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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.
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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/.
Alex Sanfilippo shares how a childhood marked by dyslexia and self-doubt evolved into a leadership platform spanning podcasting, public speaking, and entrepreneurship. As the founder of PodMatch, Alex has enabled thousands of leaders to get their voices heard, but his path started with personal healing and self-expression.In this episode, Alex details how podcasting became his tool for leadership—helping him own his voice, refine his message, and grow his confidence. He makes the case for why CEOs and founders shouldn’t delegate guest appearances or hosting duties. Alex argues that being the voice of your company is irreplaceable when building connection and trust.He also explains why podcasting isn’t just a marketing tool—it’s an engine for clarity, learning, and growth. Whether it’s guesting to articulate your message or hosting to expand your network, Alex views podcasting as one of the most strategic moves a leader can make.Want to learn more about Alex Sanfilippo's work? Check out their website at https://podmatch.com/.Connect with Alex Sanfilippo on LinkedIn at https://www.linkedin.com/in/alexsanfilippo/.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/.
Chris Hurn, CEO of Community Bankshares, joined the show to talk straight about entrepreneurial leadership in high-stakes environments. He traces his roots to watching his single mother run a chocolate business out of their basement, an early masterclass in grit, marketing, and operations. That foundation shaped his view of what it means to lead—not just manage.Now a leader in small business financing, Chris outlines the crucial difference between being an entrepreneur and becoming a CEO. He explains how leaders must eventually move beyond scrappiness and take calculated risks with debt to scale their companies. But he’s quick to note that optimism must be balanced with pragmatism. Cash flow—not charisma—is what gets a loan approved.Chris also unpacks the coming wave of business acquisitions driven by baby boomer retirements, sharing insights on what industries are hot and where private equity is warping the landscape. His message is clear: real leadership is about seeing around corners and backing up vision with execution.Want to learn more about Chris Hurn’s work? Check out their website at https://www.phxbusiness.com.Connect with Chris Hurn on LinkedIn at https://www.linkedin.com/in/chrishurn/.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/.
Allison De Paoli joins Craig Andrews to break down how employers can lead through one of the most neglected aspects of their business—health insurance. Drawing from decades of experience and her family’s entrepreneurial legacy, Allison shows how leaders can stop hemorrhaging money on bloated health plans and start using benefits as a tool for retention, loyalty, and long-term cost control.She argues the system isn’t broken—it’s rigged. But with the right strategy, employers can bypass middlemen, reclaim fiduciary control, and offer high-quality care without budget blowouts. Allison walks through real-world examples of employers who’ve turned skyrocketing premiums into savings—without shifting the cost burden onto employees.If you lead a team and think better healthcare is out of reach, this episode will challenge that belief—and give you a roadmap to lead differently.Want to learn more about Allison De Paoli's work? Check out their website at https://www.altiqe.com.Connect with Allison De Paoli on LinkedIn at https://www.linkedin.com/in/allison-de-paoli/.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/.
Everett O’Keefe shares the origin story of Ignite Press, from a chance reconnection to a publishing powerhouse. His leadership was tested early when co-founder John tragically passed away, forcing Everett to carry the vision forward alone. Instead of folding, he doubled down. That decision sparked the launch of nearly 200 bestselling books and reshaped how thought leaders share their message.In this episode, Everett unpacks the power of books as a leadership tool—helping entrepreneurs build credibility, refine their message, and amplify their impact. He also offers a practical roadmap through the complex publishing landscape, covering ghostwriting, hybrid models, and the importance of editorial integrity.His message is clear: authorship is leadership. A book is more than a marketing tool—it’s a durable asset that outlives trends, outlasts platforms, and outperforms expectations. For Everett, real leadership means using your voice to unlock someone else’s potential.Want to learn more about Everett O’Keefe's work? Check out their website at https://IgnitePress.us.Connect with Everett O’Keefe on LinkedIn at https://www.linkedin.com/in/everettokeefe/.Get a complimentary copy of The Power of the Published: https://mypodcastperk.com/.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/.
