Leaders & Legacies
The Leaders & Legacies Podcast honors owners and founders who are making an impact beyond themselves. Host Craig Andrews was inspired by his own experience in 2021 when a six-week coma made him realize how his team and freelancers stepped up to run the company. The show shares stories of leaders who lead others and create lasting legacies. Craig Andrews is the founder of allies4me and has spent over two decades in marketing.
Episodes
294 - Why “We Screwed Up” Can Be the Start of Greater Trust with Craig Andrews
Many leaders fear that admitting a miss will destroy a client relationship. Craig Andrews argues that delaying the truth is often far more damaging. Delivering bad news early gives customers options, reduces downstream harm, and creates an opportunity to demonstrate integrity when it matters most.Craig shares a four-part framework for handling failure: state and own the bad news, explain what brok
293 - Why Your CPA and Tax Lawyer Play Different Roles with Josh Lowenthal
Business owners face a costly tension when planning an eventual exit: the decisions that may shape taxes and deal outcomes often need attention years before a buyer appears, yet the legal language and tax rules can be difficult to understand. Josh Lowenthal joins Craig Andrews to explain why effective advisors should translate complexity into clear choices so owners can make informed decisions abo
292 - Why Growing Revenue Won’t Fix a Profitability Problem with Arron Bennett
Revenue can climb while cash gets tighter, margins shrink, and the owner ends up working harder for less. Arron Bennett explains why trying to outgrow a profitability problem usually magnifies it: when the economics are broken at $1 million, adding more sales can simply scale the damage.Arron introduces a framework built around 60% gross margins, 15% for sales and marketing, and 15% for general an
291 - How Marketing Cuts Can Damage Business Value with Craig Andrews
When business gets tight, marketing often becomes one of the first expenses on the chopping block. Craig Andrews opens with the contrast at the heart of that decision: Henry Ford was frugal enough to reuse shipping-crate boards as car floorboards, yet he warned that cutting advertising to save money was like stopping a watch to save time.How much should a company spend? Craig compares examples cit
290 - The Live Oak Lesson: Authenticity in the Age of AI with Craig Andrews
AI can make work faster, cheaper, and more efficient. But when leaders start handing AI the parts of the business that require trust, empathy, and human connection, efficiency turns into erosion. In this solo episode of Leaders & Legacies, Craig Andrews challenges the tempting belief that AI can replace the people responsible for customer service, sales, marketing, and storytelling.Standing am
289 - What Business Owners Should Fix Before the Buyer Shows Up with Adam Marshall
Business owners often treat legal work like a fire alarm: wait until something starts burning, then call for help. Adam Marshall, Managing Member at Lorium Law, joins Leaders & Legacies to explain why that approach costs more, creates more stress, and leaves owners with fewer options when the moment matters most.Adam shares the story behind leaving Big Law and building a firm around teamwork,
288 - Five Stars or Nothing: Scaling Through Service with Paul H. Graham
The hard part of scaling is not always strategy, capital, or market timing. Sometimes the constraint is the owner's grip. Paul Graham joins Craig Andrews to talk about what happens when business owners want bigger outcomes but keep operating from the same limits, roles, and control patterns that got them to their current level.Paul traces that thinking back through a life of calculated risk, seven
287 - Systems Don't Fail. Standards Do with Richard Walsh
A business can install the right system, build the right dashboards, and still bleed profit because nobody is holding the standard. Richard Walsh returns to Leaders & Legacies to explain why structurally sound operating systems often fail on the floor: not because the framework is bad, but because small deviations go unchallenged until they become expensive failures.Richard calls the problem c
286 - Built From the Customer Backward with Sheldon Wolf
Real estate customers now do much of the work that once justified the old brokerage model. They find the house, research neighborhoods, compare mortgage options, write stronger listing copy, and still often pay commissions built around assumptions from another era. Sheldon Wolf sees the tension clearly: the customer has moved forward, but too much of the transaction is still organized around agent
285 - Why Product-First Selling Breaks High-Trust Pipeline with Steve Wallace
