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/