Leaders & Legacies

PODCAST · business

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 impact greater than we realize and wants to honor owners and founders as they lead others.Craig Andrews is the founder and Principal Ally at allies4me. He’s been in the marketing space for more than two decades and has driven over a half-billion dollars of revenue. He’s spoken on dozens of podcast as well as conferences including Conversion Conference.

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    272 - Why US Manufacturing Can Still Compete Globally with David Solomon

    David Solomon built and ran a $100 million toy manufacturing company in the 1990s with 840,000 square feet of facilities in Montreal and Plattsburgh, New York, successfully competing against China at a time when conventional wisdom said it couldn't be done. Today, as founder of SERO Growth, he helps manufacturers expand into international markets and supports international organizations entering North America.In this episode, David challenges the myth that US manufacturing can't compete globally. He shares his "just-in-time" manufacturing approach that eliminated warehousing costs, explains why unit cost is only part of the equation, and reveals how his company achieved 40-45% gross margins while competitors struggled. David also breaks down the hidden costs of offshoring - from supply chain disruptions to cash flow tied up in goods on the water - and offers practical advice for manufacturers looking to enter new markets, including why starting small beats going big.Want to learn more about David Solomon's work? Check out their website at https://www.serogrowth.com/.Connect with David Solomon on LinkedIn at https://www.linkedin.com/in/davidsolomon13/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    271 - The "Double Wind" Strategy: How to Pick Industries and Clients that Fuel Growth with Jon Morris

    Jon Morris built Rise Interactive from a solo operation to one of the largest independent digital marketing agencies in the world, scaling it to nearly $40 million in revenue over 16 years. He started with prize money from the University of Chicago's New Venture Challenge in 2004 and rode the wave of digital advertising's explosive growth.Today, Jon is the founder and CEO of The Fiscal Advocate, where he serves as a fractional CFO for professional service firms. In this episode, Jon shares his "double wind" framework - the idea that success comes from having wind at your back in both your service offerings and your client selection. He explains why picking high-growth industries and rapidly growing clients matters more than raw talent, discusses the future of AI in financial planning, and reveals why structured data is the key to unlocking AI's potential. Jon also opens up about the challenges creative agency owners face when forced to become entrepreneurs and why getting into the financial weeds separates great CEOs from the rest.Want to learn more about Jon Morris's work? Check out their website at https://www.fiscaladvocate.com/.Connect with Jon Morris on LinkedIn at https://www.linkedin.com/in/jonmorrisramsayinnovations/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    270 - America's Tax Defender: How to Fight the IRS and Win with Pietro Canestrelli

    Pietro Canestrelli is a tax attorney and former IRS attorney who helps business owners and taxpayers protect their hard-earned money. As the founder of the Law Office of Pietro Canestrelli and author of America's Tax Defender, he focuses on getting the IRS out of your life as fast as possible.In this episode, Pietro breaks down the three areas of tax work: compliance, proactive planning, and tax defense. He explains why being audited is actually a "badge of success," why CPAs don't do proactive tax planning, and shares underutilized strategies like R&D tax credits and cost segregation that could save business owners tens or hundreds of thousands of dollars.Want to learn more about Pietro's work? Check out his website at https://ietaxattorney.com/.Connect with Pietro on LinkedIn at https://www.linkedin.com/in/pietro-canestrelli-18032a21.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    269 - Why Most Virtual Training Fails - and How Great Leaders Fix It with Bernie DeSantis

    In this episode of Leaders and Legacies, Craig Andrews sits down with Bernie DeSantis, CEO of Insignia Training Partners, to explore how leaders can transform virtual training from a dull obligation into a powerful leadership tool. Drawing on more than 20 years of experience in corporate learning and development, Bernie shares how organizations can deliver high-impact virtual experiences that engage people and drive real results.Bernie explains why many virtual events fail: leaders treat them like in-person presentations and simply “turn on the camera.” But virtual environments demand a different approach. Leaders must intentionally create interaction, structure engagement, and guide participants through meaningful learning moments.The conversation also covers the psychology of audience engagement, why attention spans are shrinking, and how simple tools like polling, chat prompts, and structured interaction can dramatically improve participation. Bernie also highlights common mistakes leaders make—such as overwhelming audiences with too much information and failing to provide a clear call to action.Ultimately, great virtual experiences come down to intentional leadership. When leaders design training and events that prioritize engagement and clarity, they build stronger relationships, deeper trust, and better business outcomes.Want to learn more about Bernie DeSantis's work? Check out their website at https://insigniatraining.com/.Connect with Bernie DeSantis on LinkedIn at https://www.linkedin.com/in/badiii/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    268 - The Micro-Moments That Build - or Break - Trust in Leadership with Kim Bohr

