.Nick explains how AI and smart automation are eliminating low-value work like data cleanup, financial modeling, and report creation. That shift frees leaders to focus on judgment, relationships, and strategic decisions. Instead of spending weeks analyzing spreadsheets, leaders can now generate insights in hours—and act

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31:42

264 - From Conflict to Cohesion - Turning Strong...

Leaders & Legacies ·

2026/04/02

Sriram Mangudi believes leadership reveals itself in moments of pressure. In this episode, he shares hard-earned lessons from global HR leadership, M&A integrations, and navigating COVID while running essential pharmaceutical operations.He explains why most leaders fail during transformation: they push agendas instead of listening. In one high-stakes acquisition, Sriram walked into a room filled with suspicion. Instead of forcing integration plans, he listened. That shift built trust, preserved

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31:22

263 - Building a Firm That Outlives You - Erik...

Leaders & Legacies ·

2026/03/31

Erik Brenner doesn’t lead from theory. He leads from structure.As President and CEO of Hilltop Wealth & Tax Solutions, Erik built a firm that integrates advanced tax strategy with wealth management. He saw what others missed: reactive advice was failing clients. CPAs focused on last year. Advisors focused on investments. No one owned the full picture.So he changed it.Erik shares how a defining client case exposed the cost of disconnected advice. Required minimum distributions were set to create

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28:21

262 - Why Smart Leaders Don’t Outsource Thinking to...

Leaders & Legacies ·

2026/03/26

Leadership isn’t just vision. It’s responsibility. In this episode, Catrina M. Craft challenges business owners to rethink what leadership really means when it comes to money, decisions, and long-term impact.Catrina explains why most entrepreneurs unknowingly overpay the IRS—not because the law requires it, but because they were never taught how the system actually works. She draws a sharp line between compliance and strategy, arguing that true leaders don’t just “file correctly,” they plan

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27:47

261 - Leadership Means Planning the Exit Before You...

Leaders & Legacies ·

2026/03/24

In this episode of Leaders and Legacies, Craig Andrews speaks with Brett Swarts, founder of Capital Gains Tax Solutions, about what leadership looks like when business owners think beyond today.Brett makes the case that strong leaders plan for exits long before they happen. Most owners focus on growth, customers, and operations, but fail to prepare for the financial reality of selling. That lack of foresight can cost 20–50% of their wealth in capital gains taxes.Brett explains why leadership is

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30:26

260 - Heidi DeCoux on Leadership, Cash Flow, and Why...

Leaders & Legacies ·

2026/03/19

Most leadership failures don’t start with people. They start with poor visibility into the business. In this episode, Heidi DeCoux explains why leaders who don’t understand their numbers end up working longer hours while making less money.Heidi breaks down the leadership trap of chasing top-line revenue without understanding profitability. She explains why many founders scale chaos instead of results and how unclear financial data leads to bad decisions, burnout, and broken teams. Drawing from

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29:23

259 - Why Modern Leaders Must Think Like Security...

Leaders & Legacies ·

2026/03/17

Leadership today demands more than vision and execution. It requires the ability to protect people, data, and trust in an increasingly hostile digital environment.In this episode, Craig Andrews sits down with Robert Siciliano, a leading authority on identity theft, cybersecurity, and personal risk management. Robert breaks down why security is no longer an IT issue—it’s a leadership responsibility. He explains how leaders who ignore cyber and identity risks expose their teams, customers, and brands

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26:13

258 - From Startups to Slam Dunks - Adam House on...

Leaders & Legacies ·

2026/03/12

Adam House doesn’t believe in waiting for the right moment—he builds momentum. In this episode of Leaders and Legacies, Adam shares how his “Why Not?” mindset propelled him from serial entrepreneur to professional basketball player at 32—and later, to becoming CEO and co-owner of the very team he joined.Craig Andrews explores Adam’s leadership journey through seven ventures, including a healthcare analytics platform that went public. Adam reflects on the real value of failure, timing, and using

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35:27

257 - The Hidden Cost of Bad Hires - and How to Avoid...

Leaders & Legacies ·

2026/03/10

Jennifer Bookspan knows that leadership isn’t about filling seats—it’s about shaping the future of an organization. In this episode, she joins Craig Andrews to discuss how her firm, Bookspan Search Partners, goes beyond typical executive recruiting to help companies build intentional, aligned leadership teams.Jennifer shares why the best leaders are usually the best listeners, and how humility, clarity, and vision all factor into successful hiring. She explains what most founders get wrong when

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30:49

256 - Why Your Business Won’t Scale Until You Stop...