Mike Jesowshek, founder of TaxElm, delivers a masterclass on leadership by eliminating one of the biggest pain points for entrepreneurs: tax confusion. His leadership style centers on simplifying complexity and empowering clients and employees through clear strategy and execution. On the Leaders and Legacies podcast, Mike breaks down how he uses transparency, consistency, and responsiveness to lead both a growing team and a national client base.Mike shares how most accountants are overworked or hesitant to charge for high-value advice, leaving business owners in the dark. His leadership challenge was to change that. By launching TaxElm and building a proactive software tool backed by expert support, he created a system that doesn’t just educate—it equips.He explains how he built trust through consistent communication, set clear expectations with his team, and scaled impact with tech and systems. His leadership isn’t about doing more—it’s about doing the right things and making those repeatable.Want to learn more about Mike Jesowshek’s work? Check out their website at https://www.TaxElm.com.Connect with Mike Jesowshek on LinkedIn at https://www.linkedin.com/in/mikejesowshek/.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/.
Michael Cole, President of Next Level Technician, shares how he turned a failed Subway franchise and a few unlikely training classes into a thriving staffing and training company in the low-voltage trades. In a field plagued by high turnover and unpredictability, Cole stands out by building systems that value integrity and grit over credentials. His leadership journey is rooted in real-world trial and error—like discovering too late that some recruits are afraid of ladders or can’t pass drug tests.Michael’s leadership sharpens through adversity: he reshaped his business model after nearly every early mistake. His approach to staffing centers on deep vetting, video interviews, and second chances for people who own their past mistakes. He’s built a company that sets clear expectations, values honesty, and adapts without lowering standards. This episode is a masterclass in leading imperfect people to create powerful outcomes.Want to learn more about Michael Cole's work? Check out their website at https://www.nextleveltechnician.com.Connect with Michael Cole on LinkedIn at https://www.linkedin.com/in/coles-corner/.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/.
Vance Morris doesn’t just deliver services—he designs unforgettable experiences. In this episode, he shares how Disney’s obsession with systems shaped his philosophy for building customer loyalty and price elasticity. Morris breaks down his transition from security guard at a birth control factory to Disney executive, then to bankrupt entrepreneur, and finally to the founder of Deliver Service Now. His key insight? Competing on price kills service.Instead, Morris urges business owners to map every customer touchpoint and turn each one into a moment of delight. He explains how even something as small as baking cookies in a dentist’s office or FedExing a proposal can shift your brand from transactional to relational. Whether you’re in retail, B2B, or professional services, Morris shows how intentional design builds brand loyalty, repels price shoppers, and increases profitability.Want to learn more about Vance Morris's work? Check out their website at https://vancemorris.com.Connect with Vance Morris on LinkedIn at https://www.linkedin.com/in/vancemorris/.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/.
Tom Dillon, founder of Frak Finance, joins Craig Andrews to break down how smart financial leadership unlocks business growth. As a fractional CFO, Tom helps companies escape the trap of gut-based decisions and start leading with data. He exposes the cost of common blind spots—like selling at a loss, underestimating hiring costs, or ignoring traction metrics.Tom shows how predictable revenue isn’t a myth—it’s a method. From analyzing ROI on marketing channels to knowing when to hire ahead of growth, he explains how leaders can build confidence through numbers. He also tackles the tension between branding and financial metrics, arguing that long-term value often looks unpredictable in a spreadsheet but is crucial to sustained success.Leadership, Tom says, is about accountability—not just managing costs but owning outcomes. His insights push leaders to stop hiding from the financials and start using them as tools to scale.Want to learn more about Tom Dillon's work? Check out their website at https://www.frakfinance.com.Connect with Tom Dillon on LinkedIn at https://www.linkedin.com/in/tom-dillon-cfa/.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/.
Kirk Spahn brings leadership to life at ICL Academy, a school built for students who aim higher—on the court, on the stage, or in their communities. In this conversation, Kirk breaks down what it takes to lead with purpose. He shares how ICL moves beyond academics to develop discipline, resilience, and character. The goal? To build champions for life.Kirk reveals how elite athletes and performers grow not just through hard work but through intentional structure and mindset. He details how ICL pairs students with mentors, designs custom curriculum around passions, and instills the habits of high-performance leadership. Whether training with Novak Djokovic or guiding a student to the French Open, Kirk’s focus stays the same: build people who lead with integrity and impact.He also addresses equity in education, explaining how ICL delivers personalized, values-driven schooling to students—90% of whom are on scholarship. The model blends traditional respect with forward-thinking tech, ensuring students thrive both online and in the world.Want to learn more about Kirk Spahn's work? Check out their website at https://www.iclacademy.org.Connect with Kirk Spahn on LinkedIn at https://www.linkedin.com/in/kirk-spahn-10a913/.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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