    Trust is often treated as a vague leadership ideal, but Kim Bohr argues it’s one of the most measurable and practical drivers of performance inside organizations.As President and CEO of SparkEffect, Kim works with executive teams navigating disruption without breaking trust. In this conversation, she explains how leadership failures rarely come from malicious intent. Instead, they stem from blind spots—small behaviors, missed signals, and unexamined habits that slowly erode trust within teams.Kim shares how leaders can recognize these “micro-moments” that shape trust every day. Whether it’s acknowledging mistakes quickly, demonstrating transparency during difficult decisions, or showing curiosity instead of judgment, leaders have constant opportunities to strengthen relationships.She also highlights why organizations often overlook leadership development at the frontline level, where trust issues frequently begin. Without the right skills and emotional intelligence, leaders unintentionally damage the culture they’re responsible for building.Ultimately, Kim’s message is clear: trust is not abstract. It can be measured, strengthened, repaired, and intentionally built into how organizations operate.Want to learn more about Kim Bohr's work? Check out their website at https://sparkeffect.com/.Connect with Kim Bohr on LinkedIn at https://www.linkedin.com/in/kimbohr/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    267 - The Strategic CIO: How Leaders Turn Technology Into a Growth Engine with Jeremy Fennema

    In this episode of Leaders and Legacies, Craig Andrews sits down with Jeremy Fennema, founder of Fennema.io and a fractional CIO/CTO who helps growth-stage companies bring order to chaotic technology environments.Jeremy explains why most companies struggle with technology—not because of poor tools, but because they lack strategy. Leaders often buy solutions to solve isolated problems, creating a patchwork of systems that don’t work together. Jeremy’s role is to step in, align technology decisions with business goals, and build a clear roadmap for execution.He also breaks down the difference between tactical IT support and true technology leadership. Instead of simply fixing problems when systems fail, strategic leaders design environments where those problems rarely happen in the first place.Jeremy also tackles one of today’s biggest leadership challenges: AI adoption. Too many companies start with the question, “How can we use AI?” when the real question should be, “What problem are we trying to solve?” Technology should follow strategy—not drive it.Through stories from international business expansion and years of technology leadership, Jeremy shows how leaders can build systems that scale, reduce chaos, and support long-term growth.Want to learn more about Jeremy Fennema's work? Check out their website at https://fennema.io.Connect with Jeremy Fennema on LinkedIn at https://linkedin.com/in/fennema.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    266 - Financial Leadership for Law Firms: Turning Numbers into Strategy with John Scott

    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 planning, uneven partner distributions, and missed opportunities to reinvest in growth.John explains how law firms can shift from reactive accounting to proactive financial leadership. Instead of looking backward at reports, leaders should forecast cash flow, set operating cash targets, and plan distributions strategically. This forward-looking discipline helps firms avoid cash crunches and operate with confidence.The conversation also explores leadership culture inside professional services firms. John emphasizes the importance of hiring smart people, building flexible work environments, and creating a culture where employees choose to stay. Leaders who treat their people well build organizations that thrive beyond themselves.For law firm leaders—and any professional services owner—this episode highlights how financial discipline, thoughtful leadership, and strong culture combine to create long-term success.Want to learn more about John C. Scott's work? Check out their website at https://anderscpa.com/virtual-cfo-legal/.Connect with John C. Scott on LinkedIn at https://www.linkedin.com/in/john-c-scott-cpa/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    265 - AI-Driven Leadership: How Smart Operators 10x Their Impact with Nick Jain

    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 faster than competitors.He shares how AI can compress consulting-level analysis into a fraction of the time and cost, making elite financial insight accessible to small and mid-sized businesses. From predicting cash flow risks to uncovering hidden cost savings, technology now surfaces what most humans would miss.Nick also challenges leaders to rethink roles. Coders become architects. Analysts become decision-makers. Owners become system designers. The future belongs to leaders who adapt quickly, expand their capabilities, and use AI as a force multiplier.Want to learn more about Nick Jain's work? Check out their website at https://eaglerockcfo.com.Connect with Nick Jain on LinkedIn at https://www.linkedin.com/in/nickmjain/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    264 - From Conflict to Cohesion - Turning Strong Personalities into Strong Teams with Sriram Mangudi

    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 value, and turned a tense acquisition into a long-term success.Sriram breaks down what separates reactive managers from strategic leaders. Strong leaders create space for dialogue. They protect autonomy. They focus on root causes instead of surface symptoms. During COVID, while others reacted daily to chaos, his team focused on preventive health and long-term workforce stability. That decision preserved operations and saved lives.He also challenges private equity’s habit of replacing executives too quickly. Sustainable performance requires governance, alignment, and transparent communication—not constant leadership churn.Leadership is not about control. It’s about clarity, calm, and disciplined execution when the ground shifts beneath you.Want to learn more about Sriram Mangudi's work? Check out their website at https://consultmsg.com/.Connect with Sriram Mangudi on LinkedIn at https://www.linkedin.com/in/srirammangudi/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    263 - Building a Firm That Outlives You - Erik Brenner on Leadership Through Integration