Too many leaders say they sell through relationships, then walk into the next discovery call and make the product the center of the room. The result is a pipeline full of pressure, weak referrals, and prospects who can feel they are being processed instead of understood.Steve Wallace, CEO of Back to Basics Revenue Company / B2B Rev, learned that lesson in one of the hardest sales classrooms: 100%
284 - Build Your Brand and Media Presence with Ted Jenkin
Most leaders say they want a stronger brand, but many still judge every decision by this quarter’s direct ROI. That tension runs through Craig’s conversation with Ted Jenkin, President of ESL Advisors: the businesses that become memorable rarely do it by copying the industry playbook or measuring only the fastest return.Ted shares how Oxygen Financial grew by going after the market most financial
283 - Financial Clarity, Operating Discipline, and the Business That Runs Without You
Too many business owners build companies that depend on them for every important decision, every customer save, every operational fix, and every financial answer. The business may be profitable, but it still feels fragile. It owns the owner instead of the other way around.In this episode, Craig talks with Rob Johnson and Steve Thornton about how financial clarity and operating discipline work toge
282 - The CFO Who Helps You Say Yes with Fred Kosnac
Revenue can make a business owner feel like the company is winning, even while cash, margin, and operational drag are quietly telling a different story. In this episode, Craig Andrews talks with Fred Kosnac about why growth without financial context can create blind spots, especially for owners who are moving fast and trying to make decisions from incomplete numbers.Fred pushes back on the idea th
281 - Your Best AI Strategy May Already Be Inside Your Business with Stephan Bajaio
AI has made search feel new again, but Stephan Bajaio warns leaders not to mistake new acronyms for a new strategy. Whether people call it SEO, AEO, GEO, or AI search, the real question is still whether your market can find useful, credible answers from you and about you. Chasing a mention inside ChatGPT or Claude is a shaky substitute for understanding what your customers need and what the web is
280 - Private-Equity-Grade Finance for Owner-Led Companies with Salvatore Tirabassi
Most business owners do not need prettier dashboards. They need financial reporting that helps them make better decisions, faster.In this episode of Leaders & Legacies, Craig talks with Salvatore Tirabassi about what founder-led and family-owned companies often miss in their finance function. Sal explains why useful reporting starts with a single source of truth, not another spreadsheet or vis
279 - Stop Treating Your Business Lawyer Like a Vending Machine with Matt Bracy
Matt Bracy helps business owners make better legal decisions before those decisions become expensive problems. As a partner at Scheef & Stone, former litigator, former general counsel, and corporate business lawyer, Matt brings the perspective of someone who has both provided and purchased legal services.In this episode, Matt explains why business owners often misuse legal counsel by treating
278: Scaling Without Breaking the Business with Gary Leeman
Gary Leeman helps leadership teams break through the ceilings that stall growth. As a Professional EOS Implementer with EOS Worldwide and a former integrator and COO, he brings a practical operator's perspective to the messy moment when a company has outgrown improvisation but has not yet built the structure needed to scale.In this episode, Gary shares how living in Ireland reshaped his view of pa
277: The Legal Advice Business Owners Actually Need with Aron Phillips
Aron Phillips is an attorney and founder of the Law Office of Aron Phillips in the Stockyards of Fort Worth, where he advises business owners on entity formation, mergers and acquisitions, and commercial real estate. From a century-old building overlooking the daily cattle drive, Aron brings a practical legal perspective shaped by business realities rather than courtroom theatrics.In this episode,
276: The Human Intelligence Behind Scaling Your Business with Courtney DeRonde
Courtney DeRonde is the CEO of Forge Financial and Management Consulting and creator of the Simple Scale Up System, a framework built to help already-successful businesses navigate the complexity that growth creates. A CPA by training and an operator shaped by hard leadership lessons, she now helps founders and leadership teams scale both the business and the leader behind it.In this episode, Cour
275 - Why Too Much Software Is Killing Your Margins with Chad King
Chad King helps businesses stop bending themselves around rigid software. Today, as VP at Ayoka Systems, he focuses on automation, integration, and custom software strategies that make operations simpler, faster, and more profitable.In this episode, Chad breaks down why so many companies are trapped between overpriced off-the-shelf tools and expensive full-custom builds. He explains how AI is chan
