Claim OwnershipLeaders & Legacies
Subscribed: 3Played: 0
Subscribe
© Copyright 2025 Craig Andrews
Description
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.
240 Episodes
Reverse
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/
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
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/.
Hillary Gale didn’t just pivot careers—she rewrote the script entirely. A former college writing teacher, she stepped away from academia, launched a one-woman marketing firm, and then discovered she was pregnant—all within days. With nine months on the clock, she had to lead fast, build smart, and carve out space for maternity leave while launching Moneta Copy.In this episode, Hillary breaks down how strong writing skills are foundational to leadership. She challenges the myth that good writing must follow rigid rules, arguing instead for authenticity, emotion, and real connection. Craig and Hillary dig into what makes content persuasive, how AI is changing the writing landscape, and why personal voice still matters.Her story is a lesson in resilience and resourcefulness. She didn’t wait for permission to lead—she made the deadline non-negotiable. If you’re a business owner relying on stale content and ChatGPT shortcuts, this conversation will remind you that powerful words—and clear leadership—still win.Want to learn more about Hillary Gale's work? Check out her website at https://monetacopy.com.Connect with Hillary Gale on LinkedIn at https://www.linkedin.com/in/hillary-meehan/.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/.
Donovan Ryckis is leading a healthcare revolution—one grounded in leadership, accountability, and total transparency. As CEO of Ethos Benefits, he exposes the broken incentives in traditional benefits brokerage, where rising premiums often pad broker commissions. His fiduciary approach flips the model: no backdoor deals, no hidden fees, and no vague renewals. Just clear numbers and bold decisions.In this episode, Donovan walks through how he saved a client from a 37% rate hike—without cutting coverage. He explains how ERISA laws make employers responsible for plan decisions, even if they don't understand them. He also breaks down how healthcare lawsuits are forcing CEOs, CFOs, and HR leaders to take their fiduciary duties seriously—or face legal consequences.Donovan doesn’t talk about leadership in theory—he practices it by telling hard truths, navigating complex data, and challenging a system rigged for opacity. This episode is a must-listen for any leader responsible for a company’s healthcare decisions.Want to learn more about Donovan Ryckis' work? Check out his website at https://www.EthosBenefits.com.Connect with Donovan Ryckis on LinkedIn at https://www.linkedin.com/in/donovanryckis.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/.
Comments
Download from Google Play
Download from App Store
United States