    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 a future tax crisis. The CPA didn’t see it. Erik did. That moment led him to build an in-house tax business designed to be proactive, not seasonal.He also explains how leadership means developing people. Early hires weren’t advisors. They were detail-driven operators who freed him to focus on strategy. He built a residency model to train future advisors the same way doctors train surgeons—through immersion and repetition.His philosophy is clear: delegate paperwork, never advice. Hire opposites. Build sustainable systems. Anticipate where the puck is going.Leadership, for Erik, means taking responsibility for outcomes before they become problems.Want to learn more about Erik Brenner's work? Check out their website at https://hilltopwealthtax.com/Connect with Erik Brenner on LinkedIn at https://www.linkedin.com/in/erikbrenner/Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    262 - Why Smart Leaders Don’t Outsource Thinking to Their CPA

    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 intentionally.The discussion covers why relying solely on a CPA can limit growth, how leaders use the tax code as a tool rather than a constraint, and why proactive decision-making separates owners from operators. Catrina also breaks down overlooked strategies—like retirement planning, family employment, and asset structuring—and shows how disciplined leaders turn them into leverage.At its core, this conversation is about ownership. Leaders don’t wait to be told what’s possible. They ask better questions, demand clarity, and act early. If leadership means stewarding resources wisely—for your business, your team, and your future—this episode delivers a clear blueprint.Want to learn more about Catrina M. Craft's work? Check out their website at https://www.catrinamcraft.com/.Connect with Catrina M. Craft on LinkedIn at https://www.linkedin.com/in/catrinamcraft/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrews' work at allies4me? Check out his website at https://allies4me.com/.

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    261 - Leadership Means Planning the Exit Before You Need It with Brett Swarts

    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 about optionality—building a business that can run without you, scale cleanly, and exit efficiently. He walks through how disciplined planning, clear systems, and early tax strategy protect both families and legacies.The conversation also explores why many owners delay planning until a health crisis or unexpected offer forces a rushed decision. Brett argues that leaders who slow down, ask better questions, and plan early create leverage, not pressure.This episode is a must-listen for founders and advisors who want leadership decisions today to compound into freedom tomorrow.Want to learn more about Brett Swarts's work? Check out their website at https://capitalgainstaxsolutions.com/.Connect with Brett Swarts on LinkedIn at https://www.linkedin.com/in/brett-swarts/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    260 - Heidi DeCoux on Leadership, Cash Flow, and Why Most Businesses Fly Blind

    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 decades as a serial entrepreneur, she shows how leaders can use simple KPIs to identify what actually drives profit—and what quietly drains it.The conversation also covers why automation is now a leadership advantage, how incentive structures impact productivity, and why white space is essential for good decision-making. Heidi makes a clear case: leaders who want freedom, impact, and sustainability must build systems that surface truth, not noise.This episode is a practical look at leadership through the lens of financial discipline, clarity, and intentional design.Want to learn more about Heidi DeCoux's work? Check out their website at https://heididecoux.com.Connect with Heidi DeCoux on LinkedIn at https://www.linkedin.com/in/heididecoux/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    259 - Why Modern Leaders Must Think Like Security Experts with Robert Siciliano

    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 to avoidable damage.Robert shares how strong leaders think proactively about risk, build security-aware cultures, and make prevention part of everyday operations. He also outlines common mistakes executives make when they assume security can be delegated or delayed. The conversation focuses on decision-making under uncertainty, accountability, and the leadership mindset required to stay ahead of evolving threats.This episode challenges leaders to rethink how they define responsibility, resilience, and preparedness. If you lead a team, a company, or a growing organization, this conversation will change how you approach risk—and how seriously you take your role in protecting what matters most.Want to learn more about Robert Siciliano's work? Check out their website at https://protectnowllc.com/.Connect with Robert Siciliano on LinkedIn at https://www.linkedin.com/in/robertsiciliano.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    258 - From Startups to Slam Dunks - Adam House on Leading with Grit and Vision

    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 outsider perspective as an advantage. His businesses span tech, marketing, supplements, roofing, and more—but his leadership playbook stays consistent: build better, move faster, serve others.At the core of House of Bricks is a belief that leadership is about self-awareness, legacy, and service. Adam now advises founders across industries, helping them scale and grow with clarity and confidence. His latest mission? Supporting veterans in their transition to civilian leadership through the “What the Truck” initiative.Adam lives what he teaches—every decision is a brick in the legacy he’s building.Want to learn more about Adam House's work? Check out his website at https://houseofbricks.io.Connect with Adam House on LinkedIn: https://www.linkedin.com/in/adamhousesr/Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/

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    257 - The Hidden Cost of Bad Hires - and How to Avoid Them with Jennifer Bookspan

    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 searching for executive talent and how her team helps them avoid costly misfires.From hard-earned lessons to practical hiring frameworks, Jennifer breaks down how to approach leadership with discipline, empathy, and a long-game mindset. If you're building a leadership team—or trying to level up your own leadership skills—this episode delivers real takeaways you can apply today.Want to learn more about Jennifer Bookspan's work? Check out their website at https://bookspansearchpartners.com/about/.Connect with Jennifer Bookspan on LinkedIn at https://www.linkedin.com/in/jenniferbookspan/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    256 - Why Your Business Won’t Scale Until You Stop Solving Every Problem