274 - From Kyiv to the Boardroom - Bob Nienaber on Retaining Top Talent
Bob Nienaber has spent more than three decades helping companies design executive benefit plans that retain top talent and strengthen long-term business value. Today, as CEO of BenefitRFP and a partner at Simplicity Group, he advises boards and leadership teams on retention, succession, and the financial structures that keep key people committed.In this episode, Bob shares what going behind enemy
273 - Building Businesses That Last: Operational Excellence with Jake Isaacs
Jake Isaacs is a serial integrator and co-founder of Gathering the Kings, an entrepreneurial mastermind and coaching group. As a champion of operational clarity, team leadership, and community-driven growth, Jake shares real-world strategies for building businesses and people that last.In this episode, Jake discusses his journey from breaking his neck playing football to becoming a "fixer" for Hil
272 - Why US Manufacturing Can Still Compete Globally with David Solomon
David Solomon built and ran a $100 million toy manufacturing company in the 1990s with 840,000 square feet of facilities in Montreal and Plattsburgh, New York, successfully competing against China at a time when conventional wisdom said it couldn't be done. Today, as founder of SERO Growth, he helps manufacturers expand into international markets and supports international organizations entering N
271 - The "Double Wind" Strategy: How to Pick Industries and Clients that Fuel Growth with Jon Morris
Jon Morris built Rise Interactive from a solo operation to one of the largest independent digital marketing agencies in the world, scaling it to nearly $40 million in revenue over 16 years. He started with prize money from the University of Chicago's New Venture Challenge in 2004 and rode the wave of digital advertising's explosive growth.Today, Jon is the founder and CEO of The Fiscal Advocate, w
270 - America's Tax Defender: How to Fight the IRS and Win with Pietro Canestrelli
Pietro Canestrelli is a tax attorney and former IRS attorney who helps business owners and taxpayers protect their hard-earned money. As the founder of the Law Office of Pietro Canestrelli and author of America's Tax Defender, he focuses on getting the IRS out of your life as fast as possible.In this episode, Pietro breaks down the three areas of tax work: compliance, proactive planning, and tax d
269 - Why Most Virtual Training Fails - and How Great Leaders Fix It with Bernie DeSantis
In this episode of Leaders and Legacies, Craig Andrews sits down with Bernie DeSantis, CEO of Insignia Training Partners, to explore how leaders can transform virtual training from a dull obligation into a powerful leadership tool. Drawing on more than 20 years of experience in corporate learning and development, Bernie shares how organizations can deliver high-impact virtual experiences that enga
268 - The Micro-Moments That Build - or Break - Trust in Leadership with Kim Bohr
Trust is often treated as a vague leadership ideal, but Kim Bohr argues it’s one of the most measurable and practical drivers of performance inside organizations.As President and CEO of SparkEffect, Kim works with executive teams navigating disruption without breaking trust. In this conversation, she explains how leadership failures rarely come from malicious intent. Instead, they stem from blind
267 - The Strategic CIO: How Leaders Turn Technology Into a Growth Engine with Jeremy Fennema
In this episode of Leaders and Legacies, Craig Andrews sits down with Jeremy Fennema, founder of Fennema.io and a fractional CIO/CTO who helps growth-stage companies bring order to chaotic technology environments.Jeremy explains why most companies struggle with technology—not because of poor tools, but because they lack strategy. Leaders often buy solutions to solve isolated problems, creating a p
266 - Financial Leadership for Law Firms: Turning Numbers into Strategy with John Scott
Leadership often hinges on decisions made with incomplete information. In this episode of Leaders and Legacies, John C. Scott explains why strong leaders build financial clarity into their organizations rather than relying on intuition or a bank balance.John, a CPA and partner at Anders, specializes in helping law firms understand the business side of their practice. Many attorneys excel in legal
265 - AI-Driven Leadership: How Smart Operators 10x Their Impact with Nick Jain
Nick Jain, co-founder of Eagle Rock CFO, believes leadership in the AI era comes down to leverage. The best leaders won’t be replaced by AI—they’ll use it to multiply their impact.Nick explains how AI and smart automation are eliminating low-value work like data cleanup, financial modeling, and report creation. That shift frees leaders to focus on judgment, relationships, and strategic decisions.
