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© Copyright 2026 Craig Andrews
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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.
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.
254 Episodes
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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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/
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/.
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/
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/.
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/.
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/.
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/.
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/
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/.
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/.
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/
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