    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? Clear systems, strong core values, and a culture that encourages decision-making and allows room for failure.Greg and Craig dive into leadership as mentorship—not control. They challenge perfectionism, unpack the cost of micromanagement, and drive home the ROI of empowering your team. If your business relies on you to function, this episode is your wake-up call.Want to learn more about Greg Giniel's work? Check out his website at https://www.eosworldwide.com/greg-giniel.Connect with Greg Giniel on LinkedIn at https://www.linkedin.com/in/greg-giniel/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    255 - The Real Cost of Talent and the Hidden Goldmine in Latin America with Chris Brown

    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 hiring—language capabilities, time zone alignment, and deep professional talent. He also exposes the limits of AI in customer support, highlighting the irreplaceable value of human connection.Leadership, in Chris’s view, means building systems that adapt fast, scale responsibly, and serve both customers and team members well. He didn't just outsource—he restructured for performance, proving leadership is about leverage, not micromanagement.Want to learn more about Chris Brown's work? Check out their website at https://wowremoteteams.com/.Connect with Chris Brown on LinkedIn at https://www.linkedin.com/in/wowcto/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    254 - The Power of Asking Better Questions with David Kreeger

    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 saw commodity. One $1,700 job turned into $600,000 in revenue because he treated every customer like gold.Now, David uses his legal training to dissect complex business challenges and help companies focus on what really matters. His superpower? Asking the right questions. He explains why leaders often miss what’s obvious—and how the right data can shift everything. If you're facing tough decisions or struggling with clarity, David’s approach offers a fresh blueprint for forward momentum.Want to learn more about David Kreeger's work? Check out their website at https://www.thegopedal.net.Connect with David Kreeger on LinkedIn at https://www.linkedin.com/in/david-kreeger-b1264b4/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    253 - The Hidden Dangers Lurking in Your 401(k) Plan with Alex Langan

    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) Exposed, Alex reveals the legal shifts making it easier than ever to sue employers who fail their fiduciary duty. He outlines how proactive leadership can head off lawsuits and improve employee outcomes. His “fee forensics” process shows leaders how to detect hidden charges, ask the right questions, and demand transparency.Alex isn’t just warning employers—he’s giving them a blueprint for doing better. Because leaders don’t just offer benefits. They protect them.Want to learn more about Alex Langan's work? Check out his website at https://langanfinancialgroup.com.Connect with Alex Langan on LinkedIn at https://www.linkedin.com/in/alexander-langan-26017b40.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    252 - Inside the Hilton Family Office - Mark Miller on Leading with Clarity and Purpose

    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 up to fail, driven by emotion and overexposed to risk. The wealthy, on the other hand, take a safety-first approach—prioritizing protection over flashy returns. Mark challenges the mainstream obsession with chasing gains, instead advocating for disciplined, long-term strategies built on experience and balance.Craig and Mark also unpack the emotional psychology of money, exploring how trauma, ego, and ignorance impact financial decisions—and how leaders can rise above it. Mark’s ultimate goal? Helping clients find “true wealth,” defined not just by financial success, but by peace, freedom, and life balance.Want to learn more about Mark Miller's work? Check out their website at https://www.hiltonwealth.com/.Connect with Mark Miller on LinkedIn at https://www.linkedin.com/in/markmiller-hiltonfo/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    251 - The Hidden ROI of Kindness in Business - A CX Masterclass with Ty Givens

    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 instead of the brand itself. That shift in mindset launched a career helping brands—from startups to Fortune 500s—reshape how they engage customers at every level.Ty also opens up about the power of leadership that sees potential in others. A former bookstore manager changed her trajectory with one simple act of belief, reminding us that leadership isn’t always flashy—sometimes it’s about sending someone to a job fair.This episode challenges companies in every industry to rethink how they listen, act, and lead through customer experience.Want to learn more about Ty Givens' work? Check out their website at https://cxcollective.com.Connect with Ty Givens on LinkedIn at https://www.linkedin.com/in/tybryantgivens/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    250 - The IRS Calls You 'Low-Hanging Fruit' - Sherry Peel Jackson Says Not Anymore

    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 backing down, she doubled down. Now, she helps six-figure professionals keep more of what they earn without crossing legal lines.Craig and Sherry discuss the importance of standing up to institutional overreach and why leadership sometimes means challenging broken systems. Sherry shares practical advice for anyone looking to reduce their tax burden legally, including the necessity of having a home-based business and meticulous record-keeping.This isn’t about tax evasion—it’s about tax education, justice, and reclaiming financial freedom. Sherry’s mission is clear: empower people with knowledge and help them escape financial bondage.Want to learn more about Sherry Peel Jackson's work? Check out her website at https://sherrypeeljackson.com/.Connect with Sherry Peel Jackson on LinkedIn at https://www.linkedin.com/in/sherrypeeljackson/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  24. 250

    249 - The Power of Alignment - How Leadership Teams Accelerate Growth with Nils Vinje