264 - From Conflict to Cohesion - Turning Strong Personalities into Strong Teams with Sriram Mangudi
Sriram Mangudi believes leadership reveals itself in moments of pressure. In this episode, he shares hard-earned lessons from global HR leadership, M&A integrations, and navigating COVID while running essential pharmaceutical operations.He explains why most leaders fail during transformation: they push agendas instead of listening. In one high-stakes acquisition, Sriram walked into a room fill
263 - Building a Firm That Outlives You - Erik Brenner on Leadership Through Integration
Erik Brenner doesn’t lead from theory. He leads from structure.As President and CEO of Hilltop Wealth & Tax Solutions, Erik built a firm that integrates advanced tax strategy with wealth management. He saw what others missed: reactive advice was failing clients. CPAs focused on last year. Advisors focused on investments. No one owned the full picture.So he changed it.Erik shares how a defining
262 - Why Smart Leaders Don’t Outsource Thinking to Their CPA
Leadership isn’t just vision. It’s responsibility. In this episode, Catrina M. Craft challenges business owners to rethink what leadership really means when it comes to money, decisions, and long-term impact.Catrina explains why most entrepreneurs unknowingly overpay the IRS—not because the law requires it, but because they were never taught how the system actually works. She draws a sharp line be
261 - Leadership Means Planning the Exit Before You Need It with Brett Swarts
In this episode of Leaders and Legacies, Craig Andrews speaks with Brett Swarts, founder of Capital Gains Tax Solutions, about what leadership looks like when business owners think beyond today.Brett makes the case that strong leaders plan for exits long before they happen. Most owners focus on growth, customers, and operations, but fail to prepare for the financial reality of selling. That lack o
260 - Heidi DeCoux on Leadership, Cash Flow, and Why Most Businesses Fly Blind
Most leadership failures don’t start with people. They start with poor visibility into the business. In this episode, Heidi DeCoux explains why leaders who don’t understand their numbers end up working longer hours while making less money.Heidi breaks down the leadership trap of chasing top-line revenue without understanding profitability. She explains why many founders scale chaos instead of resu
259 - Why Modern Leaders Must Think Like Security Experts with Robert Siciliano
Leadership today demands more than vision and execution. It requires the ability to protect people, data, and trust in an increasingly hostile digital environment.In this episode, Craig Andrews sits down with Robert Siciliano, a leading authority on identity theft, cybersecurity, and personal risk management. Robert breaks down why security is no longer an IT issue—it’s a leadership responsibility
258 - From Startups to Slam Dunks - Adam House on Leading with Grit and Vision
Adam House doesn’t believe in waiting for the right moment—he builds momentum. In this episode of Leaders and Legacies, Adam shares how his “Why Not?” mindset propelled him from serial entrepreneur to professional basketball player at 32—and later, to becoming CEO and co-owner of the very team he joined.Craig Andrews explores Adam’s leadership journey through seven ventures, including a healthcare
257 - The Hidden Cost of Bad Hires - and How to Avoid Them with Jennifer Bookspan
Jennifer Bookspan knows that leadership isn’t about filling seats—it’s about shaping the future of an organization. In this episode, she joins Craig Andrews to discuss how her firm, Bookspan Search Partners, goes beyond typical executive recruiting to help companies build intentional, aligned leadership teams.Jennifer shares why the best leaders are usually the best listeners, and how humility, cl
256 - Why Your Business Won’t Scale Until You Stop Solving Every Problem
Greg Giniel, Professional EOS Implementer, joins Craig Andrews to break down the mindset shift every business owner must make: stop being the easy button for your team. In this candid conversation, Greg explains how the EOS framework builds leaders at every level, freeing business owners from the daily grind while increasing performance across the organization.He shares personal stories, including