Leaders & Legacies ·

2026/03/05

Greg Giniel, Professional EOS Implementer, joins Craig Andrews to break down the mindset shift every business owner must make: stop being the easy button for your team. In this candid conversation, Greg explains how the EOS framework builds leaders at every level, freeing business owners from the daily grind while increasing performance across the organization.He shares personal stories, including how his team kept his business thriving while he was sidelined with COVID for a month. The reason

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37:54

255 - The Real Cost of Talent and the Hidden Goldmine...

Leaders & Legacies ·

2026/02/26

Chris Brown, CTO of Wow Remote Teams, shares how Latin America became his go-to talent solution—and why more U.S. businesses should follow. After running a booming medical e-commerce operation during the pandemic, Chris needed scalable, affordable, and reliable help. His wife Julie, originally from Bogotá and now CEO of Wow Remote Teams, helped him build a nearshore workforce that outperformed U.S.-based teams at a fraction of the cost.Chris breaks down the real-world benefits of remote

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34:51

254 - The Power of Asking Better Questions with David...

Leaders & Legacies ·

2026/02/19

David Kreeger traded legal briefs for business breakthroughs. In this episode, the founder of GoPedal shares his journey from practicing law at WilmerHale and IBM to owning a painting franchise and now leading strategic transformations for companies that feel stuck.David reveals what drew him away from the legal grind—a desire to make decisions, improve quality of life, and be present for his family. His pivot into entrepreneurship wasn’t just about freedom; it was about creating value where others

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26:52

253 - The Hidden Dangers Lurking in Your 401(k) Plan...

Leaders & Legacies ·

2026/02/12

Alex Langan blends law and finance to protect employees from the hidden traps inside their company retirement plans. As founder of Langan Financial Group and a practicing attorney, Alex has seen the worst—plans charging over 4% in fees with little to no service. In this episode, he explains how poor plan design and ignorance—not malice—often sabotage employee retirements. True leadership, he argues, means protecting your team from this kind of financial abuse.Drawing from his upcoming book 401(k)

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26:59

252 - Inside the Hilton Family Office - Mark Miller...

Leaders & Legacies ·

2026/02/05

Mark Miller doesn’t just manage money—he manages legacies. As the managing partner of Hilton Wealth and co-leader of the Hilton family office, Mark helps business owners and high-net-worth individuals make smarter, safer financial decisions. In this episode, Mark breaks down the misunderstood world of family offices and how they function as a “general contractor” for wealth—coordinating top-tier advisors across tax, investments, legal, and insurance.He explains how the average investor is often set

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34:10

251 - The Hidden ROI of Kindness in Business - A CX...

Leaders & Legacies ·

2026/01/29

Ty Givens, founder and CEO of CX Collective, joins Craig Andrews to break down the overlooked power of customer experience. Ty argues that customer experience isn’t just about fixing problems—it’s about preventing them. Through real-world examples, from Starbucks to five-star restaurants, Ty highlights how small touches—like empathy and initiative—can turn a moment of friction into long-term loyalty.She shares her early career misstep that changed everything: thinking she was just an employee

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33:15

250 - The IRS Calls You 'Low-Hanging Fruit' - Sherry...

Leaders & Legacies ·

2026/01/22

Dr. Sherry Peel Jackson, former IRS agent turned tax strategist, pulls back the curtain on how small business owners are unfairly targeted by the system. In this hard-hitting episode, Sherry explains why the IRS considers entrepreneurs “low-hanging fruit” and how to legally protect yourself through strategic deductions and proper business structuring.After leaving the IRS, Sherry discovered deep flaws in the tax system—ones that led to a federal prison sentence when she spoke out. But instead of

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29:47

249 - The Power of Alignment - How Leadership Teams...

Leaders & Legacies ·

2026/01/15

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: People, Purpose, Playbooks, Performance, and Profit. He argues that most

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24:46

248 - Why Simplicity Wins - James Elliman’s Blueprint...

Leaders & Legacies ·

2026/01/08

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 plans fall apart. He opens up about the early days, charging $14 an hour

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11:27

247 - From ICU to Camp Gladiator - Setting and...

Leaders & Legacies ·

2026/01/01

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. From being too weak to raise the blinds to showing up at a

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266 results

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