    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 dysfunction goes unnoticed because it feels normal from the inside. His job is to bring clarity—often by asking the questions no one else is asking. From working with fence installers to Fortune 100s, Nils shows that scaling is less about tactics and more about mindset and structure.This episode is a must-listen for leaders who feel stuck despite working harder than ever. If your team is talented but directionless, Nils offers a clear, proven path forward.Want to learn more about Nils Vinje's work? Check out their website at https://nilsvinje.com.Connect with Nils Vinje on LinkedIn at https://www.linkedin.com/in/nilsvinje/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  25. 249

    248 - Why Simplicity Wins - James Elliman’s Blueprint for Small Business IT Leadership

    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 and fixing printers via Facebook. Over time, he learned how to price value, not time, and transitioned to a scalable MSP model. That shift not only stabilized his business—it turned him into a more strategic leader.James discusses how overwhelming tech stacks taught him the importance of standardization, the role of empathy in customer service, and why flexible pricing models build trust. He also unpacks the chaos from recent tech outages, and how proactive leadership helped clients stay calm while the internet burned.Want to learn more about James Elliman's work? Check out their website at https://ellimantech.com.Connect with James Elliman on LinkedIn at https://www.linkedin.com/in/james-elliman-a7667212a/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    247 - From ICU to Camp Gladiator - Setting and Achieving Outrageous Goals with Craig Andrews

    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 high-intensity workout in a wheelchair and on oxygen, Craig shares the mental framework that got him through it: map the path, no matter how outrageous, and execute.He urges listeners to apply the same strategy for the new year. Set goals that scare you. Set goals that excite you. Then plan the path to make them real—physically, professionally, or personally.This is a candid, high-impact episode about resilience, leadership, and growth through adversity.Want to learn more about Craig Andrews' work? Check out their website at https://allies4me.com/.Connect with Craig Andrews on LinkedIn at https://www.linkedin.com/in/craig-andrews/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  27. 247

    246 - Choosing the Right Relationships - A Leader’s Priority with Craig Andrews

    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 and the relationships that mattered most. From struggling to climb stairs to re-learning how to stand, he talks candidly about physical weakness and emotional clarity. Coming back from the brink helped him separate genuine, reciprocal relationships from those that were only surface deep.Craig urges leaders to evaluate who’s really in their corner and to invest in people who show up when it counts. His story is both personal and powerful—an unfiltered look at legacy through leadership.Want to learn more about Craig Andrews' work? Check out their website at https://allies4me.com.Connect with Craig Andrews on LinkedIn at https://www.linkedin.com/in/craig-andrews.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  28. 246

    245 - From Ballroom to Boardroom - Camille Diaz on Leading Through Reinvention

    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 create sustainable wealth through financial education and strategic benefits planning. Her leadership style is direct, process-driven, and focused on giving people tools to regain control of their lives. In this episode, she shares how clear exit plans, humility after failure, and unshakable curiosity shaped her journey. She also unpacks how employers can offer zero-net-cost health benefits through smart tax strategies, breaking the cycle of annual cost hikes.Whether she’s mentoring clients or challenging the status quo in healthcare, Camille leads by empowering others to think differently and act with intention.Want to learn more about Camille Diaz's work? Check out her website at https://camillediaz.com.Connect with Camille Diaz on LinkedIn: https://www.linkedin.com/in/camillediaz/Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/Want to learn more about Craig Andrew's work at allies4me? Visit https://allies4me.com/

  29. 245

    244 - Reclaiming the American Dream Through Smarter Health Benefits with Chris Mathew.mp3

    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 wellness programs that bypass traditional insurance models. The results? Employers cut healthcare spend by up to 50% while improving retention with life-enhancing benefits like childcare and college scholarships.His leadership is rooted in advocacy. Chris believes employees need champions in a system that prioritizes paperwork over people. By creating real alternatives to the broken status quo, he's helping businesses escape the trap of year-over-year rate hikes—and he's inviting others to do the same.Want to learn more about Chris Mathew’s work? Check out their website at https://www.well-genie.com.Connect with Chris Mathew on LinkedIn at https://www.linkedin.com/in/chrismathew/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  30. 244

    243 - From Purple Branding to Powerful Follow-Up: Ely Delaney’s Playbook

    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 his personal quirks, like his Renaissance fair obsession and dog love, helped him build stronger business relationships. The real leadership win? Ely’s ability to systematize authentic communication that continues building trust—even when he’s offline.Ely explains how his “Ultimate Follow-Up” system boosts engagement not with gimmicks, but with real conversation. His emails feel personal because they are. The result: higher open rates, stronger replies, and deeper relationships.Want to learn more about Ely Delaney's work? Check out his website at https://ElyDelaney.com.Connect with Ely Delaney on LinkedIn at https://www.linkedin.com/in/elydelaney/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/

  31. 243

    242 - Leadership Born in the ICU - Kimberly Carleson’s Mission to Fix Health Care Billing