255 - The Real Cost of Talent and the Hidden Goldmine in Latin America with Chris Brown
Chris Brown, CTO of Wow Remote Teams, shares how Latin America became his go-to talent solution—and why more U.S. businesses should follow. After running a booming medical e-commerce operation during the pandemic, Chris needed scalable, affordable, and reliable help. His wife Julie, originally from Bogotá and now CEO of Wow Remote Teams, helped him build a nearshore workforce that outperformed U.S
254 - The Power of Asking Better Questions with David Kreeger
David Kreeger traded legal briefs for business breakthroughs. In this episode, the founder of GoPedal shares his journey from practicing law at WilmerHale and IBM to owning a painting franchise and now leading strategic transformations for companies that feel stuck.David reveals what drew him away from the legal grind—a desire to make decisions, improve quality of life, and be present for his fami
253 - The Hidden Dangers Lurking in Your 401(k) Plan with Alex Langan
Alex Langan blends law and finance to protect employees from the hidden traps inside their company retirement plans. As founder of Langan Financial Group and a practicing attorney, Alex has seen the worst—plans charging over 4% in fees with little to no service. In this episode, he explains how poor plan design and ignorance—not malice—often sabotage employee retirements. True leadership, he argue
252 - Inside the Hilton Family Office - Mark Miller on Leading with Clarity and Purpose
Mark Miller doesn’t just manage money—he manages legacies. As the managing partner of Hilton Wealth and co-leader of the Hilton family office, Mark helps business owners and high-net-worth individuals make smarter, safer financial decisions. In this episode, Mark breaks down the misunderstood world of family offices and how they function as a “general contractor” for wealth—coordinating top-tier a
251 - The Hidden ROI of Kindness in Business - A CX Masterclass with Ty Givens
Ty Givens, founder and CEO of CX Collective, joins Craig Andrews to break down the overlooked power of customer experience. Ty argues that customer experience isn’t just about fixing problems—it’s about preventing them. Through real-world examples, from Starbucks to five-star restaurants, Ty highlights how small touches—like empathy and initiative—can turn a moment of friction into long-term loyal
250 - The IRS Calls You 'Low-Hanging Fruit' - Sherry Peel Jackson Says Not Anymore
Dr. Sherry Peel Jackson, former IRS agent turned tax strategist, pulls back the curtain on how small business owners are unfairly targeted by the system. In this hard-hitting episode, Sherry explains why the IRS considers entrepreneurs “low-hanging fruit” and how to legally protect yourself through strategic deductions and proper business structuring.After leaving the IRS, Sherry discovered deep f
249 - The Power of Alignment - How Leadership Teams Accelerate Growth with Nils Vinje
Nils Vinje helps CEOs scale by aligning their leadership teams. In this episode, he breaks down how misalignment at the top quietly drains momentum—and what to do about it. Drawing from his time in Silicon Valley, where leadership teams were swapped out like batteries, Nils explains why true alignment starts with shared understanding and ruthless simplicity.Nils outlines the five principles that p
248 - Why Simplicity Wins - James Elliman’s Blueprint for Small Business IT Leadership
James Elliman planned to be a Marine officer, following a family legacy of military service. But a last-minute medical disqualification forced a hard pivot. Instead of serving in uniform, he leaned into his lifelong love of tech and launched Elliman Technologies to simplify IT for small businesses.In this episode, James shares how leadership isn't just about titles—it’s about clarity, adaptability
247 - From ICU to Camp Gladiator - Setting and Achieving Outrageous Goals with Craig Andrews
Craig Andrews opens up about the most defining moment of his life—a six-week coma after a severe case of COVID-19. Doctors told his wife he wouldn’t survive. But he beat the odds. When he woke, he discovered that his team and community kept his business running. That, he says, is his proudest leadership moment.In this solo episode, Craig reflects on the radical recovery process and the outrageous
246 - Choosing the Right Relationships - A Leader’s Priority with Craig Andrews
Craig Andrews opens up about the most defining leadership moment of his life—one he wasn’t even conscious for. After slipping into a six-week coma from COVID-19, doctors told his wife he wouldn’t survive. But his team kept the business running. Freelancers stepped in unasked. That’s when Craig knew he had built something more than a company—he built loyalty.In this special Christmas episode, Craig
245 - From Ballroom to Boardroom - Camille Diaz on Leading Through Reinvention
Camille Diaz’s leadership story is rooted in reinvention. A science teacher turned ballroom dance studio co-founder, she built a thriving business—until a partner change derailed everything. Faced with debt, a lawsuit, and burnout, Camille hit rock bottom. But when friends began asking her for business advice, she discovered a new path: optimization coaching.Camille now leads Serenity Financial, h
244 - Reclaiming the American Dream Through Smarter Health Benefits with Chris Mathew.mp3
Chris Mathew, Chief Growth Officer at Well-Genie, joins Craig Andrews to reveal how his father’s tragic and avoidable death shaped his mission to transform American healthcare. With deep family roots in Kerala and a legacy of firstborn leadership, Chris channels that sense of duty into helping employers radically cut costs while increasing wellness benefits for their teams.Chris doesn’t just talk
243 - From Purple Branding to Powerful Follow-Up: Ely Delaney’s Playbook
Ely Delaney doesn’t just teach follow-up marketing—he lives it. On this episode of Leaders & Legacies, Ely shares how authenticity and consistency transformed his business and leadership style. From his signature purple branding to a three-year evergreen email campaign, Ely leans into what makes him different—and encourages others to do the same.He and host Craig Andrews explore the leadership
242 - Leadership Born in the ICU - Kimberly Carleson’s Mission to Fix Health Care Billing
Kimberly Carleson didn’t set out to become a leader in health care reform. Life forced her into it.When her husband was diagnosed with stage four metastatic bladder cancer, Kimberly found herself navigating a health care system built for confusion, not care. Pregnant and raising a young daughter, she refused to accept the death sentence doctors gave her husband. Her advocacy, persistence, and lead
241 - From HR Hater to Growth Strategist - DeeAnn Palin’s Bold Pivot
DeeAnn Palin doesn’t just fix companies — she rebuilds them from the inside out. In this episode, Craig Andrews talks with the founder and CEO of OnPoint Business Solutions about her radical journey from corporate HR skeptic to trusted strategic partner for CEOs.Palin pulls back the curtain on toxic culture, ethical blind spots, and the cost of keeping the wrong people in leadership. She explains
240 - From Marine to Media Mogul - Jesse Sieff on Leading with Precision
Jesse Sieff is no stranger to reinvention. From military barracks to media production, he’s built a career on sharp pivots and sharper leadership. In this episode, Jesse breaks down how his time in the Marine Corps Drum & Bugle Corps instilled in him a deep respect for discipline, detail, and public representation—skills that now fuel his work at Sieff Studios.Jesse’s leadership style blends s
239 - The Power of Presence - Why Fathers Matter More Than Ever with Marquess Dennis
Marquess Dennis doesn’t just talk about fatherhood—he’s on a mission to redefine it. As the founder of Birthright Living Legacy, he joins Craig Andrews to challenge cultural narratives, unpack generational trauma, and spotlight the deep systemic impact of absent fathers. Dennis shares his own journey from poverty in North Tulsa to building a nonprofit dedicated to helping fathers of all background
238 -Why Your CPA Isn’t Your Tax Strategist - And What to Do About It with Paden Squires