    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. Beacon, the company she founded to fight bloated medical billing and protect employers from skyrocketing health costs. Kimberly’s team reviews claims for self-funded plans, finding and eliminating ineligible charges—often cutting 20–40% from monthly claims. Her work restores fairness and trust in a system where both are in short supply.Her leadership isn’t just professional. It’s deeply personal. Kimberly speaks with clarity, strength, and purpose—because she’s lived what most only fear.Want to learn more about Kimberly Carleson’s work? Check out their website at https://www-us-beacon.com.Connect with Kimberly Carleson on LinkedIn at https://linkedin.com/in/kimberlycarleson.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  32. 242

    241 - From HR Hater to Growth Strategist - DeeAnn Palin’s Bold Pivot

    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 company’s growth engine.Drawing from her experience with brands like Motorola and the Phoenix Suns, Palin shares real-world examples of betrayal, ethical breakdowns, and executive blind spots. She makes the case for firing fast, leading with values, and building cultures that actually perform.Her boldest leadership moment? Walking away from her largest client — and $1.3 million in savings — to protect her team. That’s not HR. That’s leadership.Want to learn more about DeeAnn Palin’s work? Check out her website at https://www.onptbiz.com.Connect with DeeAnn Palin on LinkedIn: https://www.linkedin.com/in/deeannpalin/Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Visit https://allies4me.com/.

  33. 241

    240 - From Marine to Media Mogul - Jesse Sieff on Leading with Precision

    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 about crafting media that moves people and delivers results. He shares how his military background helped him lead high-performing teams and why leaders should master the art of storytelling if they want to build trust and drive action.Listeners get a behind-the-scenes look at how Jesse helps clients show up confidently on camera and how he integrates AI tools to strengthen internal communication and branding. Whether you're a business owner navigating change or a leader scaling your message, Jesse offers actionable insight on building systems that support clarity, confidence, and growth.Want to learn more about Jesse Sieff's work? Check out their website at https://www.sieffstudios.com.Connect with Jesse Sieff on LinkedIn at https://www.linkedin.com/in/jessesieff/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  34. 240

    239 - The Power of Presence - Why Fathers Matter More Than Ever with Marquess Dennis

    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 one race or class—“it affects the poor house all the way to the White House.” He weaves together personal stories, sobering statistics, and sharp social commentary, revealing how pop culture has eroded the public perception of fatherhood and how leadership begins at home.Dennis makes a compelling case: fatherhood isn’t a footnote in a child’s life—it’s the framework. He urges dads to treat their families like million-dollar clients: full attention, consistent engagement, and intentional presence.Want to learn more about Marquess Dennis's work? Check out their website at https://brlivinglegacy.com.Connect with Marquess Dennis on LinkedIn at https://www.linkedin.com/in/marquessdennis/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  35. 239

    238 -Why Your CPA Isn’t Your Tax Strategist - And What to Do About It with Paden Squires

    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 advertising: as an ROI tool, not an expense. With deep insight into entrepreneurial finance, Paden emphasizes building advisory relationships that prioritize long-term planning over reactive compliance.He also sheds light on why so many accountants undervalue their work, run generic firms, and fail to deliver real value to business owners. If you’re running a 7-figure business and feel like you're leaving money on the table, this episode is your wake-up call.Want to learn more about Paden Squires' work? Check out their website at https://www.squirestaxplanning.com/Connect with Paden Squires on LinkedIn at https://www.linkedin.com/in/paden-squires-cpa-cfp-19681a1a/Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/

  36. 238

    237 - Ashley Connell on Unlocking Hidden Ops Talent for Scalable Leadership

    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; they’re looking for impact and flexibility. And they deliver, often increasing profits, improving team dynamics, and freeing CEOs to focus on growth.Ashley and Craig explore how emotional intelligence should be compensated like hard skills, why leadership means letting go, and the power of empathy in business. Ashley also reveals how Prowess Project uses data—not gut instinct—to match CEOs with the right operators, transforming overwhelmed founders into confident leaders.This is a must-listen for any business owner ready to lead with intention and build a legacy of empowered teams.Want to learn more about Ashley Connell's work? Check out their website at https://www.prowessproject.com.Connect with Ashley Connell on LinkedIn at https://www.linkedin.com/in/ashley-connell-ceo/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  37. 237

    236 - Why Justin Dixon Quit a Six-Figure Job to Build a Recruiting Firm During a Crisis

    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 one was hiring, and how that generosity paid off later.He also dives into how most business owners misunderstand recruiters—and the small moves that can drastically improve your odds of landing A-players. From running triathlons to running a company, Justin reveals the parallels between endurance sports and entrepreneurial grit.Want to learn more about Justin Dixon's work? Check out their website at https://www.hiretomorrow.com.Connect with Justin Dixon on LinkedIn at https://www.linkedin.com/in/jmdixon15/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  38. 236

    235 - Why “Scared Money Doesn’t Make Money” - Sonny Grappone’s Leadership Mindset

    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, Sonny bet on himself and launched Precision Accounting & Consulting. His leadership mindset is clear: invest in yourself, know your value, and make bold decisions—even when they seem risky.He now advises law firms, construction companies, and business owners on how to treat accounting as an investment, not an expense. Sonny doesn’t just run numbers—he helps clients fund growth, make strategic hires, and unlock hidden savings with federal tax programs.His leadership mantra? “Scared money doesn’t make money.”Want to learn more about Sonny Grappone's work? Check out his website athttps://precisionaccountingconsulting.comConnect with Sonny Grappone on LinkedIn athttps://www.linkedin.com/in/sonny-grappone-24536312aThink you'd be a great guest on the show? Apply athttps://podcast.allies4me.com/podcast-guest/Want to learn more about Craig Andrews’ work at allies4me? Visithttps://allies4me.com/

  39. 235

    234 - Why Transparency in Pharmacy Benefits is a Leadership Imperative with Justin Jasniewski

    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 responsibilities employers often overlook and the lawsuits now surfacing when health plan mismanagement drains employee benefits. Justin stresses the importance of understanding what your PBM is really doing with your money and lays out how transparency and better contracts can unlock serious cost savings—sometimes enough to fund new hires or expansion without touching top-line revenue.This episode is a wake-up call for business leaders: your PBM could be silently bleeding your budget. The good news? You can fix it—and Justin shows you how.Want to learn more about Justin Jasniewski's work? Check out their website at https://ServeYouRx.com.Connect with Justin Jasniewski on LinkedIn at https://www.linkedin.com/in/justin-jasniewski/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  40. 234

    233 - The ABCs of Charisma - Leadership Lessons from Milam Miller

    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 Welch and Sam Walton mastered connection through confidence and kindness—not through dominance or ego. Whether it’s helping sales teams outperform AI or guiding executives to connect instead of command, Milam’s approach is rooted in relational leadership, not transactional tactics.This episode is packed with practical tools for modern leaders who want to elevate influence, build trust, and create high-performing teams that thrive on human connection.Want to learn more about Milam Miller's work? Check out their website at https://beconfidentandkind.com.Connect with Milam Miller on LinkedIn at https://www.linkedin.com/in/milam-miller-bck.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  41. 233

    232 - Reinventing Voice of the Customer with AI - Eli Portnoy's Leadership Playbook

    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 conversations. He explains how BackEngine uses large language models to surface actionable feedback from client interactions—email threads, Zoom calls, and more—giving leaders a fuller, more accurate picture.His leadership philosophy? You can’t solve the right problems if you’re asking the wrong questions. Eli makes a compelling case for empowering decision-makers with authentic customer sentiment—without the distortion of surveys or false memories.Want to learn more about Eli Portnoy's work? Check out their website at https://backengine.ai.Connect with Eli Portnoy on LinkedIn at https://www.linkedin.com/in/eliportnoy/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  42. 232

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

    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 ones.That realization got him fired… and fired up. He launched Health Compass Consulting to give employers a path out. Donovan outlines how business leaders can cut costs without slashing benefits. In fact, the key to savings is often improving employee care, not reducing it.This conversation is a must-listen for CFOs, HR leaders, and CEOs who want to transform their benefits from a financial liability into a strategic advantage.Want to learn more about Donovan Pyle's work? Check out their website at https://www.donovanpyle.com.Connect with Donovan Pyle on LinkedIn at https://linkedin.com/in/donovanpyle.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  43. 231

    230 - From Solo Act to Sustainable Business - William Bissett on Leadership

    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 let go. William shares his approach to building high-performance teams using tools like the Culture Index, but emphasizes that real success comes from empowering people to grow—even if that means they eventually leave.For William, leadership isn’t about control—it’s about legacy. That means creating wins for your people, investing in their growth, and building a culture that celebrates progress. It’s leadership with humility and a long view.Want to learn more about William Bissett's work? Check out their website at http://www.portusadvisors.com.Connect with William Bissett on LinkedIn at https://www.linkedin.com/in/williambissett/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  44. 230

    229 - The Ezra Principle - Leadership Lessons That Scaled a Referral Empire with Brian McRae

    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 feel seen. Within three years, 60% of his business came through that event, and he never once asked for referrals.Brian shares the "Ezra Principle"—study, practice, teach—as his guiding framework. He also talks about how building community led to the creation of The Boardroom, a mastermind group for financial professionals looking to lead with heart, not hustle.His story is a masterclass in leadership through generosity and consistency. If you want to grow by helping others win, this episode is your playbook.Want to learn more about Brian McRae's work? Check out their website at https://www.briankmcrae.com.Connect with Brian McRae on LinkedIn at https://www.linkedin.com/in/briankmcrae/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