Paden Squires grew up in rural Missouri with firsthand experience of financial insecurity. That early exposure shaped his mission: help entrepreneurs grow wealth with clarity and confidence. In this episode, Paden breaks down why relying on your CPA for tax strategy is a mistake. Most CPAs are set up to file returns—not proactively plan.He walks through high-impact tax strategies like the Augusta
237 - Ashley Connell on Unlocking Hidden Ops Talent for Scalable Leadership
Ashley Connell, CEO of Prowess Project, joins Leaders and Legacies to unpack a bold truth: leaders don’t need another version of themselves. They need a “not you”—a skilled operator who thrives on structure, details, and execution.In this episode, Ashley shares how she built a talent pipeline of highly qualified caregivers—primarily mothers and sandwich-generation women—who bring unmatched emotion
236 - Why Justin Dixon Quit a Six-Figure Job to Build a Recruiting Firm During a Crisis
Justin Dixon walked away from a comfortable six-figure job and launched a recruiting firm—just weeks before the world shut down. In this episode, he joins Craig Andrews to unpack what it really takes to lead when the timing couldn’t be worse.Justin shares the personal finance moves he and his wife made to de-risk the leap, and why reading Rich Dad Poor Dad flipped his entire outlook on life and ca
235 - Why “Scared Money Doesn’t Make Money” - Sonny Grappone’s Leadership Mindset
Sonny Grappone didn’t follow a straight path to success. Raised by a single mother from Guyana and a hardworking Italian-American stepfather, Sonny grew up in Queens, New York, sharing a bed with his mom and sister. That early scarcity drove his work ethic—bagging groceries at 12, building computers in high school, and running an auto detailing business in college.At 25, he pivoted. He went back t
234 - Why Transparency in Pharmacy Benefits is a Leadership Imperative with Justin Jasniewski
Justin Jasniewski, CEO of Serve You Rx, breaks down one of healthcare’s murkiest corners—pharmacy benefit managers (PBMs). In this episode, he exposes how PBMs sit at the crossroads of drug manufacturers, employers, and pharmacies—often inflating costs instead of controlling them. With plain talk and sharp insights, Justin walks through how the system evolved from a simple IT add-on to a high-stak
233 - The ABCs of Charisma - Leadership Lessons from Milam Miller
Milam Miller, founder of Be Confident and Kind and author of The Charisma Craft, joins Craig Andrews to challenge everything we think we know about charisma. A former executive for a billionaire sports team owner and affectionately nicknamed the “real-life Ted Lasso,” Milam shares how charisma isn’t innate—it’s a skill any leader can develop.Through bold stories and sharp insight, Milam breaks dow
232 - Reinventing Voice of the Customer with AI - Eli Portnoy's Leadership Playbook
Eli Portnoy, CEO and co-founder of BackEngine, joins Craig Andrews to expose the flaws in traditional customer feedback systems—and why leadership demands better data. A seasoned entrepreneur and Harvard Business School Executive Fellow, Eli dives into how B2B companies often make strategic decisions using flawed insights from biased surveys.Eli unpacks how leadership in the AI era means throwing
231 - 25% of Waste Hiding in Your P&L with Donovan Pyle
Donovan Pyle pulls back the curtain on an industry most business leaders misunderstand: employer-sponsored health care. In this episode, Donovan explains how companies are overpaying by as much as 25%—often without realizing it—and why the current broker model keeps them trapped. Drawing on his own experience inside a major insurance company and later as a broker, Donovan saw firsthand how incenti
230 - From Solo Act to Sustainable Business - William Bissett on Leadership
William Bissett, founder of Portus Wealth Advisors, joins Craig Andrews to unpack what it really takes to lead a company that survives and thrives beyond its founder. William shares how watching his father struggle in solo practice shaped his commitment to team building. His insight is simple but powerful: don’t just hire talent—hire people who fill your gaps, not mirror them.The episode cuts thro
229 - The Ezra Principle - Leadership Lessons That Scaled a Referral Empire with Brian McRae