  45. 229

    228 - Why Leadership Isn’t Taught - It’s Lived - Lessons from Kyle Schwarz

    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 apply in business. He draws sharp lines between managers and leaders, emphasizing the need for tough conversations, personal accountability, and seeing people as humans—not transactions. His approach at Risus Talent Partners rejects the churn-and-burn model. Instead, it prioritizes connection, fit, and long-term relationships.Craig and Kyle discuss the dangers of avoiding confrontation, the flaws in transactional thinking, and how real leadership requires self-awareness and emotional intelligence. Kyle doesn’t just talk about leadership—he embodies it.Want to learn more about Kyle Schwarz’s work? Check out his website at https://risustalent.com.Connect with Kyle Schwarz on LinkedIn at https://www.linkedin.com/in/kyle-t-schwarz/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    227 - The Wisdom of Ignorance - Why Not Knowing Can Be the Key to Innovation with Alan Gregerman

    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 smartest people in the room may not be the answer. His latest book, The Wisdom of Ignorance, argues that not knowing is often the key to seeing clearly and moving boldly. He introduces his six-part framework for unlocking genius: be purposeful, curious, humble, respectful, future-focused, and yes—just a bit paranoid.With stories from his own life and business consulting career, Alan makes a compelling case for breaking with expertise, embracing fresh perspectives, and looking outside your industry for inspiration.Want to learn more about Alan Gregerman's work? Check out their website at https://www.alangregerman.com.Connect with Alan Gregerman on LinkedIn at https://www.linkedin.com/in/alan-gregerman-a33b236/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    226 - From Hospice to High Impact - How Emily Erstad Builds Resilient Teams

    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 great leaders don’t just give direction—they create safety, clarity, and alignment in moments of fear or uncertainty.Drawing from her book It’s Not That Deep, Emily discusses how her own struggles and leadership pivots helped her shape a human-centric approach to influence and impact. She also reveals how building teams that thrive without her has become her quiet legacy.Want to learn more about Emily Erstad’s work? Check out her website at https://eepublicationsllc.wixsite.com/ee-publications.Connect with Emily Erstad on LinkedIn at https://www.linkedin.com/in/emily-erstad-m-a-ccc-slp-381346135/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    225 - Why Great Leaders Set the Strategy - Then Get Out of the Way with Lee Pepper

    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 like Patton, Schwarzkopf, and Ross Perot, Lee calls out the real enemy: indecision. Whether in combat or campaign strategy, action wins. Leadership isn’t about managing from a spreadsheet—it’s about removing barriers and letting your people attack the mission.Lee also dives into how old-school intelligence gathering—listening to 10,000+ sales calls—has given him insights that most companies miss. His advice is simple and sharp: stop micromanaging, start trusting, and use history as your manual.Want to learn more about Lee Pepper's work? Check out their website at https://www.NeverOutmatchedBook.com.Connect with Lee Pepper on LinkedIn at https://www.linkedin.com/in/leepepper/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    224 - From Moscow to Main Street - How Stan Sukhinin Helps Clinics Thrive

    Stan Sukhinin knows what it’s like to rebuild from scratch. After a meteoric rise in Eastern Europe’s finance world—managing a $450M mezzanine loan portfolio—he moved to New York to launch a hedge fund. It didn’t survive the pandemic. What did survive? His ability to spot financial blind spots and fix them fast.Now, as founder of The Sorso, Stan serves as a fractional CFO for outpatient clinics across the U.S. He combines deep financial rigor with AI-powered forecasting to help healthcare providers operate with precision. In this episode, Stan breaks down the unique challenges in the outpatient clinic model—especially the widespread misreporting of revenue due to insurance reimbursement complexity.He shares why many seemingly healthy businesses collapse overnight, and how bad debt, shallow risk planning, and poor scenario modeling are usually to blame. For clinic owners and business leaders alike, Stan offers practical insight into financial structure, AI use cases, and creating stability in volatile times.Want to learn more about Stan Sukhinin's work? Check out their website at https://www.thesorso.com.Connect with Stan Sukhinin on LinkedIn at https://www.linkedin.com/in/stan-sukhinin/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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    223 - From Iraq to EOS - Why Every Leader Needs a Coaching Team with Hark Herold

    Hark Herold brings three decades of military precision to the entrepreneurial world. As a retired U.S. Air Force colonel turned EOS implementer, Hark shares how his leadership experience in high-stakes environments—from serving in Desert Storm to overseeing base recovery during rocket attacks in Iraq—shaped his approach to business.Now, he empowers small and medium-sized businesses to build clarity, cohesion, and execution with the Entrepreneurial Operating System (EOS). In this episode, Hark explains why leadership alignment is non-negotiable, how ego can cripple growth, and what it means to have the “right people in the right seats.” He also highlights resources available for veteran-owned businesses and shares why coaching is essential, even when all the tools are already at your fingertips.Want to learn more about Hark Herold's work? Check out their website at https://www.eosworldwide.com/hark-herold.Connect with Hark Herold on LinkedIn at https://www.linkedin.com/in/joeharkherold/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

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ABOUT THIS SHOW

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 impact greater than we realize and wants to honor owners and founders as they lead others.Craig Andrews is the founder and Principal Ally at allies4me. He’s been in the marketing space for more than two decades and has driven over a half-billion dollars of revenue. He’s spoken on dozens of podcast as well as conferences including Conversion Conference.

HOSTED BY

Craig Andrews

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