Brian McRae walked away from a comfortable W-2 job to chase something more fulfilling—control, freedom, and impact. What followed was a leadership journey rooted in service. In this episode, Brian shares how he transitioned from the mortgage world to building a coaching and mastermind business that thrives on authentic relationships.He didn’t advertise. He didn’t pitch. Instead, he launched a free
228 - Why Leadership Isn’t Taught - It’s Lived - Lessons from Kyle Schwarz
Kyle Schwarz brings clarity to what leadership really looks like. A U.S. Naval Academy graduate and surface warfare officer, Kyle shares how a blunt rejection from his blue and gold officer nearly derailed his academy ambitions—but ultimately became a catalyst for transformation. He didn't quit. He trained, returned, and earned one of the strongest recommendations in years.Now with 17 years of lea
227 - The Wisdom of Ignorance - Why Not Knowing Can Be the Key to Innovation with Alan Gregerman
Alan Gregerman nearly lost everything after a stroke robbed him of his ability to speak and see. But instead of giving in, he turned that moment into one of his greatest leadership lessons. In this episode, Alan shares how navigating life without communication forced him to rethink how leaders engage, innovate, and lead. Through his recovery, he uncovered deeper truths about humility, clarity, and
226 - From Hospice to High Impact - How Emily Erstad Builds Resilient Teams
Emily Erstad joins Craig Andrews for a candid conversation about the real heart of leadership—emotional intelligence. A former speech-language pathologist turned hospice leader, Emily shares how leading in high-stakes environments taught her the power of trust, vulnerability, and consistency.She explains why leadership isn’t about commanding—it’s about partnering. Whether guiding patients through
225 - Why Great Leaders Set the Strategy - Then Get Out of the Way with Lee Pepper
Lee Pepper brings battlefield-tested leadership into the boardroom. In this episode, Lee breaks down how military strategies—some dating back to the Romans—can drive success in today’s marketing and business landscape. Drawing from his Army background, time at Fort Knox, and career in behavioral healthcare marketing, Lee explains how setting clear intent and empowering teams to execute leads to su
224 - From Moscow to Main Street - How Stan Sukhinin Helps Clinics Thrive
Stan Sukhinin knows what it’s like to rebuild from scratch. After a meteoric rise in Eastern Europe’s finance world—managing a $450M mezzanine loan portfolio—he moved to New York to launch a hedge fund. It didn’t survive the pandemic. What did survive? His ability to spot financial blind spots and fix them fast.Now, as founder of The Sorso, Stan serves as a fractional CFO for outpatient clinics ac
223 - From Iraq to EOS - Why Every Leader Needs a Coaching Team with Hark Herold
Hark Herold brings three decades of military precision to the entrepreneurial world. As a retired U.S. Air Force colonel turned EOS implementer, Hark shares how his leadership experience in high-stakes environments—from serving in Desert Storm to overseeing base recovery during rocket attacks in Iraq—shaped his approach to business.Now, he empowers small and medium-sized businesses to build clarit
222 - Copy that Persuades for Leaders with Hillary Gale
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
221 - From Financial Advisor to Healthcare Disruptor -The Donovan Ryckis Story
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.
220 - From Dyslexic Kid to Podcasting Visionary - The Leadership Journey of Alex Sanfilippo
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—
219 - Chris Hurn on Why Entrepreneurs Need Courage - and Cash Flow
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 finan
218 - From Budget Buster to Loyalty Builder - Rethinking Employer Health Plans with Allison De Paoli
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 argu
217 - Why Every Leader Should Write a Book - Insights from Everett O’Keefe
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 th
216 - Empowering Business Owners - Tax Strategies with Mike Jesowshek
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 lea
215 - Building a Workforce from Scratch - Michael Cole’s Leadership in the Trades
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
